Roo to main

src/core/prompts/tools/native-tools/__tests__/read_file.spec.ts

@@ -96,6 +96,48 @@ describe("createReadFileTool", () => {
 		})
 	})
 
+	describe("supportsImages option", () => {
+		it("should include image format documentation when supportsImages is true", () => {
+			const tool = createReadFileTool({ supportsImages: true })
+			const description = getFunctionDef(tool).description
+
+			expect(description).toContain(
+				"Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis",
+			)
+		})
+
+		it("should not include image format documentation when supportsImages is false", () => {
+			const tool = createReadFileTool({ supportsImages: false })
+			const description = getFunctionDef(tool).description
+
+			expect(description).not.toContain(
+				"Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis",
+			)
+			expect(description).toContain("may not handle other binary files properly")
+		})
+
+		it("should default supportsImages to false", () => {
+			const tool = createReadFileTool({})
+			const description = getFunctionDef(tool).description
+
+			expect(description).not.toContain(
+				"Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis",
+			)
+		})
+
+		it("should always include PDF and DOCX support in description", () => {
+			const toolWithImages = createReadFileTool({ supportsImages: true })
+			const toolWithoutImages = createReadFileTool({ supportsImages: false })
+
+			expect(getFunctionDef(toolWithImages).description).toContain(
+				"Supports text extraction from PDF and DOCX files",
+			)
+			expect(getFunctionDef(toolWithoutImages).description).toContain(
+				"Supports text extraction from PDF and DOCX files",
+			)
+		})
+	})
+
 	describe("combined options", () => {
 		it("should correctly combine low maxConcurrentFileReads with partialReadsEnabled", () => {
 			const tool = createReadFileTool({
@@ -120,6 +162,49 @@ describe("createReadFileTool", () => {
 			expect(description).not.toContain("line_ranges")
 			expect(description).not.toContain("Example multiple files")
 		})
+
+		it("should correctly combine partialReadsEnabled and supportsImages", () => {
+			const tool = createReadFileTool({
+				partialReadsEnabled: true,
+				supportsImages: true,
+			})
+			const description = getFunctionDef(tool).description
+
+			// Should have both line_ranges and image support
+			expect(description).toContain("line_ranges")
+			expect(description).toContain(
+				"Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis",
+			)
+		})
+
+		it("should work with partialReadsEnabled=false and supportsImages=true", () => {
+			const tool = createReadFileTool({
+				partialReadsEnabled: false,
+				supportsImages: true,
+			})
+			const description = getFunctionDef(tool).description
+
+			// Should have image support but no line_ranges
+			expect(description).not.toContain("line_ranges")
+			expect(description).toContain(
+				"Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis",
+			)
+		})
+
+		it("should correctly combine all three options", () => {
+			const tool = createReadFileTool({
+				maxConcurrentFileReads: 3,
+				partialReadsEnabled: true,
+				supportsImages: true,
+			})
+			const description = getFunctionDef(tool).description
+
+			expect(description).toContain("maximum of 3 files")
+			expect(description).toContain("line_ranges")
+			expect(description).toContain(
+				"Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis",
+			)
+		})
 	})
 
 	describe("tool structure", () => {

src/core/prompts/tools/native-tools/index.ts

@@ -34,6 +34,8 @@ export interface NativeToolsOptions {
 	partialReadsEnabled?: boolean
 	/** Maximum number of files that can be read in a single read_file request (default: 5) */
 	maxConcurrentFileReads?: number
+	/** Whether the model supports image processing (default: false) */
+	supportsImages?: boolean
 }
 
 /**
@@ -43,11 +45,12 @@ export interface NativeToolsOptions {
  * @returns Array of native tool definitions
  */
 export function getNativeTools(options: NativeToolsOptions = {}): OpenAI.Chat.ChatCompletionTool[] {
-	const { partialReadsEnabled = true, maxConcurrentFileReads = 5 } = options
+	const { partialReadsEnabled = true, maxConcurrentFileReads = 5, supportsImages = false } = options
 
 	const readFileOptions: ReadFileToolOptions = {
 		partialReadsEnabled,
 		maxConcurrentFileReads,
+		supportsImages,
 	}
 
 	return [

src/core/prompts/tools/native-tools/read_file.ts

@@ -1,6 +1,17 @@
 import type OpenAI from "openai"
 
-const READ_FILE_SUPPORTS_NOTE = `Supports text extraction from PDF and DOCX files, but may not handle other binary files properly.`
+/**
+ * Generates the file support note, optionally including image format support.
+ *
+ * @param supportsImages - Whether the model supports image processing
+ * @returns Support note string
+ */
+function getReadFileSupportsNote(supportsImages: boolean): string {
+	if (supportsImages) {
+		return `Supports text extraction from PDF and DOCX files. Automatically processes and returns image files (PNG, JPG, JPEG, GIF, BMP, SVG, WEBP, ICO, AVIF) for visual analysis. May not handle other binary files properly.`
+	}
+	return `Supports text extraction from PDF and DOCX files, but may not handle other binary files properly.`
+}
 
 /**
  * Options for creating the read_file tool definition.
@@ -10,6 +21,8 @@ export interface ReadFileToolOptions {
 	partialReadsEnabled?: boolean
 	/** Maximum number of files that can be read in a single request (default: 5) */
 	maxConcurrentFileReads?: number
+	/** Whether the model supports image processing (default: false) */
+	supportsImages?: boolean
 }
 
 /**
@@ -20,7 +33,7 @@ export interface ReadFileToolOptions {
  * @returns Native tool definition for read_file
  */
 export function createReadFileTool(options: ReadFileToolOptions = {}): OpenAI.Chat.ChatCompletionTool {
-	const { partialReadsEnabled = true, maxConcurrentFileReads = 5 } = options
+	const { partialReadsEnabled = true, maxConcurrentFileReads = 5, supportsImages = false } = options
 	const isMultipleReadsEnabled = maxConcurrentFileReads > 1
 
 	// Build description intro with concurrent reads limit message
@@ -50,7 +63,8 @@ export function createReadFileTool(options: ReadFileToolOptions = {}): OpenAI.Ch
 				? `Example multiple files (within ${maxConcurrentFileReads}-file limit): { files: [{ path: 'file1.ts' }, { path: 'file2.ts' }] }`
 				: "")
 
-	const description = baseDescription + optionalRangesDescription + READ_FILE_SUPPORTS_NOTE + " " + examples
+	const description =
+		baseDescription + optionalRangesDescription + getReadFileSupportsNote(supportsImages) + " " + examples
 
 	// Build the properties object conditionally
 	const fileProperties: Record<string, any> = {

src/core/task/Task.ts

@@ -1444,6 +1444,10 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		this.handleWebviewAskResponse("noButtonClicked", text, images)
 	}
 
+	public supersedePendingAsk(): void {
+		this.lastMessageTs = Date.now()
+	}
+
 	/**
 	 * Updates the API configuration but preserves the locked tool protocol.
 	 * The task's tool protocol is locked at creation time and should NOT change

src/core/task/__tests__/validateToolResultIds.spec.ts

@@ -482,6 +482,96 @@ describe("validateAndFixToolResultIds", () => {
 			expect(resultContent[1].type).toBe("text")
 			expect((resultContent[1] as Anthropic.TextBlockParam).text).toBe("Some additional context")
 		})
+
+		// Verifies fix for GitHub #10465: Terminal fallback race condition can generate
+		// duplicate tool_results with the same valid tool_use_id, causing API protocol violations.
+		it("should filter out duplicate tool_results with identical valid tool_use_ids (terminal fallback scenario)", () => {
+			const assistantMessage: Anthropic.MessageParam = {
+				role: "assistant",
+				content: [
+					{
+						type: "tool_use",
+						id: "tooluse_QZ-pU8v2QKO8L8fHoJRI2g",
+						name: "execute_command",
+						input: { command: "ps aux | grep test", cwd: "/path/to/project" },
+					},
+				],
+			}
+
+			// Two tool_results with the SAME valid tool_use_id from terminal fallback race condition
+			const userMessage: Anthropic.MessageParam = {
+				role: "user",
+				content: [
+					{
+						type: "tool_result",
+						tool_use_id: "tooluse_QZ-pU8v2QKO8L8fHoJRI2g", // First result from command execution
+						content: "No test processes found",
+					},
+					{
+						type: "tool_result",
+						tool_use_id: "tooluse_QZ-pU8v2QKO8L8fHoJRI2g", // Duplicate from user approval during fallback
+						content: '{"status":"approved","message":"The user approved this operation"}',
+					},
+				],
+			}
+
+			const result = validateAndFixToolResultIds(userMessage, [assistantMessage])
+
+			expect(Array.isArray(result.content)).toBe(true)
+			const resultContent = result.content as Anthropic.ToolResultBlockParam[]
+
+			// Only ONE tool_result should remain to prevent API protocol violation
+			expect(resultContent.length).toBe(1)
+			expect(resultContent[0].tool_use_id).toBe("tooluse_QZ-pU8v2QKO8L8fHoJRI2g")
+			expect(resultContent[0].content).toBe("No test processes found")
+		})
+
+		it("should preserve text blocks while deduplicating tool_results with same valid ID", () => {
+			const assistantMessage: Anthropic.MessageParam = {
+				role: "assistant",
+				content: [
+					{
+						type: "tool_use",
+						id: "tool-123",
+						name: "read_file",
+						input: { path: "test.txt" },
+					},
+				],
+			}
+
+			const userMessage: Anthropic.MessageParam = {
+				role: "user",
+				content: [
+					{
+						type: "tool_result",
+						tool_use_id: "tool-123",
+						content: "First result",
+					},
+					{
+						type: "text",
+						text: "Environment details here",
+					},
+					{
+						type: "tool_result",
+						tool_use_id: "tool-123", // Duplicate with same valid ID
+						content: "Duplicate result from fallback",
+					},
+				],
+			}
+
+			const result = validateAndFixToolResultIds(userMessage, [assistantMessage])
+
+			expect(Array.isArray(result.content)).toBe(true)
+			const resultContent = result.content as Array<Anthropic.ToolResultBlockParam | Anthropic.TextBlockParam>
+
+			// Should have: 1 tool_result + 1 text block (duplicate filtered out)
+			expect(resultContent.length).toBe(2)
+			expect(resultContent[0].type).toBe("tool_result")
+			expect((resultContent[0] as Anthropic.ToolResultBlockParam).tool_use_id).toBe("tool-123")
+			expect((resultContent[0] as Anthropic.ToolResultBlockParam).content).toBe("First result")
+			expect(resultContent[1].type).toBe("text")
+			expect((resultContent[1] as Anthropic.TextBlockParam).text).toBe("Environment details here")
+		})
 	})
 
 	describe("when there are more tool_uses than tool_results", () => {

src/core/task/build-tools.ts

@@ -64,10 +64,14 @@ export async function buildNativeToolsArray(options: BuildToolsOptions): Promise
 	// Determine if partial reads are enabled based on maxReadFileLine setting.
 	const partialReadsEnabled = maxReadFileLine !== -1
 
+	// Check if the model supports images for read_file tool description.
+	const supportsImages = modelInfo?.supportsImages ?? false
+
 	// Build native tools with dynamic read_file tool based on settings.
 	const nativeTools = getNativeTools({
 		partialReadsEnabled,
 		maxConcurrentFileReads,
+		supportsImages,
 	})
 
 	// Filter native tools based on mode restrictions.

src/core/task/validateToolResultIds.ts

@@ -78,7 +78,31 @@ export function validateAndFixToolResultIds(
 	}
 
 	// Find tool_result blocks in the user message
-	const toolResults = userMessage.content.filter(
+	let toolResults = userMessage.content.filter(
+		(block): block is Anthropic.ToolResultBlockParam => block.type === "tool_result",
+	)
+
+	// Deduplicate tool_result blocks to prevent API protocol violations (GitHub #10465)
+	// Terminal fallback race conditions can generate duplicate tool_results with the same tool_use_id.
+	// Filter out duplicates before validation since Set-based checks below would miss them.
+	const seenToolResultIds = new Set<string>()
+	const deduplicatedContent = userMessage.content.filter((block) => {
+		if (block.type !== "tool_result") {
+			return true
+		}
+		if (seenToolResultIds.has(block.tool_use_id)) {
+			return false // Duplicate - filter out
+		}
+		seenToolResultIds.add(block.tool_use_id)
+		return true
+	})
+
+	userMessage = {
+		...userMessage,
+		content: deduplicatedContent,
+	}
+
+	toolResults = deduplicatedContent.filter(
 		(block): block is Anthropic.ToolResultBlockParam => block.type === "tool_result",
 	)
 
@@ -139,15 +163,12 @@ export function validateAndFixToolResultIds(
 		)
 	}
 
-	// Create a mapping of tool_result IDs to corrected IDs
-	// Strategy: Match by position (first tool_result -> first tool_use, etc.)
-	// This handles most cases where the mismatch is due to ID confusion
-	//
-	// Track which tool_use IDs have been used to prevent duplicates
+	// Match tool_results to tool_uses by position and fix incorrect IDs
 	const usedToolUseIds = new Set<string>()
+	const contentArray = userMessage.content as Anthropic.Messages.ContentBlockParam[]
 
-	const correctedContent = userMessage.content
-		.map((block) => {
+	const correctedContent = contentArray
+		.map((block: Anthropic.Messages.ContentBlockParam) => {
 			if (block.type !== "tool_result") {
 				return block
 			}
@@ -177,17 +198,18 @@ export function validateAndFixToolResultIds(
 			}
 
 			// No corresponding tool_use for this tool_result, or the ID is already used
-			// Filter out this orphaned tool_result by returning null
 			return null
 		})
 		.filter((block): block is NonNullable<typeof block> => block !== null)
 
 	// Add missing tool_result blocks for any tool_use that doesn't have one
-	// After the ID correction above, recalculate which tool_use IDs are now covered
 	const coveredToolUseIds = new Set(
 		correctedContent
-			.filter((b): b is Anthropic.ToolResultBlockParam => b.type === "tool_result")
-			.map((r) => r.tool_use_id),
+			.filter(
+				(b: Anthropic.Messages.ContentBlockParam): b is Anthropic.ToolResultBlockParam =>
+					b.type === "tool_result",
+			)
+			.map((r: Anthropic.ToolResultBlockParam) => r.tool_use_id),
 	)
 
 	const stillMissingToolUseIds = toolUseBlocks.filter((toolUse) => !coveredToolUseIds.has(toolUse.id))

src/core/tools/ExecuteCommandTool.ts

@@ -117,6 +117,9 @@ export class ExecuteCommandTool extends BaseTool<"execute_command"> {
 				provider?.postMessageToWebview({ type: "commandExecutionStatus", text: JSON.stringify(status) })
 				await task.say("shell_integration_warning")
 
+				// Invalidate pending ask from first execution to prevent race condition
+				task.supersedePendingAsk()
+
 				if (error instanceof ShellIntegrationError) {
 					const [rejected, result] = await executeCommandInTerminal(task, {
 						...options,