osx mail not synchronizing with gmail in "outbound" direction

Hey akfromnyc,

We see your Gmail account on your Mac sync changes made from other devices, but not changes made on the Mac itself.

To aid us in isolating this issue, take a look at the Connection Doctor feature built into the Mail app. It will check the status for the inbound and outbound connections for your accounts. If there is an issue, it will display a red dot with the problem vs a green one.

• Use Connection Doctor in Mail on Mac

If Connection Doctor does report an issue, let us know the error you receive.

Cheers!

Some have reported that this sort of thing can be resolved by deleting the GMAIL account entirely from your Mac and then re-adding it again. If all your GMAIL email is all on the GMAIL server, it should then all re-synchronize (including sent and deleted messages). If you have moved some of your Mail or Calendar items to "on my Mac" (local storage), then some care might be needed to avoid losing those when the account is temporarily deleted.