There are two Email sections in the app - which one am I supposed to use?

You went looking for the place to plug your email in and found the word Email in two different places. One performer described it exactly: "Here is one place I'm getting hung up. There are two places for Email as far as I can tell. One, the Inbox, Calendar and Files section. This option shows an Open Sign-In Button." Then, a few lines later: "The other place where I see Mail in Connections is in the Mail and Calendars section. Here I attempted to add my email address, but I suspect this is more related to calendar clashes." If you have been going back and forth between the two trying to work out which one is the real one, here is the answer.

They are two different mechanisms, not two routes to the same thing

Neither one is a duplicate of the other, and setting up one does not set up the other. They sit on the same screen, one above the other, which is most of why they look like siblings. Open the More menu in the right pane and choose Connections (some older support notes call this tab Connectors, it is the same tab). Then:

• On that tab the connector cards are grouped by category. One of those groups is Inbox, calendar & files, and the Gmail card inside it is an account connector. It rides your Claude account through a Google sign-in.
• Further down the same tab is the Mail & calendars section with an Add an email account button. That is a direct mailbox connection over IMAP, made with an app password from your mail provider. It has nothing to do with your Claude account.

Different plumbing, different powers. Here is what each one actually buys you.

Place 1: Connections > Inbox, calendar & files > Gmail

This is the account-based one. It does not use an Anthropic API key and it never asks for your mail password. Its button reads Open sign-in, and clicking it opens Claude's own connectors page in your browser, because that is where this kind of connection gets finished.

What it buys you: Otto can read your inquiries and draft replies when you ask him to. That is the whole scope. It is on demand only. It does not watch Gmail in the background, so nothing lands on your desk by itself through this connector.

Two things about its badge, because they cost people hours. Linked is history, not a live check: it means this was linked at some point, nothing more. And a green checkmark next to Gmail on the claude.ai website is not proof either. The one control that actually asks the question is Check it's live on the Gmail card. It puts the question to Otto directly, right now, and answers in plain words: working now, needs sign-in again, or could not confirm.

Place 2: Connections > Mail & calendars > Add an email account

This is a separate connection to the mailbox itself, over IMAP, with an app password. For Gmail that means a Google App Password from your Google security settings, not your normal Google password.

What it buys you, and this is the difference that matters: background listening. The app watches that inbox on its own and surfaces new inquiries to you instead of waiting to be asked. It is also what lets Otto work and send from your own address, and you can add several inboxes with a purpose tag on each, so booking mail goes out from your booking address and personal mail stays personal.

The full walkthrough, including custom-domain Google accounts, is in Connect your Gmail with an app password (step by step).

Side by side

• Reads your inbox and drafts a reply when you ask: both of them do this.
• Watches the inbox on its own and surfaces new inquiries: only the account added under Mail & calendars. The Gmail connector card does not do background listening at all.
• What it signs in with: the Gmail card uses a Google sign-in on your Claude account. The Mail & calendars account uses an app password issued by your mail provider.
• What an Anthropic API key does to it: while a key is active, the Gmail card cannot connect at all. The Mail & calendars account keeps working with or without one.

Which one do I use for email?

If all you want is to open Chat and type "Otto check my inbox" and have him read it and draft something back, Place 1 covers that on its own. You do not need to add an email account under Mail & calendars to make that sentence work.

Set up Place 2 anyway. In practice the account connector has been the least dependable part of email setup: performers have authorized Gmail on the claude.ai site, set its permissions to always allow, watched the checkmark appear, and still had Otto report that Gmail was not connected. The app-password inbox does not depend on any of that, it is the path support walks people through, and it is the only one of the two that gives you background listening. If you only ever finish one of these, finish Place 2.

The dead end: authorizing Gmail on the website and waiting for the card to change

Almost everyone tries this first, and on its own it is a dead end. Clicking Open sign-in takes you to Claude's connectors page. Authorising Gmail there, setting read and write to always allow, and seeing a checkmark appear does not flip the Gmail card inside Booked Solid. The app counts Gmail as connected only once Otto himself has connected it, and that happens through the Approve button that appears in Chat when Otto actually reaches for Gmail. Repeating the website authorization, removing the connector and adding it again, or signing out of Claude and back in will not change the card. Skip all of that.

One version note. On builds before 1.11.12, that sign-in link opened claude.ai's old connectors page, the one that shows a notice saying connectors have moved, and connecting there never reached Otto no matter how many times you did it. That is fixed in 1.11.12 and newer. If your app is older than that, update it before you try anything else.

And once your inbox is connected under Mail & calendars, the Gmail card up top can keep saying Open sign-in forever without costing you a thing. Adding an email account does not change that card, and it is not meant to. Your email works regardless of what that card says.

The calendars in that same section do a different job

The calendar entries under Mail & calendars are not part of the email question at all. They are there so Otto can check booking conflicts: connect a bookings calendar and a personal calendar, and the app warns you when dates collide before you double-book a Saturday. Adding a calendar there does nothing for your inbox, and adding an inbox does nothing for your dates. The details are in Add email accounts and calendars (so gig dates never clash).

If you pasted an Anthropic API key, remove it

This one is easy to miss and it silently switches Place 1 off. Gmail as an account connector runs on a Google sign-in on your Claude account and never uses an API key. Otto always prefers your account login, which is already covered by the Claude plan you pay for. While an Anthropic API key is active, claude.ai account connectors do not load at all - that is by design on Claude's side, not a Booked Solid choice. So a stray key means no amount of relinking will ever bring Gmail through, and nothing in the app will tell you that is why.

1. Open the Connections tab.
2. Find the Claude card under Your AI. That is the AI that runs Otto. Some of Otto's own chat messages call it the Claude Code card, and it is the same one.
3. If it shows Key saved with a masked key, click Remove key.

If the key is set on the computer itself rather than pasted into the app, the same card says so in its own description line, along the lines of "an Anthropic API key is set on this computer, which switches account connections like Gmail off". In that case the key has to come out of your computer's environment variables, not out of the app. Either way, inboxes you added under Mail & calendars are unaffected, because they never touched your Claude account. And if Otto says he is signed out after the key is gone, sign back into Claude. No key needed.

If it still does not work

Tell us which of the two places you set up and what happened at the point it stopped. The most useful things to send: the exact words Check it's live gave back on the Gmail card, or the exact error from Check it if an IMAP account will not save, plus your app version. Submit a ticket from this help center, or email bookedsolid@kivimedia.freshdesk.com, and a person will take it from there.