diff --git a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts
new file mode 100644
index 00000000..610c21a4
--- /dev/null
+++ b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.test.ts
@@ -0,0 +1,105 @@
+import { beforeEach, describe, expect, mock, test } from "bun:test"
+import type { PluginInput } from "@opencode-ai/plugin"
+
+const executeCompactMock = mock(async () => {})
+const getLastAssistantMock = mock(async () => ({
+  providerID: "anthropic",
+  modelID: "claude-sonnet-4-5",
+}))
+const parseAnthropicTokenLimitErrorMock = mock(() => ({
+  providerID: "anthropic",
+  modelID: "claude-sonnet-4-5",
+}))
+
+mock.module("./executor", () => ({
+  executeCompact: executeCompactMock,
+  getLastAssistant: getLastAssistantMock,
+}))
+
+mock.module("./parser", () => ({
+  parseAnthropicTokenLimitError: parseAnthropicTokenLimitErrorMock,
+}))
+
+mock.module("../../shared/logger", () => ({
+  log: () => {},
+}))
+
+function createMockContext(): PluginInput {
+  return {
+    client: {
+      session: {
+        messages: mock(() => Promise.resolve({ data: [] })),
+      },
+      tui: {
+        showToast: mock(() => Promise.resolve()),
+      },
+    },
+    directory: "/tmp",
+  } as PluginInput
+}
+
+function setupDelayedTimeoutMocks(): {
+  restore: () => void
+  getClearTimeoutCalls: () => Array<ReturnType<typeof setTimeout>>
+} {
+  const originalSetTimeout = globalThis.setTimeout
+  const originalClearTimeout = globalThis.clearTimeout
+  const clearTimeoutCalls: Array<ReturnType<typeof setTimeout>> = []
+  let timeoutCounter = 0
+
+  globalThis.setTimeout = ((_: () => void, _delay?: number) => {
+    timeoutCounter += 1
+    return timeoutCounter as ReturnType<typeof setTimeout>
+  }) as typeof setTimeout
+
+  globalThis.clearTimeout = ((timeoutID: ReturnType<typeof setTimeout>) => {
+    clearTimeoutCalls.push(timeoutID)
+  }) as typeof clearTimeout
+
+  return {
+    restore: () => {
+      globalThis.setTimeout = originalSetTimeout
+      globalThis.clearTimeout = originalClearTimeout
+    },
+    getClearTimeoutCalls: () => clearTimeoutCalls,
+  }
+}
+
+describe("createAnthropicContextWindowLimitRecoveryHook", () => {
+  beforeEach(() => {
+    executeCompactMock.mockClear()
+    getLastAssistantMock.mockClear()
+    parseAnthropicTokenLimitErrorMock.mockClear()
+  })
+
+  test("cancels pending timer when session.idle handles compaction first", async () => {
+    //#given
+    const { restore, getClearTimeoutCalls } = setupDelayedTimeoutMocks()
+    const { createAnthropicContextWindowLimitRecoveryHook } = await import("./recovery-hook")
+    const hook = createAnthropicContextWindowLimitRecoveryHook(createMockContext())
+
+    try {
+      //#when
+      await hook.event({
+        event: {
+          type: "session.error",
+          properties: { sessionID: "session-race", error: "prompt is too long" },
+        },
+      })
+
+      await hook.event({
+        event: {
+          type: "session.idle",
+          properties: { sessionID: "session-race" },
+        },
+      })
+
+      //#then
+      expect(getClearTimeoutCalls()).toEqual([1 as ReturnType<typeof setTimeout>])
+      expect(executeCompactMock).toHaveBeenCalledTimes(1)
+      expect(executeCompactMock.mock.calls[0]?.[0]).toBe("session-race")
+    } finally {
+      restore()
+    }
+  })
+})
diff --git a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.ts b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.ts
index f4bcb0f2..556f9b45 100644
--- a/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.ts
+++ b/src/hooks/anthropic-context-window-limit-recovery/recovery-hook.ts
@@ -28,6 +28,7 @@ export function createAnthropicContextWindowLimitRecoveryHook(
 ) {
   const autoCompactState = createRecoveryState()
   const experimental = options?.experimental
+  const pendingCompactionTimeoutBySession = new Map<string, ReturnType<typeof setTimeout>>()
 
   const eventHandler = async ({ event }: { event: { type: string; properties?: unknown } }) => {
     const props = event.properties as Record<string, unknown> | undefined
@@ -35,6 +36,12 @@ export function createAnthropicContextWindowLimitRecoveryHook(
     if (event.type === "session.deleted") {
       const sessionInfo = props?.info as { id?: string } | undefined
       if (sessionInfo?.id) {
+        const timeoutID = pendingCompactionTimeoutBySession.get(sessionInfo.id)
+        if (timeoutID !== undefined) {
+          clearTimeout(timeoutID)
+          pendingCompactionTimeoutBySession.delete(sessionInfo.id)
+        }
+
         autoCompactState.pendingCompact.delete(sessionInfo.id)
         autoCompactState.errorDataBySession.delete(sessionInfo.id)
         autoCompactState.retryStateBySession.delete(sessionInfo.id)
@@ -76,7 +83,8 @@ export function createAnthropicContextWindowLimitRecoveryHook(
           })
           .catch(() => {})
 
-        setTimeout(() => {
+        const timeoutID = setTimeout(() => {
+          pendingCompactionTimeoutBySession.delete(sessionID)
           executeCompact(
             sessionID,
             { providerID, modelID },
@@ -86,6 +94,8 @@ export function createAnthropicContextWindowLimitRecoveryHook(
             experimental,
           )
         }, 300)
+
+        pendingCompactionTimeoutBySession.set(sessionID, timeoutID)
       }
       return
     }
@@ -114,6 +124,12 @@ export function createAnthropicContextWindowLimitRecoveryHook(
 
       if (!autoCompactState.pendingCompact.has(sessionID)) return
 
+      const timeoutID = pendingCompactionTimeoutBySession.get(sessionID)
+      if (timeoutID !== undefined) {
+        clearTimeout(timeoutID)
+        pendingCompactionTimeoutBySession.delete(sessionID)
+      }
+
       const errorData = autoCompactState.errorDataBySession.get(sessionID)
       const lastAssistant = await getLastAssistant(sessionID, ctx.client, ctx.directory)
 
diff --git a/src/hooks/preemptive-compaction.test.ts b/src/hooks/preemptive-compaction.test.ts
index 81bb6bc7..4ef001e3 100644
--- a/src/hooks/preemptive-compaction.test.ts
+++ b/src/hooks/preemptive-compaction.test.ts
@@ -1,5 +1,12 @@
 import { describe, it, expect, mock, beforeEach } from "bun:test"
-import { createPreemptiveCompactionHook } from "./preemptive-compaction"
+
+const logMock = mock(() => {})
+
+mock.module("../shared/logger", () => ({
+  log: logMock,
+}))
+
+const { createPreemptiveCompactionHook } = await import("./preemptive-compaction")
 
 function createMockCtx() {
   return {
@@ -21,6 +28,7 @@ describe("preemptive-compaction", () => {
 
   beforeEach(() => {
     ctx = createMockCtx()
+    logMock.mockClear()
   })
 
   // #given event caches token info from message.updated
@@ -152,4 +160,45 @@ describe("preemptive-compaction", () => {
 
     expect(ctx.client.session.summarize).not.toHaveBeenCalled()
   })
+
+  it("should log summarize errors instead of swallowing them", async () => {
+    //#given
+    const hook = createPreemptiveCompactionHook(ctx as never)
+    const sessionID = "ses_log_error"
+    const summarizeError = new Error("summarize failed")
+    ctx.client.session.summarize.mockRejectedValueOnce(summarizeError)
+
+    await hook.event({
+      event: {
+        type: "message.updated",
+        properties: {
+          info: {
+            role: "assistant",
+            sessionID,
+            providerID: "anthropic",
+            modelID: "claude-sonnet-4-5",
+            finish: true,
+            tokens: {
+              input: 170000,
+              output: 0,
+              reasoning: 0,
+              cache: { read: 10000, write: 0 },
+            },
+          },
+        },
+      },
+    })
+
+    //#when
+    await hook["tool.execute.after"](
+      { tool: "bash", sessionID, callID: "call_log" },
+      { title: "", output: "test", metadata: null }
+    )
+
+    //#then
+    expect(logMock).toHaveBeenCalledWith("[preemptive-compaction] Compaction failed", {
+      sessionID,
+      error: String(summarizeError),
+    })
+  })
 })
diff --git a/src/hooks/preemptive-compaction.ts b/src/hooks/preemptive-compaction.ts
index 87190415..fd617ccf 100644
--- a/src/hooks/preemptive-compaction.ts
+++ b/src/hooks/preemptive-compaction.ts
@@ -1,3 +1,5 @@
+import { log } from "../shared/logger"
+
 const DEFAULT_ACTUAL_LIMIT = 200_000
 
 const ANTHROPIC_ACTUAL_LIMIT =
@@ -76,8 +78,8 @@ export function createPreemptiveCompactionHook(ctx: PluginInput) {
       })
 
       compactedSessions.add(sessionID)
-    } catch {
-      // best-effort; do not disrupt tool execution
+    } catch (error) {
+      log("[preemptive-compaction] Compaction failed", { sessionID, error: String(error) })
     } finally {
       compactionInProgress.delete(sessionID)
     }