diff --git a/apps/server/src/core/ai-chat/ai-chat.service.spec.ts b/apps/server/src/core/ai-chat/ai-chat.service.spec.ts
index d007c546..20650457 100644
--- a/apps/server/src/core/ai-chat/ai-chat.service.spec.ts
+++ b/apps/server/src/core/ai-chat/ai-chat.service.spec.ts
@@ -97,4 +97,13 @@ describe('prepareAgentStep', () => {
     // The synthesis instruction is appended.
     expect(result?.system).toContain(FINAL_STEP_INSTRUCTION);
   });
+
+  it('pins the off-by-one boundary (MAX-2 is not final, MAX-1 is)', () => {
+    // Boundary expressed via the constant, not a hardcoded 18/19, so the test
+    // tracks MAX_AGENT_STEPS if the cap ever changes.
+    expect(prepareAgentStep(MAX_AGENT_STEPS - 2, 'SYS')).toBeUndefined();
+    const atBoundary = prepareAgentStep(MAX_AGENT_STEPS - 1, 'SYS');
+    expect(atBoundary).toBeDefined();
+    expect(atBoundary?.toolChoice).toBe('none');
+  });
 });
diff --git a/apps/server/src/core/ai-chat/ai-chat.service.ts b/apps/server/src/core/ai-chat/ai-chat.service.ts
index 1b274238..cd62b5f6 100644
--- a/apps/server/src/core/ai-chat/ai-chat.service.ts
+++ b/apps/server/src/core/ai-chat/ai-chat.service.ts
@@ -38,6 +38,9 @@ const FINAL_STEP_INSTRUCTION =
 // `system` is the in-scope system prompt; we CONCATENATE so the original
 // persona/context is preserved — a bare `system` override would REPLACE the
 // whole system prompt for the step.
+//
+// NOTE: at AI SDK v7 the per-step `system` field is renamed to `instructions`.
+// On v6 (`^6.0.134`) `system` is the correct field — adjust when bumping.
 export function prepareAgentStep(
   stepNumber: number,
   system: string,