My foreskin might be too long to stay retracted without some device be it a glans ring or something to keep it pulled back all the way. I don't have the issue of it rolling forward when I retract but keeping it retracted causes the foreskin that you know rolls up under the head to start to swell.
Does the swelling subside over time?
Evening,
When I use the spoon method I'm pretty well tucked in even at the frenulum but because I leave it tucked in for 3-4 days the area under the frenulum swells up a bit and covering my glans again for a bit makes it go down and I just re-spoon.
Hope this gives you some answer
How long do you keep the glans covered before retracting again?
Usually about an hour? For example if I wake up and its swollen I pull it forward when I get up and keep it forward until I've had breakfast, showered and then retract it when I'm getting dressed