diff --git a/CHANGELOG.md b/CHANGELOG.md
index dfe246fd5..8362d29c3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,7 @@ Docs: https://docs.clawd.bot
 - BlueBubbles: stop typing indicator on idle/no-reply. (#1439) Thanks @Nicell.
 - Message tool: keep path/filePath as-is for send; hydrate buffers only for sendAttachment. (#1444) Thanks @hopyky.
 - Auto-reply: only report a model switch when session state is available. (#1465) Thanks @robbyczgw-cla.
+- Compaction: harden oversized summarization handling and gate UI compaction status by verbose level. (#1466) Thanks @dlauer.
 - Control UI: resolve local avatar URLs with basePath across injection + identity RPC. (#1457) Thanks @dlauer.
 - Agents: surface concrete API error details instead of generic AI service errors.
 - Exec approvals: allow per-segment allowlists for chained shell commands on gateway + node hosts. (#1458) Thanks @czekaj.
diff --git a/src/agents/pi-extensions/compaction-safeguard.ts b/src/agents/pi-extensions/compaction-safeguard.ts
index a6a66637a..3cbce0061 100644
--- a/src/agents/pi-extensions/compaction-safeguard.ts
+++ b/src/agents/pi-extensions/compaction-safeguard.ts
@@ -15,6 +15,15 @@ const TURN_PREFIX_INSTRUCTIONS =
 const MAX_TOOL_FAILURES = 8;
 const MAX_TOOL_FAILURE_CHARS = 240;
 
+function isAbortError(err: unknown): boolean {
+  if (!err || typeof err !== "object") return false;
+  const name = "name" in err ? String(err.name) : "";
+  if (name === "AbortError") return true;
+  const message =
+    "message" in err && typeof err.message === "string" ? err.message.toLowerCase() : "";
+  return message.includes("aborted");
+}
+
 type ToolFailure = {
   toolCallId: string;
   toolName: string;
@@ -251,6 +260,9 @@ async function summarizeWithFallback(params: {
   try {
     return await summarizeChunks(params);
   } catch (fullError) {
+    if (params.signal.aborted || isAbortError(fullError)) {
+      throw fullError;
+    }
     console.warn(
       `Full summarization failed, trying partial: ${
         fullError instanceof Error ? fullError.message : String(fullError)
@@ -283,6 +295,9 @@ async function summarizeWithFallback(params: {
       const notes = oversizedNotes.length > 0 ? `\n\n${oversizedNotes.join("\n")}` : "";
       return partialSummary + notes;
     } catch (partialError) {
+      if (params.signal.aborted || isAbortError(partialError)) {
+        throw partialError;
+      }
       console.warn(
         `Partial summarization also failed: ${
           partialError instanceof Error ? partialError.message : String(partialError)
diff --git a/src/gateway/server-chat.ts b/src/gateway/server-chat.ts
index 9ef62e688..0604d6e44 100644
--- a/src/gateway/server-chat.ts
+++ b/src/gateway/server-chat.ts
@@ -173,7 +173,7 @@ export function createAgentEventHandler({
     nodeSendToSession(sessionKey, "chat", payload);
   };
 
-  const shouldEmitToolEvents = (runId: string, sessionKey?: string) => {
+  const shouldEmitVerboseEvents = (runId: string, sessionKey?: string) => {
     const runContext = getAgentRunContext(runId);
     const runVerbose = normalizeVerboseLevel(runContext?.verboseLevel);
     if (runVerbose) return runVerbose === "on";
@@ -198,7 +198,10 @@ export function createAgentEventHandler({
     // Include sessionKey so Control UI can filter tool streams per session.
     const agentPayload = sessionKey ? { ...evt, sessionKey } : evt;
     const last = agentRunSeq.get(evt.runId) ?? 0;
-    if (evt.stream === "tool" && !shouldEmitToolEvents(evt.runId, sessionKey)) {
+    if (
+      (evt.stream === "tool" || evt.stream === "compaction") &&
+      !shouldEmitVerboseEvents(evt.runId, sessionKey)
+    ) {
       agentRunSeq.set(evt.runId, evt.seq);
       return;
     }
diff --git a/src/gateway/server.agent.gateway-server-agent.test.ts b/src/gateway/server.agent.gateway-server-agent.test.ts
index d5cdc5b48..2017ae1fb 100644
--- a/src/gateway/server.agent.gateway-server-agent.test.ts
+++ b/src/gateway/server.agent.gateway-server-agent.test.ts
@@ -77,6 +77,22 @@ describe("gateway server agent", () => {
     {
       registerAgentRunContext("run-tool-off", { sessionKey: "agent:main:main" });
 
+      const compactionEvtP = onceMessage(
+        ws,
+        (o) =>
+          o.type === "event" &&
+          o.event === "agent" &&
+          o.payload?.runId === "run-tool-off" &&
+          o.payload?.stream === "compaction",
+        1000,
+      );
+
+      emitAgentEvent({
+        runId: "run-tool-off",
+        stream: "compaction",
+        data: { phase: "start" },
+      });
+
       emitAgentEvent({
         runId: "run-tool-off",
         stream: "tool",
@@ -98,6 +114,8 @@ describe("gateway server agent", () => {
           ? (evt.payload as Record<string, unknown>)
           : {};
       expect(payload.stream).toBe("assistant");
+
+      await expect(compactionEvtP).rejects.toThrow("timeout");
     }
 
     {
diff --git a/ui/src/ui/app-tool-stream.ts b/ui/src/ui/app-tool-stream.ts
index 5c83c3a79..4898b2779 100644
--- a/ui/src/ui/app-tool-stream.ts
+++ b/ui/src/ui/app-tool-stream.ts
@@ -142,6 +142,7 @@ export type CompactionStatus = {
   active: boolean;
   startedAt: number | null;
   completedAt: number | null;
+  retryingAt: number | null;
 };
 
 type CompactionHost = ToolStreamHost & {
@@ -154,6 +155,7 @@ const COMPACTION_TOAST_DURATION_MS = 5000;
 export function handleCompactionEvent(host: CompactionHost, payload: AgentEventPayload) {
   const data = payload.data ?? {};
   const phase = typeof data.phase === "string" ? data.phase : "";
+  const willRetry = Boolean(data.willRetry);
   
   // Clear any existing timer
   if (host.compactionClearTimer != null) {
@@ -166,12 +168,14 @@ export function handleCompactionEvent(host: CompactionHost, payload: AgentEventP
       active: true,
       startedAt: Date.now(),
       completedAt: null,
+      retryingAt: null,
     };
   } else if (phase === "end") {
     host.compactionStatus = {
-      active: false,
+      active: willRetry,
       startedAt: host.compactionStatus?.startedAt ?? null,
-      completedAt: Date.now(),
+      completedAt: willRetry ? null : Date.now(),
+      retryingAt: willRetry ? Date.now() : null,
     };
     // Auto-clear the toast after duration
     host.compactionClearTimer = window.setTimeout(() => {
@@ -183,13 +187,19 @@ export function handleCompactionEvent(host: CompactionHost, payload: AgentEventP
 
 export function handleAgentEvent(host: ToolStreamHost, payload?: AgentEventPayload) {
   if (!payload) return;
-  
+
   // Handle compaction events
   if (payload.stream === "compaction") {
+    const sessionKey =
+      typeof payload.sessionKey === "string" ? payload.sessionKey : undefined;
+    if (sessionKey && sessionKey !== host.sessionKey) return;
+    if (!sessionKey && host.chatRunId && payload.runId !== host.chatRunId) return;
+    if (host.chatRunId && payload.runId !== host.chatRunId) return;
+    if (!host.chatRunId) return;
     handleCompactionEvent(host as CompactionHost, payload);
     return;
   }
-  
+
   if (payload.stream !== "tool") return;
   const sessionKey =
     typeof payload.sessionKey === "string" ? payload.sessionKey : undefined;
diff --git a/ui/src/ui/views/chat.ts b/ui/src/ui/views/chat.ts
index 97ce9d4ec..70c95f6df 100644
--- a/ui/src/ui/views/chat.ts
+++ b/ui/src/ui/views/chat.ts
@@ -20,6 +20,7 @@ export type CompactionIndicatorStatus = {
   active: boolean;
   startedAt: number | null;
   completedAt: number | null;
+  retryingAt: number | null;
 };
 
 export type ChatProps = {
@@ -80,6 +81,17 @@ function renderCompactionIndicator(status: CompactionIndicatorStatus | null | un
     `;
   }
   
+  if (status.retryingAt) {
+    const elapsed = Date.now() - status.retryingAt;
+    if (elapsed < COMPACTION_TOAST_DURATION_MS) {
+      return html`
+        <div class="callout info compaction-indicator compaction-indicator--active">
+          🧹 Retrying compaction...
+        </div>
+      `;
+    }
+  }
+
   // Show "compaction complete" briefly after completion
   if (status.completedAt) {
     const elapsed = Date.now() - status.completedAt;