I already sent the draft myself, but the lead still says "review and send"

You sent those drafts yourself, hours ago, and the desk still lists them as work you owe. The performer who first reported it put it exactly: "13 library leads still said next action: review and send, but those drafts went out this afternoon." If your version of it is leads still say review and send after I sent them, or simply the app doesn't know I already sent it, you are in the right place. He also said the part that matters most: "I want to make sure that I'm not missing a step, or that you're not programmed wrong." You were not missing a step. This one was ours, and it has been fixed. Below is what was happening, the one line that clears stuck leads today, and the single setup requirement the fix depends on.

Why is that happening?

A lead record only ever knows what Otto has actually written onto its lines. Booked Solid has no Send button for your mail, on purpose: Otto drafts, you send. But the app also does not watch the Send button in your Gmail. So when you sent that batch of drafts from your own inbox, nothing told the app it had happened. Each lead kept the last thing filed on it, Review and send, and it stays that way until Otto next re-reads those threads, sees the message left, and moves the lead on.

Before version 1.11.14, nothing caught that lag automatically. Not a patrol, not the app. The line sat there until you noticed it yourself. That was a real gap in the product, not a mistake in your setup.

What a stale "review and send" can and cannot cost you

This is the part that decides whether you should be worried, so here it is plainly. The mistake is a lead showing as still-to-do when you already did it. It is a nag, not a wrong action.

Otto cannot send anything at all. The worst a stale line can produce is Otto later drafting a nudge on a thread you already handled, and that nudge still lands as a draft in front of you, where you would catch it as already sent. It never becomes a wrong message to a buyer, a wrong date on a contract, or a dollar moved. Annoying, yes. Dangerous, no.

Clear the stuck leads right now (works on any version)

1. Open a chat with Otto.
2. Tell him, in your own words: "These already went out - re-read those threads and bring the leads up to date."

He re-reads the threads, sees the sent messages, and advances those leads off review and send. This works no matter which version you are on, and it is still the fastest way to clear a batch that has been sitting for weeks.

The permanent fix: sent detection, version 1.11.14 and newer

On each inbox sync, the app now also reads your Sent mail. When it finds a message you sent to an address one of your leads knows, and that lead's next action reads as a send you still owe, it marks the outreach sent for you.

• The lead's next action flips from something like Review and send the proposal to Sent by you on 2026-07-25 - watch for their reply.
• One dated line goes into that gig's log recording exactly what was detected, in the form Detected in your Sent mail: "Proposal for the library event" to booking@example.com; marked the outreach sent. So you can always see why a lead moved.
• Nothing is deleted and no other field on the record is touched.
• Running the sync again changes nothing. A message already recorded against a lead never fires a second time.

You do not have to wait for the next automatic pass. Open the Connections tab, scroll to Mail & calendars, and click Check now next to Email accounts to run a sweep on demand.

Worth saying how this was checked before it was announced, because trust is the whole point here: a real message was sent to a lead's address from that account's own Gmail, a sync was run, and the lead was watched flipping to the sent state with its log line. Then the run was repeated to confirm a second pass changes nothing.

The requirement nobody would guess: the inbox must be connected the direct way

Sent detection reads a Sent folder, which means it only works on inboxes the app can open by itself:

• Gmail, or any other mailbox, added by Any email (IMAP). For Gmail that means a Google app password.
• Microsoft 365 connected by device-code sign-in.

If your Gmail rides only on the claude.ai link, sent detection cannot work at all, and no amount of resyncing will change that - there is no Sent folder for the app to open. Almost everyone tries another sync first when nothing flips. On a claude.ai-linked Gmail that is a dead end. Skip it and connect the inbox properly instead: Connections > Mail & calendars > Add an email account, method Any email (IMAP), with a Google app password. You get sent detection and the more reliable Gmail path in one move. The full walkthrough is in Connect your Gmail with an app password (step by step), and the Outlook side is in Connect Outlook and desktop mail (Microsoft 365).

Two more of the connection methods cannot do it either, and it is better you know now than wonder later: Any email (POP3) has no folders to read, and Outlook app on this computer reads only your inbox.

Why some leads still will not flip, on purpose

Sent detection is deliberately conservative. A wrong flip would hide work you still owe, so when anything is unclear it leaves the card for you. These cases are the design working, not failures to report:

• The next action has to read as a send you owe. Review and send the proposal or Re-send the quote qualify. Follow up with Dana does not, because there is no send wording in it, and it will not auto-flip even when a matching send is detected.
• Hedged or conditional wording is left alone too. A next action that says wait, hold, not yet, or once or until something else happens is never flipped by a detected send.
• The address you sent to has to already appear on the lead record. If you wrote to a colleague's address the lead has never mentioned, nothing connects the two.
• Only recent mail is read: roughly the last two weeks, and up to fifty messages per inbox per pass. Leads that went stale months ago will not move on their own, so use the one line to Otto above for those.
• An inbox tagged with the personal purpose is not read at all. Personal mail stays private and is never filed, so nothing sent from it can advance a lead. If your booking inbox is tagged personal, edit the account under Mail & calendars and set its purpose to bookings.

The other half of the same update: counts you can check

The same release changed how Otto reports numbers. When he tells you how many leads are due, he now quotes the desk's own computed list rather than counting in a sentence, so the number in chat and the number on your board can no longer disagree. If you ever see them differ again, that is worth a ticket.

If it still does not work

1. Check your version. Click Check for updates in the top bar; you need 1.11.14 or newer, and installing takes one Restart & install click.
2. Confirm the inbox in question is connected by IMAP with an app password, or by Microsoft 365, and that it is not tagged personal.
3. Run Check now under Mail & calendars and give it a moment to finish.
4. Open the lead and read its next action wording. If it does not name a send, that is the conservative rule above, and clearing it by hand or telling Otto is the answer.

If a lead whose next action clearly says review and send, to an address that is on the record, still has not moved after a Check now on a directly connected inbox, we want to see it. Submit a ticket from this help center with the lead's name, the address you sent to, and the date you sent it, and we'll take it from there.