diff --git a/app/src/providers/CoreStateProvider.tsx b/app/src/providers/CoreStateProvider.tsx
index ad0578b2e..30c237904 100644
--- a/app/src/providers/CoreStateProvider.tsx
+++ b/app/src/providers/CoreStateProvider.tsx
@@ -75,6 +75,19 @@ export function coreStatePollFailureWarningMessage(failureCount: number): string
   return null;
 }
 
+export function coreStatePollFailureDebugMessage(failureCount: number): string | null {
+  if (failureCount <= 0) {
+    return null;
+  }
+  if (failureCount < MAX_BOOTSTRAP_RETRIES) {
+    return `refresh failed during bootstrap retry ${failureCount}/${MAX_BOOTSTRAP_RETRIES}; nextAction=retrying`;
+  }
+  if (failureCount === MAX_BOOTSTRAP_RETRIES) {
+    return `refresh failed during bootstrap retry ${failureCount}/${MAX_BOOTSTRAP_RETRIES}; nextAction=marking-ready-with-fallback`;
+  }
+  return `refresh failed after ${failureCount} consecutive poll failures; bootstrapRetryLimit=${MAX_BOOTSTRAP_RETRIES}; nextAction=continuing-background-polling-with-warnings-suppressed`;
+}
+
 function decodeJwtPayload(token: string): Record<string, unknown> | null {
   const [, payload] = token.split('.');
   if (!payload) return null;
@@ -425,12 +438,10 @@ export default function CoreStateProvider({ children }: { children: ReactNode })
         if (!cancelled) {
           bootstrapFailCountRef.current += 1;
           const safe = sanitizeError(error);
-          log(
-            'refresh failed attempt=%d/%d error=%O',
-            bootstrapFailCountRef.current,
-            MAX_BOOTSTRAP_RETRIES,
-            safe
-          );
+          const debugMessage = coreStatePollFailureDebugMessage(bootstrapFailCountRef.current);
+          if (debugMessage) {
+            log('%s error=%O', debugMessage, safe);
+          }
           const warningMessage = coreStatePollFailureWarningMessage(bootstrapFailCountRef.current);
           if (warningMessage) {
             console.warn(warningMessage, safe);
diff --git a/app/src/providers/__tests__/CoreStateProvider.test.tsx b/app/src/providers/__tests__/CoreStateProvider.test.tsx
index 26da31e29..499035596 100644
--- a/app/src/providers/__tests__/CoreStateProvider.test.tsx
+++ b/app/src/providers/__tests__/CoreStateProvider.test.tsx
@@ -7,6 +7,7 @@ import * as tauriCommands from '../../utils/tauriCommands';
 import { getCoreStateSnapshot, setCoreStateSnapshot } from '../../lib/coreState/store';
 import { setActiveUserId } from '../../store/userScopedStorage';
 import CoreStateProvider, {
+  coreStatePollFailureDebugMessage,
   coreStatePollFailureWarningMessage,
   useCoreState,
 } from '../CoreStateProvider';
@@ -524,4 +525,20 @@ describe('coreStatePollFailureWarningMessage', () => {
     );
     expect(coreStatePollFailureWarningMessage(7)).toBeNull();
   });
+
+  it('describes post-bootstrap poll failures without impossible retry counters', () => {
+    expect(coreStatePollFailureDebugMessage(0)).toBeNull();
+    expect(coreStatePollFailureDebugMessage(1)).toBe(
+      'refresh failed during bootstrap retry 1/5; nextAction=retrying'
+    );
+    expect(coreStatePollFailureDebugMessage(5)).toBe(
+      'refresh failed during bootstrap retry 5/5; nextAction=marking-ready-with-fallback'
+    );
+
+    const postBootstrapMessage = coreStatePollFailureDebugMessage(11);
+    expect(postBootstrapMessage).toBe(
+      'refresh failed after 11 consecutive poll failures; bootstrapRetryLimit=5; nextAction=continuing-background-polling-with-warnings-suppressed'
+    );
+    expect(postBootstrapMessage).not.toContain('11/5');
+  });
 });