diff --git a/packages/core/src/core/client.test.ts b/packages/core/src/core/client.test.ts
index e362243054..f6f8e98c40 100644
--- a/packages/core/src/core/client.test.ts
+++ b/packages/core/src/core/client.test.ts
@@ -511,6 +511,31 @@ describe('Gemini Client (client.ts)', () => {
         );
       });
     });
+    it('should correctly latch hasFailedCompressionAttempt flag', async () => {
+      // 1. Setup: Call setup() from this test file
+      // This helper function mocks the compression service for us.
+      const { client } = setup({
+        originalTokenCount: 100,
+        newTokenCount: 200, // Inflated
+        compressionStatus:
+          CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
+      });
+
+      // 2. Test Step 1: Trigger a non-forced failure
+      await client.tryCompressChat('prompt-1', false); // force = false
+
+      // 3. Assert Step 1: Check that the flag became true
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
+      expect((client as any).hasFailedCompressionAttempt).toBe(true);
+
+      // 4. Test Step 2: Trigger a forced failure
+
+      await client.tryCompressChat('prompt-2', true); // force = true
+
+      // 5. Assert Step 2: Check that the flag REMAINS true
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
+      expect((client as any).hasFailedCompressionAttempt).toBe(true);
+    });
 
     it('should not trigger summarization if token count is below threshold', async () => {
       const MOCKED_TOKEN_LIMIT = 1000;
diff --git a/packages/core/src/core/client.ts b/packages/core/src/core/client.ts
index 43a8a5ae00..f7d915bc9a 100644
--- a/packages/core/src/core/client.ts
+++ b/packages/core/src/core/client.ts
@@ -742,7 +742,8 @@ export class GeminiClient {
       info.compressionStatus ===
       CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT
     ) {
-      this.hasFailedCompressionAttempt = !force && true;
+      this.hasFailedCompressionAttempt =
+        this.hasFailedCompressionAttempt || !force;
     } else if (info.compressionStatus === CompressionStatus.COMPRESSED) {
       if (newHistory) {
         this.chat = await this.startChat(newHistory);