diff --git a/src/hooks/preemptive-compaction.test.ts b/src/hooks/preemptive-compaction.test.ts
index ef6e695b0..09cbf83dc 100644
--- a/src/hooks/preemptive-compaction.test.ts
+++ b/src/hooks/preemptive-compaction.test.ts
@@ -284,10 +284,57 @@ describe("preemptive-compaction", () => {
     //#then
     expect(logMock).toHaveBeenCalledWith("[preemptive-compaction] Compaction failed", {
       sessionID,
+      providerID: "anthropic",
+      modelID: "claude-sonnet-4-6",
       error: String(summarizeError),
     })
   })
 
+  // #given compaction fails
+  // #when tool.execute.after completes the catch block
+  // #then should show a warning toast explaining the failure to the user
+  it("should show a warning toast when preemptive compaction fails", async () => {
+    //#given
+    const hook = createPreemptiveCompactionHook(ctx as never, {} as never)
+    const sessionID = "ses_toast_on_failure"
+    const summarizeError = new Error("upstream rate limited")
+    ctx.client.session.summarize.mockRejectedValueOnce(summarizeError)
+
+    await hook.event({
+      event: {
+        type: "message.updated",
+        properties: {
+          info: {
+            role: "assistant",
+            sessionID,
+            providerID: "anthropic",
+            modelID: "claude-sonnet-4-6",
+            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_toast" },
+      { title: "", output: "test", metadata: null },
+    )
+
+    //#then
+    expect(ctx.client.tui.showToast).toHaveBeenCalledTimes(1)
+    const toastCall = ctx.client.tui.showToast.mock.calls[0]?.[0]
+    expect(toastCall?.body?.title).toBe("Preemptive compaction failed")
+    expect(toastCall?.body?.variant).toBe("warning")
+    expect(String(toastCall?.body?.message)).toContain("upstream rate limited")
+  })
+
   // #given compaction fails
   // #when tool.execute.after is called again immediately
   // #then should NOT retry due to cooldown
@@ -475,6 +522,8 @@ describe("preemptive-compaction", () => {
       expect(ctx.client.session.summarize).toHaveBeenCalledTimes(1)
       expect(logMock).toHaveBeenCalledWith("[preemptive-compaction] Compaction failed", {
         sessionID,
+        providerID: "anthropic",
+        modelID: "claude-sonnet-4-6",
         error: expect.stringContaining("Compaction summarize timed out"),
       })
 
diff --git a/src/hooks/preemptive-compaction.ts b/src/hooks/preemptive-compaction.ts
index ef58b1a95..ecab70676 100644
--- a/src/hooks/preemptive-compaction.ts
+++ b/src/hooks/preemptive-compaction.ts
@@ -8,7 +8,7 @@ import {
 import { resolveCompactionModel } from "./shared/compaction-model-resolver"
 import { createPostCompactionDegradationMonitor } from "./preemptive-compaction-degradation-monitor"
 
-const PREEMPTIVE_COMPACTION_TIMEOUT_MS = 120_000
+const PREEMPTIVE_COMPACTION_TIMEOUT_MS = 60_000
 const PREEMPTIVE_COMPACTION_THRESHOLD = 0.78
 const PREEMPTIVE_COMPACTION_COOLDOWN_MS = 60_000
 
@@ -134,7 +134,25 @@ export function createPreemptiveCompactionHook(
 
       compactedSessions.add(sessionID)
     } catch (error) {
-      log("[preemptive-compaction] Compaction failed", { sessionID, error: String(error) })
+      log("[preemptive-compaction] Compaction failed", {
+        sessionID,
+        providerID: cached.providerID,
+        modelID: cached.modelID,
+        error: String(error),
+      })
+      ctx.client.tui.showToast({
+        body: {
+          title: "Preemptive compaction failed",
+          message: `Context window is above ${Math.round(PREEMPTIVE_COMPACTION_THRESHOLD * 100)}% and auto-compaction could not run. The session may grow large. Error: ${String(error)}`,
+          variant: "warning",
+          duration: 10000,
+        },
+      }).catch((toastError: unknown) => {
+        log("[preemptive-compaction] Failed to show toast", {
+          sessionID,
+          toastError: String(toastError),
+        })
+      })
     } finally {
       compactionInProgress.delete(sessionID)
     }