OS X repeatedly stops syncing contacts and calendar with Gmail For what feels like forever (but is probably only a year or two), OS X constantly ‘loses’ my Gmail password. This is particularly annoying, because I use two-factor-authentication with my Google account, and have to go generate a new password every time I see this bug:



Even worse, I don't know there's any problem until I actually open the Contacts application (a thing I never do). I'll get text messages on my Mac, and wonder who the hell's messaging me, because it'll show up as a phone-number; meanwhile, I created a new contact for that person months ago on my iPhone, and it turns out Google hasn't synced to my computer in that entire time.

I clear all the Google/Gmail entries out of my keychain, generate a new one-use password with Google, and put it in OS X, every time I see this. It just happens again a couple months later.

Does anybody know what could be causing this?
Usually an easy fix is to remove the google account from your mac all together so that all info is taken off. Then re-add the account from scratch, it should resync everything and this usually stops it constantly asking for the password.