diff --git a/.changeset/fix-cast-error-cause-message.md b/.changeset/fix-cast-error-cause-message.md
new file mode 100644
index 00000000000..453a243509e
--- /dev/null
+++ b/.changeset/fix-cast-error-cause-message.md
@@ -0,0 +1,7 @@
+---
+"wrangler": patch
+---
+
+Surface the original error message, name and stack when the dev server reports an internal error
+
+Errors reported by the ProxyWorker cross a JSON channel, so they arrived as plain objects and were previously wrapped in a message-less `Error`, causing `wrangler dev` to exit with an empty `✘ [ERROR]` log. Such errors (e.g. `Network connection lost.`, see #14641) are now rehydrated with their original message, name and stack so the failure is actually diagnosable.
diff --git a/packages/wrangler/src/__tests__/api/startDevWorker/ProxyController.test.ts b/packages/wrangler/src/__tests__/api/startDevWorker/ProxyController.test.ts
index 3af59552994..f5a08b65136 100644
--- a/packages/wrangler/src/__tests__/api/startDevWorker/ProxyController.test.ts
+++ b/packages/wrangler/src/__tests__/api/startDevWorker/ProxyController.test.ts
@@ -1,11 +1,38 @@
 import { describe, test } from "vitest";
+import { serialiseError } from "../../../api/startDevWorker/events";
 import { ProxyController } from "../../../api/startDevWorker/ProxyController";
 import { FakeBus } from "../../helpers/fake-bus";
 import { mockConsoleMethods } from "../../helpers/mock-console";
+import type { SerializedError } from "../../../api/startDevWorker/events";
 
 describe("ProxyController", () => {
 	mockConsoleMethods();
 
+	test("ProxyWorker error reports preserve message/name/stack across the JSON channel", async ({
+		expect,
+	}) => {
+		// Regression test for https://github.com/cloudflare/workers-sdk/issues/14641:
+		// the ProxyWorker's error reports arrive as JSON-serialized plain objects,
+		// and used to be re-wrapped in a message-less Error, so the resulting
+		// fatal log was an empty `✘ [ERROR]` with no clue about the failure.
+		const bus = new FakeBus();
+		const controller = new ProxyController(bus);
+		const waited = bus.waitFor("error");
+
+		const original = new Error("Network connection lost.");
+		const serialized = JSON.parse(
+			JSON.stringify(serialiseError(original))
+		) as SerializedError;
+		controller.onProxyWorkerMessage({ type: "error", error: serialized });
+
+		const event = await waited;
+		expect(event.source).toBe("ProxyController");
+		expect(event.reason).toBe("Error inside ProxyWorker");
+		expect(event.cause).toBeInstanceOf(Error);
+		expect(event.cause.message).toBe("Network connection lost.");
+		expect(event.cause.stack).toBe(original.stack);
+	});
+
 	test("Runtime.exceptionThrown dispatches a typed runtimeError event", async ({
 		expect,
 	}) => {
diff --git a/packages/wrangler/src/__tests__/api/startDevWorker/events.test.ts b/packages/wrangler/src/__tests__/api/startDevWorker/events.test.ts
new file mode 100644
index 00000000000..1d5cd3ce65b
--- /dev/null
+++ b/packages/wrangler/src/__tests__/api/startDevWorker/events.test.ts
@@ -0,0 +1,74 @@
+import { describe, it } from "vitest";
+import {
+	castErrorCause,
+	serialiseError,
+} from "../../../api/startDevWorker/events";
+
+describe("castErrorCause", () => {
+	it("returns Error instances unchanged", ({ expect }) => {
+		const cause = new TypeError("boom");
+		expect(castErrorCause(cause)).toBe(cause);
+	});
+
+	it("rehydrates a SerializedError, preserving message/name/stack", ({
+		expect,
+	}) => {
+		// Regression test for https://github.com/cloudflare/workers-sdk/issues/14641:
+		// the ProxyWorker's error reports cross a JSON channel, so they arrive as
+		// plain objects. castErrorCause used to wrap them in a message-less
+		// `new Error()`, making the fatal log an empty `✘ [ERROR]` with no clue
+		// about the actual failure (e.g. "Network connection lost.").
+		const original = new Error("Network connection lost.");
+		const serialized = JSON.parse(
+			JSON.stringify(serialiseError(original))
+		) as unknown;
+
+		const error = castErrorCause(serialized);
+
+		expect(error).toBeInstanceOf(Error);
+		expect(error.message).toBe("Network connection lost.");
+		expect(error.name).toBe("Error");
+		expect(error.stack).toBe(original.stack);
+		// No own `cause: undefined` property that would render as
+		// `{ cause: undefined }` in util.format-based debug logs
+		expect(Object.hasOwn(error, "cause")).toBe(false);
+	});
+
+	it("rehydrates the serialized nested cause chain into Error instances", ({
+		expect,
+	}) => {
+		const original = new Error("outer", { cause: new TypeError("inner") });
+		const serialized = JSON.parse(
+			JSON.stringify(serialiseError(original))
+		) as unknown;
+
+		const error = castErrorCause(serialized);
+
+		expect(error.message).toBe("outer");
+		expect(error.cause).toBeInstanceOf(Error);
+		const inner = error.cause as Error;
+		expect(inner.message).toBe("inner");
+		expect(inner.name).toBe("TypeError");
+	});
+
+	it("wraps other non-Error causes, keeping them as `cause`", ({ expect }) => {
+		const error = castErrorCause("string cause");
+
+		expect(error).toBeInstanceOf(Error);
+		expect(error.message).toBe("");
+		expect(error.cause).toBe("string cause");
+	});
+
+	it("preserves message-bearing objects with extra properties verbatim", ({
+		expect,
+	}) => {
+		// Not a SerializedError (extra `code` key): rehydrating would silently
+		// drop `code`, so the object must be kept whole as `cause` instead
+		const cause = { message: "failed", code: "E_CUSTOM" };
+
+		const error = castErrorCause(cause);
+
+		expect(error.message).toBe("");
+		expect(error.cause).toBe(cause);
+	});
+});
diff --git a/packages/wrangler/src/api/startDevWorker/events.ts b/packages/wrangler/src/api/startDevWorker/events.ts
index 79ce57502f5..876b4244858 100644
--- a/packages/wrangler/src/api/startDevWorker/events.ts
+++ b/packages/wrangler/src/api/startDevWorker/events.ts
@@ -34,12 +34,54 @@ export function castErrorCause(cause: unknown) {
 		return cause;
 	}
 
+	// Errors that cross a JSON channel (e.g. the ProxyWorker's and
+	// InspectorProxyWorker's error reports) arrive as SerializedError plain
+	// objects — rehydrate them so their message/name/stack are surfaced
+	// instead of an empty `new Error()`.
+	if (isSerializedError(cause)) {
+		const error = new Error(cause.message);
+		if (cause.name !== undefined) {
+			error.name = cause.name;
+		}
+		if (cause.stack !== undefined) {
+			error.stack = cause.stack;
+		}
+		if (cause.cause !== undefined) {
+			// Rehydrate serialized cause chains (serialiseError recurses) so the
+			// `instanceof Error` cause-chain classifiers in handle-errors.ts work
+			// across the channel; leave non-SerializedError causes untouched.
+			error.cause = isSerializedError(cause.cause)
+				? castErrorCause(cause.cause)
+				: cause.cause;
+		}
+		return error;
+	}
+
 	const error = new Error();
 	error.cause = cause;
 
 	return error;
 }
 
+const serializedErrorKeys = new Set(["message", "name", "stack", "cause"]);
+
+// Matches exactly the shape produced by serialiseError() and the
+// ProxyWorker's error reports. Kept strict (no extra keys) so that arbitrary
+// message-bearing objects passed to castErrorCause() are still preserved
+// verbatim as `cause` rather than lossily rehydrated.
+function isSerializedError(value: unknown): value is SerializedError {
+	if (typeof value !== "object" || value === null) {
+		return false;
+	}
+	const record = value as Record<string, unknown>;
+	return (
+		typeof record.message === "string" &&
+		(record.name === undefined || typeof record.name === "string") &&
+		(record.stack === undefined || typeof record.stack === "string") &&
+		Object.keys(record).every((key) => serializedErrorKeys.has(key))
+	);
+}
+
 // ConfigController
 export type ConfigUpdateEvent = {
 	type: "configUpdate";