Just an update to close my post. I wound up rotating the gland ring with a pipe wrench and retried driving it in. After trying a couple small rotations and re-driving attempts, I was successful driving the gland ring in past the groove. Did not apply any heat.
I have a John Deere 250 Skid. Did seals on the right tilt cylinder a few weeks ago. had to really drive it hard but was able to get the gland ring in enough to insert filler and pull out rod. Now the left tilt cylinder is leaking a bit and want to do same to that one. Cannot drive the gland...