I cannot imagine stuffing a wet, dirty tent into my pack! If the tent bag is too small, just replace it with a larger sack, or at least use a plastic garbage bag. Or just get a large square of waterproof rip-stop nylon and roll the tent in it like a burrito.

I have read that it is better to roll up a tent if it is made of certain coated fabrics. Repeated stuffing causes the waterproof coating to break down sooner. I recall that sil-nylon does not have this problem, but many other light tents are made with fabric that is better rolled than stuffed.