Why an Anthropic API key on your computer switches off Gmail, Calendar and Drive

Modified on Tue, 4 Aug at 4:34 PM

Your Gmail card in Connections reads Linked, you have relinked Gmail on claude.ai three or four times, and Otto still will not draft an email. Google Calendar and Google Drive sit there with the same stubborn badge. On current versions the app says it out loud: tap Check it's live on that Gmail card and the status line reads "off while an API key is in use - remove the key to use Gmail". If you ever created an Anthropic (Claude) API key and pasted it into the app, or set one on this computer for something else, that key is the reason, and no amount of relinking will get you past it.

The rule, in one sentence

Booked Solid does its thinking on Claude, through your own Claude account. You sign in once during the Get Otto ready setup, and a paid Claude plan powers everything: Claude Pro, about $20 a month, covers most performers, and if you run Autopilot hard every day you may need Claude Max, about $100 a month. No API key is needed and nothing has to be pasted.

When an Anthropic API key is active, Otto runs on the key instead of your sign-in, and the claude.ai account connections - Gmail, Google Calendar and Google Drive - are switched off. Customers ask it in almost exactly these words. If you have an Anthropic (Claude) API key active on your computer, why do Gmail and other account connections stop working? Because that is a rule on Claude's side, not a Booked Solid choice. Those connectors never load while a key is the session credential, and that stays true even if you previously ran /login. Relinking on claude.ai cannot bring them back while the key is there. The key also bills you per use, on top of the Claude plan you are already paying for.

First, check whether any of this applies to you

Most people who land on this article are not actually affected, and it is worth thirty seconds to find that out before you go hunting for a key. An API key only reaches the connections that ride your claude.ai account. It cannot touch any of these:

Gmail added directly in the app as an Any email (IMAP) account with a Google App Password.
Any other inbox added under Connections > Mail & calendars, including Microsoft 365.
Calendars added as a Calendar feed (ICS link), or with the Private calendar sign-in (iCloud / CalDAV).

Those are independent of claude.ai entirely, and they keep working with or without a key. The direct app-password route is also the supported path for Otto's email work. So if your mail is set up that way and something is failing, an API key is not your problem and this is the wrong article: read Connect your Gmail with an app password (step by step), or Gmail shows Linked but drafts stopped working: switch to an app password if you are still on the old linked-account method.

What counts as "an API key"

Three different credentials all put Otto into key mode, and any one of them silently takes priority over your Claude sign-in:

An ANTHROPIC_API_KEY environment variable on your computer.
An apiKeyHelper configured for Claude Code.
A CLAUDE_CODE_OAUTH_TOKEN.

How to check whether a key is active

Start with the fast check. It answers the question outright.

On Windows, open PowerShell and run echo $env:ANTHROPIC_API_KEY. If anything at all prints, that is your culprit. A blank line means no key is set that way.
On Mac, Linux, or in Git Bash, run echo $ANTHROPIC_API_KEY instead.

There is a deeper check if you want to see exactly which credential Otto's engine is running on:

Open a terminal. Booked Solid has one built in: in Chat, switch to Power view. Type claude and press Enter.
Type /status and press Enter. Read the account line: it tells you whether the session is signed in with your Claude account or running on an API key.
Type /mcp and press Enter to list connectors. There may be a Show unused connectors row to expand. Look for claude.ai Gmail. In key mode it is not there.
Type /exit to leave.

Be ready for that second check to be unavailable to you, especially on Windows. The claude command is often not on your PATH, and PowerShell answers with "The term 'claude' is not recognized as the name of a cmdlet, function, script file, or operable program." That is not a symptom of anything and nothing is broken. It means the diagnostic is not available on your machine. Skip it and trust the first check.

One more place the app spells it out, if the key is set in your computer's environment: when your Gmail is listed under Connections > Mail & calendars as a Gmail (linked account) row, tap Check it on that row and you get the whole story: "Linked before, but an Anthropic API key is active on this computer, and account Gmail stays switched off while a key is in use - relinking cannot bring it back. Remove the key, then ask Otto for a harmless Gmail draft."

How to remove the key

The instruction is short. Remove the API key so the app uses your Claude sign-in, then retry the draft. Where the key lives decides how you remove it.

If you pasted the key into Booked Solid

Open the Connections tab.
Find the Claude Code card. When a key is saved on it, the card shows a Key saved badge and a masked preview of the key.
Click Remove key.
Ask Otto in chat for a harmless Gmail draft, ideally the same one that failed, and see whether it goes through this time.

This normally costs you nothing. Otto is account-first and always prefers your account login, and that login is included with the Claude Pro plan you already pay for. Removing the key hands the work back to your subscription and stops the per-use billing in the same action.

If the key is set in your computer's environment

A key living in an environment variable was never saved by Booked Solid, so the Remove key button cannot clear it. It has to come out where it was put in: the environment variables for your Windows user account, or the shell profile file on Mac and Linux that exports it. If you did not set it yourself and cannot find where it came from, send us a ticket rather than guessing at system settings.

The app does tell you when this is the case. With a key in your environment, the Claude Code card reads "Installed - but an Anthropic API key is set on this computer, which switches account connections like Gmail off." Once you have cleared the variable, quit Booked Solid completely and open it again. The app reads your environment when it starts, so a copy that is already running keeps seeing the old key until you restart it.

Do not reach for an API key to get past a different error

This is the trap that creates most of these tickets. If Otto shows you "Your organization has disabled Claude subscription access for Claude Code - Use an Anthropic API key instead, or ask your admin to enable access.", that message is pushing you toward the key route. Take it and you will break Gmail drafting on the claude.ai path, then spend the following week relinking Gmail and wondering why nothing sticks.

Two better ways out of that error, both of which leave Gmail intact:

If that Claude account belongs to an organization you own - including one Claude created on its own for your custom-domain email address - sign in at claude.ai as the owner and switch Claude Code access back on for members. Then quit Booked Solid completely and reopen it.
If it is a work or team account that someone else manages, run Otto on a personal Claude account with its own paid plan instead.

If you need Otto touching Gmail at all, we recommend against the API key. It is a real way to pay for the thinking, and it is the wrong trade for a performer whose email is the whole point.

Does my Claude account have to match my Gmail?

This question arrives in the same breath as the connector problem, every time. One performer put it this way: "Wondering if I should eventually cancel Claude Pro with the frontier email and sign up with the gmail account." Another asked: "As far as signing in on different Claude accounts, I don't believe that I am... but how can I check in Booked Solid?"

The plain answer to does my Claude account have to match my Gmail: no. Keep your Booked Solid licence and your Claude subscription on the same email as each other and leave both alone. The Google account you connect for mail or calendar is a separate thing and does not need to match your Claude login at all. Cancelling or switching Claude accounts to chase a connector problem fixes nothing, and it tangles your licence and your billing on the way.

One thing here genuinely does matter, and only if you are still on the claude.ai connector path: when you authorise Gmail on Claude's connectors page, be signed in there with the exact same Claude account Booked Solid is running under. Gmail authorised under one Claude login while Otto runs under another is a real failure mode, and from the outside it looks identical to the key problem.

As for checking it inside the app: in honesty, there is no screen in Booked Solid today that names which Claude account Otto is signed in with, or lets you switch it. The /status check above is the only reliable way, and only when the claude command is available on your machine. That gap is on us.

Google Calendar and Google Drive: the honest picture

Worth knowing before you lose an evening to it. Even with no API key anywhere on the machine, Google Calendar and Google Drive linked through claude.ai do not reach Otto. Calendar tools are not enabled for him, so that connection can only ever show as Linked and never finishes into anything usable. The app's own note says as much: "Linked before, but Calendar tools are not enabled for Otto yet; add a private calendar link for conflict checks." Almost everyone disconnects and reconnects it several times first, and it is a dead end. Skip that step.

For real conflict checks, hand Booked Solid the calendar's private feed instead:

In Google Calendar on the web, open Settings, click the calendar you want in the left-hand list, and scroll to Secret address in iCal format. Copy that link.
In Booked Solid, open Connections > Mail & calendars and click Add a calendar.
Choose Calendar feed (ICS link), paste the link, and save.

That gives Otto a working view of your dates and sidesteps the connector entirely.

What else lives on the Connections screen

You may see ChatGPT (Codex CLI) and Gemini CLI listed there. Booked Solid's safety checks, the guard that keeps drafts as drafts and never lets money move on its own, run on Claude today, so those assistants cannot carry your booking work yet - the picker marks them "can't run Otto yet". Claude is the one to use. If you prefer a fully local option, Local AI (Ollama) appears in the same assistant list and runs through the same safety checks.

Some optional connections, like lead research tools, are set up by pasting that provider's key on a card here. Two things are worth knowing before you paste anything:

Keys are encrypted in the vault and never shown again. Once saved, the app uses the key on your behalf but will not display it. If you need the raw key later, get it from the provider's key page, not from the app.
The app warns you if secure storage is unavailable. On machines where the vault cannot be used, a banner appears so you can decide whether to proceed. If you see that banner and are unsure, hold off and contact support.

The other half of setup is telling the app how hard to think. Click Advanced in the top bar, use the Assistant select to choose which assistant handles chats and tasks (Claude is the recommended one), and use the Thoroughness select to pick the tier, quicker and lighter or slower and more careful. You can change both at any time. A common setup is low thoroughness for everyday drafting, turned up when the work matters, like a tricky quote or a long client thread.

If it still does not work

If the key check printed nothing, the Claude Code card shows no saved key, and Gmail still will not draft, then a key is not your problem and you should stop looking for one. The next move is to leave the claude.ai path behind and add that inbox directly with a Google App Password, which does not depend on your Claude account in any way.

Still stuck? Email bookedsolid@kivimedia.freshdesk.com and a person will help. Tell us four things and we can usually answer in one reply: what the key check printed, whether the Claude Code card shows Key saved, the exact words Otto gives back when you ask him for a Gmail draft, and the version number shown in Settings.