diff --git a/src/hooks/anthropic-context-window-limit-recovery/executor.test.ts b/src/hooks/anthropic-context-window-limit-recovery/executor.test.ts
index 8c958aa..8ddd397 100644
--- a/src/hooks/anthropic-context-window-limit-recovery/executor.test.ts
+++ b/src/hooks/anthropic-context-window-limit-recovery/executor.test.ts
@@ -1,6 +1,7 @@
-import { describe, test, expect, mock, beforeEach } from "bun:test"
+import { describe, test, expect, mock, beforeEach, spyOn } from "bun:test"
 import { executeCompact } from "./executor"
 import type { AutoCompactState } from "./types"
+import * as storage from "./storage"
 
 describe("executeCompact lock management", () => {
   let autoCompactState: AutoCompactState
@@ -224,4 +225,86 @@ describe("executeCompact lock management", () => {
     // The continuation happens in setTimeout, but lock is cleared in finally before that
     expect(autoCompactState.compactionInProgress.has(sessionID)).toBe(false)
   })
+
+  test("falls through to summarize when truncation is insufficient", async () => {
+    // #given: Over token limit with truncation returning insufficient
+    autoCompactState.errorDataBySession.set(sessionID, {
+      errorType: "token_limit",
+      currentTokens: 250000,
+      maxTokens: 200000,
+    })
+
+    const truncateSpy = spyOn(storage, "truncateUntilTargetTokens").mockReturnValue({
+      success: true,
+      sufficient: false,
+      truncatedCount: 3,
+      totalBytesRemoved: 10000,
+      targetBytesToRemove: 50000,
+      truncatedTools: [
+        { toolName: "Grep", originalSize: 5000 },
+        { toolName: "Read", originalSize: 3000 },
+        { toolName: "Bash", originalSize: 2000 },
+      ],
+    })
+
+    // #when: Execute compaction
+    await executeCompact(sessionID, msg, autoCompactState, mockClient, directory)
+
+    // #then: Truncation was attempted
+    expect(truncateSpy).toHaveBeenCalled()
+
+    // #then: Summarize should be called (fall through from insufficient truncation)
+    expect(mockClient.session.summarize).toHaveBeenCalledWith(
+      expect.objectContaining({
+        path: { id: sessionID },
+        body: { providerID: "anthropic", modelID: "claude-opus-4-5" },
+      }),
+    )
+
+    // #then: Lock should be cleared
+    expect(autoCompactState.compactionInProgress.has(sessionID)).toBe(false)
+
+    truncateSpy.mockRestore()
+  })
+
+  test("does NOT call summarize when truncation is sufficient", async () => {
+    // #given: Over token limit with truncation returning sufficient
+    autoCompactState.errorDataBySession.set(sessionID, {
+      errorType: "token_limit",
+      currentTokens: 250000,
+      maxTokens: 200000,
+    })
+
+    const truncateSpy = spyOn(storage, "truncateUntilTargetTokens").mockReturnValue({
+      success: true,
+      sufficient: true,
+      truncatedCount: 5,
+      totalBytesRemoved: 60000,
+      targetBytesToRemove: 50000,
+      truncatedTools: [
+        { toolName: "Grep", originalSize: 30000 },
+        { toolName: "Read", originalSize: 30000 },
+      ],
+    })
+
+    // #when: Execute compaction
+    await executeCompact(sessionID, msg, autoCompactState, mockClient, directory)
+
+    // Wait for setTimeout callback
+    await new Promise((resolve) => setTimeout(resolve, 600))
+
+    // #then: Truncation was attempted
+    expect(truncateSpy).toHaveBeenCalled()
+
+    // #then: Summarize should NOT be called (early return from sufficient truncation)
+    expect(mockClient.session.summarize).not.toHaveBeenCalled()
+
+    // #then: prompt_async should be called (Continue after successful truncation)
+    expect(mockClient.session.prompt_async).toHaveBeenCalled()
+
+    // #then: Lock should be cleared
+    expect(autoCompactState.compactionInProgress.has(sessionID)).toBe(false)
+
+    truncateSpy.mockRestore()
+  })
 })
diff --git a/src/hooks/anthropic-context-window-limit-recovery/executor.ts b/src/hooks/anthropic-context-window-limit-recovery/executor.ts
index 09608f4..1c5abd6 100644
--- a/src/hooks/anthropic-context-window-limit-recovery/executor.ts
+++ b/src/hooks/anthropic-context-window-limit-recovery/executor.ts
@@ -401,21 +401,31 @@ export async function executeCompact(
 
         log("[auto-compact] aggressive truncation completed", aggressiveResult);
 
-        clearSessionState(autoCompactState, sessionID);
-        setTimeout(async () => {
-          try {
-            await (client as Client).session.prompt_async({
-              path: { sessionID },
-              body: { parts: [{ type: "text", text: "Continue" }] },
-              query: { directory },
-            });
-          } catch {}
-        }, 500);
-        return;
+        // Only return early if truncation was sufficient to get under token limit
+        // Otherwise fall through to PHASE 3 (Summarize)
+        if (aggressiveResult.sufficient) {
+          clearSessionState(autoCompactState, sessionID);
+          setTimeout(async () => {
+            try {
+              await (client as Client).session.prompt_async({
+                path: { sessionID },
+                body: { parts: [{ type: "text", text: "Continue" }] },
+                query: { directory },
+              });
+            } catch {}
+          }, 500);
+          return;
+        }
+        // Truncation was insufficient - fall through to Summarize
+        log("[auto-compact] truncation insufficient, falling through to summarize", {
+          sessionID,
+          truncatedCount: aggressiveResult.truncatedCount,
+          sufficient: aggressiveResult.sufficient,
+        });
       }
     }
 
-    // PHASE 3: Summarize - fallback when no tool outputs to truncate
+    // PHASE 3: Summarize - fallback when truncation insufficient or no tool outputs
     const retryState = getOrCreateRetryState(autoCompactState, sessionID);
 
     if (errorData?.errorType?.includes("non-empty content")) {
diff --git a/src/hooks/anthropic-context-window-limit-recovery/types.ts b/src/hooks/anthropic-context-window-limit-recovery/types.ts
index 5a3ec73..024fd54 100644
--- a/src/hooks/anthropic-context-window-limit-recovery/types.ts
+++ b/src/hooks/anthropic-context-window-limit-recovery/types.ts
@@ -44,5 +44,5 @@ export const TRUNCATE_CONFIG = {
   maxTruncateAttempts: 20,
   minOutputSizeToTruncate: 500,
   targetTokenRatio: 0.5,
-  charsPerToken: 2,
+  charsPerToken: 4,
 } as const