ITM options are auto-executed at expiration.
But rarely do options get executed prior to expiration, for this reason if none other. The further out in time, and the lower the extrinsic value, the more likely an early exercise.
My own approach with DITM options is that I keep an eye on the extrinsic and roll earlier than something closer to the money. In practice that often looked like rolling options a week before expiration. In these cases I would also roll by at least 2 weeks, and strongly consider 1-12 months (for me, heavy bias towards 1 month at a time). I do the monthly roll instead of weekly for a couple of reasons - I don't have to roll again in a week, and with a 1 month roll I might even pick up enough time value to trade it in for a strike improvement, where 4x 1 week rolls wouldn't.
Deep enough ITM, and I REALLY don't want to be assigned, I've done 1 - 2 year rolls. If nothing else rolling into next year can move the tax impact at assignment if I want to do that.