diff --git a/src/core/prompts/responses.ts b/src/core/prompts/responses.ts
index 60b5b4123ac..7a678de56ea 100644
--- a/src/core/prompts/responses.ts
+++ b/src/core/prompts/responses.ts
@@ -66,6 +66,21 @@ Otherwise, if you have not completed the task and do not need additional informa
 		return `Missing value for required parameter '${paramName}'. Please retry with complete response.\n\n${instructions}`
 	},
 
+	writeToFileMissingContentError: () => {
+		const instructions = getToolInstructionsReminder()
+
+		return `Missing value for required parameter 'content'. This most commonly happens when the file content is too large and your response was truncated before the 'content' parameter could be fully generated.
+
+To recover, try one of these approaches:
+1. **Create a smaller file first**: Write a minimal version of the file with write_to_file, then use edit_file or apply_diff to add the remaining content incrementally.
+2. **Use edit_file instead**: If modifying an existing file, use edit_file with targeted changes rather than rewriting the entire file.
+3. **Split into multiple files**: If the content is genuinely large, consider splitting it across multiple smaller files.
+
+Do NOT simply retry write_to_file with the same large content — it will likely fail again for the same reason.
+
+${instructions}`
+	},
+
 	invalidMcpToolArgumentError: (serverName: string, toolName: string) =>
 		JSON.stringify({
 			status: "error",
diff --git a/src/core/tools/WriteToFileTool.ts b/src/core/tools/WriteToFileTool.ts
index c8455ef3d97..4c7fa333a09 100644
--- a/src/core/tools/WriteToFileTool.ts
+++ b/src/core/tools/WriteToFileTool.ts
@@ -42,7 +42,13 @@ export class WriteToFileTool extends BaseTool<"write_to_file"> {
 		if (newContent === undefined) {
 			task.consecutiveMistakeCount++
 			task.recordToolError("write_to_file")
-			pushToolResult(await task.sayAndCreateMissingParamError("write_to_file", "content"))
+			await task.say(
+				"error",
+				`Roo tried to use write_to_file${
+					relPath ? ` for '${relPath.toPosix()}'` : ""
+				} without value for required parameter 'content'. This is likely due to output token limits. Retrying...`,
+			)
+			pushToolResult(formatResponse.toolError(formatResponse.writeToFileMissingContentError()))
 			await task.diffViewProvider.reset()
 			return
 		}
diff --git a/src/core/tools/__tests__/writeToFileTool.spec.ts b/src/core/tools/__tests__/writeToFileTool.spec.ts
index 6c63387ee10..78c5f024bbb 100644
--- a/src/core/tools/__tests__/writeToFileTool.spec.ts
+++ b/src/core/tools/__tests__/writeToFileTool.spec.ts
@@ -36,6 +36,10 @@ vi.mock("../../prompts/responses", () => ({
 		toolError: vi.fn((msg) => `Error: ${msg}`),
 		rooIgnoreError: vi.fn((path) => `Access denied: ${path}`),
 		createPrettyPatch: vi.fn(() => "mock-diff"),
+		writeToFileMissingContentError: vi.fn(
+			() =>
+				"Missing value for required parameter 'content'. This most commonly happens when the file content is too large and your response was truncated.",
+		),
 	},
 }))
 
@@ -442,6 +446,63 @@ describe("writeToFileTool", () => {
 		})
 	})
 
+	describe("missing parameter handling", () => {
+		it("returns enhanced error when content is missing, suggesting alternatives to large file writes", async () => {
+			// Directly build a toolUse with nativeArgs.content = undefined to simulate truncation
+			const toolUse: ToolUse = {
+				type: "tool_use",
+				name: "write_to_file",
+				params: { path: testFilePath },
+				nativeArgs: { path: testFilePath, content: undefined } as any,
+				partial: false,
+			}
+
+			mockPushToolResult = vi.fn()
+
+			await writeToFileTool.handle(mockCline, toolUse as ToolUse<"write_to_file">, {
+				askApproval: mockAskApproval,
+				handleError: mockHandleError,
+				pushToolResult: mockPushToolResult,
+			})
+
+			expect(mockCline.consecutiveMistakeCount).toBe(1)
+			expect(mockCline.recordToolError).toHaveBeenCalledWith("write_to_file")
+			expect(mockCline.say).toHaveBeenCalledWith(
+				"error",
+				expect.stringContaining("without value for required parameter 'content'"),
+			)
+			expect(mockCline.say).toHaveBeenCalledWith("error", expect.stringContaining("output token limits"))
+			expect(mockPushToolResult).toHaveBeenCalledWith(expect.stringContaining("truncated"))
+			expect(mockCline.diffViewProvider.reset).toHaveBeenCalled()
+			// Should NOT call the generic sayAndCreateMissingParamError
+			expect(mockCline.sayAndCreateMissingParamError).not.toHaveBeenCalled()
+		})
+
+		it("returns generic error when path is missing", async () => {
+			// Directly build a toolUse with nativeArgs.path = undefined
+			const toolUse: ToolUse = {
+				type: "tool_use",
+				name: "write_to_file",
+				params: {},
+				nativeArgs: { path: undefined, content: testContent } as any,
+				partial: false,
+			}
+
+			mockPushToolResult = vi.fn()
+
+			await writeToFileTool.handle(mockCline, toolUse as ToolUse<"write_to_file">, {
+				askApproval: mockAskApproval,
+				handleError: mockHandleError,
+				pushToolResult: mockPushToolResult,
+			})
+
+			expect(mockCline.consecutiveMistakeCount).toBe(1)
+			expect(mockCline.recordToolError).toHaveBeenCalledWith("write_to_file")
+			expect(mockCline.sayAndCreateMissingParamError).toHaveBeenCalledWith("write_to_file", "path")
+			expect(mockCline.diffViewProvider.reset).toHaveBeenCalled()
+		})
+	})
+
 	describe("error handling", () => {
 		it("handles general file operation errors", async () => {
 			mockCline.diffViewProvider.open.mockRejectedValue(new Error("General error"))