When a Reply Fails
Sometimes a reply doesn't land. The AI provider behind your chat has a bad minute, a request is too big to send, or the server drops it before your Chief of Staff ever sees it. When that happens you get a card explaining what went wrong instead of a half-finished answer.
Your message is never lost. It's still in the conversation, and Edit & retry puts the text back in the box so you can change it and resend.
What the card tells you
It names the actual problem. "That took longer than expected" is a different situation from "That message is too large to send" or "That request didn't get through", and each one has a different fix. The card says which one you hit.
Try again is a real second attempt, not a repeat. Each retry is routed to a different connection than the one that just failed, so a provider having a bad moment usually clears on the first tap.
It stops offering retries once they stop helping. After two, the card tells you so instead of letting you tap forever. It also doesn't show a retry button at all for problems retrying can't fix — an attachment that's over the size limit, a scanned PDF with no readable text, or an expired session.
Long chats get a different button. If the conversation itself has grown too big to send, the card offers Summarize older messages & continue instead. That folds the older part of the thread into a summary and keeps you going in the same chat.
What to do if it keeps failing
- Tap Try again once. Most single failures clear right there.
- If the second attempt fails the same way, switch models in the picker under the message box — a different model routes through different infrastructure. See Models.
- Still failing? Start a new chat and paste your question in. A conversation can pick up a state that keeps breaking every reply in it; a fresh one won't have it.
- If the card says your session expired, reload the page to sign back in. Your chat is saved.
If a reply starts repeating itself
Your Chief of Staff checks its own replies while it writes them. If one starts looping — repeating a phrase, or tacking the same bracketed label onto sentence after sentence — it stops that reply and writes it again from the start, in the same message. You'll see a short line saying so, and the new answer replaces the broken one. You don't need to tap anything.
If the rewrite fails too, you get the usual note with a Try again button. Once a chat has looped like that, the rest of the conversation is answered on a steadier setup, so it doesn't keep happening in the same thread. Your CoS also won't save a document whose text repeats a label like that; it writes a clean version first.
If a reply stops mid-sentence
That's a different thing, and it isn't an error — the reply hit its length limit. You'll see a Continue button on that message instead of an error card. Tap it and your Chief of Staff picks up exactly where it stopped, in the same reply. Don't re-ask the question; you'd get the answer from the top again.
If you only do one thing today: when a chat starts failing every reply, stop tapping retry and switch models. That fixes it far more often than a third attempt does.