diff --git a/packages/ui/src/sync/event-pipeline.ts b/packages/ui/src/sync/event-pipeline.ts
index 83741854..331ef9e6 100644
--- a/packages/ui/src/sync/event-pipeline.ts
+++ b/packages/ui/src/sync/event-pipeline.ts
@@ -20,6 +20,8 @@ export type QueuedEvent = {
 export type FlushHandler = (events: QueuedEvent[]) => void
 
 const FLUSH_FRAME_MS = 33
+const BACKPRESSURE_FLUSH_FRAME_MS = 200
+const BACKPRESSURE_MODE_MS = 10_000
 const STREAM_YIELD_MS = 8
 const DEFAULT_RECONNECT_DELAY_MS = 250
 const DEFAULT_HEARTBEAT_TIMEOUT_MS = 30_000
@@ -44,7 +46,7 @@ export type EventPipelineInput = {
 }
 
 type MessageStreamWsFrame = {
-  type: "ready" | "event" | "error"
+  type: "ready" | "event" | "error" | "backpressure"
   payload?: unknown
   eventId?: string
   directory?: string
@@ -254,7 +256,8 @@ export function createEventPipeline(input: EventPipelineInput) {
     const d = getOrCreateDir(directory)
     if (d.timer) return
     const elapsed = Date.now() - d.last
-    d.timer = setTimeout(() => flushDir(directory), Math.max(0, FLUSH_FRAME_MS - elapsed))
+    const flushFrameMs = Date.now() < backpressureUntil ? BACKPRESSURE_FLUSH_FRAME_MS : FLUSH_FRAME_MS
+    d.timer = setTimeout(() => flushDir(directory), Math.max(0, flushFrameMs - elapsed))
   }
 
   const wait = (ms: number) => new Promise<void>((resolve) => setTimeout(resolve, ms))
@@ -269,6 +272,7 @@ export function createEventPipeline(input: EventPipelineInput) {
   let activeTransport: "ws" | "sse" = transport === "ws" ? "ws" : "sse"
   let attemptAbortReason: AttemptAbortReason = null
   let consecutiveFailures = 0
+  let backpressureUntil = 0
 
   const notifyDisconnected = (reason: string) => {
     if (disconnected) {
@@ -489,6 +493,11 @@ export function createEventPipeline(input: EventPipelineInput) {
           return
         }
 
+        if (frame.type === "backpressure") {
+          backpressureUntil = Date.now() + BACKPRESSURE_MODE_MS
+          return
+        }
+
         if (frame.type !== "event") {
           return
         }
diff --git a/packages/web/server/lib/event-stream/global-hub.js b/packages/web/server/lib/event-stream/global-hub.js
index 1bc98abe..86f28b3f 100644
--- a/packages/web/server/lib/event-stream/global-hub.js
+++ b/packages/web/server/lib/event-stream/global-hub.js
@@ -1,6 +1,8 @@
 import { createUpstreamSseReader } from './upstream-reader.js';
 
-export const MESSAGE_STREAM_GLOBAL_REPLAY_LIMIT = 512;
+// Raised from 512 → 2048 to improve recovery after brief disconnects during
+// long-running agent sessions where many events accumulate quickly.
+export const MESSAGE_STREAM_GLOBAL_REPLAY_LIMIT = 2048;
 
 export function createGlobalMessageStreamHub({
   buildOpenCodeUrl,
diff --git a/packages/web/server/lib/event-stream/protocol.js b/packages/web/server/lib/event-stream/protocol.js
index d92ea485..394fa502 100644
--- a/packages/web/server/lib/event-stream/protocol.js
+++ b/packages/web/server/lib/event-stream/protocol.js
@@ -3,7 +3,13 @@ export const MESSAGE_STREAM_DIRECTORY_WS_PATH = '/api/event/ws';
 export const MESSAGE_STREAM_WS_HEARTBEAT_INTERVAL_MS = 15 * 1000;
 // Per-client pending outbound WS buffer, not a payload or stream-size limit.
 // Healthy clients stay near 0; this only trips when a client is far behind.
-export const MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES = 4 * 1024 * 1024;
+// Raised from 4 MB → 16 MB to tolerate bursts during long agent sessions
+// (e.g. ultrawork / multi-tool loops) where the browser briefly falls behind.
+export const MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES = 16 * 1024 * 1024;
+
+// Threshold at which we emit a backpressure warning frame so the client can
+// proactively start shedding low-priority updates before the hard disconnect.
+export const MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES = 12 * 1024 * 1024;
 
 export function parseSseEventEnvelope(block) {
   if (!block || typeof block !== 'string') {
@@ -67,7 +73,9 @@ export function sendMessageStreamWsFrame(socket, payload) {
     return false;
   }
 
-  if (typeof socket.bufferedAmount === 'number' && socket.bufferedAmount > MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES) {
+  const buffered = typeof socket.bufferedAmount === 'number' ? socket.bufferedAmount : 0;
+
+  if (buffered > MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES) {
     try {
       socket.close(1013, 'Message stream client is too slow');
     } catch {
@@ -77,13 +85,36 @@ export function sendMessageStreamWsFrame(socket, payload) {
 
   try {
     socket.send(JSON.stringify(payload));
-    if (typeof socket.bufferedAmount === 'number' && socket.bufferedAmount > MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES) {
+    const bufferedAfter = typeof socket.bufferedAmount === 'number' ? socket.bufferedAmount : 0;
+    if (bufferedAfter > MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES) {
       try {
         socket.close(1013, 'Message stream client is too slow');
       } catch {
       }
       return false;
     }
+
+    // Emit a one-shot backpressure warning when the buffer is building up.
+    // The flag prevents sending repeated warnings that would themselves
+    // increase the buffer.  It resets once the buffer drains below the
+    // threshold.
+    if (bufferedAfter > MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES) {
+      if (!socket._ocBackpressureWarned) {
+        socket._ocBackpressureWarned = true;
+        try {
+          socket.send(JSON.stringify({
+            type: 'backpressure',
+            bufferedBytes: bufferedAfter,
+            maxBytes: MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES,
+          }));
+        } catch {
+          // Best-effort warning — ignore send failures.
+        }
+      }
+    } else if (socket._ocBackpressureWarned) {
+      socket._ocBackpressureWarned = false;
+    }
+
     return true;
   } catch {
     return false;
diff --git a/packages/web/server/lib/event-stream/protocol.test.js b/packages/web/server/lib/event-stream/protocol.test.js
index a3b1417e..ec8c7aaf 100644
--- a/packages/web/server/lib/event-stream/protocol.test.js
+++ b/packages/web/server/lib/event-stream/protocol.test.js
@@ -4,6 +4,7 @@ import {
   MESSAGE_STREAM_DIRECTORY_WS_PATH,
   MESSAGE_STREAM_GLOBAL_WS_PATH,
   MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES,
+  MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES,
   parseSseEventEnvelope,
   sendMessageStreamWsEvent,
   sendMessageStreamWsFrame,
@@ -88,6 +89,73 @@ describe('event stream protocol helpers', () => {
     });
   });
 
+  it('emits a backpressure warning when buffer exceeds the warn threshold', () => {
+    const sentPayloads = [];
+    const socket = {
+      readyState: 1,
+      bufferedAmount: MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES + 1,
+      send(payload) {
+        sentPayloads.push(payload);
+      },
+    };
+
+    const sent = sendMessageStreamWsFrame(socket, { type: 'test' });
+
+    expect(sent).toBe(true);
+    expect(sentPayloads).toHaveLength(2);
+
+    const warning = JSON.parse(sentPayloads[1]);
+    expect(warning.type).toBe('backpressure');
+    expect(warning.bufferedBytes).toBeGreaterThan(0);
+    expect(warning.maxBytes).toBe(MESSAGE_STREAM_WS_MAX_BUFFERED_BYTES);
+  });
+
+  it('does not repeat backpressure warnings while still above threshold', () => {
+    const sentPayloads = [];
+    const socket = {
+      readyState: 1,
+      bufferedAmount: MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES + 1,
+      send(payload) {
+        sentPayloads.push(payload);
+      },
+    };
+
+    sendMessageStreamWsFrame(socket, { type: 'test1' });
+    sendMessageStreamWsFrame(socket, { type: 'test2' });
+
+    // First call: data + warning = 2 sends.  Second call: data only = 1 send.
+    expect(sentPayloads).toHaveLength(3);
+    expect(JSON.parse(sentPayloads[1]).type).toBe('backpressure');
+    expect(JSON.parse(sentPayloads[2])).toEqual({ type: 'test2' });
+  });
+
+  it('resets backpressure warning flag when buffer drains', () => {
+    const sentPayloads = [];
+    const socket = {
+      readyState: 1,
+      bufferedAmount: MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES + 1,
+      send(payload) {
+        sentPayloads.push(payload);
+      },
+    };
+
+    sendMessageStreamWsFrame(socket, { type: 'first' });
+    expect(socket._ocBackpressureWarned).toBe(true);
+
+    // Buffer drains
+    socket.bufferedAmount = 100;
+    sendMessageStreamWsFrame(socket, { type: 'recovered' });
+    expect(socket._ocBackpressureWarned).toBe(false);
+
+    // Buffer spikes again — warning should fire again
+    socket.bufferedAmount = MESSAGE_STREAM_WS_BACKPRESSURE_WARN_BYTES + 1;
+    sendMessageStreamWsFrame(socket, { type: 'again' });
+    const backpressureFrames = sentPayloads
+      .map((p) => JSON.parse(p))
+      .filter((p) => p.type === 'backpressure');
+    expect(backpressureFrames).toHaveLength(2);
+  });
+
   it('serializes event frames with routing metadata', () => {
     let rawPayload = null;
     const socket = {