Mail Trash only deletes on second attempt

In Mailbox Behaviors I have 'Move Deleted Messages to Trash mailbox' selected. I also have 'permanently erase deleted messages when Quitting Mail' selected.
Thing is, when I quit Mail and then relaunch Mail, the trash is still there. If I quit Mail and relaunch a second time, the trash will be empty.
This happens 'most' of the time.

Is this an imap account?

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