Gmail shows Linked but drafts stopped working: how to relink

Created by Ziv Raviv, Modified on Sat, 11 Jul at 6:53 PM by Ziv Raviv

Your Gmail card on the Connections tab says Linked, but when Otto tries to draft an email it fails. This article explains why that happens and how to get drafts working again in a couple of minutes.

Why "Linked" does not mean "working right now"

Gmail, Google Calendar, and Google Drive are connected through your own claude.ai account connectors, not through a key you paste into the app. The dim Linked badge means the account was linked at some point. It is never checked live. So the badge really says "linked before", not "working now".

That link can go stale on Google's side. When it does, the badge still reads Linked, but a draft fails. The Gmail card itself warns about exactly this: "Linked before, but not checked live - if a draft fails, choose Manage and relink Gmail; restarting does not reconnect it."

The Connections screen showing connector cards with their status badges

How to relink Gmail

Open the Connections tab and find the Gmail card.
Choose Manage. This opens your connector settings at claude.ai/settings/connectors.
Relink Gmail there, following the prompts on the claude.ai page.
Come back to Booked Solid and ask Otto for the same draft again.

Do not bother restarting the app first. The connection lives in your claude.ai account, not inside Booked Solid, so restarting does not reconnect it.

How to confirm it works again

The link is only proven when it is used. So the real test is the task that failed: ask Otto to draft that email again. If the draft goes through, you are relinked. The badge itself is not the proof, because it is never checked live.

Good to know

The Gmail connection is on-demand only. It does not watch your Gmail in the background. If you want Booked Solid to listen to an inbox automatically, add that inbox under Accounts instead.
The same applies to Google Calendar: the linked account is not a background calendar feed. For automatic conflict checks, add its private calendar link under Accounts.
Google Calendar and Google Drive use the same claude.ai account link, so if one of them fails the same Manage and relink fix applies.

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.

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