I put the headgear on as soon as my ears feel tender or if I'm rolling against somebody that I know to be a rough spaz. It does a great job staying in place and my ears couldn't feel any safer. Even when they are tender, red, and warm I know I they won't get damaged while I wear these. The problem is that they do kind of a weak air choke sometimes. I don't have them choking me when I put them on but I think the nature of rolling just causes them to tighten up a bit. It's not really a big deal but between my mouth guard and my headgear it can make a difference in my breathing. I spoke a friend that uses the same kind and he said he gets the same thing. Is that just the nature of headgear or would another brand work better? I use these.