diff --git a/packages/cli/api-importers/asyncapi-to-ir/package.json b/packages/cli/api-importers/asyncapi-to-ir/package.json
index 74a051b105a..3dd559ff1a0 100644
--- a/packages/cli/api-importers/asyncapi-to-ir/package.json
+++ b/packages/cli/api-importers/asyncapi-to-ir/package.json
@@ -33,6 +33,7 @@
   "dependencies": {
     "@fern-api/ir-sdk": "workspace:*",
     "@fern-api/ir-utils": "workspace:*",
+    "@fern-api/task-context": "workspace:*",
     "@fern-api/v3-importer-commons": "workspace:*",
     "lodash-es": "catalog:",
     "openapi-types": "^12.1.3",
diff --git a/packages/cli/api-importers/asyncapi-to-ir/src/3.0/channel/ChannelConverter3_0.ts b/packages/cli/api-importers/asyncapi-to-ir/src/3.0/channel/ChannelConverter3_0.ts
index 7be9f889f43..dc8775a670b 100644
--- a/packages/cli/api-importers/asyncapi-to-ir/src/3.0/channel/ChannelConverter3_0.ts
+++ b/packages/cli/api-importers/asyncapi-to-ir/src/3.0/channel/ChannelConverter3_0.ts
@@ -1,5 +1,6 @@
 import { HttpHeader, PathParameter, QueryParameter, WebSocketMessage, WebSocketMessageBody } from "@fern-api/ir-sdk";
 import { constructHttpPath } from "@fern-api/ir-utils";
+import { CliError } from "@fern-api/task-context";
 import { Converters } from "@fern-api/v3-importer-commons";
 import { OpenAPIV3 } from "openapi-types";
 import { AbstractChannelConverter } from "../../converters/AbstractChannelConverter.js";
@@ -310,7 +311,10 @@ export class ChannelConverter3_0 extends AbstractChannelConverter<AsyncAPIV3.Cha
 
     private getChannelPathFromOperation(operation: AsyncAPIV3.Operation): string {
         if (!operation.channel.$ref.startsWith(CHANNEL_REFERENCE_PREFIX)) {
-            throw new Error(`Failed to resolve channel path from operation ${operation.channel.$ref}`);
+            throw new CliError({
+                message: `Failed to resolve channel path from operation ${operation.channel.$ref}`,
+                code: CliError.Code.ReferenceError
+            });
         }
         return operation.channel.$ref.substring(CHANNEL_REFERENCE_PREFIX.length);
     }
diff --git a/packages/cli/api-importers/commons/src/utils/FernDefinitionDirectory.ts b/packages/cli/api-importers/commons/src/utils/FernDefinitionDirectory.ts
index 02b71a076c6..3fa2c051c41 100644
--- a/packages/cli/api-importers/commons/src/utils/FernDefinitionDirectory.ts
+++ b/packages/cli/api-importers/commons/src/utils/FernDefinitionDirectory.ts
@@ -1,5 +1,6 @@
 import { RawSchemas } from "@fern-api/fern-definition-schema";
 import { RelativeFilePath, sep } from "@fern-api/path-utils";
+import { CliError } from "@fern-api/task-context";
 
 export class FernDefinitionDirectory {
     private files: Record<RelativeFilePath, RawSchemas.DefinitionFileSchema> = {};
@@ -41,7 +42,10 @@ export class FernDefinitionDirectory {
         }
         const [directory, ...remainingPath] = pathParts;
         if (directory == null) {
-            throw new Error(`Internal error; cannot add file with path: ${pathParts}`);
+            throw new CliError({
+                message: `Internal error; cannot add file with path: ${pathParts}`,
+                code: CliError.Code.InternalError
+            });
         }
         if (!this.directories[directory]) {
             this.directories[directory] = new FernDefinitionDirectory();
diff --git a/packages/cli/api-importers/conjure/conjure-to-fern/package.json b/packages/cli/api-importers/conjure/conjure-to-fern/package.json
index 12aa0a6852d..cffff7caa40 100644
--- a/packages/cli/api-importers/conjure/conjure-to-fern/package.json
+++ b/packages/cli/api-importers/conjure/conjure-to-fern/package.json
@@ -37,6 +37,7 @@
     "@fern-api/fern-definition-schema": "workspace:*",
     "@fern-api/fs-utils": "workspace:*",
     "@fern-api/importer-commons": "workspace:*",
+    "@fern-api/task-context": "workspace:*",
     "js-yaml": "catalog:"
   },
   "devDependencies": {
diff --git a/packages/cli/api-importers/conjure/conjure-to-fern/src/ConjureImporter.ts b/packages/cli/api-importers/conjure/conjure-to-fern/src/ConjureImporter.ts
index 718e4ef9192..7f0acedeb87 100644
--- a/packages/cli/api-importers/conjure/conjure-to-fern/src/ConjureImporter.ts
+++ b/packages/cli/api-importers/conjure/conjure-to-fern/src/ConjureImporter.ts
@@ -3,6 +3,7 @@ import { parseEndpointLocator, removeSuffix } from "@fern-api/core-utils";
 import { RawSchemas } from "@fern-api/fern-definition-schema";
 import { AbsoluteFilePath, dirname, getFilename, join, RelativeFilePath, relativize } from "@fern-api/fs-utils";
 import { APIDefinitionImporter, FernDefinitionBuilderImpl, HttpServiceInfo } from "@fern-api/importer-commons";
+import { CliError } from "@fern-api/task-context";
 
 import { listConjureFiles } from "./utils/listConjureFiles.js";
 import { visitConjureTypeDeclaration } from "./utils/visitConjureTypeDeclaration.js";
@@ -77,7 +78,10 @@ export class ConjureImporter extends APIDefinitionImporter<ConjureImporter.Args>
             if (definition.services == null || Object.keys(definition.services ?? {}).length === 0) {
                 const fernFilePath = this.conjureFilepathToFernFilepath[filepath];
                 if (fernFilePath == null) {
-                    throw new Error(`Failed to find corresponding fern filepath for conjure file ${filepath}`);
+                    throw new CliError({
+                        message: `Failed to find corresponding fern filepath for conjure file ${filepath}`,
+                        code: CliError.Code.InternalError
+                    });
                 }
 
                 for (const [import_, importedFilepath] of Object.entries(definition.types?.conjureImports ?? {})) {
@@ -151,9 +155,10 @@ export class ConjureImporter extends APIDefinitionImporter<ConjureImporter.Args>
                         for (const pathParameter of endpointLocator.pathParameters) {
                             const pathParameterType = endpointDeclaration.args[pathParameter];
                             if (pathParameterType == null) {
-                                throw new Error(
-                                    `Failed to find path parameter ${pathParameter} in ${endpointDeclaration.http}`
-                                );
+                                throw new CliError({
+                                    message: `Failed to find path parameter ${pathParameter} in ${endpointDeclaration.http}`,
+                                    code: CliError.Code.InternalError
+                                });
                             }
                             pathParameters[pathParameter] =
                                 typeof pathParameterType === "string"
@@ -338,9 +343,10 @@ export class ConjureImporter extends APIDefinitionImporter<ConjureImporter.Args>
         );
         const correspondingFernFilePath = this.conjureFilepathToFernFilepath[relativeFilePathToImportedFile];
         if (correspondingFernFilePath == null) {
-            throw new Error(
-                `Failed to find corresponding fern filepath for conjure file ${relativeFilePathToImportedFile}`
-            );
+            throw new CliError({
+                message: `Failed to find corresponding fern filepath for conjure file ${relativeFilePathToImportedFile}`,
+                code: CliError.Code.InternalError
+            });
         }
         return correspondingFernFilePath;
     }
diff --git a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildEndpoint.ts b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildEndpoint.ts
index 3c39cb7912b..6dba3b578ba 100644
--- a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildEndpoint.ts
+++ b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildEndpoint.ts
@@ -3,6 +3,7 @@ import { assertNever, MediaType } from "@fern-api/core-utils";
 import { RawSchemas } from "@fern-api/fern-definition-schema";
 import { Endpoint, EndpointExample, Request, RetriesConfiguration, Schema, SchemaId } from "@fern-api/openapi-ir";
 import { RelativeFilePath } from "@fern-api/path-utils";
+import { CliError } from "@fern-api/task-context";
 import { buildEndpointExample } from "./buildEndpointExample.js";
 import { ERROR_DECLARATIONS_FILENAME, EXTERNAL_AUDIENCE } from "./buildFernDefinition.js";
 import { buildHeader } from "./buildHeader.js";
@@ -283,7 +284,10 @@ export function buildEndpoint({
                 };
             },
             _other: () => {
-                throw new Error("Unrecognized Response type: " + endpoint.response?.type);
+                throw new CliError({
+                    message: "Unrecognized Response type: " + endpoint.response?.type,
+                    code: CliError.Code.InternalError
+                });
             }
         });
     }
diff --git a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildWebhooks.ts b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildWebhooks.ts
index ceca44ade35..b69772ab07d 100644
--- a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildWebhooks.ts
+++ b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/buildWebhooks.ts
@@ -13,6 +13,7 @@ import {
     WebhookTimestampFormat
 } from "@fern-api/openapi-ir";
 import { join, RelativeFilePath } from "@fern-api/path-utils";
+import { CliError } from "@fern-api/task-context";
 import { camelCase, isEqual } from "lodash-es";
 import { buildHeader } from "./buildHeader.js";
 import { buildTypeReference } from "./buildTypeReference.js";
@@ -142,7 +143,10 @@ export function buildWebhooks(context: OpenApiIrConverterContext): void {
                     };
                 },
                 _other: () => {
-                    throw new Error("Unrecognized Response type: " + webhook.response?.type);
+                    throw new CliError({
+                        message: "Unrecognized Response type: " + webhook.response?.type,
+                        code: CliError.Code.InternalError
+                    });
                 }
             });
         }
diff --git a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/convertToHttpMethod.ts b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/convertToHttpMethod.ts
index 6c2a8977d68..468cdaf246a 100644
--- a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/convertToHttpMethod.ts
+++ b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/convertToHttpMethod.ts
@@ -1,5 +1,6 @@
 import { RawSchemas } from "@fern-api/fern-definition-schema";
 import { HttpMethod } from "@fern-api/openapi-ir";
+import { CliError } from "@fern-api/task-context";
 
 export function convertToHttpMethod(httpMethod: HttpMethod): RawSchemas.HttpMethodSchema {
     return HttpMethod._visit<RawSchemas.HttpMethodSchema>(httpMethod, {
@@ -10,13 +11,13 @@ export function convertToHttpMethod(httpMethod: HttpMethod): RawSchemas.HttpMeth
         delete: () => RawSchemas.HttpMethodSchema.Delete,
         head: () => RawSchemas.HttpMethodSchema.Head,
         options: () => {
-            throw new Error("OPTIONS is unsupported");
+            throw new CliError({ message: "OPTIONS is unsupported", code: CliError.Code.ConfigError });
         },
         trace: () => {
-            throw new Error("TRACE is unsupported");
+            throw new CliError({ message: "TRACE is unsupported", code: CliError.Code.ConfigError });
         },
         _other: () => {
-            throw new Error("Unknown http method is unsupported");
+            throw new CliError({ message: "Unknown http method is unsupported", code: CliError.Code.ConfigError });
         }
     });
 }
diff --git a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/getEndpointLocation.ts b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/getEndpointLocation.ts
index 17b3f307f1f..76be6ce0842 100644
--- a/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/getEndpointLocation.ts
+++ b/packages/cli/api-importers/openapi/openapi-ir-to-fern/src/utils/getEndpointLocation.ts
@@ -1,8 +1,8 @@
 import { FERN_PACKAGE_MARKER_FILENAME } from "@fern-api/configuration";
 import { Endpoint, HttpMethod } from "@fern-api/openapi-ir";
 import { join, RelativeFilePath } from "@fern-api/path-utils";
+import { CliError } from "@fern-api/task-context";
 import { camelCase, compact, isEqual } from "lodash-es";
-
 import { convertEndpointSdkNameToFileWithoutExtension } from "./convertSdkGroupName.js";
 
 export interface EndpointLocation {
@@ -108,7 +108,10 @@ function getUnresolvedEndpointLocation(endpoint: Endpoint): EndpointLocation {
     }
 
     if (fileParts.length >= operationIdTokens.length) {
-        throw new Error(`Cannot get file for endpoint ${JSON.stringify(endpoint)}`);
+        throw new CliError({
+            message: `Cannot get file for endpoint ${JSON.stringify(endpoint)}`,
+            code: CliError.Code.InternalError
+        });
     }
 
     return {
diff --git a/packages/cli/api-importers/v3-importer-commons/package.json b/packages/cli/api-importers/v3-importer-commons/package.json
index 4e9c4b24905..471818b6a8e 100644
--- a/packages/cli/api-importers/v3-importer-commons/package.json
+++ b/packages/cli/api-importers/v3-importer-commons/package.json
@@ -40,6 +40,7 @@
     "@fern-api/ir-sdk": "workspace:*",
     "@fern-api/ir-utils": "workspace:*",
     "@fern-api/logger": "workspace:*",
+    "@fern-api/task-context": "workspace:*",
     "js-yaml": "catalog:",
     "js-yaml-source-map": "catalog:",
     "lodash-es": "catalog:",
diff --git a/packages/cli/api-importers/v3-importer-commons/src/utils/CreateTypeReferenceFromFernType.ts b/packages/cli/api-importers/v3-importer-commons/src/utils/CreateTypeReferenceFromFernType.ts
index 06a830fddb8..6c15ace87bc 100644
--- a/packages/cli/api-importers/v3-importer-commons/src/utils/CreateTypeReferenceFromFernType.ts
+++ b/packages/cli/api-importers/v3-importer-commons/src/utils/CreateTypeReferenceFromFernType.ts
@@ -1,5 +1,6 @@
 import { recursivelyVisitRawTypeReference } from "@fern-api/fern-definition-schema";
 import * as FernIr from "@fern-api/ir-sdk";
+import { CliError } from "@fern-api/task-context";
 
 export function createTypeReferenceFromFernType(fernType: string): FernIr.TypeReference | undefined {
     return recursivelyVisitRawTypeReference<FernIr.TypeReference | undefined>({
@@ -153,7 +154,10 @@ export function createTypeReferenceFromFernType(fernType: string): FernIr.TypeRe
                             string: (value) => FernIr.Literal.string(value),
                             boolean: (value) => FernIr.Literal.boolean(value),
                             _other: () => {
-                                throw new Error("Unexpected literal type");
+                                throw new CliError({
+                                    message: "Unexpected literal type",
+                                    code: CliError.Code.InternalError
+                                });
                             }
                         })
                     )
diff --git a/packages/cli/cli/src/cli.ts b/packages/cli/cli/src/cli.ts
index 41ff3025a50..c227a7b1540 100644
--- a/packages/cli/cli/src/cli.ts
+++ b/packages/cli/cli/src/cli.ts
@@ -1869,10 +1869,16 @@ function addDocsPreviewDeleteCommand(cli: Argv<GlobalCliOptions>, cliContext: Cl
                 .check((argv) => {
                     const sources = [argv.target, argv.url, argv.id].filter(Boolean);
                     if (sources.length === 0) {
-                        throw new Error("Must provide a preview URL or --id.");
+                        throw new CliError({
+                            message: "Must provide a preview URL or --id.",
+                            code: CliError.Code.ConfigError
+                        });
                     }
                     if (sources.length > 1) {
-                        throw new Error("Provide only one of: [target], --url, or --id.");
+                        throw new CliError({
+                            message: "Provide only one of: [target], --url, or --id.",
+                            code: CliError.Code.ConfigError
+                        });
                     }
                     return true;
                 }),
diff --git a/packages/cli/cli/src/commands/docs-preview/deleteDocsPreview.ts b/packages/cli/cli/src/commands/docs-preview/deleteDocsPreview.ts
index 40f0ccee156..89141364196 100644
--- a/packages/cli/cli/src/commands/docs-preview/deleteDocsPreview.ts
+++ b/packages/cli/cli/src/commands/docs-preview/deleteDocsPreview.ts
@@ -45,7 +45,10 @@ function resolveTarget({
         return { type: "id", value: id };
     }
     if (target == null) {
-        throw new Error("Must provide a preview URL or --id.");
+        throw new CliError({
+            message: "Must provide a preview URL or --id.",
+            code: CliError.Code.ConfigError
+        });
     }
     if (isPreviewUrl(target)) {
         return { type: "url", value: target };
diff --git a/packages/cli/cli/src/commands/upgrade/migrations/__test__/loader.test.ts b/packages/cli/cli/src/commands/upgrade/migrations/__test__/loader.test.ts
index 3564f171077..c94d7de3bd7 100644
--- a/packages/cli/cli/src/commands/upgrade/migrations/__test__/loader.test.ts
+++ b/packages/cli/cli/src/commands/upgrade/migrations/__test__/loader.test.ts
@@ -434,6 +434,10 @@ describe("loadAndRunMigrations", () => {
             ).rejects.toThrow("Invalid generator configuration");
         });
 
+        // Timeout bumped to 60s because these two happy-path tests fall through
+        // to loadMigrationModule, which performs a real `npm install
+        // @fern-api/generator-migrations@latest`. That call is network-bound and
+        // regularly exceeds the 5s vitest default on CI (observed 2s–5s+).
         it("should accept valid config with name property", async () => {
             const mockLogger = {
                 debug: vi.fn(),
@@ -456,7 +460,7 @@ describe("loadAndRunMigrations", () => {
             expect(mockLogger.warn).not.toHaveBeenCalledWith(
                 expect.stringContaining("Invalid generator configuration structure")
             );
-        });
+        }, 60000);
 
         it("should accept config with additional properties", async () => {
             const mockLogger = {
@@ -483,6 +487,6 @@ describe("loadAndRunMigrations", () => {
             expect(mockLogger.warn).not.toHaveBeenCalledWith(
                 expect.stringContaining("Invalid generator configuration structure")
             );
-        });
+        }, 60000);
     });
 });
diff --git a/packages/cli/docs-importers/commons/src/FernDocsBuilderImpl.ts b/packages/cli/docs-importers/commons/src/FernDocsBuilderImpl.ts
index 94458f11452..1a3943cbeaa 100644
--- a/packages/cli/docs-importers/commons/src/FernDocsBuilderImpl.ts
+++ b/packages/cli/docs-importers/commons/src/FernDocsBuilderImpl.ts
@@ -7,9 +7,9 @@ import {
 } from "@fern-api/configuration";
 import { FdrAPI as CjsFdrSdk } from "@fern-api/fdr-sdk";
 import { AbsoluteFilePath, dirname, join, RelativeFilePath } from "@fern-api/fs-utils";
+import { CliError } from "@fern-api/task-context";
 import { cp, mkdir, writeFile } from "fs/promises";
 import yaml from "js-yaml";
-
 import { FernDocsBuilder, FernDocsNavigationBuilder } from "./FernDocsBuilder.js";
 
 interface MarkdownPage {
@@ -88,7 +88,7 @@ export class FernDocsBuilderImpl extends FernDocsBuilder {
         versionConfig: docsYml.RawSchemas.VersionConfig;
         navigation: docsYml.RawSchemas.VersionFileConfig;
     }): void {
-        throw new Error("Method not implemented.");
+        throw new CliError({ message: "Method not implemented.", code: CliError.Code.InternalError });
     }
 
     public addNavbarLink({ link }: { link: docsYml.RawSchemas.NavbarLink }): void {
diff --git a/packages/cli/docs-importers/mintlify/src/MintlifyImporter.ts b/packages/cli/docs-importers/mintlify/src/MintlifyImporter.ts
index 7a2dd4f0dd7..8de427e0fb4 100644
--- a/packages/cli/docs-importers/mintlify/src/MintlifyImporter.ts
+++ b/packages/cli/docs-importers/mintlify/src/MintlifyImporter.ts
@@ -7,6 +7,7 @@ import {
     TabInfo
 } from "@fern-api/docs-importer-commons";
 import { AbsoluteFilePath, dirname, join, RelativeFilePath } from "@fern-api/fs-utils";
+import { CliError } from "@fern-api/task-context";
 import { readFile } from "fs/promises";
 
 import { convertColors } from "./convertColors.js";
@@ -154,7 +155,11 @@ export class MintlifyImporter extends DocsImporter<MintlifyImporter.Args> {
         if (Object.keys(this.tabUrlToInfo).length > 0) {
             const tabUrl = getTabForMintItem({ mintItem });
             if (tabUrl == null) {
-                return this.context.failAndThrow(`Failed to assign navigation item to a tab group: ${mintItem.group}`);
+                return this.context.failAndThrow(
+                    `Failed to assign navigation item to a tab group: ${mintItem.group}`,
+                    undefined,
+                    { code: CliError.Code.ConfigError }
+                );
             }
             const tab = this.tabUrlToInfo[tabUrl] ?? this.getDefaultDocumentationTab(builder);
             return tab.navigationBuilder;
diff --git a/packages/cli/docs-importers/readme/src/assert.ts b/packages/cli/docs-importers/readme/src/assert.ts
index 10818108a59..1aa6c00276a 100644
--- a/packages/cli/docs-importers/readme/src/assert.ts
+++ b/packages/cli/docs-importers/readme/src/assert.ts
@@ -1,3 +1,4 @@
+import { CliError } from "@fern-api/task-context";
 import type { Element, Root } from "hast";
 import { CONTINUE, EXIT, visit } from "unist-util-visit";
 import { z } from "zod";
@@ -10,7 +11,7 @@ export function assertIsNumber(val: unknown): asserts val is number {
 
 export function assertIsDefined<T>(val: T): asserts val is NonNullable<T> {
     if (val === undefined || val == null) {
-        throw new Error("Value is nullable.");
+        throw new CliError({ message: "Value is nullable.", code: CliError.Code.InternalError });
     }
 }
 
diff --git a/packages/cli/docs-importers/readme/src/utils/files/file.ts b/packages/cli/docs-importers/readme/src/utils/files/file.ts
index 38bdfa7ce7c..ab45f9e2c6e 100644
--- a/packages/cli/docs-importers/readme/src/utils/files/file.ts
+++ b/packages/cli/docs-importers/readme/src/utils/files/file.ts
@@ -1,5 +1,6 @@
 import { mkdirSync, writeFileSync } from "node:fs";
 import { dirname } from "node:path";
+import { CliError } from "@fern-api/task-context";
 import { join } from "path";
 
 export function createFilename(
@@ -73,7 +74,10 @@ export function writePage({
             })
         );
     } catch (error) {
-        throw new Error(`${cleanedWritePath}: failed to download to disk`);
+        throw new CliError({
+            message: `${cleanedWritePath}: failed to download to disk`,
+            code: CliError.Code.NetworkError
+        });
     }
 }
 
diff --git a/packages/cli/docs-importers/readme/src/utils/files/images.ts b/packages/cli/docs-importers/readme/src/utils/files/images.ts
index 1785e130e0b..ef95f6bc657 100644
--- a/packages/cli/docs-importers/readme/src/utils/files/images.ts
+++ b/packages/cli/docs-importers/readme/src/utils/files/images.ts
@@ -1,6 +1,6 @@
 import { existsSync, mkdirSync } from "node:fs";
 import { dirname, join } from "node:path";
-
+import { CliError } from "@fern-api/task-context";
 import type { Result } from "../../types/result.js";
 import { fetchImage } from "../network.js";
 import { write } from "./file.js";
@@ -42,7 +42,10 @@ async function writeImageToFile(src: string, rootPath: string): Promise<string>
     const imagePath = join(rootPath, filename);
 
     if (!isValidImageSrc(filename)) {
-        throw new Error(`${filename} - file extension not supported`);
+        throw new CliError({
+            message: `${filename} - file extension not supported`,
+            code: CliError.Code.InternalError
+        });
     }
     if (existsSync(imagePath)) {
         return imagePath;
@@ -51,7 +54,7 @@ async function writeImageToFile(src: string, rootPath: string): Promise<string>
     try {
         mkdirSync(dirname(imagePath), { recursive: true });
     } catch (error) {
-        throw new Error(`${imagePath} - failed to create directory`);
+        throw new CliError({ message: `${imagePath} - failed to create directory`, code: CliError.Code.InternalError });
     }
 
     try {
@@ -59,7 +62,10 @@ async function writeImageToFile(src: string, rootPath: string): Promise<string>
         write(imagePath, imageData);
         return imagePath;
     } catch (error) {
-        throw new Error(`${imagePath}: failed to download file from source`);
+        throw new CliError({
+            message: `${imagePath}: failed to download file from source`,
+            code: CliError.Code.NetworkError
+        });
     }
 }
 
diff --git a/packages/cli/docs-importers/readme/src/utils/network.ts b/packages/cli/docs-importers/readme/src/utils/network.ts
index 70c8384944e..9eed54d4aab 100644
--- a/packages/cli/docs-importers/readme/src/utils/network.ts
+++ b/packages/cli/docs-importers/readme/src/utils/network.ts
@@ -1,3 +1,4 @@
+import { CliError } from "@fern-api/task-context";
 import { Browser, launch } from "puppeteer";
 
 const userAgent =
@@ -34,7 +35,7 @@ export async function startPuppeteer(): Promise<Browser> {
     try {
         return await launch({ headless: true, args: ["--ignore-certificate-errors"] });
     } catch (error) {
-        throw new Error("Could not create a Puppeteer instance");
+        throw new CliError({ message: "Could not create a Puppeteer instance", code: CliError.Code.EnvironmentError });
     }
 }
 
@@ -63,7 +64,7 @@ export async function getHtmlWithPuppeteer(browser: Browser, url: string | URL):
         await page.close();
         return content;
     } catch (error) {
-        throw new Error("Failed to download page from Puppeteer");
+        throw new CliError({ message: "Failed to download page from Puppeteer", code: CliError.Code.NetworkError });
     }
 }
 
@@ -71,11 +72,11 @@ async function fetchPageResponse(url: string | URL): Promise<string> {
     try {
         const res = await fetch(url);
         if (!res.ok) {
-            throw new Error(`${res.status} ${res.statusText}`);
+            throw new CliError({ message: `${res.status} ${res.statusText}`, code: CliError.Code.NetworkError });
         }
         return await res.text();
     } catch (error) {
-        throw new Error("Failed to fetch page from source");
+        throw new CliError({ message: "Failed to fetch page from source", code: CliError.Code.NetworkError });
     }
 }
 
@@ -90,9 +91,12 @@ export async function fetchPageHtml({ url, browser }: { url: string | URL; brows
         if (res) {
             return res;
         }
-        throw new Error("An unknown error occurred.");
+        throw new CliError({ message: "An unknown error occurred.", code: CliError.Code.NetworkError });
     } catch (error) {
-        throw new Error(`Error retrieving HTML for ${url.toString()}`);
+        throw new CliError({
+            message: `Error retrieving HTML for ${url.toString()}`,
+            code: CliError.Code.NetworkError
+        });
     }
 }
 
@@ -100,7 +104,7 @@ export async function fetchImage(url: string): Promise<NodeJS.TypedArray> {
     try {
         const res = await exponentialBackoff(() => fetch(url));
         if (!res.ok) {
-            throw new Error(`${res.status} ${res.statusText}`);
+            throw new CliError({ message: `${res.status} ${res.statusText}`, code: CliError.Code.NetworkError });
         }
 
         const imageBuffer = await res.arrayBuffer();
@@ -108,6 +112,9 @@ export async function fetchImage(url: string): Promise<NodeJS.TypedArray> {
 
         return imageData;
     } catch (error) {
-        throw new Error(`Failed to retrieve image from source url ${url}`);
+        throw new CliError({
+            message: `Failed to retrieve image from source url ${url}`,
+            code: CliError.Code.NetworkError
+        });
     }
 }
diff --git a/packages/cli/docs-preview/src/downloadLocalDocsBundle.ts b/packages/cli/docs-preview/src/downloadLocalDocsBundle.ts
index ff3d6dfdb65..410612a773b 100644
--- a/packages/cli/docs-preview/src/downloadLocalDocsBundle.ts
+++ b/packages/cli/docs-preview/src/downloadLocalDocsBundle.ts
@@ -1,6 +1,7 @@
 import { AbsoluteFilePath, doesPathExist, join, RelativeFilePath } from "@fern-api/fs-utils";
 import { Logger } from "@fern-api/logger";
 import { loggingExeca } from "@fern-api/logging-execa";
+import { CliError } from "@fern-api/task-context";
 import chalk from "chalk";
 import { execSync } from "child_process";
 import cliProgress from "cli-progress";
@@ -305,7 +306,10 @@ export async function downloadBundle({
     try {
         const docsBundleZipResponse = await fetch(docsBundleUrl);
         if (!docsBundleZipResponse.ok) {
-            throw new Error(`Failed to download docs preview bundle. Status code: ${docsBundleZipResponse.status}`);
+            throw new CliError({
+                message: `Failed to download docs preview bundle. Status code: ${docsBundleZipResponse.status}`,
+                code: CliError.Code.NetworkError
+            });
         }
         const outputZipPath = join(
             absoluteDirectoryToTmpDir,
@@ -482,9 +486,11 @@ export async function downloadBundle({
                     doNotPipeOutput: true
                 });
             } catch (error) {
-                throw new Error(
-                    "Requires [pnpm] to run local development. Please run: npm install -g pnpm, and then: fern docs dev"
-                );
+                throw new CliError({
+                    message:
+                        "Requires [pnpm] to run local development. Please run: npm install -g pnpm, and then: fern docs dev",
+                    code: CliError.Code.EnvironmentError
+                });
             }
 
             try {
diff --git a/packages/cli/docs-preview/src/previewDocs.ts b/packages/cli/docs-preview/src/previewDocs.ts
index dd980fa0448..6d588ddff8c 100644
--- a/packages/cli/docs-preview/src/previewDocs.ts
+++ b/packages/cli/docs-preview/src/previewDocs.ts
@@ -26,7 +26,8 @@ import { AbsoluteFilePath, convertToFernHostAbsoluteFilePath, doesPathExist, rel
 import { IntermediateRepresentation } from "@fern-api/ir-sdk";
 import { Project } from "@fern-api/project-loader";
 import { convertIrToFdrApi } from "@fern-api/register";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
+
 import { readFile } from "fs/promises";
 import grayMatter from "gray-matter";
 import { v4 as uuidv4 } from "uuid";
@@ -128,7 +129,7 @@ export async function getPreviewDocsDefinition({
     const docsWorkspace = project.docsWorkspaces;
     const apiWorkspaces = project.apiWorkspaces;
     if (docsWorkspace == null) {
-        throw new Error("No docs workspace found in project");
+        throw new CliError({ message: "No docs workspace found in project", code: CliError.Code.ConfigError });
     }
 
     if (editedAbsoluteFilepaths != null && previousDocsDefinition != null) {
diff --git a/packages/cli/docs-preview/src/previewUrlUtils.ts b/packages/cli/docs-preview/src/previewUrlUtils.ts
index dbd54a0f2e2..7487b105402 100644
--- a/packages/cli/docs-preview/src/previewUrlUtils.ts
+++ b/packages/cli/docs-preview/src/previewUrlUtils.ts
@@ -1,3 +1,5 @@
+import { CliError } from "@fern-api/task-context";
+
 /**
  * Preview URLs follow the pattern: {org}-preview-{id}.docs.buildwithfern.com
  */
@@ -63,7 +65,10 @@ export function buildPreviewDomain({ orgId, previewId }: { orgId: string; previe
 
     const minIdLength = 8;
     if (availableSpace < minIdLength) {
-        throw new Error(`Organization name "${orgId}" is too long to generate a valid preview URL`);
+        throw new CliError({
+            message: `Organization name "${orgId}" is too long to generate a valid preview URL`,
+            code: CliError.Code.ValidationError
+        });
     }
 
     const truncatedId = sanitizedId.slice(0, availableSpace).replace(/-+$/, "");
diff --git a/packages/cli/docs-preview/src/runAppPreviewServer.ts b/packages/cli/docs-preview/src/runAppPreviewServer.ts
index 3fed8741628..014bc5bd7c1 100644
--- a/packages/cli/docs-preview/src/runAppPreviewServer.ts
+++ b/packages/cli/docs-preview/src/runAppPreviewServer.ts
@@ -4,7 +4,8 @@ import { DocsV1Read, DocsV2Read, FernNavigation } from "@fern-api/fdr-sdk";
 import { AbsoluteFilePath, dirname, doesPathExist, listFiles, RelativeFilePath, resolve } from "@fern-api/fs-utils";
 import { runExeca } from "@fern-api/logging-execa";
 import { Project } from "@fern-api/project-loader";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
+
 import chalk from "chalk";
 import { execSync } from "child_process";
 import cors from "cors";
@@ -495,9 +496,10 @@ export async function runAppPreviewServer({
         try {
             const url = process.env.APP_DOCS_TAR_PREVIEW_BUCKET;
             if (url == null) {
-                throw new Error(
-                    "Failed to connect to the docs preview server. Please contact support@buildwithfern.com"
-                );
+                throw new CliError({
+                    message: "Failed to connect to the docs preview server. Please contact support@buildwithfern.com",
+                    code: CliError.Code.InternalError
+                });
             }
             await downloadBundle({
                 bucketUrl: url,
@@ -516,9 +518,11 @@ export async function runAppPreviewServer({
             try {
                 const url = process.env.APP_DOCS_PREVIEW_BUCKET;
                 if (url == null) {
-                    throw new Error(
-                        "Failed to connect to the docs preview server. Please contact support@buildwithfern.com"
-                    );
+                    throw new CliError({
+                        message:
+                            "Failed to connect to the docs preview server. Please contact support@buildwithfern.com",
+                        code: CliError.Code.InternalError
+                    });
                 }
                 await downloadBundle({
                     bucketUrl: url,
diff --git a/packages/cli/docs-preview/src/runPreviewServer.ts b/packages/cli/docs-preview/src/runPreviewServer.ts
index 427239928f8..f8d036701f2 100644
--- a/packages/cli/docs-preview/src/runPreviewServer.ts
+++ b/packages/cli/docs-preview/src/runPreviewServer.ts
@@ -2,7 +2,8 @@ import { wrapWithHttps } from "@fern-api/docs-resolver";
 import { DocsV1Read, DocsV2Read, FernNavigation } from "@fern-api/fdr-sdk";
 import { AbsoluteFilePath, dirname, doesPathExist } from "@fern-api/fs-utils";
 import { Project } from "@fern-api/project-loader";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
+
 import chalk from "chalk";
 import cors from "cors";
 import express from "express";
@@ -77,9 +78,10 @@ export async function runPreviewServer({
         try {
             const url = process.env.DOCS_PREVIEW_BUCKET;
             if (url == null) {
-                throw new Error(
-                    "Failed to connect to the docs preview server. Please contact support@buildwithfern.com"
-                );
+                throw new CliError({
+                    message: "Failed to connect to the docs preview server. Please contact support@buildwithfern.com",
+                    code: CliError.Code.InternalError
+                });
             }
             await downloadBundle({ bucketUrl: url, logger: context.logger, preferCached: true, tryTar: false });
         } catch (err) {
diff --git a/packages/cli/docs-resolver/src/ApiReferenceNodeConverter.ts b/packages/cli/docs-resolver/src/ApiReferenceNodeConverter.ts
index 520ff98454d..c0d7111c556 100644
--- a/packages/cli/docs-resolver/src/ApiReferenceNodeConverter.ts
+++ b/packages/cli/docs-resolver/src/ApiReferenceNodeConverter.ts
@@ -2,7 +2,7 @@ import { docsYml } from "@fern-api/configuration-loader";
 import { isNonNullish, titleCase } from "@fern-api/core-utils";
 import { APIV1Read, FdrAPI, FernNavigation } from "@fern-api/fdr-sdk";
 import { AbsoluteFilePath } from "@fern-api/fs-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { visitDiscriminatedUnion } from "@fern-api/ui-core-utils";
 import { DocsWorkspace, FernWorkspace } from "@fern-api/workspace-loader";
 import { camelCase, kebabCase } from "lodash-es";
@@ -1356,7 +1356,9 @@ export class ApiReferenceNodeConverter {
     private getFileId(filepath: AbsoluteFilePath): string {
         const fileId = this.collectedFileIds.get(filepath);
         if (fileId == null) {
-            return this.taskContext.failAndThrow("Failed to locate file after uploading: " + filepath);
+            return this.taskContext.failAndThrow("Failed to locate file after uploading: " + filepath, undefined, {
+                code: CliError.Code.InternalError
+            });
         }
         return fileId;
     }
diff --git a/packages/cli/docs-resolver/src/DocsDefinitionResolver.ts b/packages/cli/docs-resolver/src/DocsDefinitionResolver.ts
index e3ade737042..8b31b33d4aa 100644
--- a/packages/cli/docs-resolver/src/DocsDefinitionResolver.ts
+++ b/packages/cli/docs-resolver/src/DocsDefinitionResolver.ts
@@ -25,7 +25,8 @@ import { generateIntermediateRepresentation } from "@fern-api/ir-generator";
 import { IntermediateRepresentation } from "@fern-api/ir-sdk";
 import { getSnakeCaseUnsafe } from "@fern-api/ir-utils";
 import { OSSWorkspace } from "@fern-api/lazy-fern-workspace";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
+
 import { AbstractAPIWorkspace, DocsWorkspace, FernWorkspace } from "@fern-api/workspace-loader";
 import dayjs from "dayjs";
 import utc from "dayjs/plugin/utc";
@@ -246,7 +247,7 @@ export class DocsDefinitionResolver {
     private _parsedDocsConfig: WithoutQuestionMarks<docsYml.ParsedDocsConfiguration> | undefined;
     private get parsedDocsConfig(): WithoutQuestionMarks<docsYml.ParsedDocsConfiguration> {
         if (this._parsedDocsConfig == null) {
-            throw new Error("parsedDocsConfig is not set");
+            throw new CliError({ message: "parsedDocsConfig is not set", code: CliError.Code.InternalError });
         }
         return this._parsedDocsConfig;
     }
@@ -912,7 +913,7 @@ export class DocsDefinitionResolver {
         const errorMessage = apiSection.apiName
             ? `Failed to load API Definition '${apiSection.apiName}' referenced in docs.\nA valid API configuration was not found at the path: fern/apis/${apiSection.apiName}.\nLearn more about project structure:\nhttps://buildwithfern.com/learn/docs/getting-started/project-structure#api-definitions`
             : "Failed to load API Definition referenced in docs.\nLearn more about project structure:\nhttps://buildwithfern.com/learn/docs/getting-started/project-structure#api-definitions";
-        throw new Error(errorMessage);
+        throw new CliError({ message: errorMessage, code: CliError.Code.ConfigError });
     }
 
     private getOpenApiWorkspaceForApiSection(apiSection: docsYml.DocsNavigationItem.ApiSection): OSSWorkspace {
@@ -927,7 +928,7 @@ export class DocsDefinitionResolver {
         const errorMessage = apiSection.apiName
             ? `Failed to load API Definition '${apiSection.apiName}' referenced in docs.\nA valid API configuration was not found at the path: fern/apis/${apiSection.apiName}.\nLearn more about project structure:\nhttps://buildwithfern.com/learn/docs/getting-started/project-structure#api-definitions`
             : "Failed to load API Definition referenced in docs.\nLearn more about project structure:\nhttps://buildwithfern.com/learn/docs/getting-started/project-structure#api-definitions";
-        throw new Error(errorMessage);
+        throw new CliError({ message: errorMessage, code: CliError.Code.ConfigError });
     }
 
     private async toRootNode(): Promise<FernNavigation.V1.RootNode> {
@@ -1035,9 +1036,10 @@ export class DocsDefinitionResolver {
 
         const defaultVersion = versioned.versions[0];
         if (defaultVersion?.hidden === true) {
-            throw new Error(
-                `The default version "${defaultVersion.version}" cannot be hidden. Please set a non-hidden version as the first version in your versions list, or remove the hidden flag from the default version.`
-            );
+            throw new CliError({
+                message: `The default version "${defaultVersion.version}" cannot be hidden. Please set a non-hidden version as the first version in your versions list, or remove the hidden flag from the default version.`,
+                code: CliError.Code.ConfigError
+            });
         }
 
         // Process versions in batches to reduce memory usage for customers with many API versions.
@@ -1469,7 +1471,11 @@ export class DocsDefinitionResolver {
                 ir,
                 {
                     onError: (e) =>
-                        this.taskContext.failAndThrow(`Error substituting environment variables in API spec: ${e}`)
+                        this.taskContext.failAndThrow(
+                            `Error substituting environment variables in API spec: ${e}`,
+                            undefined,
+                            { code: CliError.Code.EnvironmentError }
+                        )
                 },
                 { substituteAsEmpty: false }
             );
@@ -2096,7 +2102,9 @@ export class DocsDefinitionResolver {
         }
         const fileId = this.collectedFileIds.get(filepath);
         if (fileId == null) {
-            return this.taskContext.failAndThrow("Failed to locate file after uploading: " + filepath);
+            return this.taskContext.failAndThrow("Failed to locate file after uploading: " + filepath, undefined, {
+                code: CliError.Code.InternalError
+            });
         }
         return DocsV1Write.FileId(fileId);
     }
@@ -2282,7 +2290,10 @@ export class DocsDefinitionResolver {
                 value: this.getFileId(value)
             }),
             url: ({ value }) => ({ type: "url", value: DocsV1Write.Url(value) }),
-            _other: () => this.taskContext.failAndThrow("Invalid metadata configuration")
+            _other: () =>
+                this.taskContext.failAndThrow("Invalid metadata configuration", undefined, {
+                    code: CliError.Code.ConfigError
+                })
         });
     }
 
diff --git a/packages/cli/docs-resolver/src/NodeIdGenerator.ts b/packages/cli/docs-resolver/src/NodeIdGenerator.ts
index 27c5867a907..4751a1fcee9 100644
--- a/packages/cli/docs-resolver/src/NodeIdGenerator.ts
+++ b/packages/cli/docs-resolver/src/NodeIdGenerator.ts
@@ -1,4 +1,5 @@
 import { FernNavigation } from "@fern-api/fdr-sdk";
+import { CliError } from "@fern-api/task-context";
 import crypto from "crypto";
 
 function hash(id: string): string {
@@ -28,7 +29,10 @@ export class NodeIdGenerator {
             hashedId = this.#getHashedId(id);
             loop++;
             if (loop > 100) {
-                throw new Error(`Infinite loop detected for id: ${id}`);
+                throw new CliError({
+                    message: `Infinite loop detected for id: ${id}`,
+                    code: CliError.Code.ReferenceError
+                });
             }
         }
         return hashedId;
diff --git a/packages/cli/docs-resolver/src/utils/mergeEndpointPairs.ts b/packages/cli/docs-resolver/src/utils/mergeEndpointPairs.ts
index 61b22876e8f..263508596bc 100644
--- a/packages/cli/docs-resolver/src/utils/mergeEndpointPairs.ts
+++ b/packages/cli/docs-resolver/src/utils/mergeEndpointPairs.ts
@@ -1,4 +1,5 @@
 import { FernNavigation } from "@fern-api/fdr-sdk";
+import { CliError } from "@fern-api/task-context";
 
 export function mergeEndpointPairs<EndpointType extends { method: string }>({
     children,
@@ -28,7 +29,10 @@ export function mergeEndpointPairs<EndpointType extends { method: string }>({
 
         const endpoint = findEndpointById(child.endpointId);
         if (endpoint == null) {
-            throw new Error(`Endpoint ${child.endpointId} not found`);
+            throw new CliError({
+                message: `Endpoint ${child.endpointId} not found`,
+                code: CliError.Code.InternalError
+            });
         }
 
         const methodAndPath = `${endpoint.method} ${stringifyEndpointPathParts(endpoint)}`;
diff --git a/packages/cli/fern-definition/formatter/src/formatWorkspace.ts b/packages/cli/fern-definition/formatter/src/formatWorkspace.ts
index e7d380c3bc5..bc9df1cb760 100644
--- a/packages/cli/fern-definition/formatter/src/formatWorkspace.ts
+++ b/packages/cli/fern-definition/formatter/src/formatWorkspace.ts
@@ -1,6 +1,6 @@
 import { FernWorkspace } from "@fern-api/api-workspace-commons";
 import { entries } from "@fern-api/core-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import chalk from "chalk";
 import { writeFile } from "fs/promises";
 
@@ -25,7 +25,7 @@ export async function formatFernWorkspace({
                 context.logger.info(chalk.green(`Formatted ${chalk.bold(relativeFilepath)}`));
             } else {
                 context.logger.info(chalk.red(`Invalid formatting: ${chalk.bold(relativeFilepath)}`));
-                context.failWithoutThrowing();
+                context.failWithoutThrowing(undefined, undefined, { code: CliError.Code.ValidationError });
             }
         }
     }
diff --git a/packages/cli/fern-definition/ir-to-jsonschema/src/JsonSchemaConverterContext.ts b/packages/cli/fern-definition/ir-to-jsonschema/src/JsonSchemaConverterContext.ts
index 6cddea99744..e306342a55c 100644
--- a/packages/cli/fern-definition/ir-to-jsonschema/src/JsonSchemaConverterContext.ts
+++ b/packages/cli/fern-definition/ir-to-jsonschema/src/JsonSchemaConverterContext.ts
@@ -1,6 +1,6 @@
 import { IntermediateRepresentation, TypeDeclaration, TypeId, TypeReference } from "@fern-api/ir-sdk";
 import { getOriginalName } from "@fern-api/ir-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { JSONSchema4 } from "json-schema";
 
 export class JsonSchemaConverterContext {
@@ -20,7 +20,7 @@ export class JsonSchemaConverterContext {
             } else {
                 // context.logger.error(`Type declaration not found for ${typeName}`);
             }
-            return this.context.failAndThrow();
+            return this.context.failAndThrow(undefined, undefined, { code: CliError.Code.ReferenceError });
         }
         return typeDeclaration;
     }
diff --git a/packages/cli/fern-definition/validator/src/rules/valid-navigation/valid-navigation.ts b/packages/cli/fern-definition/validator/src/rules/valid-navigation/valid-navigation.ts
index 68ffcb8a8d8..9bf2f093dc8 100644
--- a/packages/cli/fern-definition/validator/src/rules/valid-navigation/valid-navigation.ts
+++ b/packages/cli/fern-definition/validator/src/rules/valid-navigation/valid-navigation.ts
@@ -2,6 +2,7 @@ import { getAllDefinitionFiles, getAllNamedDefinitionFiles } from "@fern-api/api
 import { FERN_PACKAGE_MARKER_FILENAME } from "@fern-api/configuration-loader";
 import { keys } from "@fern-api/core-utils";
 import { dirname, join, RelativeFilePath, relative } from "@fern-api/fs-utils";
+import { CliError } from "@fern-api/task-context";
 import path from "path";
 
 import { Rule, RuleViolation } from "../../Rule.js";
@@ -51,7 +52,10 @@ export const ValidNavigationRule: Rule = {
 
                     const expectedItems = directoryToChildren[dirname(relativeFilepath)];
                     if (expectedItems == null) {
-                        throw new Error(`Could not find expected contents of ${relativeFilepath}`);
+                        throw new CliError({
+                            message: `Could not find expected contents of ${relativeFilepath}`,
+                            code: CliError.Code.InternalError
+                        });
                     }
 
                     const violations: RuleViolation[] = [];
diff --git a/packages/cli/fern-definition/validator/src/rules/valid-pagination/valid-pagination.ts b/packages/cli/fern-definition/validator/src/rules/valid-pagination/valid-pagination.ts
index 7f7c675dd33..f281ba449c7 100644
--- a/packages/cli/fern-definition/validator/src/rules/valid-pagination/valid-pagination.ts
+++ b/packages/cli/fern-definition/validator/src/rules/valid-pagination/valid-pagination.ts
@@ -5,6 +5,7 @@ import {
     isRawUriPaginationSchema,
     TypeResolverImpl
 } from "@fern-api/ir-generator";
+import { CliError } from "@fern-api/task-context";
 
 import { Rule } from "../../Rule.js";
 import { CASINGS_GENERATOR } from "../../utils/casingsGenerator.js";
@@ -77,7 +78,10 @@ export const ValidPaginationRule: Rule = {
                             pathPagination: endpointPagination
                         });
                     }
-                    throw new Error("Invalid pagination schema");
+                    throw new CliError({
+                        message: "Invalid pagination schema",
+                        code: CliError.Code.ValidationError
+                    });
                 }
             }
         };
diff --git a/packages/cli/generation/ir-generator-tests/src/loadApisOrThrow.ts b/packages/cli/generation/ir-generator-tests/src/loadApisOrThrow.ts
index 8045f719a99..512b0a9d3b0 100644
--- a/packages/cli/generation/ir-generator-tests/src/loadApisOrThrow.ts
+++ b/packages/cli/generation/ir-generator-tests/src/loadApisOrThrow.ts
@@ -1,9 +1,13 @@
 import { loadApis } from "@fern-api/project-loader";
+import { CliError } from "@fern-api/task-context";
 
 export async function loadApisOrThrow(...args: Parameters<typeof loadApis>): ReturnType<typeof loadApis> {
     const result = await loadApis(...args);
     if (result.length === 0) {
-        throw new Error("No APIs found. Args: " + JSON.stringify(args, null, 2));
+        throw new CliError({
+            message: "No APIs found. Args: " + JSON.stringify(args, null, 2),
+            code: CliError.Code.ConfigError
+        });
     }
     return result;
 }
diff --git a/packages/cli/generation/ir-migrations/src/IntermediateRepresentationMigrator.ts b/packages/cli/generation/ir-migrations/src/IntermediateRepresentationMigrator.ts
index 52d3966532b..4355cf6047c 100644
--- a/packages/cli/generation/ir-migrations/src/IntermediateRepresentationMigrator.ts
+++ b/packages/cli/generation/ir-migrations/src/IntermediateRepresentationMigrator.ts
@@ -1,7 +1,7 @@
 import { GeneratorName } from "@fern-api/configuration-loader";
 import { IntermediateRepresentation, serialization as IrSerialization } from "@fern-api/ir-sdk";
 import { isVersionAhead } from "@fern-api/semver-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { GENERATOR_MINIMUM_VERSIONS, MINIMUM_SUPPORTED_IR_VERSION } from "./generatorVersionMap.js";
 import { GeneratorNameAndVersion } from "./IrMigrationContext.js";
 import { V54_TO_V53_MIGRATION } from "./migrations/v54-to-v53/migrateFromV54ToV53.js";
@@ -137,17 +137,21 @@ class IntermediateRepresentationMigratorImpl implements IntermediateRepresentati
             if (targetGenerator != null) {
                 const minVersion = this.getMinimumGeneratorVersion(targetGenerator.name);
                 if (minVersion != null) {
-                    throw new Error(
-                        `${targetGenerator.name}@${targetGenerator.version} is not compatible with CLI v4.x.x+. ` +
-                            `Please upgrade to ${targetGenerator.name}@${minVersion} or later using 'fern generator upgrade --include-major'.`
-                    );
+                    throw new CliError({
+                        message:
+                            `${targetGenerator.name}@${targetGenerator.version} is not compatible with CLI v4.x.x+. ` +
+                            `Please upgrade to ${targetGenerator.name}@${minVersion} or later using 'fern generator upgrade --include-major'.`,
+                        code: CliError.Code.VersionError
+                    });
                 }
             }
 
-            throw new Error(
-                "This generator version is not compatible with CLI v4.x.x+. " +
-                    "Please upgrade your generator using 'fern generator upgrade --include-major'."
-            );
+            throw new CliError({
+                message:
+                    "This generator version is not compatible with CLI v4.x.x+. " +
+                    "Please upgrade your generator using 'fern generator upgrade --include-major'.",
+                code: CliError.Code.VersionError
+            });
         }
     }
 
@@ -191,7 +195,7 @@ class IntermediateRepresentationMigratorImpl implements IntermediateRepresentati
 
         // eslint-disable-next-line @typescript-eslint/no-unnecessary-condition
         if (!hasEncounteredMigrationYet) {
-            context.failAndThrow(`IR ${version} does not exist`);
+            context.failAndThrow(`IR ${version} does not exist`, undefined, { code: CliError.Code.VersionError });
         }
 
         return migrated;
@@ -244,21 +248,30 @@ class IntermediateRepresentationMigratorImpl implements IntermediateRepresentati
             migration.firstGeneratorVersionToConsumeNewIR[targetGenerator.name as GeneratorName];
 
         if (minVersionToExclude == null) {
-            throw new Error(
-                `Cannot migrate intermediate representation. Unrecognized generator: ${targetGenerator.name}. If leveraging a custom generator, ensure you are specifying "ir-version" within the generator configuration.`
-            );
+            throw new CliError({
+                message: `Cannot migrate intermediate representation. Unrecognized generator: ${targetGenerator.name}. If leveraging a custom generator, ensure you are specifying "ir-version" within the generator configuration.`,
+                code: CliError.Code.ConfigError
+            });
         }
 
         switch (minVersionToExclude) {
             case GeneratorWasNeverUpdatedToConsumeNewIR:
                 return true;
             case GeneratorWasNotCreatedYet:
-                throw new Error(
-                    `Cannot migrate intermediate representation. Generator was created after intermediate representation ${migration.laterVersion}.`
-                );
+                throw new CliError({
+                    message: `Cannot migrate intermediate representation. Generator was created after intermediate representation ${migration.laterVersion}.`,
+                    code: CliError.Code.VersionError
+                });
         }
 
-        return isVersionAhead(minVersionToExclude, targetGenerator.version);
+        try {
+            return isVersionAhead(minVersionToExclude, targetGenerator.version);
+        } catch (error) {
+            throw new CliError({
+                message: `Failed to compare versions: ${error instanceof Error ? error.message : String(error)}`,
+                code: CliError.Code.VersionError
+            });
+        }
     }
 
     public getIRVersionForGenerator({
diff --git a/packages/cli/generation/ir-migrations/src/migrations/v55-to-v54/migrateFromV55ToV54.ts b/packages/cli/generation/ir-migrations/src/migrations/v55-to-v54/migrateFromV55ToV54.ts
index c30af39344a..652782280ce 100644
--- a/packages/cli/generation/ir-migrations/src/migrations/v55-to-v54/migrateFromV55ToV54.ts
+++ b/packages/cli/generation/ir-migrations/src/migrations/v55-to-v54/migrateFromV55ToV54.ts
@@ -1,7 +1,8 @@
 import { GeneratorName } from "@fern-api/configuration-loader";
 import { assertNever } from "@fern-api/core-utils";
-import { mapValues } from "lodash-es";
+import { CliError } from "@fern-api/task-context";
 
+import { mapValues } from "lodash-es";
 import { IrSerialization } from "../../ir-serialization/index.js";
 import { IrVersions } from "../../ir-versions/index.js";
 import {
@@ -122,7 +123,7 @@ function convertTypes(
                     );
                 },
                 _other: () => {
-                    throw new Error("Encountered unknown shape");
+                    throw new CliError({ message: "Encountered unknown shape", code: CliError.Code.InternalError });
                 }
             })
         };
@@ -333,7 +334,10 @@ function convertTypeReference(typeReference: IrVersions.V55.types.TypeReference)
         named: IrVersions.V54.types.TypeReference.named,
         unknown: IrVersions.V54.types.TypeReference.unknown,
         _other: () => {
-            throw new Error("Unknown type reference: " + typeReference.type);
+            throw new CliError({
+                message: "Unknown type reference: " + typeReference.type,
+                code: CliError.Code.InternalError
+            });
         }
     });
 }
@@ -370,7 +374,10 @@ function convertContainerType(container: IrVersions.V55.types.ContainerType): Ir
             }),
         literal: IrVersions.V54.types.ContainerType.literal,
         _other: () => {
-            throw new Error("Unknown ContainerType: " + container.type);
+            throw new CliError({
+                message: "Unknown ContainerType: " + container.type,
+                code: CliError.Code.InternalError
+            });
         }
     });
 }
@@ -399,7 +406,10 @@ function convertSingleUnionTypeProperties(
                 }),
             noProperties: IrVersions.V54.types.SingleUnionTypeProperties.noProperties,
             _other: () => {
-                throw new Error(`Unknown SingleUnionTypeProperties: ${JSON.stringify(properties)}`);
+                throw new CliError({
+                    message: `Unknown SingleUnionTypeProperties: ${JSON.stringify(properties)}`,
+                    code: CliError.Code.InternalError
+                });
             }
         }
     );
@@ -415,7 +425,10 @@ function convertResolvedType(
             IrVersions.V54.types.ResolvedTypeReference.primitive(convertPrimitiveType(primitiveType)),
         unknown: IrVersions.V54.types.ResolvedTypeReference.unknown,
         _other: () => {
-            throw new Error("Unknown ResolvedTypeReference: " + resolvedType.type);
+            throw new CliError({
+                message: "Unknown ResolvedTypeReference: " + resolvedType.type,
+                code: CliError.Code.InternalError
+            });
         }
     });
 }
@@ -664,7 +677,10 @@ function convertSdkRequestShape(shape: IrVersions.V55.http.SdkRequestShape): IrV
             IrVersions.V54.http.SdkRequestShape.justRequestBody(convertSdkRequestBodyType(reference)),
         wrapper: IrVersions.V54.http.SdkRequestShape.wrapper,
         _other: () => {
-            throw new Error("Unknown SdkRequestShape: " + shape.type);
+            throw new CliError({
+                message: "Unknown SdkRequestShape: " + shape.type,
+                code: CliError.Code.InternalError
+            });
         }
     });
 }
@@ -723,7 +739,10 @@ function convertRequestBody(requestBody: IrVersions.V55.http.HttpRequestBody): I
             return IrVersions.V54.http.HttpRequestBody.bytes(bytes);
         },
         _other: () => {
-            throw new Error("Unknown HttpRequestBody: " + requestBody.type);
+            throw new CliError({
+                message: "Unknown HttpRequestBody: " + requestBody.type,
+                code: CliError.Code.InternalError
+            });
         }
     });
 }
diff --git a/packages/cli/generation/ir-migrations/src/migrations/v63-to-v62/migrateFromV63ToV62.ts b/packages/cli/generation/ir-migrations/src/migrations/v63-to-v62/migrateFromV63ToV62.ts
index 73f1d8bda0e..7747cd36c7d 100644
--- a/packages/cli/generation/ir-migrations/src/migrations/v63-to-v62/migrateFromV63ToV62.ts
+++ b/packages/cli/generation/ir-migrations/src/migrations/v63-to-v62/migrateFromV63ToV62.ts
@@ -1,4 +1,5 @@
 import { GeneratorName } from "@fern-api/configuration-loader";
+import { CliError } from "@fern-api/task-context";
 import { mapValues } from "lodash-es";
 import { IrSerialization } from "../../ir-serialization/index.js";
 import { IrVersions } from "../../ir-versions/index.js";
@@ -161,7 +162,7 @@ function convertAuthScheme(scheme: IrVersions.V63.AuthScheme): IrVersions.V62.Au
             // in the serializer, we can pass it through with a type assertion
             return IrVersions.V62.AuthScheme.inferred(scheme as unknown as IrVersions.V62.auth.InferredAuthScheme);
         default:
-            throw new Error("Unknown AuthScheme type");
+            throw new CliError({ message: "Unknown AuthScheme type", code: CliError.Code.InternalError });
     }
 }
 
diff --git a/packages/cli/init/src/__test__/initializeWithMintlify.test.ts b/packages/cli/init/src/__test__/initializeWithMintlify.test.ts
index 286dbd6ac76..b29ca8e9725 100644
--- a/packages/cli/init/src/__test__/initializeWithMintlify.test.ts
+++ b/packages/cli/init/src/__test__/initializeWithMintlify.test.ts
@@ -1,6 +1,7 @@
 /* eslint-disable @typescript-eslint/no-explicit-any */
 import { AbsoluteFilePath, cwd, resolve } from "@fern-api/fs-utils";
 import { runMintlifyMigration } from "@fern-api/mintlify-importer";
+import { CliError } from "@fern-api/task-context";
 import { vi } from "vitest";
 
 import { initializeWithMintlify } from "../initializeWithMintlify.js";
@@ -29,7 +30,9 @@ describe("initializeWithMintlify", () => {
         ).rejects.toThrow();
 
         expect(taskContext.failAndThrow).toHaveBeenCalledWith(
-            "Clone the repo locally and run this command again by referencing the path to the local mint.json file"
+            "Clone the repo locally and run this command again by referencing the path to the local mint.json file",
+            undefined,
+            { code: CliError.Code.ConfigError }
         );
     });
 
@@ -50,7 +53,9 @@ describe("initializeWithMintlify", () => {
             })
         ).rejects.toThrow();
 
-        expect(taskContext.failAndThrow).toHaveBeenCalledWith("Provide a path to a mint.json file");
+        expect(taskContext.failAndThrow).toHaveBeenCalledWith("Provide a path to a mint.json file", undefined, {
+            code: CliError.Code.ConfigError
+        });
     });
 
     it("Throws an error if the mint.json file does not exist", async () => {
@@ -72,7 +77,9 @@ describe("initializeWithMintlify", () => {
 
         const absolutePathToMintJson = resolve(cwd(), "./mint.json");
 
-        expect(taskContext.failAndThrow).toHaveBeenCalledWith(`${absolutePathToMintJson} does not exist`);
+        expect(taskContext.failAndThrow).toHaveBeenCalledWith(`${absolutePathToMintJson} does not exist`, undefined, {
+            code: CliError.Code.ConfigError
+        });
     });
 
     it("Successfully runs the mintlify migration if a proper mint.json file is provided", async () => {
diff --git a/packages/cli/init/src/createFernDirectoryAndOrganization.ts b/packages/cli/init/src/createFernDirectoryAndOrganization.ts
index 7552c6a5427..8b9a946787b 100644
--- a/packages/cli/init/src/createFernDirectoryAndOrganization.ts
+++ b/packages/cli/init/src/createFernDirectoryAndOrganization.ts
@@ -8,7 +8,7 @@ import {
 import { createVenusService } from "@fern-api/core";
 import { AbsoluteFilePath, cwd, doesPathExist, join, RelativeFilePath } from "@fern-api/fs-utils";
 import { askToLogin } from "@fern-api/login";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import chalk from "chalk";
 import { mkdir, writeFile } from "fs/promises";
 import { kebabCase } from "lodash-es";
@@ -46,7 +46,9 @@ export async function createFernDirectoryAndWorkspace({
                 if (response.ok) {
                     organization = response.body.organizationId;
                 } else {
-                    taskContext.failAndThrow("Unauthorized. FERN_TOKEN is invalid.");
+                    taskContext.failAndThrow("Unauthorized. FERN_TOKEN is invalid.", undefined, {
+                        code: CliError.Code.AuthError
+                    });
                     // dummy return value to appease the linter. won't actually ever get run.
                     return { absolutePathToFernDirectory: AbsoluteFilePath.of("/dummy"), organization: "dummy" };
                 }
diff --git a/packages/cli/init/src/createWorkspace.ts b/packages/cli/init/src/createWorkspace.ts
index 61609fd311a..4963753b315 100644
--- a/packages/cli/init/src/createWorkspace.ts
+++ b/packages/cli/init/src/createWorkspace.ts
@@ -10,7 +10,7 @@ import {
 import { formatDefinitionFile } from "@fern-api/fern-definition-formatter";
 import { RootApiFileSchema } from "@fern-api/fern-definition-schema";
 import { AbsoluteFilePath, doesPathExist, join, RelativeFilePath, relative } from "@fern-api/fs-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { mkdir, writeFile } from "fs/promises";
 import yaml from "js-yaml";
 
@@ -185,10 +185,19 @@ async function writeSampleApiDefinition({
     await writeFile(join(directoryOfDefinition, RelativeFilePath.of(ROOT_API_FILENAME)), yaml.dump(rootApi));
 
     const absoluteFilepathToImdbYaml = join(directoryOfDefinition, RelativeFilePath.of("imdb.yml"));
-    await writeFile(
-        absoluteFilepathToImdbYaml,
-        await formatDefinitionFile({
+    let formattedContent: string;
+    try {
+        formattedContent = await formatDefinitionFile({
             fileContents: SAMPLE_IMDB_API
-        })
-    );
+        });
+    } catch (error) {
+        if (error instanceof CliError) {
+            throw error;
+        }
+        throw new CliError({
+            message: `Failed to format definition file: ${error instanceof Error ? error.message : String(error)}`,
+            code: CliError.Code.ParseError
+        });
+    }
+    await writeFile(absoluteFilepathToImdbYaml, formattedContent);
 }
diff --git a/packages/cli/init/src/initializeWithMintlify.ts b/packages/cli/init/src/initializeWithMintlify.ts
index 4b26507211c..5d41ac8254b 100644
--- a/packages/cli/init/src/initializeWithMintlify.ts
+++ b/packages/cli/init/src/initializeWithMintlify.ts
@@ -1,6 +1,6 @@
 import { AbsoluteFilePath, cwd, doesPathExist, isURL, resolve } from "@fern-api/fs-utils";
 import { runMintlifyMigration } from "@fern-api/mintlify-importer";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 
 export const initializeWithMintlify = async ({
     pathToMintJson,
@@ -15,7 +15,9 @@ export const initializeWithMintlify = async ({
 }): Promise<void> => {
     // The file path should include `mint.json` in it
     if (!pathToMintJson?.includes("mint.json")) {
-        taskContext.failAndThrow("Provide a path to a mint.json file");
+        taskContext.failAndThrow("Provide a path to a mint.json file", undefined, {
+            code: CliError.Code.ConfigError
+        });
         return;
     }
 
@@ -24,7 +26,9 @@ export const initializeWithMintlify = async ({
     // @todo get urls to work - for now, throw an error if the user provides a URL
     if (isURL(pathToMintJson)) {
         taskContext.failAndThrow(
-            "Clone the repo locally and run this command again by referencing the path to the local mint.json file"
+            "Clone the repo locally and run this command again by referencing the path to the local mint.json file",
+            undefined,
+            { code: CliError.Code.ConfigError }
         );
         return;
     } else {
@@ -34,7 +38,9 @@ export const initializeWithMintlify = async ({
     const pathExists = await doesPathExist(absolutePathToMintJson);
 
     if (!pathExists || !absolutePathToMintJson) {
-        taskContext.failAndThrow(`${absolutePathToMintJson} does not exist`);
+        taskContext.failAndThrow(`${absolutePathToMintJson} does not exist`, undefined, {
+            code: CliError.Code.ConfigError
+        });
         return;
     }
 
diff --git a/packages/cli/init/src/initializeWithReadme.ts b/packages/cli/init/src/initializeWithReadme.ts
index 3e8bb700408..eb71b5fa0e8 100644
--- a/packages/cli/init/src/initializeWithReadme.ts
+++ b/packages/cli/init/src/initializeWithReadme.ts
@@ -1,6 +1,6 @@
 import { AbsoluteFilePath, cwd, isURL } from "@fern-api/fs-utils";
 import { runReadmeMigration } from "@fern-api/readme-importer";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 
 export const initializeWithReadme = async ({
     readmeUrl,
@@ -14,7 +14,9 @@ export const initializeWithReadme = async ({
     versionOfCli: string;
 }): Promise<void> => {
     if (!readmeUrl || !isURL(readmeUrl)) {
-        taskContext.failAndThrow("Provide a URL to a readme-generated site");
+        taskContext.failAndThrow("Provide a URL to a readme-generated site", undefined, {
+            code: CliError.Code.ConfigError
+        });
         return;
     }
 
diff --git a/packages/cli/library-docs-generator/cpp/src/renderers/CompoundPageRenderer.ts b/packages/cli/library-docs-generator/cpp/src/renderers/CompoundPageRenderer.ts
index 21a53e92816..2dce1173f6c 100644
--- a/packages/cli/library-docs-generator/cpp/src/renderers/CompoundPageRenderer.ts
+++ b/packages/cli/library-docs-generator/cpp/src/renderers/CompoundPageRenderer.ts
@@ -4,6 +4,7 @@
  * Handles: class, concept, function, enum, typedef, variable
  */
 
+import { CliError } from "@fern-api/task-context";
 import type {
     CppClassIr,
     CppConceptIr,
@@ -50,7 +51,10 @@ export function renderCompoundPage(compound: CppCompoundIr, meta: CompoundMeta):
             return renderVariablePage(compound.data, meta);
         default: {
             const _exhaustive: never = compound;
-            throw new Error(`Unknown compound kind: ${JSON.stringify(_exhaustive)}`);
+            throw new CliError({
+                message: `Unknown compound kind: ${JSON.stringify(_exhaustive)}`,
+                code: CliError.Code.InternalError
+            });
         }
     }
 }
diff --git a/packages/cli/library-docs-generator/package.json b/packages/cli/library-docs-generator/package.json
index 11ec38b3e34..5a0cdc51e52 100644
--- a/packages/cli/library-docs-generator/package.json
+++ b/packages/cli/library-docs-generator/package.json
@@ -33,6 +33,7 @@
   },
   "dependencies": {
     "@fern-api/fdr-sdk": "catalog:",
+    "@fern-api/task-context": "workspace:*",
     "js-yaml": "catalog:"
   },
   "devDependencies": {
diff --git a/packages/cli/library-docs-generator/src/CppDocsGenerator.ts b/packages/cli/library-docs-generator/src/CppDocsGenerator.ts
index d4efc006dd2..76b74fc9583 100644
--- a/packages/cli/library-docs-generator/src/CppDocsGenerator.ts
+++ b/packages/cli/library-docs-generator/src/CppDocsGenerator.ts
@@ -11,6 +11,7 @@
  * currentPagePath) requires that pages are rendered one at a time.
  */
 
+import { CliError } from "@fern-api/task-context";
 import type { CompoundMeta } from "../cpp/src/context.js";
 import {
     clearEntityRegistry,
@@ -244,7 +245,10 @@ function categoryFolderForCompound(collected: CollectedCompound): string {
             return "variables";
         default: {
             const _exhaustive: never = collected.compound;
-            throw new Error(`Unknown compound kind: ${JSON.stringify(_exhaustive)}`);
+            throw new CliError({
+                message: `Unknown compound kind: ${JSON.stringify(_exhaustive)}`,
+                code: CliError.Code.InternalError
+            });
         }
     }
 }
diff --git a/packages/cli/login/src/askToLogin.ts b/packages/cli/login/src/askToLogin.ts
index 10686c6b857..cd976d66bb1 100644
--- a/packages/cli/login/src/askToLogin.ts
+++ b/packages/cli/login/src/askToLogin.ts
@@ -1,5 +1,5 @@
 import { FernToken, getToken, isLoggedIn } from "@fern-api/auth";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import inquirer, { ConfirmQuestion } from "inquirer";
 
 import { login } from "./login.js";
@@ -8,7 +8,7 @@ export async function askToLogin(context: TaskContext): Promise<FernToken> {
     if (!(await isLoggedIn()) && process.stdout.isTTY) {
         await context.takeOverTerminal(async () => {
             if (!(await askForConfirmation("Login required. Continue?"))) {
-                context.failAndThrow();
+                context.failAndThrow(undefined, undefined, { code: CliError.Code.AuthError });
             }
         });
         await login(context);
@@ -16,7 +16,9 @@ export async function askToLogin(context: TaskContext): Promise<FernToken> {
     const token = await getToken();
     if (token == null) {
         context.failAndThrow(
-            "Authentication required. Please run 'fern login' or set the FERN_TOKEN environment variable."
+            "Authentication required. Please run 'fern login' or set the FERN_TOKEN environment variable.",
+            undefined,
+            { code: CliError.Code.AuthError }
         );
     }
 
diff --git a/packages/cli/login/src/auth0-login/doAuth0DeviceAuthorizationFlow.ts b/packages/cli/login/src/auth0-login/doAuth0DeviceAuthorizationFlow.ts
index 74d168559ed..3913064936c 100644
--- a/packages/cli/login/src/auth0-login/doAuth0DeviceAuthorizationFlow.ts
+++ b/packages/cli/login/src/auth0-login/doAuth0DeviceAuthorizationFlow.ts
@@ -1,5 +1,5 @@
 import { delay } from "@fern-api/core-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import axios from "axios";
 import boxen from "boxen";
 import open from "open";
@@ -48,7 +48,7 @@ export async function doAuth0DeviceAuthorizationFlow({
     });
 
     if (deviceCodeResponse.status !== 200) {
-        context.failAndThrow("Failed to authenticate", deviceCodeResponse.data);
+        context.failAndThrow("Failed to authenticate", deviceCodeResponse.data, { code: CliError.Code.AuthError });
     }
 
     await open(deviceCodeResponse.data.verification_uri_complete);
@@ -134,6 +134,6 @@ async function pollForToken({
         case "access_denied":
         case "expired_token":
         default:
-            return context.failAndThrow("Failed to authenticate", data);
+            return context.failAndThrow("Failed to authenticate", data, { code: CliError.Code.AuthError });
     }
 }
diff --git a/packages/cli/login/src/auth0-login/doAuth0LoginFlow.ts b/packages/cli/login/src/auth0-login/doAuth0LoginFlow.ts
index c3b6890160c..4ba22070546 100644
--- a/packages/cli/login/src/auth0-login/doAuth0LoginFlow.ts
+++ b/packages/cli/login/src/auth0-login/doAuth0LoginFlow.ts
@@ -1,7 +1,7 @@
+import { CliError } from "@fern-api/task-context";
 import axios from "axios";
 import { IncomingMessage, Server } from "http";
 import open from "open";
-
 import { createServer } from "./createServer.js";
 
 /**
@@ -127,10 +127,10 @@ async function getTokenFromCode({
     );
     const { access_token: accessToken, id_token: idToken } = response.data;
     if (accessToken == null) {
-        throw new Error("Access token is not defined");
+        throw new CliError({ message: "Access token is not defined", code: CliError.Code.AuthError });
     }
     if (idToken == null) {
-        throw new Error("ID token is not defined");
+        throw new CliError({ message: "ID token is not defined", code: CliError.Code.AuthError });
     }
     return { accessToken, idToken };
 }
diff --git a/packages/cli/login/src/auth0-login/resolveSsoConnection.ts b/packages/cli/login/src/auth0-login/resolveSsoConnection.ts
index bcda5c11d48..760a569d994 100644
--- a/packages/cli/login/src/auth0-login/resolveSsoConnection.ts
+++ b/packages/cli/login/src/auth0-login/resolveSsoConnection.ts
@@ -1,3 +1,4 @@
+import { CliError } from "@fern-api/task-context";
 import axios from "axios";
 
 export async function resolveSsoConnection({
@@ -18,17 +19,26 @@ export async function resolveSsoConnection({
         );
     } catch (error) {
         if (axios.isAxiosError(error) && error.response?.status === 404) {
-            throw new Error(`No SSO connection associated with email: ${email}`);
+            throw new CliError({
+                message: `No SSO connection associated with email: ${email}`,
+                code: CliError.Code.AuthError
+            });
         }
         throw error;
     }
     const responseData = response.data;
     if (typeof responseData !== "object" || responseData == null) {
-        throw new Error("Invalid response format from SSO resolve endpoint");
+        throw new CliError({
+            message: "Invalid response format from SSO resolve endpoint",
+            code: CliError.Code.AuthError
+        });
     }
     const { connection } = responseData;
     if (typeof connection !== "string" || connection.length === 0) {
-        throw new Error("No SSO connection found for this email");
+        throw new CliError({
+            message: "No SSO connection found for this email",
+            code: CliError.Code.AuthError
+        });
     }
     return connection;
 }
diff --git a/packages/cli/project-loader/src/loadProject.ts b/packages/cli/project-loader/src/loadProject.ts
index ad25a059fbf..b5d01acdaa3 100644
--- a/packages/cli/project-loader/src/loadProject.ts
+++ b/packages/cli/project-loader/src/loadProject.ts
@@ -13,7 +13,7 @@ import {
     OPENAPI_DIRECTORY
 } from "@fern-api/configuration-loader";
 import { AbsoluteFilePath, doesPathExist, join, RelativeFilePath } from "@fern-api/fs-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { handleFailedWorkspaceParserResult, loadAPIWorkspace, loadDocsWorkspace } from "@fern-api/workspace-loader";
 import chalk from "chalk";
 import { readdir } from "fs/promises";
@@ -44,7 +44,9 @@ export declare namespace loadProject {
 export async function loadProject({ context, nameOverride, ...args }: loadProject.Args): Promise<Project> {
     const fernDirectory = await getFernDirectory(nameOverride);
     if (fernDirectory == null) {
-        return context.failAndThrow(`Directory "${nameOverride ?? FERN_DIRECTORY}" not found.`);
+        return context.failAndThrow(`Directory "${nameOverride ?? FERN_DIRECTORY}" not found.`, undefined, {
+            code: CliError.Code.ConfigError
+        });
     }
 
     return await loadProjectFromDirectory({
@@ -101,7 +103,9 @@ export async function loadProjectFromDirectory({
                 ` › ${ASYNCAPI_DIRECTORY}/\n` +
                 `For more information:\n` +
                 ` › SDK project structure: https://buildwithfern.com/learn/api-definitions/overview/project-structure\n` +
-                ` › Docs project structure: https://buildwithfern.com/learn/docs/getting-started/project-structure`
+                ` › Docs project structure: https://buildwithfern.com/learn/docs/getting-started/project-structure`,
+            undefined,
+            { code: CliError.Code.ConfigError }
         );
     }
 
@@ -147,10 +151,12 @@ export async function loadApis({
 
         if (commandLineApiWorkspace != null) {
             if (!apiWorkspaceDirectoryNames.includes(commandLineApiWorkspace)) {
-                return context.failAndThrow("API does not exist: " + commandLineApiWorkspace);
+                return context.failAndThrow("API does not exist: " + commandLineApiWorkspace, undefined, {
+                    code: CliError.Code.ConfigError
+                });
             }
         } else if (apiWorkspaceDirectoryNames.length === 0) {
-            return context.failAndThrow("No APIs found.");
+            return context.failAndThrow("No APIs found.", undefined, { code: CliError.Code.ConfigError });
         } else if (apiWorkspaceDirectoryNames.length > 1 && !defaultToAllApiWorkspaces) {
             let message = "There are multiple workspaces. You must specify one with --api:\n";
             const longestWorkspaceName = Math.max(
@@ -164,7 +170,7 @@ export async function loadApis({
                     )}`;
                 })
                 .join("\n");
-            return context.failAndThrow(message);
+            return context.failAndThrow(message, undefined, { code: CliError.Code.ConfigError });
         }
 
         const apiWorkspaces: AbstractAPIWorkspace<unknown>[] = [];
@@ -188,7 +194,7 @@ export async function loadApis({
                     apiWorkspaces.push(workspace.workspace);
                 } else {
                     handleFailedWorkspaceParserResult(workspace, context.logger);
-                    context.failAndThrow();
+                    context.failAndThrow(undefined, undefined, { code: CliError.Code.ConfigError });
                 }
             })
         );
diff --git a/packages/cli/workspace/api-workspace-validator/src/validateAPIWorkspaceAndLogIssues.ts b/packages/cli/workspace/api-workspace-validator/src/validateAPIWorkspaceAndLogIssues.ts
index e5fea63f8ed..6f253103438 100644
--- a/packages/cli/workspace/api-workspace-validator/src/validateAPIWorkspaceAndLogIssues.ts
+++ b/packages/cli/workspace/api-workspace-validator/src/validateAPIWorkspaceAndLogIssues.ts
@@ -3,7 +3,7 @@ import { ValidationViolation, validateFernWorkspace } from "@fern-api/fern-defin
 import { validateGeneratorsWorkspace } from "@fern-api/generators-validator";
 import { OSSWorkspace } from "@fern-api/lazy-fern-workspace";
 import { validateOSSWorkspace } from "@fern-api/oss-validator";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import validatePackageName from "validate-npm-package-name";
 
 import { logViolations } from "./logViolations.js";
@@ -25,7 +25,7 @@ export async function collectAPIWorkspaceViolations({
     ossWorkspace?: OSSWorkspace;
 }): Promise<CollectedApiViolations> {
     if (!validatePackageName(workspace.definition.rootApiFile.contents.name).validForNewPackages) {
-        context.failAndThrow("API name is not valid.");
+        context.failAndThrow("API name is not valid.", undefined, { code: CliError.Code.ValidationError });
     }
 
     const startTime = performance.now();
@@ -91,7 +91,7 @@ export async function validateAPIWorkspaceAndLogIssues({
     ossWorkspace?: OSSWorkspace;
 }): Promise<void> {
     if (!validatePackageName(workspace.definition.rootApiFile.contents.name).validForNewPackages) {
-        context.failAndThrow("API name is not valid.");
+        context.failAndThrow("API name is not valid.", undefined, { code: CliError.Code.ValidationError });
     }
 
     const { hasErrors } = await validateAPIWorkspaceWithoutExiting({
@@ -102,6 +102,6 @@ export async function validateAPIWorkspaceAndLogIssues({
     });
 
     if (hasErrors) {
-        context.failAndThrow();
+        context.failAndThrow(undefined, undefined, { code: CliError.Code.ValidationError });
     }
 }
diff --git a/packages/cli/workspace/browser-compatible-fern-workspace/src/InMemoryOpenAPILoader.ts b/packages/cli/workspace/browser-compatible-fern-workspace/src/InMemoryOpenAPILoader.ts
index d40049c0127..209992847f4 100644
--- a/packages/cli/workspace/browser-compatible-fern-workspace/src/InMemoryOpenAPILoader.ts
+++ b/packages/cli/workspace/browser-compatible-fern-workspace/src/InMemoryOpenAPILoader.ts
@@ -1,8 +1,8 @@
 import { isOpenAPIV2 } from "@fern-api/api-workspace-commons";
 import { applyOpenAPIOverlay, mergeWithOverrides as coreMergeWithOverrides, type Overlay } from "@fern-api/core-utils";
 import { getParseOptions, OpenAPIDocument } from "@fern-api/openapi-ir-parser";
+import { CliError } from "@fern-api/task-context";
 import { OpenAPI, OpenAPIV3 } from "openapi-types";
-
 import { OpenAPIWorkspace } from "./OpenAPIWorkspace.js";
 
 export class InMemoryOpenAPILoader {
@@ -28,7 +28,10 @@ export class InMemoryOpenAPILoader {
         overlays: Overlay | undefined;
     }): OpenAPIV3.Document {
         if (isOpenAPIV2(openapi)) {
-            throw new Error("Swagger v2.0 is not supported in the browser");
+            throw new CliError({
+                message: "Swagger v2.0 is not supported in the browser",
+                code: CliError.Code.ConfigError
+            });
         }
         let result = openapi as OpenAPIV3.Document;
 
diff --git a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertApiSpecToFdrDefinition.ts b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertApiSpecToFdrDefinition.ts
index e384d772b75..0bb9e100e1c 100644
--- a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertApiSpecToFdrDefinition.ts
+++ b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertApiSpecToFdrDefinition.ts
@@ -1,8 +1,8 @@
 import { generatorsYml } from "@fern-api/configuration";
 import { FdrAPI } from "@fern-api/fdr-sdk";
+import { CliError } from "@fern-api/task-context";
 import { OpenrpcDocument } from "@open-rpc/meta-schema";
 import { OpenAPIV3_1 } from "openapi-types";
-
 import { convertAsyncApiSpecToFdrDefinition } from "./convertAsyncApiSpecToFdrDefinition.js";
 import { convertOpenApiSpecToFdrDefinition } from "./convertOpenApiSpecToFdrDefinition.js";
 import { convertOpenRpcSpecToFdrDefinition } from "./convertOpenRpcSpecToFdrDefinition.js";
@@ -78,17 +78,20 @@ export async function apiSpecToFdr({
     const detectedType = detectApiSpecType(spec);
 
     if (detectedType == null) {
-        throw new Error(
-            "Unable to detect API spec type. Expected a document with an 'openapi', 'swagger', 'asyncapi', or 'openrpc' top-level field."
-        );
+        throw new CliError({
+            message:
+                "Unable to detect API spec type. Expected a document with an 'openapi', 'swagger', 'asyncapi', or 'openrpc' top-level field.",
+            code: CliError.Code.ConfigError
+        });
     }
 
     switch (detectedType) {
         case "openapi": {
             if (typeof spec.swagger === "string") {
-                throw new Error(
-                    `Swagger v2.0 is not supported. Please convert your spec to OpenAPI 3.x first. Detected swagger version: ${spec.swagger}`
-                );
+                throw new CliError({
+                    message: `Swagger v2.0 is not supported. Please convert your spec to OpenAPI 3.x first. Detected swagger version: ${spec.swagger}`,
+                    code: CliError.Code.ConfigError
+                });
             }
             return convertOpenApiSpecToFdrDefinition({
                 spec: spec as unknown as OpenAPIV3_1.Document,
diff --git a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertAsyncApiSpecToFdrDefinition.ts b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertAsyncApiSpecToFdrDefinition.ts
index 9f609ba886e..4b73ef99069 100644
--- a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertAsyncApiSpecToFdrDefinition.ts
+++ b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertAsyncApiSpecToFdrDefinition.ts
@@ -4,7 +4,8 @@ import { generatorsYml } from "@fern-api/configuration";
 import { FdrAPI } from "@fern-api/fdr-sdk";
 import { IntermediateRepresentation } from "@fern-api/ir-sdk";
 import { convertIrToFdrApi } from "@fern-api/register";
-import { createMockTaskContext } from "@fern-api/task-context";
+import { CliError, createMockTaskContext } from "@fern-api/task-context";
+
 import { ErrorCollector } from "@fern-api/v3-importer-commons";
 
 import { OpenAPIWorkspace } from "./OpenAPIWorkspace.js";
@@ -84,7 +85,10 @@ async function convertAsyncApiSpecToIr({
     const result = await converter.convert();
 
     if (result == null) {
-        throw new Error("Failed to convert AsyncAPI spec to intermediate representation");
+        throw new CliError({
+            message: "Failed to convert AsyncAPI spec to intermediate representation",
+            code: CliError.Code.IrConversionError
+        });
     }
 
     if (errorCollector.hasErrors()) {
diff --git a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenApiSpecToFdrDefinition.ts b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenApiSpecToFdrDefinition.ts
index 308eb04dd20..e8c2213f32b 100644
--- a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenApiSpecToFdrDefinition.ts
+++ b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenApiSpecToFdrDefinition.ts
@@ -4,7 +4,8 @@ import { FdrAPI } from "@fern-api/fdr-sdk";
 import { IntermediateRepresentation } from "@fern-api/ir-sdk";
 import { OpenAPI3_1Converter, OpenAPIConverterContext3_1 } from "@fern-api/openapi-to-ir";
 import { convertIrToFdrApi } from "@fern-api/register";
-import { createMockTaskContext } from "@fern-api/task-context";
+import { CliError, createMockTaskContext } from "@fern-api/task-context";
+
 import { ErrorCollector } from "@fern-api/v3-importer-commons";
 import { OpenAPIV3_1 } from "openapi-types";
 
@@ -98,7 +99,10 @@ async function convertOpenApiSpecToIr({
     const result = await converter.convert();
 
     if (result == null) {
-        throw new Error("Failed to convert OpenAPI spec to intermediate representation");
+        throw new CliError({
+            message: "Failed to convert OpenAPI spec to intermediate representation",
+            code: CliError.Code.IrConversionError
+        });
     }
 
     if (errorCollector.hasErrors()) {
diff --git a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenRpcSpecToFdrDefinition.ts b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenRpcSpecToFdrDefinition.ts
index bb425bad0ff..93ee19f92d2 100644
--- a/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenRpcSpecToFdrDefinition.ts
+++ b/packages/cli/workspace/browser-compatible-fern-workspace/src/convertOpenRpcSpecToFdrDefinition.ts
@@ -4,7 +4,8 @@ import { FdrAPI } from "@fern-api/fdr-sdk";
 import { IntermediateRepresentation } from "@fern-api/ir-sdk";
 import { OpenRPCConverter, OpenRPCConverterContext3_1 } from "@fern-api/openrpc-to-ir";
 import { convertIrToFdrApi } from "@fern-api/register";
-import { createMockTaskContext } from "@fern-api/task-context";
+import { CliError, createMockTaskContext } from "@fern-api/task-context";
+
 import { ErrorCollector } from "@fern-api/v3-importer-commons";
 import { OpenrpcDocument } from "@open-rpc/meta-schema";
 
@@ -87,7 +88,10 @@ async function convertOpenRpcSpecToIr({
     const result = await converter.convert();
 
     if (result == null) {
-        throw new Error("Failed to convert OpenRPC spec to intermediate representation");
+        throw new CliError({
+            message: "Failed to convert OpenRPC spec to intermediate representation",
+            code: CliError.Code.IrConversionError
+        });
     }
 
     if (errorCollector.hasErrors()) {
diff --git a/packages/cli/workspace/loader/src/loadAsyncAPIFile.ts b/packages/cli/workspace/loader/src/loadAsyncAPIFile.ts
index d69772270f9..c70161882fb 100644
--- a/packages/cli/workspace/loader/src/loadAsyncAPIFile.ts
+++ b/packages/cli/workspace/loader/src/loadAsyncAPIFile.ts
@@ -1,5 +1,5 @@
 import { AbsoluteFilePath, doesPathExist, join, RelativeFilePath } from "@fern-api/fs-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { readdir } from "fs/promises";
 
 export async function getValidAbsolutePathToAsyncAPIFromFolder(
@@ -8,7 +8,9 @@ export async function getValidAbsolutePathToAsyncAPIFromFolder(
 ): Promise<AbsoluteFilePath> {
     const files = await readdir(absolutePathToAsyncAPIFolder);
     if (files.length < 1 || files[0] == null) {
-        context.failAndThrow(`No AsyncAPI found in directory ${absolutePathToAsyncAPIFolder}`);
+        context.failAndThrow(`No AsyncAPI found in directory ${absolutePathToAsyncAPIFolder}`, undefined, {
+            code: CliError.Code.ConfigError
+        });
     }
     const absolutePathToAsyncAPIFile = join(absolutePathToAsyncAPIFolder, RelativeFilePath.of(files[0]));
     return absolutePathToAsyncAPIFile;
@@ -21,7 +23,9 @@ export async function getValidAbsolutePathToAsyncAPI(
     const absolutePathToAsyncAPIExists = await doesPathExist(absolutePathToAsyncAPI);
     if (!absolutePathToAsyncAPIExists) {
         context.failAndThrow(
-            `AsyncAPI spec not found at ${absolutePathToAsyncAPIExists}. Please update the path in generators.yml`
+            `AsyncAPI spec not found at ${absolutePathToAsyncAPIExists}. Please update the path in generators.yml`,
+            undefined,
+            { code: CliError.Code.ConfigError }
         );
     }
     return absolutePathToAsyncAPI;
diff --git a/packages/cli/workspace/loader/src/loadDocsWorkspace.ts b/packages/cli/workspace/loader/src/loadDocsWorkspace.ts
index 2b08ce6df77..123cdf55234 100644
--- a/packages/cli/workspace/loader/src/loadDocsWorkspace.ts
+++ b/packages/cli/workspace/loader/src/loadDocsWorkspace.ts
@@ -1,7 +1,8 @@
 import { DOCS_CONFIGURATION_FILENAME, docsYml } from "@fern-api/configuration-loader";
 import { extractErrorMessage, sanitizeNullValues, validateAgainstJsonSchema } from "@fern-api/core-utils";
 import { AbsoluteFilePath, doesPathExist, join, RelativeFilePath } from "@fern-api/fs-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
+
 import { readFile } from "fs/promises";
 import yaml from "js-yaml";
 
@@ -90,9 +91,15 @@ export async function loadRawDocsConfiguration({
             context.logger.error(`Parsing failed even after sanitization: ${extractErrorMessage(err)}`);
             // Log the JSON structure to debug
             context.logger.debug(`Sanitized JSON structure: ${JSON.stringify(sanitizedJson, null, 2)}`);
-            throw new Error(`Failed to parse ${absolutePathOfConfiguration}: ${extractErrorMessage(err)}`);
+            throw new CliError({
+                message: `Failed to parse ${absolutePathOfConfiguration}: ${extractErrorMessage(err)}`,
+                code: CliError.Code.ParseError
+            });
         }
     } else {
-        throw new Error(`Failed to parse docs.yml:\n${result.error?.message ?? "Unknown error"}`);
+        throw new CliError({
+            message: `Failed to parse docs.yml:\n${result.error?.message ?? "Unknown error"}`,
+            code: CliError.Code.ParseError
+        });
     }
 }
diff --git a/packages/cli/workspace/loader/src/loadOpenAPIFile.ts b/packages/cli/workspace/loader/src/loadOpenAPIFile.ts
index 68eedfac1e0..78d24536662 100644
--- a/packages/cli/workspace/loader/src/loadOpenAPIFile.ts
+++ b/packages/cli/workspace/loader/src/loadOpenAPIFile.ts
@@ -1,5 +1,5 @@
 import { AbsoluteFilePath, doesPathExist, join, RelativeFilePath } from "@fern-api/fs-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 import { readdir } from "fs/promises";
 
 export async function getValidAbsolutePathToOpenAPIFromFolder(
@@ -8,7 +8,9 @@ export async function getValidAbsolutePathToOpenAPIFromFolder(
 ): Promise<AbsoluteFilePath> {
     const files = await readdir(absolutePathToOpenAPIFolder);
     if (files.length < 1 || files[0] == null) {
-        context.failAndThrow(`No OpenAPI found in directory ${absolutePathToOpenAPIFolder}`);
+        context.failAndThrow(`No OpenAPI found in directory ${absolutePathToOpenAPIFolder}`, undefined, {
+            code: CliError.Code.ConfigError
+        });
     }
     const absolutePathToOpenAPIFile = join(absolutePathToOpenAPIFolder, RelativeFilePath.of(files[0]));
     return absolutePathToOpenAPIFile;
@@ -21,7 +23,9 @@ export async function getValidAbsolutePathToOpenAPI(
     const absolutePathToOpenAPIExists = await doesPathExist(absolutePathToOpenAPI);
     if (!absolutePathToOpenAPIExists) {
         context.failAndThrow(
-            `OpenAPI spec not found at ${absolutePathToOpenAPI}. Please update the path in generators.yml`
+            `OpenAPI spec not found at ${absolutePathToOpenAPI}. Please update the path in generators.yml`,
+            undefined,
+            { code: CliError.Code.ConfigError }
         );
     }
     return absolutePathToOpenAPI;
diff --git a/packages/cli/workspace/oss-validator/src/testing-utils/getViolationsForRule.ts b/packages/cli/workspace/oss-validator/src/testing-utils/getViolationsForRule.ts
index a5cd5218869..dded78832d4 100644
--- a/packages/cli/workspace/oss-validator/src/testing-utils/getViolationsForRule.ts
+++ b/packages/cli/workspace/oss-validator/src/testing-utils/getViolationsForRule.ts
@@ -1,6 +1,7 @@
 import { AbsoluteFilePath } from "@fern-api/fs-utils";
 import { OSSWorkspace } from "@fern-api/lazy-fern-workspace";
-import { createMockTaskContext } from "@fern-api/task-context";
+import { CliError, createMockTaskContext } from "@fern-api/task-context";
+
 import { loadAPIWorkspace } from "@fern-api/workspace-loader";
 import stripAnsi from "strip-ansi";
 
@@ -30,11 +31,14 @@ export async function getViolationsForRule({
     });
 
     if (!result.didSucceed) {
-        throw new Error("API workspace failed to load");
+        throw new CliError({ message: "API workspace failed to load", code: CliError.Code.InternalError });
     }
 
     if (!(result.workspace instanceof OSSWorkspace)) {
-        throw new Error("Expected an OSS workspace but got a different type");
+        throw new CliError({
+            message: "Expected an OSS workspace but got a different type",
+            code: CliError.Code.InternalError
+        });
     }
 
     const violations = await runRulesOnOSSWorkspace({
diff --git a/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/collect-links.ts b/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/collect-links.ts
index c844b383a98..0247a77534a 100644
--- a/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/collect-links.ts
+++ b/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/collect-links.ts
@@ -7,6 +7,7 @@ import {
     walkEstreeJsxAttributes
 } from "@fern-api/docs-markdown-utils";
 import { AbsoluteFilePath, dirname, RelativeFilePath, resolve } from "@fern-api/fs-utils";
+import { CliError } from "@fern-api/task-context";
 import type { Node as EstreeNode } from "estree";
 import { walk } from "estree-walker";
 import type { Root as HastRoot } from "hast";
@@ -62,7 +63,10 @@ export function collectLinksAndSources({
     do {
         loopCount++;
         if (loopCount > LOOP_LIMIT) {
-            throw new Error("Infinite loop detected while collecting links and sources");
+            throw new CliError({
+                message: "Infinite loop detected while collecting links and sources",
+                code: CliError.Code.ReferenceError
+            });
         }
         const popped = contentQueue.shift();
         if (popped == null) {
@@ -74,7 +78,10 @@ export function collectLinksAndSources({
         // NOTE: we don't want to visit the same file multiple times
         if (absoluteFilepath != null) {
             if (visitedAbsoluteFilepaths.has(absoluteFilepath)) {
-                throw new Error(`Circular import detected: ${absoluteFilepath}`);
+                throw new CliError({
+                    message: `Circular import detected: ${absoluteFilepath}`,
+                    code: CliError.Code.ReferenceError
+                });
             }
             visitedAbsoluteFilepaths.add(absoluteFilepath);
         }
diff --git a/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/valid-markdown-link.ts b/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/valid-markdown-link.ts
index 8f6fa27951b..dda1e1ec326 100644
--- a/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/valid-markdown-link.ts
+++ b/packages/cli/yaml/docs-validator/src/rules/valid-markdown-link/valid-markdown-link.ts
@@ -6,7 +6,8 @@ import { APIV1Read, ApiDefinition, FernNavigation } from "@fern-api/fdr-sdk";
 import { AbsoluteFilePath, join, RelativeFilePath, relative } from "@fern-api/fs-utils";
 import { generateIntermediateRepresentation } from "@fern-api/ir-generator";
 import { createLogger } from "@fern-api/logger";
-import { createMockTaskContext } from "@fern-api/task-context";
+import { CliError, createMockTaskContext } from "@fern-api/task-context";
+
 import chalk from "chalk";
 import { randomUUID } from "crypto";
 import path from "path";
@@ -47,7 +48,7 @@ export const ValidMarkdownLinks: Rule = {
 
         const configRoot = resolvedDocsDefinition.config.root;
         if (!configRoot || !isV1RootNode(configRoot)) {
-            throw new Error("Root node not found");
+            throw new CliError({ message: "Root node not found", code: CliError.Code.InternalError });
         }
 
         // TODO: this is a bit of a hack to get the navigation tree. We should probably just use the navigation tree
diff --git a/packages/cli/yaml/docs-validator/src/testing-utils/getViolationsForRule.ts b/packages/cli/yaml/docs-validator/src/testing-utils/getViolationsForRule.ts
index 6abb3a80db9..f4ccdf1a460 100644
--- a/packages/cli/yaml/docs-validator/src/testing-utils/getViolationsForRule.ts
+++ b/packages/cli/yaml/docs-validator/src/testing-utils/getViolationsForRule.ts
@@ -1,7 +1,8 @@
 import { filterOssWorkspaces } from "@fern-api/docs-resolver";
 import { AbsoluteFilePath } from "@fern-api/fs-utils";
 import { loadProjectFromDirectory } from "@fern-api/project-loader";
-import { createMockTaskContext } from "@fern-api/task-context";
+import { CliError, createMockTaskContext } from "@fern-api/task-context";
+
 import stripAnsi from "strip-ansi";
 
 import { Rule } from "../Rule.js";
@@ -30,7 +31,10 @@ export async function getViolationsForRule({
     });
 
     if (project.docsWorkspaces == null) {
-        throw new Error("Expected docs workspace to be present, but found none");
+        throw new CliError({
+            message: "Expected docs workspace to be present, but found none",
+            code: CliError.Code.InternalError
+        });
     }
 
     const violations = await runRulesOnDocsWorkspace({
diff --git a/packages/cli/yaml/generators-validator/src/rules/compatible-ir-versions/compatible-ir-versions.ts b/packages/cli/yaml/generators-validator/src/rules/compatible-ir-versions/compatible-ir-versions.ts
index 5a9c4663e1c..ac0a523c3af 100644
--- a/packages/cli/yaml/generators-validator/src/rules/compatible-ir-versions/compatible-ir-versions.ts
+++ b/packages/cli/yaml/generators-validator/src/rules/compatible-ir-versions/compatible-ir-versions.ts
@@ -1,6 +1,7 @@
 import { addDefaultDockerOrgIfNotPresent } from "@fern-api/configuration-loader";
 import { createFdrGeneratorsSdkService, getIrVersionForGenerator } from "@fern-api/core";
 import { isVersionAhead } from "@fern-api/semver-utils";
+import { CliError } from "@fern-api/task-context";
 
 import { Rule, RuleViolation } from "../../Rule.js";
 
@@ -9,7 +10,16 @@ function getMaybeBadVersionMessage(
     minCliVersion: string,
     cliVersion: string
 ): RuleViolation[] | undefined {
-    if (!isVersionAhead(cliVersion, minCliVersion)) {
+    let isAhead: boolean;
+    try {
+        isAhead = isVersionAhead(cliVersion, minCliVersion);
+    } catch (error) {
+        throw new CliError({
+            message: `Failed to compare versions: ${error instanceof Error ? error.message : String(error)}`,
+            code: CliError.Code.VersionError
+        });
+    }
+    if (!isAhead) {
         return [
             {
                 severity: "fatal",
diff --git a/packages/cli/yaml/loader/package.json b/packages/cli/yaml/loader/package.json
index 77fefb3b992..b7bb6165bf8 100644
--- a/packages/cli/yaml/loader/package.json
+++ b/packages/cli/yaml/loader/package.json
@@ -31,6 +31,9 @@
     "test:debug": "pnpm run test --inspect --no-file-parallelism",
     "test:update": "vitest --passWithNoTests --run -u"
   },
+  "dependencies": {
+    "@fern-api/task-context": "workspace:*"
+  },
   "devDependencies": {
     "@fern-api/configs": "workspace:*",
     "@fern-api/core-utils": "workspace:*",
diff --git a/packages/cli/yaml/loader/src/YamlConfigLoader.ts b/packages/cli/yaml/loader/src/YamlConfigLoader.ts
index 46d44fd81d6..b0ecaed463f 100644
--- a/packages/cli/yaml/loader/src/YamlConfigLoader.ts
+++ b/packages/cli/yaml/loader/src/YamlConfigLoader.ts
@@ -1,6 +1,7 @@
 import { extractErrorMessage } from "@fern-api/core-utils";
 import { AbsoluteFilePath, RelativeFilePath, relative } from "@fern-api/fs-utils";
 import { type Sourced, SourceLocation } from "@fern-api/source";
+import { CliError } from "@fern-api/task-context";
 import { z } from "zod";
 import { deepStrict } from "./deepStrict.js";
 import { ReferenceResolver } from "./ReferenceResolver.js";
@@ -8,6 +9,7 @@ import { ValidationIssue } from "./ValidationIssue.js";
 import type { YamlDocument } from "./YamlDocument.js";
 import { YamlParser } from "./YamlParser.js";
 import { YamlSourceResolver } from "./YamlSourceResolver.js";
+
 export namespace YamlConfigLoader {
     export type Result<T> = Success<T> | Failure;
 
@@ -129,7 +131,10 @@ export class YamlConfigLoader {
         try {
             return await this.parser.parseDocument({ absoluteFilePath, cwd: this.cwd });
         } catch (err) {
-            throw new Error(`Failed to parse YAML file ${absoluteFilePath}: ${extractErrorMessage(err)}`);
+            throw new CliError({
+                message: `Failed to parse YAML file ${absoluteFilePath}: ${extractErrorMessage(err)}`,
+                code: CliError.Code.ParseError
+            });
         }
     }
 
diff --git a/packages/cli/yaml/loader/src/YamlSourceResolver.ts b/packages/cli/yaml/loader/src/YamlSourceResolver.ts
index ed3ee5d0e54..8f3fe3c4fc9 100644
--- a/packages/cli/yaml/loader/src/YamlSourceResolver.ts
+++ b/packages/cli/yaml/loader/src/YamlSourceResolver.ts
@@ -7,6 +7,7 @@ import {
     SourcedNumber,
     SourcedString
 } from "@fern-api/source";
+import { CliError } from "@fern-api/task-context";
 import type { YamlDocument, YamlPath } from "./YamlDocument.js";
 
 export class YamlSourceResolver {
@@ -46,7 +47,10 @@ export class YamlSourceResolver {
             case "boolean":
                 return new SourcedBoolean(value, location) as Sourced<T>;
             default:
-                throw new Error(`Unexpected value type: ${typeof value}`);
+                throw new CliError({
+                    message: `Unexpected value type: ${typeof value}`,
+                    code: CliError.Code.InternalError
+                });
         }
     }
 }
diff --git a/packages/commons/api-workspace-commons/src/checkVersionExists.ts b/packages/commons/api-workspace-commons/src/checkVersionExists.ts
index cc9fb8f2874..12acdc87e7d 100644
--- a/packages/commons/api-workspace-commons/src/checkVersionExists.ts
+++ b/packages/commons/api-workspace-commons/src/checkVersionExists.ts
@@ -1,6 +1,6 @@
 import type { generatorsYml } from "@fern-api/configuration";
 import { extractErrorMessage } from "@fern-api/core-utils";
-import { TaskContext } from "@fern-api/task-context";
+import { CliError, TaskContext } from "@fern-api/task-context";
 /**
  * Resolves the package name from the raw generator configuration.
  *
@@ -152,7 +152,9 @@ export async function checkVersionDoesNotAlreadyExist({
             context.failAndThrow(
                 `Version ${version} of ${resolvedPackageName} already exists on the ${getRegistryName(language)} registry. ` +
                     `Please use a different version number. ` +
-                    `If you want to automatically increment the version, omit the --version flag.`
+                    `If you want to automatically increment the version, omit the --version flag.`,
+                undefined,
+                { code: CliError.Code.VersionError }
             );
         } else {
             context.logger.warn(
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 038c14a002c..06b97df18ee 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -3680,6 +3680,9 @@ importers:
       '@fern-api/ir-utils':
         specifier: workspace:*
         version: link:../../../commons/ir-utils
+      '@fern-api/task-context':
+        specifier: workspace:*
+        version: link:../../task-context
       '@fern-api/v3-importer-commons':
         specifier: workspace:*
         version: link:../v3-importer-commons
@@ -3775,6 +3778,9 @@ importers:
       '@fern-api/importer-commons':
         specifier: workspace:*
         version: link:../../commons
+      '@fern-api/task-context':
+        specifier: workspace:*
+        version: link:../../../task-context
       js-yaml:
         specifier: 'catalog:'
         version: 4.1.1
@@ -4136,6 +4142,9 @@ importers:
       '@fern-api/logger':
         specifier: workspace:*
         version: link:../../logger
+      '@fern-api/task-context':
+        specifier: workspace:*
+        version: link:../../task-context
       js-yaml:
         specifier: 'catalog:'
         version: 4.1.1
@@ -6410,6 +6419,9 @@ importers:
       '@fern-api/fdr-sdk':
         specifier: 1.1.13-c1ad12a2b8
         version: 1.1.13-c1ad12a2b8(@opentelemetry/api@1.9.1)(typescript@5.9.3)
+      '@fern-api/task-context':
+        specifier: workspace:*
+        version: link:../task-context
       js-yaml:
         specifier: 'catalog:'
         version: 4.1.1
@@ -7328,6 +7340,10 @@ importers:
         version: 4.1.4(@opentelemetry/api@1.9.1)(@types/node@22.19.17)(@vitest/coverage-v8@4.1.4)(vite@7.3.2(@types/node@22.19.17)(jiti@2.6.1)(tsx@4.21.0)(yaml@2.8.3))
 
   packages/cli/yaml/loader:
+    dependencies:
+      '@fern-api/task-context':
+        specifier: workspace:*
+        version: link:../../task-context
     devDependencies:
       '@fern-api/configs':
         specifier: workspace:*