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Quick Assign Is Glitched And It Happens In A Random Chance.  I Checked They Are At My Fleet  I'll send a video later this day

The quick assign issue is a known issue. Try to avoid it for now. You have two different options to schedule flights:
Using the airliner icon next to the route, or selecting routes -> airliners in the menu.

We will rethink how we handle the auto scheduler for TAP NG.