"Linked" or "couldn't confirm" doesn't mean broken: what each Connections badge means, and how to really test a connection

You open the Connections screen, the badge next to a connector looks fine, and the thing still will not work. Or the exact opposite: everything is working and the badge looks alarming. People write to us in almost the same words every week: "In the app is says linked...I looked at the settings and seems to be fine. Maybe I'm missing something here but please help", or "Email is working even though the message next to the tab says it can't confirm". Or, in the shortest version of all: it says connected but Otto can't see it. You are not missing a switch. A Connections badge is a history record, not a live test, and it can be wrong in both directions. This article explains what each badge really promises, what couldn't confirm means, and the two ways to find out for real.

The badges, and what each one actually promises

• Connected (green): the app checked for a live presence on this computer right now, and the check passed. This is the strongest badge, and the only one that is evidence of anything happening this second.
• Key saved (amber): a key for this service is in the app's encrypted vault. The key has not been tested against the service yet. It is proven the first time Otto actually uses it, so a saved key can still turn out to be expired or wrong. Account-based connectors show Login saved instead of Key saved, but it means the same thing.
• Linked (dim): the connection lives at the account level, not on this machine, and it has never been checked live. The badge means "this was linked at some point", nothing more.
• Can't tell from here: this computer holds no record of your account's connectors at all. That is completely normal if you linked them on claude.ai in a browser. It does not mean they are off, and it is not a fault.
• Not yet: nothing is set up for this connector.

Only Connected is a statement about right now. Every other badge is either a note about the past or an admission that this computer cannot tell.

"Couldn't confirm" is not a failure

The full wording is "couldn't confirm - Otto checks when it uses it", and it worries people far more than it should. It is an unproven state, not a broken one.

The app deliberately refuses to flash a green "working" badge for a connection until it has actually watched that connection succeed. Until Otto sends or reads a message through it, it says couldn't confirm rather than claiming something works that it has not tested. That is the app being careful with you, not the app reporting damage.

If your mail is going through, that is the proof. Mail arriving in your inbox and drafts landing in your Drafts folder are a far stronger signal than any badge in any app. Nothing needs fixing, nothing needs reconnecting, and as Otto keeps using the connection the label settles on its own.

One warning worth taking seriously: do not remove and re-add a working email account because of this label. You will spend twenty minutes generating a fresh app password to arrive back at exactly the same wording, because the wording was never about your password.

Why "Linked" is not proof either

Linked means only that you linked that connector at some point. It is a has-ever-been-linked record read out of your account, and the app never checks it live. So Gmail, Google Calendar or Google Drive can sit there reading Linked while Otto genuinely cannot use them right now. Gmail is where this bites hardest: the card says linked but Otto tells you he cannot see your inbox, or asks you to reconnect Gmail, and nothing on the Connections screen agrees with him.

Almost everyone's next move is to go hunting through Settings for a switch that turns the connection properly on. There is no such switch, and the badge is neither proof of connection nor proof of disconnection. Skip that step. Disconnecting and relinking on claude.ai over and over is the same dead end wearing a different hat.

Being straight with you: a live check that runs by itself behind the badge is not built yet. Until it is, treat every badge as history and use one of the two tests below to find out what is actually true.

The two honest tests

1. Ask Otto to do the thing

This is the test that settles it, it works on any version, and it needs nothing installed. Open Chat and ask Otto for the actual job:

• "Check my Gmail and show me my most recent booking inquiry"
• "Create a test draft in Gmail"
• "Draft a reply to that inquiry"
• "Check my calendar for next week"

If he does it, you are genuinely connected. If he says he cannot see it, you are not connected, whatever the badge says. That is the whole test.

Calendar needs one extra sentence. "Check my calendar for next week" tests the calendar you saved under Connections > Mail & calendars, not the claude.ai Google Calendar connector. They are not the same thing: the Google connector's tools do not reach Otto, so a Google Calendar sitting at Linked with no calendar saved in the app leaves him with nothing to read, and relinking on claude.ai will not change that. Add the calendar's private ICS link instead. The app's own read-only calendar tool switches itself on as soon as one calendar is saved, and that is what feeds his agenda and the date conflict check.

2. "Check it's live" on the connector card

From version 1.7.19 onwards there is a button that asks Otto directly, right now, instead of reading history. Open the More menu in the right pane and choose Connections (older builds labelled this menu item Connectors), find Gmail, and press Check it's live. It shows Checking... and then answers in plain words:

• working now: Otto can use it this second. Go ahead and ask for the draft.
• needs sign-in again: the sign-in has lapsed and needs redoing.
• off while an API key is in use: an Anthropic API key on this computer switches the account connectors off. Removing the key is the way through, and relinking will not help. Background: Which AI runs Booked Solid? Your own Claude account (API keys are the exception).
• couldn't confirm: the check could not reach a verdict. The app prints the reason in plain words just above the connector rows, for example that Claude timed out. This is still not a failure verdict, so fall back to test 1.

You will find this button on the Gmail card. Calendar and Drive do not carry it, and that is on purpose: their claude.ai tools do not reach Otto yet, so a "working now" verdict there would be a claim the app cannot honestly make.

If you are on an older build, open Settings and scroll to About for your version number. A pre-handover copy (1.7.5 or older) checks the old update server, so it tells you it is up to date while every release passes it by. Installing the current app by hand fixes that for good: The app is stuck on an old version or won't update.

What "Check it" on an IMAP inbox does not tell you

There is a second, differently named button: the Check it test on the email account form under Connections > Mail & calendars. It is not the same thing, and the difference matters.

For an inbox added by IMAP, Check it only confirms that the sign-in is still good. Whether the tool is live for Otto in this session is a separate question. In Otto's own words to a customer who asked: "the app's 'Check it' button confirms the sign-in is still good, but that's separate from whether the tool is actually live for me to use right now."

So a green Check it, a working inbox and Otto saying he cannot reach Gmail can all be true at the same time, and none of them is lying. Settle it with test 1. Every individual Check it error message is explained in Add any inbox by IMAP: app passwords and every "Check it" error explained.

If the ask-Otto test fails

Now you have a real answer, and there is a real fix. For Gmail and Google Calendar, do not chase the link: the linked-account method is not the supported path anymore, and relinking on claude.ai will not make it reliable. Instead:

1. Gmail: add the inbox directly under Connections > Mail & calendars as an Any email (IMAP) account with a Google App Password. Full steps: Connect your Gmail with an app password (step by step).
2. Google Calendar: add the calendar's private ICS link under the same Mail & calendars section. That feeds Otto's agenda and date conflict checks directly.

Once those direct connections are in place, the claude.ai connectors can stay disconnected. One more Gmail note: on app versions before 1.11.5, a packaging bug left the Gmail tool programs out of every installed build, so Otto could keep saying "reconnect Gmail" even when the app-password test showed green. Update the app (1.11.5 or newer), then use Start fresh so a clean session picks up the fixed tools.

Saving a key now switches the tool on

When you paste and save a key on a connector, that key and the tool it powers are treated as one setup step. The service turns on for Otto right away. You do not have to go find a second switch to enable it, and you will not be asked for the same key again. Adopting a key the app found on your computer works the same way.

The reverse is also true: choose Remove key and the tool that needed it is switched back off in the same action.

Tool access: browsing and computer control

Two connectors under Computer + browser cover what Otto can do on your machine:

• Web browsing: switch on Web browsing (Chrome or Safari) under Tool access so Otto can open, read, and research pages in a signed-in window using your own logins. Anything that submits or posts waits for you.
• Control this computer: switch on Control this computer under Tool access. Reading the screen is on by default. Moving the mouse and typing need write permission here plus the operating-system control permission, and Otto never moves money or sends on its own.

Good to know

• A saved key is only ever shown as a masked preview. The full value stays encrypted with your computer's own keychain and is handed only to the tool that needs it, so removing one key never affects the others.
• A saved key counts as usable only if it still decrypts on this machine. After a keychain or computer change, remove the key and paste it again. The service itself is fine.
• A "Needs your decision" card asking you to approve Gmail or Calendar access cannot switch a connection on by being approved. Pressing Review this decision on one of those only drops you back into a chat that asks you to set it up again. Current builds turn that card into a hand-off with an Open Connections button that takes you straight to the right screen; if yours does not offer one, come to Connections yourself and clear the card off the board with the small x in its corner.

If it still does not work

Before you write in, press Copy diagnostics on the Connections screen, just under the Inbox, calendar & files heading. It copies exactly what the app read when it decided these statuses: your app version, whether the account record exists and is readable, which connectors are listed in it, which tools are on this computer, and the result of the last live check. It carries names and flags only, never keys or passwords.

Email bookedsolid@kivimedia.freshdesk.com, paste that in, and tell us two things: what the badge says, and what Otto says when you ask him to do the job. Those two lines together are what let a person answer you properly instead of guessing at your settings.