fix(auth): prefer stored OAuth over env token by default (#646)

When SENTRY_AUTH_TOKEN is set by build tooling (e.g. the Sentry wizard)
but lacks the scopes needed for interactive CLI commands, the CLI now
prefers stored OAuth credentials by default.

OAuth-preferred default: when the user is logged in via OAuth, env
tokens are automatically skipped. This prevents wizard-generated build
tokens from silently overriding interactive credentials. Set
SENTRY_FORCE_ENV_TOKEN=1 to restore the old env-token-first priority.

Key changes:
- getEnvToken() returns undefined when stored OAuth credentials exist,
  cascading through all consumers (isEnvTokenActive, refreshToken, etc.)
- SENTRY_FORCE_ENV_TOKEN env var to force env token priority
- sentry auth login no longer blocks when an env token is present
- sentry auth status shows env token info (active vs bypassed)
- Enhanced 401/403 error messages when env token is the only auth source

Author: BYK

src/commands/auth/login.ts

@@ -9,6 +9,7 @@ import { buildCommand, numberParser } from "../../lib/command.js";
 import {
   clearAuth,
   getActiveEnvVarName,
+  hasStoredAuthCredentials,
   isAuthenticated,
   isEnvTokenActive,
   setAuthToken,
@@ -71,11 +72,15 @@ type LoginFlags = {
 async function handleExistingAuth(force: boolean): Promise<boolean> {
   if (isEnvTokenActive()) {
     const envVar = getActiveEnvVarName();
-    log.info(
-      `Authentication is provided via ${envVar} environment variable. ` +
-        `Unset ${envVar} to use OAuth-based login instead.`
+    log.warn(
+      `${envVar} is set in your environment (likely from build tooling).\n` +
+        "  OAuth credentials will be stored separately and used for CLI commands."
     );
-    return false;
+    // If no stored OAuth token exists, proceed directly to login
+    if (!hasStoredAuthCredentials()) {
+      return true;
+    }
+    // Fall through to the re-auth confirmation logic below
   }
 
   if (!force) {

src/commands/auth/status.ts

@@ -11,8 +11,11 @@ import {
   type AuthConfig,
   type AuthSource,
   ENV_SOURCE_PREFIX,
+  getActiveEnvVarName,
   getAuthConfig,
+  getRawEnvToken,
   isAuthenticated,
+  isEnvTokenActive,
 } from "../../lib/db/auth.js";
 import {
   getDefaultOrganization,
@@ -77,6 +80,13 @@ export type AuthStatusData = {
     /** Error message if verification failed */
     error?: string;
   };
+  /** Environment variable token info (present when SENTRY_AUTH_TOKEN or SENTRY_TOKEN is set) */
+  envToken?: {
+    /** Name of the env var (e.g., "SENTRY_AUTH_TOKEN") */
+    envVar: string;
+    /** Whether the env token is the effective auth source (vs bypassed for OAuth) */
+    active: boolean;
+  };
 };
 
 /**
@@ -186,6 +196,13 @@ export const statusCommand = buildCommand({
         : undefined;
     }
 
+    // Check for env token regardless of whether it's the active source
+    // (it may be set but bypassed because stored OAuth takes priority)
+    const rawEnv = getRawEnvToken();
+    const envTokenData: AuthStatusData["envToken"] = rawEnv
+      ? { envVar: getActiveEnvVarName(), active: isEnvTokenActive() }
+      : undefined;
+
     const data: AuthStatusData = {
       authenticated: true,
       source: auth?.source ?? "oauth",
@@ -194,6 +211,7 @@ export const statusCommand = buildCommand({
       token: collectTokenInfo(auth, flags["show-token"]),
       defaults: collectDefaults(),
       verification: await verifyCredentials(),
+      envToken: envTokenData,
     };
 
     yield new CommandOutput(data);

src/lib/api/infrastructure.ts

@@ -10,6 +10,7 @@
 import * as Sentry from "@sentry/node-core/light";
 import type { z } from "zod";
 
+import { getRawEnvToken } from "../db/auth.js";
 import { getEnv } from "../env.js";
 import { ApiError, AuthError, stringifyUnknown } from "../errors.js";
 import { resolveOrgRegion } from "../region.js";
@@ -57,6 +58,29 @@ export function throwApiError(
     error && typeof error === "object" && "detail" in error
       ? stringifyUnknown((error as { detail: unknown }).detail)
       : stringifyUnknown(error);
+
+  // When an env token is set and we get 401, the HTTP-layer fallback to
+  // stored OAuth already failed (no stored credentials). Convert to AuthError
+  // so the auto-login middleware in cli.ts can trigger interactive login.
+  if (status === 401 && getRawEnvToken()) {
+    throw new AuthError(
+      "not_authenticated",
+      `${context}: ${status} ${response.statusText ?? "Unknown"}.\n` +
+        "  SENTRY_AUTH_TOKEN is set but lacks permissions for this endpoint.\n" +
+        "  Run 'sentry auth login' to authenticate with OAuth."
+    );
+  }
+
+  // For 403 with env token, keep as ApiError but add guidance
+  if (status === 403 && getRawEnvToken()) {
+    throw new ApiError(
+      `${context}: ${status} ${response.statusText ?? "Unknown"}`,
+      status,
+      `${detail}\n\n  SENTRY_AUTH_TOKEN may lack permissions for this endpoint.\n` +
+        "  Run 'sentry auth login' to authenticate with OAuth."
+    );
+  }
+
   throw new ApiError(
     `${context}: ${status} ${response.statusText ?? "Unknown"}`,
     status,

src/lib/db/auth.ts

@@ -25,6 +25,19 @@ type AuthRow = {
 /** Prefix for environment variable auth sources in {@link AuthSource} */
 export const ENV_SOURCE_PREFIX = "env:";
 
+/**
+ * Process-level cache for the hasStoredAuthCredentials result.
+ * Keyed by config dir so it auto-resets when tests change SENTRY_CONFIG_DIR.
+ * Also reset on clearAuth() (logout) and setAuthToken() (login).
+ */
+const _credentialCache = { value: null as boolean | null, configDir: "" };
+
+/** Reset the credential cache. Called from closeDatabase() during test teardown. */
+export function resetCredentialCache(): void {
+  _credentialCache.value = null;
+  _credentialCache.configDir = "";
+}
+
 /** Where the auth token originated */
 export type AuthSource = "env:SENTRY_AUTH_TOKEN" | "env:SENTRY_TOKEN" | "oauth";
 
@@ -36,21 +49,75 @@ export type AuthConfig = {
   source: AuthSource;
 };
 
+/**
+ * Read the raw token string from environment variables, ignoring all filters.
+ *
+ * Unlike {@link getEnvToken}, this always returns the env token if set, even
+ * when stored OAuth credentials would normally take priority. Used by the HTTP
+ * layer to check "was an env token provided?" independent of whether it's being
+ * used, and by the per-endpoint permission cache.
+ */
+export function getRawEnvToken(): string | undefined {
+  const authToken = getEnv().SENTRY_AUTH_TOKEN?.trim();
+  if (authToken) {
+    return authToken;
+  }
+  const sentryToken = getEnv().SENTRY_TOKEN?.trim();
+  if (sentryToken) {
+    return sentryToken;
+  }
+  return;
+}
+
 /**
  * Read token from environment variables.
  * `SENTRY_AUTH_TOKEN` takes priority over `SENTRY_TOKEN` (matches legacy sentry-cli).
  * Empty or whitespace-only values are treated as unset.
+ *
+ * **Default behavior**: When the user is logged in (stored OAuth credentials
+ * exist in the database), env tokens are skipped so OAuth takes priority. This
+ * prevents wizard-generated build tokens from silently overriding interactive
+ * CLI credentials. Set `SENTRY_FORCE_ENV_TOKEN=1` to override this and force
+ * the env token to take priority (e.g., for CI pipelines that intentionally
+ * use an env token alongside stored credentials).
  */
 function getEnvToken(): { token: string; source: AuthSource } | undefined {
+  const raw = getRawEnvToken();
+  if (!raw) {
+    return;
+  }
+
+  // When OAuth credentials are stored and env token is not forced, prefer OAuth.
+  // This is the core fix for #646: wizard-generated tokens no longer silently
+  // override the user's interactive login.
+  //
+  // The result is cached per-process to avoid repeated DB queries and to prevent
+  // opening the DB as a side effect of reading an env var on the very first call.
+  // Cache is invalidated by setAuthToken() and clearAuth().
+  const forceEnv = getEnv().SENTRY_FORCE_ENV_TOKEN?.trim();
+  if (!forceEnv) {
+    const currentDir = getEnv().SENTRY_CONFIG_DIR ?? "";
+    if (
+      _credentialCache.value === null ||
+      _credentialCache.configDir !== currentDir
+    ) {
+      _credentialCache.configDir = currentDir;
+      try {
+        _credentialCache.value = hasStoredAuthCredentials();
+      } catch {
+        _credentialCache.value = false;
+      }
+    }
+    if (_credentialCache.value) {
+      return;
+    }
+  }
+
   const authToken = getEnv().SENTRY_AUTH_TOKEN?.trim();
   if (authToken) {
     return { token: authToken, source: "env:SENTRY_AUTH_TOKEN" };
   }
-  const sentryToken = getEnv().SENTRY_TOKEN?.trim();
-  if (sentryToken) {
-    return { token: sentryToken, source: "env:SENTRY_TOKEN" };
-  }
-  return;
+  return { token: raw, source: "env:SENTRY_TOKEN" };
 }
 
 /**
@@ -62,17 +129,21 @@ export function isEnvTokenActive(): boolean {
 }
 
 /**
- * Get the name of the active env var providing authentication.
+ * Get the name of the env var providing a token, for error messages.
  * Returns the specific variable name (e.g. "SENTRY_AUTH_TOKEN" or "SENTRY_TOKEN").
  *
- * **Important**: Call only after checking {@link isEnvTokenActive} returns true.
- * Falls back to "SENTRY_AUTH_TOKEN" if no env source is active, which is a safe
- * default for error messages but may be misleading if used unconditionally.
+ * Uses {@link getRawEnvToken} (not {@link getEnvToken}) so the result is
+ * independent of whether stored OAuth takes priority.
+ * Falls back to "SENTRY_AUTH_TOKEN" if no env var is set.
  */
 export function getActiveEnvVarName(): string {
-  const env = getEnvToken();
-  if (env) {
-    return env.source.slice(ENV_SOURCE_PREFIX.length);
+  const authToken = getEnv().SENTRY_AUTH_TOKEN?.trim();
+  if (authToken) {
+    return "SENTRY_AUTH_TOKEN";
+  }
+  const sentryToken = getEnv().SENTRY_TOKEN?.trim();
+  if (sentryToken) {
+    return "SENTRY_TOKEN";
   }
   return "SENTRY_AUTH_TOKEN";
 }
@@ -133,6 +204,7 @@ export function setAuthToken(
   expiresIn?: number,
   newRefreshToken?: string
 ): void {
+  _credentialCache.value = true; // Invalidate: we're storing credentials
   withDbSpan("setAuthToken", () => {
     const db = getDatabase();
     const now = Date.now();
@@ -156,6 +228,7 @@ export function setAuthToken(
 }
 
 export async function clearAuth(): Promise<void> {
+  _credentialCache.value = null; // Invalidate: credentials being cleared
   withDbSpan("clearAuth", () => {
     const db = getDatabase();
     db.query("DELETE FROM auth WHERE id = 1").run();
@@ -179,6 +252,33 @@ export function isAuthenticated(): boolean {
   return !!token;
 }
 
+/**
+ * Check if usable OAuth credentials are stored in the database.
+ *
+ * Returns true when the `auth` table has either:
+ * - A non-expired token, or
+ * - An expired token with a refresh token (will be refreshed on next use)
+ *
+ * This is the gate for the "OAuth-preferred" default: when this returns true,
+ * {@link getEnvToken} skips the env token so OAuth takes priority. Also used
+ * by the login command to decide whether to prompt for re-authentication.
+ */
+export function hasStoredAuthCredentials(): boolean {
+  const db = getDatabase();
+  const row = db.query("SELECT * FROM auth WHERE id = 1").get() as
+    | AuthRow
+    | undefined;
+  if (!row?.token) {
+    return false;
+  }
+  // Non-expired token
+  if (!row.expires_at || Date.now() <= row.expires_at) {
+    return true;
+  }
+  // Expired but has refresh token — will be refreshed on next use
+  return !!row.refresh_token;
+}
+
 export type RefreshTokenOptions = {
   /** Bypass threshold check and always refresh */
   force?: boolean;
@@ -229,7 +329,7 @@ async function performTokenRefresh(
 export async function refreshToken(
   options: RefreshTokenOptions = {}
 ): Promise<RefreshTokenResult> {
-  // Env var tokens are assumed valid — no refresh, no expiry check
+  // Env var tokens are assumed valid — no refresh, no expiry check.
   const envToken = getEnvToken();
   if (envToken) {
     return { token: envToken.token, refreshed: false };

src/lib/db/index.ts

@@ -7,6 +7,7 @@ import { Database } from "bun:sqlite";
 import { chmodSync, mkdirSync } from "node:fs";
 import { join } from "node:path";
 import { getEnv } from "../env.js";
+import { resetCredentialCache } from "./auth.js";
 import { migrateFromJson } from "./migration.js";
 import { initSchema, runMigrations } from "./schema.js";
 
@@ -130,6 +131,7 @@ export function closeDatabase(): void {
     rawDb = null;
     dbOpenedPath = null;
   }
+  resetCredentialCache();
 }
 
 /**

src/lib/formatters/human.ts

@@ -1826,6 +1826,10 @@ export function formatAuthStatus(data: AuthStatusData): string {
     lines.push(mdKvTable(authRows));
   }
 
+  if (data.envToken) {
+    lines.push(formatEnvTokenSection(data.envToken));
+  }
+
   if (data.defaults) {
     lines.push(formatDefaultsSection(data.defaults));
   }
@@ -1837,6 +1841,24 @@ export function formatAuthStatus(data: AuthStatusData): string {
   return renderMarkdown(lines.join("\n"));
 }
 
+/**
+ * Format the env token status section.
+ * Shows whether the env token is active or bypassed, and how many endpoints
+ * have been marked insufficient.
+ */
+function formatEnvTokenSection(
+  envToken: NonNullable<AuthStatusData["envToken"]>
+): string {
+  const status = envToken.active
+    ? "active"
+    : "set but not used (using OAuth credentials)";
+  const rows: [string, string][] = [
+    ["Env var", safeCodeSpan(envToken.envVar)],
+    ["Status", status],
+  ];
+  return `\n${mdKvTable(rows, "Environment Token")}`;
+}
+
 // Project Creation Formatting
 
 /** Input for the project-created success formatter */