Nothing in my Sent mail after Otto "sent" it: Otto only ever writes drafts

You asked Otto to handle a reply, he came back and said it was taken care of, and then nothing appeared in my sent mail. You went looking a minute later and I don't see it in my sent folder either. Or you never got that far, and the question is the simpler one: will Otto send the email for me? Here is the whole answer in one line, and it is worth reading before you troubleshoot anything: Otto never sends email. He writes drafts. An empty Sent folder after a test is the system working correctly, not a failure.

What a successful test actually looks like

A working test is a draft quietly appearing in your Drafts folder. There is no banner, no confirmation screen, no green tick, and nothing lands in Sent. That is the single thing to know before you run a test, because support has had to say it in advance every single time: without it, a perfectly healthy run reads like a broken one, and people report a failure that never happened.

So the habit to build is the one customers land on themselves once they see it work: check my drafts folder, not my sent folder.

Otto does tell you in the chat. His confirmation names the inbox the draft landed in and says in the same breath that it has not been sent. If his wording read to you as it says it emailed them but I can't find it, read the message once more. He is almost certainly telling you he prepared it, not that it went out.

There is no send button, and no setting that adds one

If you have been over the connection screen twice thinking there's no send button and you must have missed it somewhere: you have not missed it. It does not exist, on any mail path, and that is deliberate.

• Gmail by app password (the supported Gmail path): Otto gets exactly four abilities on that connection. Search your mail, open one message, create a draft, create a reply draft. There is no fifth one.
• Microsoft 365: the sign-in asks Microsoft for permission to create drafts (Mail.ReadWrite) and deliberately never asks for permission to send (Mail.Send). The app does not hold the ability to send at all. See Microsoft 365 by device code: what Otto can and cannot do in Outlook.
• Outlook on your desktop: same ceiling. A draft lands in Outlook's own Drafts folder at every access level, and sending stays with you in Outlook.

The outgoing server field is not a loophole either. When you fill in an outgoing server such as smtp.gmail.com on port 465, that server is verified so the account record is complete, and then never used to send anything.

In Settings > Permissions, the widest access any tool can be given is Read & write, and there is nothing above it. For a mail tool, write means write a draft. It has never meant send. More on that screen in Settings > Permissions: how far each connected tool can reach.

Does Otto send emails automatically? No, and the autonomy dial does not change it

The worry underneath most of these tickets is really does Otto send emails automatically while you are asleep or away from the desk. He does not. There is no auto-send at any setting, and no position on the autonomy dial changes it: not Show me, not Check with me, not Run it, and not Fully Autonomous Booking. Autopilot and the morning sweep are bound by the same ceiling.

If you have read elsewhere in this help center that certain routine touches are allowed to go out on their own, that describes the app's automation permission model in general. For email it changes nothing, because no email connection in Booked Solid has a send tool for it to use. Every email touch, in every play, at every dial position, stops as a draft in your own mailbox. Where anything in the help center reads otherwise about email, this article is the correct one.

Where the draft actually is, path by path

Gmail connected with an app password

1. Open Gmail in your browser.
2. Click Drafts in the left rail.
3. Look for the reply Otto wrote. It is the newest draft on that account.
4. Read it, edit anything that is not in your voice, and press Send yourself.

If you have more than one inbox connected, Otto names which one he acted in, so you can confirm the right persona did the work before you open anything.

Microsoft 365 and desktop Outlook

The draft lands in Outlook's own Drafts folder, on the account you signed in with. Open Outlook, open Drafts, review, send.

Any other inbox: your own domain, iCloud, Fastmail

The draft lands in that account's own Drafts folder, which you open in whatever mail app or webmail you normally use for that address.

Having Otto check your Sent folder for you

Customers asked for this one and it works on the direct app-password Gmail connection: Otto can search your Sent Mail as well as your inbox. When the question is did it actually send, usually because you pressed Send by hand and want your records to agree, ask him in plain words, for example: "check the Sent folder on my Gmail app-password connection and tell me if it went out."

This works on the direct app-password connection. It does not work on the old claude.ai linked-account Gmail path.

You often will not need to ask. The app's own inbox sync reads your Sent folder too, and when it finds a message to a lead you owed a reply to, that lead's next action changes to say it was sent by you on that date and to watch for their reply.

Why it is built this way

Otto drafts, you send. He never emails a client, commits to a date, or quotes a price on his own. That one rule is what makes the rest of the app safe to leave running: a mistake in a draft is a sentence you fix before anyone sees it, never a message a buyer already received.

If no draft appears at all

That is a different problem from the one above, and worth separating. If your report is I ran the test and nothing happened and the Drafts folder really is empty, it is almost always one of these five.

• The Gmail card says Linked but drafting keeps failing. Almost everyone tries relinking Gmail on claude.ai first, and it is a dead end. The badge can read Linked while drafting fails, and reconnecting there buys you a few minutes at most. Skip that step. Move the inbox to Any email (IMAP) with a Google App Password: Gmail shows Linked but drafts stopped working: switch to an app password and Connect your Gmail with an app password (step by step).
• Check it is green, but Otto says the Gmail tools are not available in this conversation. A connection added or switched on part-way through a chat is not loaded in that chat. Click Start fresh and ask again. If a brand new chat still cannot see it, quit Booked Solid completely (close the window, not only the chat) and reopen it.
• Otto reports "reconnect Gmail" or "invalid grant" even though the password test passed green. Builds before 1.11.5 shipped without the Gmail tool programs inside them, so no amount of correct setup could work. Update to the newest build, then Start fresh.
• Otto says the Drafts folder does not exist. Mail hosts name that folder in your account's own language (Concepten in Dutch, for instance), and older builds looked only for the English name. Fixed for Gmail in 1.11.32, and for every other mail host (your own domain, iCloud, Fastmail) in 1.11.33. Update, then Start fresh and retest.
• Microsoft 365 drafts stopped short after you enabled drafts later. Microsoft fixes the permissions at the moment you sign in, so a sign-in made while the connection was read-only has no draft permission. Sign out of Microsoft on the card and sign back in.

If it still does not work

Email bookedsolid@kivimedia.freshdesk.com and a person will help. Four things make it fast: which mail path you are on (app-password Gmail, Microsoft 365, or another IMAP inbox), Otto's reply copied word for word, what Check it says on that account, and your version number, which is the line reading "You're running Booked Solid ..." in Settings under Updates.

Prefer a fully managed experience? Booked Solid OS runs on your computer and you stay hands-on. If you would rather have this handled for you on a hosted platform (lead finding, follow-ups, email sending, invoicing, all managed in one place), take a look at KM Hub from the same team.