diff --git a/packages/ai/CHANGELOG.md b/packages/ai/CHANGELOG.md
index 0f4c612a6..e31d6a88b 100644
--- a/packages/ai/CHANGELOG.md
+++ b/packages/ai/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Raised Gemini header runaway threshold to prevent premature interruption of complex reasoning loops
+
 ## [16.2.9] - 2026-06-30
 
 ### Added
diff --git a/packages/ai/src/utils/thinking-loop.ts b/packages/ai/src/utils/thinking-loop.ts
index 1810d0a1c..16c52f3cb 100644
--- a/packages/ai/src/utils/thinking-loop.ts
+++ b/packages/ai/src/utils/thinking-loop.ts
@@ -287,12 +287,17 @@ export class ThinkingLoopDetector {
  * stream that trips the tool-call reminder. Gemini occasionally narrates a long
  * chain of titled summaries ("Examining Result Handling", "Refining Result
  * Rendering", …) without ever calling a tool, burning the whole budget on
- * planning; at this many distinct titles it has almost certainly stalled. This
- * is the over-planning shape {@link ThinkingLoopDetector} misses — those titles
- * are stripped before its similarity analysis precisely because their wording
- * keeps changing, so a genuinely-distinct planning runaway never trips it.
+ * planning. This is the over-planning shape {@link ThinkingLoopDetector} misses —
+ * those titles are stripped before its similarity analysis precisely because their
+ * wording keeps changing, so a genuinely-distinct planning runaway never trips it.
+ *
+ * Set well above legitimate hard-problem depth: a capable model can emit ~10
+ * distinct, progressing hypotheses in a single reasoning block before acting (and
+ * a false trip is costly — the interrupt discards the whole reasoning turn). A
+ * real narration runaway burns dozens-to-hundreds of titles, so this still trips
+ * fast on the actual pathology.
  */
-export const GEMINI_HEADER_RUNAWAY_THRESHOLD = 10;
+export const GEMINI_HEADER_RUNAWAY_THRESHOLD = 24;
 
 /**
  * True when a single trimmed line is a Gemini reasoning-summary title: a markdown
diff --git a/packages/ai/test/thinking-loop.test.ts b/packages/ai/test/thinking-loop.test.ts
index 357da95e6..629ade660 100644
--- a/packages/ai/test/thinking-loop.test.ts
+++ b/packages/ai/test/thinking-loop.test.ts
@@ -615,6 +615,12 @@ describe("GeminiHeaderRunDetector", () => {
 		expect(feedHeaders(runaway)).toBe(true);
 	});
 
+	test("does not trip on a legitimate 10-header debugging block (regression)", () => {
+		// A real, productive debugging stretch emitted 10 distinct progressing headers; never interrupt that.
+		expect(feedHeaders(distinctPlanningRunaway(10))).toBe(false);
+		expect(feedHeaders(distinctPlanningRunaway(24))).toBe(true);
+	});
+
 	test("counts headers across intervening paragraphs (one summary = one header)", () => {
 		const detector = new GeminiHeaderRunDetector();
 		let tripped = false;
diff --git a/packages/catalog/scripts/generate-models.ts b/packages/catalog/scripts/generate-models.ts
index 0ae7cdcfe..eee29d44a 100644
--- a/packages/catalog/scripts/generate-models.ts
+++ b/packages/catalog/scripts/generate-models.ts
@@ -15,7 +15,6 @@ import type { OAuthAccess } from "@oh-my-pi/pi-ai/auth-storage";
 import type { OAuthProvider } from "@oh-my-pi/pi-ai/oauth/types";
 import { getGitLabDuoModels } from "@oh-my-pi/pi-ai/providers/gitlab-duo";
 import { $env } from "@oh-my-pi/pi-utils";
-import { buildCompat } from "../src/build";
 import { ANTIGRAVITY_PRIMARY_ENDPOINT, fetchAntigravityDiscoveryModels } from "../src/discovery/antigravity";
 import { fetchCodexModels } from "../src/discovery/codex";
 import { buildGitLabDuoWorkflowFallbackModel } from "../src/discovery/gitlab-duo-workflow";
@@ -645,7 +644,7 @@ Model Statistics:`);
 function canonicalizeModelCompat(model: ModelSpec<Api>): void {
 	if (!model.compat) return;
 
-	if (model.compat.disableStrictTools === false) {
+	if ("disableStrictTools" in model.compat && model.compat.disableStrictTools === false) {
 		delete model.compat.disableStrictTools;
 	}