diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 4a9261c4..703c3d59 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -8,6 +8,7 @@
 
 ### Fixed
 
+- Fixed auto-retry for Anthropic streams that end before `message_stop` ([#4433](https://github.com/earendil-works/pi/issues/4433)).
 - Fixed theme sharing across package scopes so extensions do not crash with `Theme not initialized` ([#4333](https://github.com/earendil-works/pi/issues/4333)).
 - Fixed keybinding hints to show Option instead of Alt on macOS ([#4289](https://github.com/earendil-works/pi/issues/4289)).
 - Fixed the interactive update notification to render the changelog as an OSC 8 hyperlink when the terminal supports hyperlinks ([#4280](https://github.com/earendil-works/pi/issues/4280)).
diff --git a/packages/coding-agent/src/core/agent-session.ts b/packages/coding-agent/src/core/agent-session.ts
index 4985779f..9868e8a6 100644
--- a/packages/coding-agent/src/core/agent-session.ts
+++ b/packages/coding-agent/src/core/agent-session.ts
@@ -2419,8 +2419,8 @@ export class AgentSession {
 		if (isContextOverflow(message, contextWindow)) return false;
 
 		const err = message.errorMessage;
-		// Match: overloaded_error, provider returned error, rate limit, 429, 500, 502, 503, 504, service unavailable, network/connection errors (including connection lost), WebSocket transport closes/errors, fetch failed, request ended without sending chunks, HTTP/2 closed before response, terminated, retry delay exceeded
-		return /overloaded|provider.?returned.?error|rate.?limit|too many requests|429|500|502|503|504|service.?unavailable|server.?error|internal.?error|network.?error|connection.?error|connection.?refused|connection.?lost|websocket.?closed|websocket.?error|other side closed|fetch failed|upstream.?connect|reset before headers|socket hang up|ended without|http2 request did not get a response|timed? out|timeout|terminated|retry delay/i.test(
+		// Match: overloaded_error, provider returned error, rate limit, 429, 500, 502, 503, 504, service unavailable, network/connection errors (including connection lost), WebSocket transport closes/errors, fetch failed, premature stream endings, HTTP/2 closed before response, terminated, retry delay exceeded
+		return /overloaded|provider.?returned.?error|rate.?limit|too many requests|429|500|502|503|504|service.?unavailable|server.?error|internal.?error|network.?error|connection.?error|connection.?refused|connection.?lost|websocket.?closed|websocket.?error|other side closed|fetch failed|upstream.?connect|reset before headers|socket hang up|ended without|stream ended before message_stop|http2 request did not get a response|timed? out|timeout|terminated|retry delay/i.test(
 			err,
 		);
 	}