Fix Azure Foundry Anthropic strict tools

packages/ai/CHANGELOG.md

@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Fixed Azure Foundry Anthropic utility requests to omit the structured-output beta whenever strict tools are disabled, preventing `structured_outputs not supported in your workspace` failures for Sonnet 5 compaction ([#4679](https://github.com/can1357/oh-my-pi/issues/4679)).
+
 ## [16.3.7] - 2026-07-05
 
 ### Fixed

packages/ai/src/providers/anthropic.ts

@@ -127,12 +127,13 @@ export function buildBetaHeader(baseBetas: readonly string[], extraBetas: readon
 
 const midConversationSystemBeta = "mid-conversation-system-2026-04-07";
 const contextManagementBeta = "context-management-2025-06-27";
+const structuredOutputsBeta = "structured-outputs-2025-12-15";
 const claudeCodeUtilityBetaDefaults = [
 	"oauth-2025-04-20",
 	"interleaved-thinking-2025-05-14",
 	contextManagementBeta,
 	"prompt-caching-scope-2026-01-05",
-	"structured-outputs-2025-12-15",
+	structuredOutputsBeta,
 ] as const;
 const claudeCodeAgentBetaDefaults = [
 	"claude-code-20250219",
@@ -159,10 +160,12 @@ function buildClaudeCodeBetas(
 	agentRequest: boolean,
 	thinkingRequest: boolean,
 	redactThinking: boolean,
+	disableStrictTools = false,
 ): readonly string[] {
-	if (!agentRequest && !redactThinking) return claudeCodeUtilityBetaDefaults;
+	if (!agentRequest && !redactThinking && !disableStrictTools) return claudeCodeUtilityBetaDefaults;
 	const betas: string[] = [];
 	for (const beta of agentRequest ? claudeCodeAgentBetaDefaults : claudeCodeUtilityBetaDefaults) {
+		if (disableStrictTools && beta === structuredOutputsBeta) continue;
 		betas.push(beta);
 		// Match CC's header order: redact-thinking immediately follows interleaved-thinking.
 		if (redactThinking && beta === interleavedThinkingBeta) betas.push(redactThinkingBeta);
@@ -1098,6 +1101,7 @@ export type AnthropicClientOptionsArgs = {
 	hasTools?: boolean;
 	thinkingEnabled?: boolean;
 	thinkingDisplay?: AnthropicThinkingDisplay;
+	disableStrictTools?: boolean;
 	fetch?: FetchImpl;
 	claudeCodeSessionId?: string;
 };
@@ -1833,6 +1837,7 @@ const streamAnthropicOnce = (
 					thinkingDisplay: options?.thinkingDisplay,
 					fetch: options?.fetch,
 					claudeCodeSessionId: options?.sessionId ?? extractClaudeMetadataSessionId(options?.metadata?.user_id),
+					disableStrictTools,
 				});
 				client = created.client;
 				isOAuthToken = created.isOAuthToken;
@@ -2648,8 +2653,10 @@ export function buildAnthropicClientOptions(args: AnthropicClientOptionsArgs): A
 		thinkingDisplay,
 		isOAuth,
 		claudeCodeSessionId,
+		disableStrictTools: disableStrictToolsOverride,
 	} = args;
 	const compat = model.compat;
+	const disableStrictTools = disableStrictToolsOverride ?? compat.disableStrictTools;
 	const needsInterleavedBeta = interleavedThinking && !model.thinking?.supportsDisplay;
 	const needsFineGrainedToolStreamingBeta = hasTools && !compat.supportsEagerToolInputStreaming;
 	const oauthToken = isOAuth ?? isAnthropicOAuthToken(apiKey);
@@ -2722,7 +2729,12 @@ export function buildAnthropicClientOptions(args: AnthropicClientOptionsArgs): A
 		isCloudflareAiGateway: model.provider === "cloudflare-ai-gateway",
 		claudeCodeSessionId,
 		claudeCodeBetas: oauthToken
-			? buildClaudeCodeBetas(hasTools || thinkingEnabled, thinkingEnabled, thinkingDisplay === "omitted")
+			? buildClaudeCodeBetas(
+					hasTools || thinkingEnabled,
+					thinkingEnabled,
+					thinkingDisplay === "omitted",
+					disableStrictTools,
+				)
 			: [],
 	});
 

packages/ai/test/issue-4679-repro.test.ts

@@ -0,0 +1,104 @@
+import { describe, expect, it } from "bun:test";
+import { buildAnthropicClientOptions, streamAnthropic } from "@oh-my-pi/pi-ai/providers/anthropic";
+import type { Context, Model, ModelSpec, TJsonSchema, Tool } from "@oh-my-pi/pi-ai/types";
+import { buildModel } from "@oh-my-pi/pi-catalog/build";
+
+const STRUCTURED_OUTPUTS_BETA = "structured-outputs-2025-12-15";
+
+const bashTool: Tool = {
+	name: "bash",
+	description: "run a bash command",
+	parameters: {
+		type: "object",
+		properties: { command: { type: "string" } },
+		required: ["command"],
+	} satisfies TJsonSchema,
+};
+
+const toolContext: Context = {
+	systemPrompt: ["Stay concise."],
+	messages: [{ role: "user", content: "Hi", timestamp: 0 }],
+	tools: [bashTool],
+};
+
+function anthropicSpec(baseUrl: string): ModelSpec<"anthropic-messages"> {
+	return {
+		id: "claude-sonnet-5",
+		name: "Claude Sonnet 5",
+		api: "anthropic-messages",
+		provider: "anthropic",
+		baseUrl,
+		reasoning: false,
+		input: ["text"],
+		cost: { input: 0, output: 0, cacheRead: 0, cacheWrite: 0 },
+		contextWindow: 200_000,
+		maxTokens: 8_192,
+	};
+}
+
+function buildOAuthUtilityBetaHeader(model: Model<"anthropic-messages">): string {
+	const options = buildAnthropicClientOptions({
+		model,
+		apiKey: "oauth-token",
+		isOAuth: true,
+		hasTools: false,
+		thinkingEnabled: false,
+	});
+	return options.defaultHeaders["anthropic-beta"] ?? "";
+}
+
+function abortedSignal(): AbortSignal {
+	const controller = new AbortController();
+	controller.abort();
+	return controller.signal;
+}
+
+async function captureToolParams(
+	model: Model<"anthropic-messages">,
+): Promise<{ tools?: Array<{ name: string; strict?: unknown }> }> {
+	const { promise, resolve } = Promise.withResolvers<{ tools?: Array<{ name: string; strict?: unknown }> }>();
+	void streamAnthropic(model, toolContext, {
+		apiKey: "sk-ant-api-test",
+		isOAuth: false,
+		signal: abortedSignal(),
+		onPayload: payload => {
+			resolve(payload as { tools?: Array<{ name: string; strict?: unknown }> });
+			return undefined;
+		},
+	});
+	return promise;
+}
+
+describe("issue #4679 Azure Foundry Anthropic strict tools", () => {
+	it.each([
+		["inference", "https://example.inference.ai.azure.com/anthropic/v1"],
+		["services", "https://example.services.ai.azure.com/anthropic/v1"],
+	])("disables strict tools and omits structured-output beta for Azure Foundry %s routes", (_kind, baseUrl) => {
+		const model = buildModel(anthropicSpec(baseUrl));
+
+		expect(model.compat.disableStrictTools).toBe(true);
+		expect(buildOAuthUtilityBetaHeader(model)).not.toContain(STRUCTURED_OUTPUTS_BETA);
+	});
+
+	it("keeps structured-output beta on direct Anthropic OAuth utility headers", () => {
+		const model = buildModel(anthropicSpec("https://api.anthropic.com"));
+
+		expect(model.compat.disableStrictTools).toBe(false);
+		expect(buildOAuthUtilityBetaHeader(model)).toContain(STRUCTURED_OUTPUTS_BETA);
+	});
+
+	it("omits strict tool schemas on Azure Foundry Anthropic requests without disabling direct Anthropic", async () => {
+		const azureParams = await captureToolParams(
+			buildModel(anthropicSpec("https://example.services.ai.azure.com/anthropic/v1")),
+		);
+		const directParams = await captureToolParams(buildModel(anthropicSpec("https://api.anthropic.com")));
+
+		const azureBashTool = azureParams.tools?.find(tool => tool.name === "bash");
+		const directBashTool = directParams.tools?.find(tool => tool.name === "bash");
+
+		expect(azureBashTool).toBeDefined();
+		expect(azureBashTool?.strict).toBeUndefined();
+		expect(directBashTool).toBeDefined();
+		expect(directBashTool?.strict).toBe(true);
+	});
+});

packages/catalog/CHANGELOG.md

@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Detected Azure AI Inference / Foundry Anthropic routes as strict-tool-incompatible so resolved Anthropic compat disables strict tools before request construction ([#4679](https://github.com/can1357/oh-my-pi/issues/4679)).
+
 ## [16.3.9] - 2026-07-06
 
 ### Fixed

packages/catalog/src/compat/anthropic.ts

@@ -99,18 +99,15 @@ export function buildAnthropicCompat(spec: ModelSpec<"anthropic-messages">): Res
 	// (issue #4192).
 	const isZenmux = modelMatchesHost(spec, "zenmux");
 	const requiresThinkingEnabled = modelMatchesHost(spec, "moonshotNative") && matchesKimiK27CodeFamily(spec);
+	const isVertex = isVertexAnthropicRoute(baseUrl);
+	const isBedrock = isBedrockAnthropicRoute(baseUrl);
+	const isAzure = isAzureAnthropicRoute(baseUrl);
 	const signingEndpoint =
-		official ||
-		isCopilot ||
-		isZenmux ||
-		isCloudflareAnthropicGateway(baseUrl) ||
-		isVertexAnthropicRoute(baseUrl) ||
-		isBedrockAnthropicRoute(baseUrl) ||
-		isAzureAnthropicRoute(baseUrl);
+		official || isCopilot || isZenmux || isCloudflareAnthropicGateway(baseUrl) || isVertex || isBedrock || isAzure;
 	const compat: ResolvedAnthropicCompat = {
 		officialEndpoint: official,
 		signingEndpoint,
-		disableStrictTools: false,
+		disableStrictTools: isAzure,
 		disableAdaptiveThinking: false,
 		supportsEagerToolInputStreaming: !isCopilot,
 		// Long cache retention is only sent to the official API by default;