diff --git a/packages/ai/CHANGELOG.md b/packages/ai/CHANGELOG.md
index 976598359..204e77408 100644
--- a/packages/ai/CHANGELOG.md
+++ b/packages/ai/CHANGELOG.md
@@ -2,6 +2,14 @@
 
 ## [Unreleased]
 
+### Added
+
+- `hasUnrepresentableStrictObjectMap()` pre-flight check in `tryEnforceStrictSchema`: schemas with `patternProperties` or schema-valued `additionalProperties` now degrade gracefully to non-strict mode instead of throwing during enforcement
+
+### Changed
+
+- Extended `ANTHROPIC_OAUTH_BETA` constant in the OpenAI-compat Anthropic route with `interleaved-thinking-2025-05-14`, `context-management-2025-06-27`, and `prompt-caching-scope-2026-01-05` beta flags
+
 ## [13.3.14] - 2026-02-28
 
 ### Added
diff --git a/packages/ai/src/provider-models/openai-compat.ts b/packages/ai/src/provider-models/openai-compat.ts
index f9587c454..3e05e8be7 100644
--- a/packages/ai/src/provider-models/openai-compat.ts
+++ b/packages/ai/src/provider-models/openai-compat.ts
@@ -10,7 +10,8 @@ import {
 
 const MODELS_DEV_URL = "https://models.dev/api.json";
 const ANTHROPIC_BASE_URL = "https://api.anthropic.com/v1";
-const ANTHROPIC_OAUTH_BETA = "claude-code-20250219,oauth-2025-04-20";
+const ANTHROPIC_OAUTH_BETA =
+	"claude-code-20250219,oauth-2025-04-20,interleaved-thinking-2025-05-14,context-management-2025-06-27,prompt-caching-scope-2026-01-05";
 
 export interface ModelsDevModel {
 	id?: string;
diff --git a/packages/ai/src/utils/schema/strict-mode.ts b/packages/ai/src/utils/schema/strict-mode.ts
index 13c5fedaa..19c0a5e8f 100644
--- a/packages/ai/src/utils/schema/strict-mode.ts
+++ b/packages/ai/src/utils/schema/strict-mode.ts
@@ -29,6 +29,61 @@ export function StringEnum<const T extends readonly string[]>(
 export const NO_STRICT = Bun.env.PI_NO_STRICT === "1";
 
 const strictSchemaCache = new WeakMap<Record<string, unknown>, { schema: Record<string, unknown>; strict: boolean }>();
+function hasUnrepresentableStrictObjectMap(schema: Record<string, unknown>, seen?: WeakSet<object>): boolean {
+	if (!seen) seen = new WeakSet();
+	if (seen.has(schema)) return false;
+	seen.add(schema);
+
+	const hasPatternProperties =
+		isJsonObject(schema.patternProperties) && Object.keys(schema.patternProperties).length > 0;
+	const additionalPropertiesValue = schema.additionalProperties;
+	const hasSchemaAdditionalProperties = additionalPropertiesValue === true || isJsonObject(additionalPropertiesValue);
+	if (hasPatternProperties || hasSchemaAdditionalProperties) {
+		return true;
+	}
+
+	if (isJsonObject(schema.properties)) {
+		for (const propertySchema of Object.values(schema.properties)) {
+			if (isJsonObject(propertySchema) && hasUnrepresentableStrictObjectMap(propertySchema, seen)) {
+				return true;
+			}
+		}
+	}
+
+	if (isJsonObject(schema.items)) {
+		if (hasUnrepresentableStrictObjectMap(schema.items, seen)) {
+			return true;
+		}
+	} else if (Array.isArray(schema.items)) {
+		for (const itemSchema of schema.items) {
+			if (isJsonObject(itemSchema) && hasUnrepresentableStrictObjectMap(itemSchema, seen)) {
+				return true;
+			}
+		}
+	}
+
+	for (const key of COMBINATOR_KEYS) {
+		const variants = schema[key];
+		if (!Array.isArray(variants)) continue;
+		for (const variant of variants) {
+			if (isJsonObject(variant) && hasUnrepresentableStrictObjectMap(variant, seen)) {
+				return true;
+			}
+		}
+	}
+
+	for (const defsKey of ["$defs", "definitions"] as const) {
+		const defs = schema[defsKey];
+		if (!isJsonObject(defs)) continue;
+		for (const defSchema of Object.values(defs)) {
+			if (isJsonObject(defSchema) && hasUnrepresentableStrictObjectMap(defSchema, seen)) {
+				return true;
+			}
+		}
+	}
+
+	return false;
+}
 export function sanitizeSchemaForStrictMode(
 	schema: Record<string, unknown>,
 	seen?: WeakSet<object>,
@@ -283,6 +338,9 @@ export function tryEnforceStrictSchema(schema: Record<string, unknown>): {
 	}
 
 	try {
+		if (hasUnrepresentableStrictObjectMap(schema)) {
+			throw new Error("Schema uses dynamic object keys that are not representable in strict mode");
+		}
 		const sanitized = sanitizeSchemaForStrictMode(schema);
 		const result = { schema: enforceStrictSchema(sanitized), strict: true };
 		strictSchemaCache.set(schema, result);
diff --git a/packages/ai/test/schema-helpers.test.ts b/packages/ai/test/schema-helpers.test.ts
index bd0d2ea7d..daf292d4a 100644
--- a/packages/ai/test/schema-helpers.test.ts
+++ b/packages/ai/test/schema-helpers.test.ts
@@ -242,4 +242,22 @@ describe("adaptSchemaForStrict", () => {
 		expect(result.strict).toBe(false);
 		expect(result.schema).toBe(schema);
 	});
+
+	it("degrades gracefully for schemas with patternProperties maps", () => {
+		const schema = {
+			type: "object",
+			properties: {
+				rewrites: {
+					type: "object",
+					patternProperties: {
+						"^(.*)$": { type: "string" },
+					},
+				},
+			},
+			required: ["rewrites"],
+		};
+		const result = adaptSchemaForStrict(schema, true);
+		expect(result.strict).toBe(false);
+		expect(result.schema).toBe(schema);
+	});
 });
diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 7ac5956dc..6c2c8a29e 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Added
+
+- Added `gemini`, `codex`, and `synthetic` as supported values for the `providers.webSearch` setting
+
 ## [13.3.14] - 2026-02-28
 
 ### Added
diff --git a/packages/coding-agent/src/config/settings-schema.ts b/packages/coding-agent/src/config/settings-schema.ts
index 93bb544cd..9e38f4b0d 100644
--- a/packages/coding-agent/src/config/settings-schema.ts
+++ b/packages/coding-agent/src/config/settings-schema.ts
@@ -737,7 +737,19 @@ export const SETTINGS_SCHEMA = {
 	// ─────────────────────────────────────────────────────────────────────────
 	"providers.webSearch": {
 		type: "enum",
-		values: ["auto", "exa", "brave", "jina", "kimi", "zai", "perplexity", "anthropic"] as const,
+		values: [
+			"auto",
+			"exa",
+			"brave",
+			"jina",
+			"kimi",
+			"zai",
+			"perplexity",
+			"anthropic",
+			"gemini",
+			"codex",
+			"synthetic",
+		] as const,
 		default: "auto",
 		ui: { tab: "services", label: "Web search provider", description: "Provider for web search tool", submenu: true },
 	},