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I was able to install the lower race without issue, but I cannot seem to get the upper one installed. I am installing a new threaded headset on a newly painted bike. There is no new paint blocking the surface. I do not have any professional tools for this installation, just a hammer and a block of wood.

Is there any trick to getting it in there or do I need to have my LBS ream it out?

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Describe specifically what problem are you having: is the upper race entering sideways or twisted? is it going partially and then blocking? Is it not entering at all? – heltonbiker Apr 3 '12 at 17:28
It is entering then blocking, once blocked it will start to go sideways if pushed further. – Carson Reinke Apr 3 '12 at 17:34
UPDATE I was able to get the race in, it required using a Dremel tool on the head to smooth it out a little, than used the home made press. – Carson Reinke Apr 6 '12 at 14:01
up vote 3 down vote accepted

I think you should use the "recommended" way to do that (even if that means using a home-made solution:

  1. Find two plates (wood, metal) which you can drill a hole through;
  2. Put each one of these (already drilled) plates on each end of the head tube, with the cups already positioned for insertion;
  3. Insert a long bolt or threaded rod through it all;
  4. Insert two nuts on each end, and press the system together, so that the cups are forced inside the frame in the proper position.

If you have a wise bench bench vise, you can do the same, but I would recommend using the plates too (not the raw jaws of the vise).

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Great suggestion, should I remove the lower cup and reinstall this way? – Carson Reinke Apr 3 '12 at 18:20
No, it is not needed to remove the lower cup. Good luck (and don't forget to accept the answer if you feel like it :o) – heltonbiker Apr 3 '12 at 18:22
It's possible that there is damage to the cup from your original attempt to install it. I hope not, but check it before ou try again. – zenbike Apr 4 '12 at 3:17
Great idea, unfortunately, the race is just too big, I am going to have to figure out something else. – Carson Reinke Apr 5 '12 at 12:15

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