Aheadset assembly after overhaul problems
 

Overhauled my 90's Aheadset on my Manitou fork and I am having trouble getting it assembled. The compression ring is my problem. It doesn't seem like it wants to fit. Every time I feed the steering tube up from the bottom, the compression ring comes part way out. If I try to put the stem on and tighten things up, the headset just gets very tight. What am I doing wrong? Thanks to anyone who can help me,
.

Usually you remove the compression ring and reinstall it before putting the top cap on.
Is it cartridge bearings or just caged bearings? Usually that is a sign that you have a caged bearing upside down.

+1
Double check your bearing orientation and then slide the compression ring (I am assuming you are referring to the centering cone) on after you have inserted the fork. Take the upper cover and flip it over or use a headset spacer slid over the steerer tube to help press the compression ring down to seat it into position then remove the upper cover/spacer and proceed with installation as normal.

-j

I tried pressing the compression ring into the upper bearing with no success. The sealed bearings are oriented with smooth side out. I ended up fitting the compression spacer into the top cap and then that seemed to work. Didn't know what else to do.

If you are still unsure/concerned about the assembly, I would recommend uninstalling everything except the cups and the fork crown race. Then do a dry fit reinstall to see if you can get things to go together properly. Look to see if the upper and lower bearings are identical or if one is smaller than the other. Double check to make sure all parts are oriented correctly. If you have a model/part number perhaps you can google a tech document showing details of installation orientation. Or perhaps open it back up and take some pictures so we have an idea what you are working with.

-j

Some desings call precisely for that. The top cap is conical and the ring engages that with the cap, and not the ring pressing the bearing. If you're still unsure remove the top cap and ring and look at the cap's ID. If it's sloppy on the steerer or at all conical, that's where the ring goes.