diff --git a/src/api/providers/__tests__/vscode-lm-content-filtering.test.ts b/src/api/providers/__tests__/vscode-lm-content-filtering.test.ts
new file mode 100644
index 00000000000..3f412ae7717
--- /dev/null
+++ b/src/api/providers/__tests__/vscode-lm-content-filtering.test.ts
@@ -0,0 +1,236 @@
+import { describe, it, expect, vi, beforeEach } from "vitest"
+import * as vscode from "vscode"
+import { VsCodeLmHandler } from "../vscode-lm"
+
+// Mock vscode module
+vi.mock("vscode", () => ({
+	workspace: {
+		onDidChangeConfiguration: vi.fn(() => ({ dispose: vi.fn() })),
+	},
+	lm: {
+		selectChatModels: vi.fn(),
+	},
+	LanguageModelChatMessage: {
+		Assistant: vi.fn((content) => ({ role: "assistant", content })),
+		User: vi.fn((content) => ({ role: "user", content })),
+	},
+	CancellationError: class extends Error {
+		constructor(message?: string) {
+			super(message)
+			this.name = "CancellationError"
+		}
+	},
+	CancellationTokenSource: vi.fn(() => ({
+		token: {},
+		cancel: vi.fn(),
+		dispose: vi.fn(),
+	})),
+}))
+
+describe("VsCodeLmHandler Content Filtering", () => {
+	let handler: VsCodeLmHandler
+	let mockClient: any
+
+	beforeEach(() => {
+		vi.clearAllMocks()
+
+		mockClient = {
+			id: "test-model",
+			name: "Test Model",
+			vendor: "test",
+			family: "test",
+			version: "1.0",
+			maxInputTokens: 8192,
+			sendRequest: vi.fn(),
+			countTokens: vi.fn().mockResolvedValue(10),
+		}
+
+		vi.mocked(vscode.lm.selectChatModels).mockResolvedValue([mockClient])
+
+		handler = new VsCodeLmHandler({
+			vsCodeLmModelSelector: { vendor: "test", family: "test" },
+		})
+	})
+
+	describe("Content Filtering Error Detection", () => {
+		it("should detect content filtering errors in Error objects", async () => {
+			const filteringError = new Error("Response was filtered by content policy")
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should detect content filtering errors with 'inappropriate' keyword", async () => {
+			const filteringError = new Error("Content deemed inappropriate")
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should detect content filtering errors with 'safety' keyword", async () => {
+			const filteringError = new Error("Safety violation detected")
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should detect content filtering errors with 'blocked' keyword", async () => {
+			const filteringError = new Error("Request blocked by policy")
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should detect content filtering errors in error objects", async () => {
+			const filteringError = {
+				message: "Content filtered",
+				code: "CONTENT_POLICY_VIOLATION",
+			}
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should detect content filtering errors in error objects with reason property", async () => {
+			const filteringError = {
+				reason: "Content policy violation",
+				type: "FILTERING_ERROR",
+			}
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should not detect content filtering for regular errors", async () => {
+			const regularError = new Error("Network timeout")
+			mockClient.sendRequest.mockRejectedValue(regularError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow("Network timeout")
+		})
+
+		it("should handle cancellation errors correctly", async () => {
+			const cancellationError = new vscode.CancellationError()
+			mockClient.sendRequest.mockRejectedValue(cancellationError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Request cancelled by user/)
+		})
+
+		it("should provide helpful error message for content filtering", async () => {
+			const filteringError = new Error("Response got filtered FIX!!")
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			try {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			} catch (error) {
+				expect(error).toBeInstanceOf(Error)
+				const errorMessage = (error as Error).message
+				expect(errorMessage).toContain("Response was filtered by VS Code's content policy")
+				expect(errorMessage).toContain("Try rephrasing your request")
+				expect(errorMessage).toContain("Original error: Response got filtered FIX!!")
+			}
+		})
+	})
+
+	describe("Case Insensitive Detection", () => {
+		it("should detect content filtering errors case-insensitively", async () => {
+			const filteringError = new Error("CONTENT POLICY VIOLATION")
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+
+		it("should detect content filtering in error name case-insensitively", async () => {
+			const filteringError = new Error("Some error")
+			filteringError.name = "CONTENT_FILTERED_ERROR"
+			mockClient.sendRequest.mockRejectedValue(filteringError)
+
+			const systemPrompt = "You are a helpful assistant"
+			const messages = [{ role: "user" as const, content: "Hello" }]
+
+			await expect(async () => {
+				const generator = handler.createMessage(systemPrompt, messages)
+				for await (const chunk of generator) {
+					// Should not reach here
+				}
+			}).rejects.toThrow(/Response was filtered by VS Code's content policy/)
+		})
+	})
+})
diff --git a/src/api/providers/vscode-lm.ts b/src/api/providers/vscode-lm.ts
index 6474371beeb..4ff748d28d7 100644
--- a/src/api/providers/vscode-lm.ts
+++ b/src/api/providers/vscode-lm.ts
@@ -287,6 +287,60 @@ export class VsCodeLmHandler extends BaseProvider implements SingleCompletionHan
 		}
 	}
 
+	private isContentFilteringError(error: Error): boolean {
+		const message = error.message.toLowerCase()
+		const name = error.name.toLowerCase()
+
+		// Common patterns that indicate content filtering
+		const filteringPatterns = [
+			"filtered",
+			"content policy",
+			"inappropriate",
+			"safety",
+			"blocked",
+			"restricted",
+			"content violation",
+			"policy violation",
+			"harmful content",
+			"unsafe content",
+		]
+
+		return filteringPatterns.some((pattern) => message.includes(pattern) || name.includes(pattern))
+	}
+
+	private isContentFilteringErrorObject(error: any): boolean {
+		if (!error || typeof error !== "object") {
+			return false
+		}
+
+		// Check various properties that might indicate content filtering
+		const checkProperties = ["message", "reason", "code", "type", "error", "description"]
+
+		for (const prop of checkProperties) {
+			if (error[prop] && typeof error[prop] === "string") {
+				const value = error[prop].toLowerCase()
+				const filteringPatterns = [
+					"filtered",
+					"content policy",
+					"inappropriate",
+					"safety",
+					"blocked",
+					"restricted",
+					"content violation",
+					"policy violation",
+					"harmful content",
+					"unsafe content",
+				]
+
+				if (filteringPatterns.some((pattern) => value.includes(pattern))) {
+					return true
+				}
+			}
+		}
+
+		return false
+	}
+
 	private async getClient(): Promise<vscode.LanguageModelChat> {
 		if (!this.client) {
 			console.debug("Roo Code <Language Model API>: Getting client with options:", {
@@ -467,12 +521,33 @@ export class VsCodeLmHandler extends BaseProvider implements SingleCompletionHan
 					name: error.name,
 				})
 
+				// Check for content filtering errors
+				if (this.isContentFilteringError(error)) {
+					throw new Error(
+						"Roo Code <Language Model API>: Response was filtered by VS Code's content policy. " +
+							"This may happen when the model's response contains content that VS Code considers inappropriate. " +
+							"Try rephrasing your request or using a different approach. " +
+							`Original error: ${error.message}`,
+					)
+				}
+
 				// Return original error if it's already an Error instance
 				throw error
 			} else if (typeof error === "object" && error !== null) {
 				// Handle error-like objects
 				const errorDetails = JSON.stringify(error, null, 2)
 				console.error("Roo Code <Language Model API>: Stream error object:", errorDetails)
+
+				// Check if the error object indicates content filtering
+				if (this.isContentFilteringErrorObject(error)) {
+					throw new Error(
+						"Roo Code <Language Model API>: Response was filtered by VS Code's content policy. " +
+							"This may happen when the model's response contains content that VS Code considers inappropriate. " +
+							"Try rephrasing your request or using a different approach. " +
+							`Original error: ${errorDetails}`,
+					)
+				}
+
 				throw new Error(`Roo Code <Language Model API>: Response stream error: ${errorDetails}`)
 			} else {
 				// Fallback for unknown error types