diff --git a/src/lib/streaming-reconnection.ts b/src/lib/streaming-reconnection.ts
new file mode 100644
index 000000000..f406bfa32
--- /dev/null
+++ b/src/lib/streaming-reconnection.ts
@@ -0,0 +1,36 @@
+import { Stream } from '../streaming';
+import { APIError } from '../error';
+
+/**
+ * Wraps a stream with automatic reconnection on timeout.
+ */
+export async function withStreamAutoReconnect<Item>(
+  streamCreator: (offset: number | undefined) => Promise<Stream<Item>>,
+  getOffset: (item: Item) => number | undefined,
+): Promise<Stream<Item>> {
+  let lastOffset: number | undefined = undefined;
+  let currentStream = await streamCreator(lastOffset);
+
+  async function* createReconnectingIterator(): AsyncIterator<Item> {
+    while (true) {
+      try {
+        for await (const item of currentStream) {
+          if (getOffset(item) !== undefined) {
+            lastOffset = getOffset(item);
+          }
+          yield item;
+        }
+        return; // Stream completed normally
+      } catch (error) {
+        if (error instanceof APIError && error.status === 408) {
+          // Reconnect with the last known offset
+          currentStream = await streamCreator(lastOffset);
+          continue;
+        }
+        throw error; // Not a timeout, rethrow
+      }
+    }
+  }
+
+  return new Stream(createReconnectingIterator, currentStream.controller);
+}
diff --git a/src/resources/devboxes/executions.ts b/src/resources/devboxes/executions.ts
index fb5d6661a..316257f72 100755
--- a/src/resources/devboxes/executions.ts
+++ b/src/resources/devboxes/executions.ts
@@ -7,6 +7,7 @@ import * as Core from '../../core';
 import * as DevboxesAPI from './devboxes';
 import { PollingOptions, poll } from '@runloop/api-client/lib/polling';
 import { Stream } from '../../streaming';
+import { withStreamAutoReconnect } from '@runloop/api-client/lib/streaming-reconnection';
 
 export class Executions extends APIResource {
   /**
@@ -153,11 +154,15 @@ export class Executions extends APIResource {
       headers: defaultHeaders,
       ...options,
     };
-    return this._client.get(`/v1/devboxes/${devboxId}/executions/${executionId}/stream_stderr_updates`, {
-      query,
-      ...mergedOptions,
-      stream: true,
-    }) as APIPromise<Stream<ExecutionUpdateChunk>>;
+    const getStream: (offset: number | undefined) => APIPromise<Stream<ExecutionUpdateChunk>> = (offset) =>
+      this._client.get(`/v1/devboxes/${devboxId}/executions/${executionId}/stream_stderr_updates`, {
+        query: { ...query, offset: offset?.toString() },
+        ...mergedOptions,
+        stream: true,
+      });
+    return withStreamAutoReconnect(getStream, (item) => item.offset) as APIPromise<
+      Stream<ExecutionUpdateChunk>
+    >;
   }
 
   /**
@@ -176,11 +181,15 @@ export class Executions extends APIResource {
       headers: defaultHeaders,
       ...options,
     };
-    return this._client.get(`/v1/devboxes/${devboxId}/executions/${executionId}/stream_stdout_updates`, {
-      query,
-      ...mergedOptions,
-      stream: true,
-    }) as APIPromise<Stream<ExecutionUpdateChunk>>;
+    const getStream: (offset: number | undefined) => APIPromise<Stream<ExecutionUpdateChunk>> = (offset) =>
+      this._client.get(`/v1/devboxes/${devboxId}/executions/${executionId}/stream_stdout_updates`, {
+        query: { ...query, offset: offset?.toString() },
+        ...mergedOptions,
+        stream: true,
+      });
+    return withStreamAutoReconnect(getStream, (item) => item.offset) as APIPromise<
+      Stream<ExecutionUpdateChunk>
+    >;
   }
 }
 
diff --git a/src/streaming.ts b/src/streaming.ts
index b056fddf6..49afd291d 100644
--- a/src/streaming.ts
+++ b/src/streaming.ts
@@ -1,5 +1,5 @@
 import { ReadableStream, type Response } from './_shims/index';
-import { RunloopError } from './error';
+import { APIError, RunloopError } from './error';
 import { findDoubleNewlineIndex, LineDecoder } from './internal/decoders/line';
 import { ReadableStreamToAsyncIterable } from './internal/stream-utils';
 
@@ -32,6 +32,18 @@ export class Stream<Item> implements AsyncIterable<Item> {
       let done = false;
       try {
         for await (const sse of _iterSSEMessages(response, controller)) {
+          if (sse.event === 'error') {
+            let error: APIError | Error | undefined = new Error(sse.data);
+            try {
+              const errorObj = JSON.parse(sse.data);
+              error = new APIError(parseInt(errorObj.code), errorObj, errorObj.message, undefined);
+            } catch (e) {
+              console.error('Could not parse error message into JSON:', sse.data);
+              error = new Error(sse.data);
+            }
+            throw error;
+          }
+
           try {
             yield JSON.parse(sse.data);
           } catch (e) {