"Check it" is green and the Gmail switch is on, but Otto still has no Gmail tools

Otto tells you that "Only the claude.ai-linked Gmail tools are available in this session", and that "the direct app-password Gmail connection (gmail-mcp) is not connected" - even though Connections shows Connected and Gmail (app password) shows ON, and it says the same thing after a restart and Start fresh. You have tested the password, you have checked the switch, and the app keeps telling you both are fine. This article is about that exact contradiction: what causes it, which versions fix it, and how to prove on your own machine that it is fixed.

If you have not connected Gmail to Booked Solid at all yet, skip ahead to Set up Gmail with an app password, start to finish below. This is the full walkthrough as well as the fix.

First: is this really your problem?

Five things have to be true. Check them in this order, because each one rules out a different wrong turn.

• Open Connections > Mail & calendars, find your Gmail account, click Check it, and it comes back green with "Connected - the address and password work".
• On the same tab, under Tool access, the Gmail (app password) card shows a green On badge.
• You have fully quit the app and reopened it, not only closed the window.
• You have clicked Start fresh so the conversation is a brand new one.
• Otto still says the direct connection is missing.

If all five are true, nothing on your side is wrong. Stop testing yourself and go straight to the two causes below.

The same failure has reached us in a lot of different words, and they are all this one thing:

• "the gmail-mcp tools (search_email, get_message) haven't come back after four separate checks this session"
• "I updated the app and when I hit Check It, it said it couldn't confirm"
• One performer wrote in the morning after an update with a single line: "upgraded to 1.10 - It cannot check gmail this morning"
• If your app runs in another language you get the same sentence in that language. In Dutch it reads "de directe app-password Gmail-koppeling (gmail-mcp) is niet aangesloten". The half that matters is gmail-mcp is niet aangesloten.

The good news buried in that message

When Otto names gmail-mcp, or "the gmail-mcp tools (search_email, get_message)", it is naming the direct app-password Gmail connection. That is the reliable path: it works in background and automatic runs, and it never waits for anything to be approved on claude.ai. Its tools are search_email, get_message, create_draft_email and create_reply_draft. So you are set up on the right road. Those tools simply did not load into that session.

Cause 1: the Gmail tool programs were missing from the installed build. Fixed in 1.11.5

On every build before 1.11.5, the small tool programs that give Otto the direct Gmail tools were left out of the installer, no matter what you configured. Otto's session started with no Gmail tools at all, so it fell back to whatever claude.ai-linked Gmail it could see, or reported that the direct connection was not connected. That is also what was behind the older wording you may have seen from Otto, "reconnect Gmail" and "invalid grant", while every check on your side passed. And every signal did keep reading green, because Check it, the On badge and the account card all read your saved settings and your saved password. None of them watched the tool program actually start. From 1.11.5 the installed build carries those programs, and a build check makes this class of miss impossible to ship again.

So here is the blunt part. Almost everyone tries these first, and against this cause every one of them is a dead end: removing and re-adding the inbox, generating a fresh Google app password, switching Gmail (app password) off and on again, disconnecting and reconnecting Gmail over on claude.ai, and reinstalling the app. None of them could ever have worked, because nothing on your side was broken. Skip all of it and update instead.

1. Click Check for updates in the top bar and let the update install.
2. Open Settings and read the Updates section. It names the version you are running. Anything older than 1.11.5 carries this bug for certain, and the later fixes in this article are worth having too, so take the newest version on offer.
3. Click Start fresh so the new conversation starts clean.
4. Ask Otto exactly this: "draft a quick test email to me, use the direct app-password Gmail connection."

The successful result is a draft appearing quietly in your Gmail Drafts folder. Otto drafts, you press send, and nothing goes out on its own. So do not wait for a sent message.

If you were already on a build newer than 1.11.5 when this started, keep reading. The next section is the cause that outlived the packaging bug.

Cause 2: your saved app password could not be unlocked after an update. Fixed in 1.11.13

This one produces the identical symptom for a completely different reason, and it is the one behind "It cannot check gmail this morning" the day after an update. Your Gmail app password is kept encrypted by your own computer. After some updates the app could fail to unlock it, and instead of saying so it started the session with no Gmail at all while the Connections card still showed a green Connected. A false green, and no way to tell from the outside.

Three things changed in version 1.11.13:

• Honest status. If the saved password cannot be unlocked, the card now shows an amber Needs attention instead of a green On, and says in plain words that the saved password could not be unlocked on this machine, that this can happen after an update, and that the password itself is still right. Never a false green again.
• A clear fix path. That same message tells you to open the account under Mail & calendars, enter the app password again, and Save.
• No restart ritual. Every new conversation re-checks and re-registers Gmail by itself, so the old quit-and-reopen habit is retired. Otto picks up a re-entered password from your next conversation.

If you are on an older build and see this, do it in this order:

1. Open Connections > Mail & calendars and open your Gmail account.
2. Re-enter the 16-character Google app password. Google shows it as four blocks of four, but it is really one 16-character string, and the app strips spaces for you.
3. Click Check it and confirm it says the address and password work.
4. Under Tool access, make sure Gmail (app password) is on.
5. Quit and reopen the app once.

Why checking again in the same chat never brought it back

On builds before 1.11.13, Otto loaded its Gmail tools once, when a work session started. If the Gmail connection was not ready at that exact moment, re-checking during the same conversation was wasted motion. It could not bring the tools back, which is why someone could check four separate times and fail four times. Only a full quit and reopen reloaded them. The same timing caught anyone who switched the connection on while a conversation was already open.

Nothing was lost while that happened. Unread mail sits safely in your Gmail the whole time, and nothing was silently missed. From 1.11.13 onward this no longer applies at all: a new conversation is enough.

Set up Gmail with an app password, start to finish

This is the supported way to connect Gmail: an IMAP account secured with a Google App Password. Otto can watch the inbox, draft replies, and always send from the right address. You do not link Gmail on claude.ai for this, and the claude.ai Gmail connector can stay disconnected.

Start here if Gmail will not connect, if it says it cannot connect or keeps failing, if Gmail is not connecting after an update, or if a Gmail inbox that used to work has stopped working. Every one of those ends at the same fix: an app password.

Before you start

• Your Google account needs 2-Step Verification turned on. Google only issues app passwords to accounts that have it, so turn it on at myaccount.google.com/security first if you have not already.
• An app password is a 16-letter code Google generates for one app only. It is not your normal Gmail password, and your normal password never enters Booked Solid.
• If Google says app passwords are not available for you, it usually means your only 2-step method is a passkey or a security key. Add a phone or an authenticator app as a second method and the app passwords page comes back.

Step 1: get your Google App Password

1. In your browser, go to myaccount.google.com/apppasswords and sign in to the Google account you want to connect.
2. Give the app password a name you will recognize, like "Booked Solid", and click Create.
3. Google shows a 16-letter code. Copy it. Do not worry about the spaces Google displays inside it, because Booked Solid strips spaces automatically when you paste.

Step 2: add the inbox in Booked Solid

1. Open the Connections tab and scroll to the Mail & calendars section.
2. Click Add an email account. The method already defaults to Any email (IMAP), so keep it there.
3. Give the account a name you will recognize and pick its purpose tag: bookings, personal, support, or business.
4. Enter your Gmail address, and paste the 16-letter app password into the password field.
5. For a normal @gmail.com address the servers fill themselves in. For a custom-domain Google account (Google Workspace, like you@yourband.com), use imap.gmail.com as the IMAP server and smtp.gmail.com port 465 for sending.
6. Click Check it. The button reads Checking... while it tests, then confirms the sign-in works.
7. Click Save.

That is the whole setup. Saving a new Gmail inbox also switches on the Gmail (app password) tool for Otto automatically, so there is no second switch to go find. And there is no restart step: adds, edits, and removals reach Otto the moment you save them.

Good to know

• Multiple inboxes are welcome. You can add several Gmail or other accounts at once, one per persona, each with its own purpose tag and its own app password. Otto names which inbox it is acting in, so you always know which address is doing the work.
• Fixing a password never means starting over. Every account card has an Edit button. To swap in a fresh app password, edit the account and paste the new code. Leaving the password field blank keeps the saved one.
• If Check it fails with "The mail server refused that sign-in", you most likely pasted your normal Gmail password instead of an app password, or the app password was revoked. Generate a fresh one at myaccount.google.com/apppasswords. Every other Check it error is decoded in Add any inbox by IMAP: app passwords and every "Check it" error explained.

One message that looks like this but is not

If Otto reaches Gmail but the draft itself fails, saying the Drafts folder does not exist ([TRYCREATE] Folder doesn't exist), that is a different bug and a different fix. Gmail names your Drafts folder in your account's own language, so a Dutch account has Concepten and not Drafts, and Otto used to look only for the English name. That was fixed in version 1.11.32: Otto now finds your real Drafts folder whatever it is called. Update and run the test draft again.

If it is still not working on the current version

Then it is ours to fix, and the fastest way to get it fixed is a support bundle from your machine.

1. Click Start fresh and ask Otto for the Gmail work again, so the failure has just happened and is in the logs.
2. Open Settings and scroll to Support logging.
3. Click Generate Support Bundle and choose where to save the file.
4. Reply to your ticket with that file attached, and say which version Settings shows and what Otto said word for word.

If we ask you for more detail, switch on Enable Support Logging in that same section first, reproduce the failure with it on, and then generate the bundle. The bundle collects app errors, system details, safe settings and counts. It does not include your messages, your client details, your passwords, or any saved keys. Two bundles and a pasted transcript are exactly what let us find the real cause of one of these and fix it at the root, instead of trading guesses for another week.

Still stuck? Email bookedsolid@kivimedia.freshdesk.com and a person will help.