diff --git a/src/auto-reply/reply/agent-runner-execution.ts b/src/auto-reply/reply/agent-runner-execution.ts
index 7fca6d4cf..166b6289a 100644
--- a/src/auto-reply/reply/agent-runner-execution.ts
+++ b/src/auto-reply/reply/agent-runner-execution.ts
@@ -18,7 +18,10 @@ import {
   updateSessionStore,
 } from "../../config/sessions.js";
 import { logVerbose } from "../../globals.js";
-import { emitAgentEvent, registerAgentRunContext } from "../../infra/agent-events.js";
+import {
+  emitAgentEvent,
+  registerAgentRunContext,
+} from "../../infra/agent-events.js";
 import { defaultRuntime } from "../../runtime.js";
 import {
   isMarkdownCapableMessageChannel,
@@ -29,11 +32,20 @@ import type { TemplateContext } from "../templating.js";
 import type { VerboseLevel } from "../thinking.js";
 import { isSilentReplyText, SILENT_REPLY_TOKEN } from "../tokens.js";
 import type { GetReplyOptions, ReplyPayload } from "../types.js";
-import { buildThreadingToolContext, resolveEnforceFinalTag } from "./agent-runner-utils.js";
-import { createBlockReplyPayloadKey, type BlockReplyPipeline } from "./block-reply-pipeline.js";
+import {
+  buildThreadingToolContext,
+  resolveEnforceFinalTag,
+} from "./agent-runner-utils.js";
+import {
+  createBlockReplyPayloadKey,
+  type BlockReplyPipeline,
+} from "./block-reply-pipeline.js";
 import type { FollowupRun } from "./queue.js";
 import { parseReplyDirectives } from "./reply-directives.js";
-import { applyReplyTagsToPayload, isRenderablePayload } from "./reply-payloads.js";
+import {
+  applyReplyTagsToPayload,
+  isRenderablePayload,
+} from "./reply-payloads.js";
 import type { TypingSignaler } from "./typing-mode.js";
 
 export type AgentRunLoopResult =
@@ -96,9 +108,12 @@ export async function runAgentTurnWithFallback(params: {
   while (true) {
     try {
       const allowPartialStream = !(
-        params.followupRun.run.reasoningLevel === "stream" && params.opts?.onReasoningStream
+        params.followupRun.run.reasoningLevel === "stream" &&
+        params.opts?.onReasoningStream
       );
-      const normalizeStreamingText = (payload: ReplyPayload): { text?: string; skip: boolean } => {
+      const normalizeStreamingText = (
+        payload: ReplyPayload,
+      ): { text?: string; skip: boolean } => {
         if (!allowPartialStream) return { skip: true };
         let text = payload.text;
         if (!params.isHeartbeat && text?.includes("HEARTBEAT_OK")) {
@@ -122,7 +137,9 @@ export async function runAgentTurnWithFallback(params: {
         if (!sanitized.trim()) return { skip: true };
         return { text: sanitized, skip: false };
       };
-      const handlePartialForTyping = async (payload: ReplyPayload): Promise<string | undefined> => {
+      const handlePartialForTyping = async (
+        payload: ReplyPayload,
+      ): Promise<string | undefined> => {
         const { text, skip } = normalizeStreamingText(payload);
         if (skip || !text) return undefined;
         await params.typingSignals.signalTextDelta(text);
@@ -157,7 +174,10 @@ export async function runAgentTurnWithFallback(params: {
                 startedAt,
               },
             });
-            const cliSessionId = getCliSessionId(params.getActiveSessionEntry(), provider);
+            const cliSessionId = getCliSessionId(
+              params.getActiveSessionEntry(),
+              provider,
+            );
             return runCliAgent({
               sessionId: params.followupRun.run.sessionId,
               sessionKey: params.sessionKey,
@@ -207,7 +227,8 @@ export async function runAgentTurnWithFallback(params: {
           return runEmbeddedPiAgent({
             sessionId: params.followupRun.run.sessionId,
             sessionKey: params.sessionKey,
-            messageProvider: params.sessionCtx.Provider?.trim().toLowerCase() || undefined,
+            messageProvider:
+              params.sessionCtx.Provider?.trim().toLowerCase() || undefined,
             agentAccountId: params.sessionCtx.AccountId,
             // Provider threading context for tool auto-injection
             ...buildThreadingToolContext({
@@ -223,7 +244,10 @@ export async function runAgentTurnWithFallback(params: {
             prompt: params.commandBody,
             extraSystemPrompt: params.followupRun.run.extraSystemPrompt,
             ownerNumbers: params.followupRun.run.ownerNumbers,
-            enforceFinalTag: resolveEnforceFinalTag(params.followupRun.run, provider),
+            enforceFinalTag: resolveEnforceFinalTag(
+              params.followupRun.run,
+              provider,
+            ),
             provider,
             model,
             authProfileId,
@@ -240,7 +264,9 @@ export async function runAgentTurnWithFallback(params: {
                 params.sessionCtx.Provider,
               );
               if (!channel) return "markdown";
-              return isMarkdownCapableMessageChannel(channel) ? "markdown" : "plain";
+              return isMarkdownCapableMessageChannel(channel)
+                ? "markdown"
+                : "plain";
             })(),
             bashElevated: params.followupRun.run.bashElevated,
             timeoutMs: params.followupRun.run.timeoutMs,
@@ -250,7 +276,11 @@ export async function runAgentTurnWithFallback(params: {
             onPartialReply: allowPartialStream
               ? async (payload) => {
                   const textForTyping = await handlePartialForTyping(payload);
-                  if (!params.opts?.onPartialReply || textForTyping === undefined) return;
+                  if (
+                    !params.opts?.onPartialReply ||
+                    textForTyping === undefined
+                  )
+                    return;
                   await params.opts.onPartialReply({
                     text: textForTyping,
                     mediaUrls: payload.mediaUrls,
@@ -261,7 +291,8 @@ export async function runAgentTurnWithFallback(params: {
               await params.typingSignals.signalMessageStart();
             },
             onReasoningStream:
-              params.typingSignals.shouldStartOnReasoning || params.opts?.onReasoningStream
+              params.typingSignals.shouldStartOnReasoning ||
+              params.opts?.onReasoningStream
                 ? async (payload) => {
                     await params.typingSignals.signalReasoningDelta();
                     await params.opts?.onReasoningStream?.({
@@ -274,14 +305,16 @@ export async function runAgentTurnWithFallback(params: {
               // Trigger typing when tools start executing.
               // Must await to ensure typing indicator starts before tool summaries are emitted.
               if (evt.stream === "tool") {
-                const phase = typeof evt.data.phase === "string" ? evt.data.phase : "";
+                const phase =
+                  typeof evt.data.phase === "string" ? evt.data.phase : "";
                 if (phase === "start" || phase === "update") {
                   await params.typingSignals.signalToolStart();
                 }
               }
               // Track auto-compaction completion
               if (evt.stream === "compaction") {
-                const phase = typeof evt.data.phase === "string" ? evt.data.phase : "";
+                const phase =
+                  typeof evt.data.phase === "string" ? evt.data.phase : "";
                 const willRetry = Boolean(evt.data.willRetry);
                 if (phase === "end" && !willRetry) {
                   autoCompactionCompleted = true;
@@ -305,14 +338,22 @@ export async function runAgentTurnWithFallback(params: {
                     params.sessionCtx.MessageSid,
                   );
                   // Let through payloads with audioAsVoice flag even if empty (need to track it)
-                  if (!isRenderablePayload(taggedPayload) && !payload.audioAsVoice) return;
-                  const parsed = parseReplyDirectives(taggedPayload.text ?? "", {
-                    currentMessageId: params.sessionCtx.MessageSid,
-                    silentToken: SILENT_REPLY_TOKEN,
-                  });
+                  if (
+                    !isRenderablePayload(taggedPayload) &&
+                    !payload.audioAsVoice
+                  )
+                    return;
+                  const parsed = parseReplyDirectives(
+                    taggedPayload.text ?? "",
+                    {
+                      currentMessageId: params.sessionCtx.MessageSid,
+                      silentToken: SILENT_REPLY_TOKEN,
+                    },
+                  );
                   const cleaned = parsed.text || undefined;
                   const hasRenderableMedia =
-                    Boolean(taggedPayload.mediaUrl) || (taggedPayload.mediaUrls?.length ?? 0) > 0;
+                    Boolean(taggedPayload.mediaUrl) ||
+                    (taggedPayload.mediaUrls?.length ?? 0) > 0;
                   // Skip empty payloads unless they have audioAsVoice flag (need to track it)
                   if (
                     !cleaned &&
@@ -326,25 +367,35 @@ export async function runAgentTurnWithFallback(params: {
                   const blockPayload: ReplyPayload = params.applyReplyToMode({
                     ...taggedPayload,
                     text: cleaned,
-                    audioAsVoice: Boolean(parsed.audioAsVoice || payload.audioAsVoice),
+                    audioAsVoice: Boolean(
+                      parsed.audioAsVoice || payload.audioAsVoice,
+                    ),
                     replyToId: taggedPayload.replyToId ?? parsed.replyToId,
                     replyToTag: taggedPayload.replyToTag || parsed.replyToTag,
-                    replyToCurrent: taggedPayload.replyToCurrent || parsed.replyToCurrent,
+                    replyToCurrent:
+                      taggedPayload.replyToCurrent || parsed.replyToCurrent,
                   });
 
                   void params.typingSignals
                     .signalTextDelta(cleaned ?? taggedPayload.text)
                     .catch((err) => {
-                      logVerbose(`block reply typing signal failed: ${String(err)}`);
+                      logVerbose(
+                        `block reply typing signal failed: ${String(err)}`,
+                      );
                     });
 
                   // Use pipeline if available (block streaming enabled), otherwise send directly
-                  if (params.blockStreamingEnabled && params.blockReplyPipeline) {
+                  if (
+                    params.blockStreamingEnabled &&
+                    params.blockReplyPipeline
+                  ) {
                     params.blockReplyPipeline.enqueue(blockPayload);
                   } else {
                     // Send directly when flushing before tool execution (no streaming).
                     // Track sent key to avoid duplicate in final payloads.
-                    directlySentBlockKeys.add(createBlockReplyPayloadKey(blockPayload));
+                    directlySentBlockKeys.add(
+                      createBlockReplyPayloadKey(blockPayload),
+                    );
                     await params.opts?.onBlockReply?.(blockPayload);
                   }
                 }
@@ -397,10 +448,17 @@ export async function runAgentTurnWithFallback(params: {
         (await params.resetSessionAfterCompactionFailure(embeddedError.message))
       ) {
         didResetAfterCompactionFailure = true;
-        continue;
+        return {
+          kind: "final",
+          payload: {
+            text: "⚠️ Context limit exceeded. I've reset our conversation to start fresh - please try again.\n\nTo prevent this, increase your compaction buffer by setting `agents.defaults.compaction.reserveTokensFloor` to 4000 or higher in your config.",
+          },
+        };
       }
       if (embeddedError?.kind === "role_ordering") {
-        const didReset = await params.resetSessionAfterRoleOrderingConflict(embeddedError.message);
+        const didReset = await params.resetSessionAfterRoleOrderingConflict(
+          embeddedError.message,
+        );
         if (didReset) {
           return {
             kind: "final",
@@ -418,8 +476,10 @@ export async function runAgentTurnWithFallback(params: {
         isContextOverflowError(message) ||
         /context.*overflow|too large|context window/i.test(message);
       const isCompactionFailure = isCompactionFailureError(message);
-      const isSessionCorruption = /function call turn comes immediately after/i.test(message);
-      const isRoleOrderingError = /incorrect role information|roles must alternate/i.test(message);
+      const isSessionCorruption =
+        /function call turn comes immediately after/i.test(message);
+      const isRoleOrderingError =
+        /incorrect role information|roles must alternate/i.test(message);
 
       if (
         isCompactionFailure &&
@@ -427,10 +487,16 @@ export async function runAgentTurnWithFallback(params: {
         (await params.resetSessionAfterCompactionFailure(message))
       ) {
         didResetAfterCompactionFailure = true;
-        continue;
+        return {
+          kind: "final",
+          payload: {
+            text: "⚠️ Context limit exceeded during compaction. I've reset our conversation to start fresh - please try again.\n\nTo prevent this, increase your compaction buffer by setting `agents.defaults.compaction.reserveTokensFloor` to 4000 or higher in your config.",
+          },
+        };
       }
       if (isRoleOrderingError) {
-        const didReset = await params.resetSessionAfterRoleOrderingConflict(message);
+        const didReset =
+          await params.resetSessionAfterRoleOrderingConflict(message);
         if (didReset) {
           return {
             kind: "final",
@@ -457,7 +523,8 @@ export async function runAgentTurnWithFallback(params: {
         try {
           // Delete transcript file if it exists
           if (corruptedSessionId) {
-            const transcriptPath = resolveSessionTranscriptPath(corruptedSessionId);
+            const transcriptPath =
+              resolveSessionTranscriptPath(corruptedSessionId);
             try {
               fs.unlinkSync(transcriptPath);
             } catch {
@@ -507,6 +574,7 @@ export async function runAgentTurnWithFallback(params: {
     fallbackModel,
     didLogHeartbeatStrip,
     autoCompactionCompleted,
-    directlySentBlockKeys: directlySentBlockKeys.size > 0 ? directlySentBlockKeys : undefined,
+    directlySentBlockKeys:
+      directlySentBlockKeys.size > 0 ? directlySentBlockKeys : undefined,
   };
 }