I am Delta PM and I usually book my flight within the 5 day upgrade window.

Whenever I book outside the window, such as 2 weeks in advance, my upgrades to and from CLE clear at the window T-5 (nearly always). If I book at say T-4 nothing clears until the gate.

Its weird because there will be 14 unselected FC seats open on booking (T-4), and then at T-3 several seats will fill up, then at T-24, a few more fill up. Its as if booking inside the window "bypasses" platinum status for confirmed upgrades.

Like I said, I usually get upgraded at the Gate Ex CLE because there's very few DMs here. Most of my connecting flights I miss the upgrade on though.

Does anyone else experience this?