"Gmail isn't responding" right after I set up a new app password

You finished the app password setup, Otto worked for a few minutes, and then he stopped with something like Well it was working. Now getting [Gmail isn't responding]. So you went back to the account card under Connections, clicked Check it, and it passed - however the connection still checks out as good. Two screens telling you opposite things, on the same day you did the setup. This pattern shows up almost exclusively within hours of creating a brand new Google app password, and it is not what it looks like.

Both screens are right, and nothing needs redoing

A green card reading Connected - the address and password work sitting next to an occasional Gmail isn't responding in chat is not a contradiction, and it is not a broken connection. When a customer sent us exactly those two screenshots together, the answer was that the pair of them is good news: the setup is right, the credential is right, and there is nothing to redo. The "isn't responding" line is a smaller, separate thing - a momentary drop on one call.

Why it works then it doesn't

This is worth understanding before you change anything, because it explains why reconnecting cannot possibly help. On the app password path there is no standing link between Booked Solid and Gmail that could break in the first place. Every single time Otto touches your mailbox, he opens a fresh, short IMAP connection, signs in with the app password, does the one job, and closes it again.

So when Gmail turns away one of those individual sign-ins, Otto has nothing to report except that Gmail is not responding. There is no connection sitting in a bad state waiting to be repaired - the next attempt is a brand new connection, and it usually goes straight through. Working, one drop, then checking out fine two minutes later is exactly the shape of this problem.

The most likely cause when the setup is brand new

If you turned on 2-Step Verification and created the app password today, Google is almost certainly the reason. Google watches new app password sign-ins closely for the first few hours and sometimes turns one away even though the password is completely correct. That is why Check it keeps passing while Otto keeps stumbling: the credential really is good, and Google is being cautious about a sign-in it has not seen before rather than rejecting a bad password.

The fix: confirm Google's security alert

This is the step that actually stops the random drops, and it happens in Gmail rather than in Booked Solid.

1. Open gmail.com signed in as the account you connected - the business address whose app password you created, not a personal Gmail you happen to already be signed into.
2. Look for a Security alert email or banner from Google dated today.
3. Open it and confirm Yes, it was me.

That teaches Google to trust the new connection, and the random drops stop. If there is no security alert sitting in that inbox, there is nothing for you to confirm - move on to the next section and give the new password the rest of the day to settle.

In the meantime, ask Otto again

When Otto says Gmail is not responding, ask him to try again a minute later. Each ask is a fresh call to Gmail, so there is nothing to reset, reconnect or restart on your side. If you want a sanity check while you wait, Check it on the account card is the right one: green means the credential is good.

One thing worth knowing while you are riding this out: Otto can verify a send himself on this path. Ask him to check the Sent folder on the Gmail app password connection and he will search Sent Mail directly, so you never have to guess whether a message actually went out during a wobbly stretch.

What not to do

Almost everyone reaches for one of these first, and every one of them is a dead end here. Skip all four.

• Do not delete and re-add the account. The account is fine, and Check it already proved it. Re-adding it gives Google another brand new sign-in to be suspicious of, which is the opposite of what you want today.
• Do not generate a new app password. The one you have has already passed. A fresh code resets the clock on Google's first-hours caution and puts you back at the start.
• Do not turn 2-Step Verification back off. This is the expensive one. Google only issues app passwords to accounts with 2-Step Verification on, so switching it off takes your app password with it and you would have to do the entire setup again.
• Do not go back to claude.ai to re-approve Gmail. If Otto ever offers you an Approve Gmail card, tap Not now. That card belongs to the old linked-account path, which is a different connection entirely and cannot fix anything on this one. From version 1.9.1 onward, a Gmail inbox saved with an app password IS the Gmail path, and a hiccup on it can no longer bounce you back to that Approve card - the loop was removed by design. If you are still being offered it, you are on an older build. Check your version under Settings > Updates and update from booked.kivimedia.co/download.

Your phone stops accepting the same mailbox

There is a side effect of switching on 2-Step Verification that has nothing to do with Booked Solid but lands the same afternoon, so it feels connected: I can no longer get to the biz Gmail account on my iPhone. I assume it's because we changed it to imap. It was set to Gmail, but it doesn't like my username and password.

The assumption is a reasonable one, and it is wrong, which is good news. Nothing about your Gmail was changed to IMAP. Booked Solid uses its own separate app password, the one you created for it during setup, and connects with that; it did not touch how your phone signs in. What actually changed is on Google's side: once 2-Step Verification is on for a mailbox, a phone mail app that had been signing in with the plain account password no longer gets in, and on screen that reads as the phone not liking your username and password.

Two ways out, depending on how the mailbox is set up on the phone:

• If the phone holds it as a Google account, remove it there and add it again as a Google account. Signing in through Google puts the second step on screen, where you can complete it.
• If the phone holds it over IMAP, give the phone its own app password. One app password per app is the entire point of them, so create a separate one for the phone rather than reusing the code you gave Booked Solid.

The customer who reported this had it sorted himself within a few hours. If your phone will not cooperate, open a ticket and tell us which phone it is and how the account is set up there, and we will walk through it with you.

If it is still dropping tomorrow

The first-few-hours explanation only covers the day you did the setup. If Otto is still telling you Gmail isn't responding a day later, that is a different problem and worth a proper look. Before you write in, collect three things: what Otto said word for word, what Check it reports on that account card right now, and your version number from Settings > Updates.

If Check it itself stops passing at any point, that is a credential problem rather than this one, and every message that button can give you is decoded in Add any inbox by IMAP: app passwords and every "Check it" error explained. If you are not sure your setup was finished correctly in the first place, walk it again with Connect your Gmail with an app password (step by step).

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