Yep, annoying. Do you have 2-step on If youre using an app password, it may be the cause.

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And for some reason, the password for the gmail account doesnt appear to be saving in the keychain.

The gmail account password box pops up on a regular basis asking me to input my password, because it cant connect.

Once I provide my password, everything is fine for a while, and then the process repeats itself.

I have also made sure to check the prevent sleep option for Outlook.

I tend to get a lot of too many simultaneous connections error which prompts a password re-entry in Outlook.

I had to set the account back up today, and havent had the problem, yet.

Although, I had this error numerous times just trying to set the account up.

The server for account Gmail returned the error ALERT Too many simultaneous connections.

Failure). Your usernamepassword or security settings may be incorrect.

Would you like to try re-entering your password That is the other error message I am getting.

After 5 times or so after hitting escape, it doesnt come for a while.

Alternatively, is it set up via pop or imap imap works better imo.

How To Connect A Gmail Account With Own Domain To Outlook 2011 For Mac