Breaking in a headset

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After responding to an earlier thread, would it make sense
to "break in" a headset?

I installed a Tioga headset in my old Fuji MTB... the races
were painted and I rotated the fork a couple times (no
cables) to get it loosened up.

My current Giants all have integrated headsets and the
compression ring sometimes wedges in the cartridge bearing
there and the headset gets loose because the top cap isn't
tightened down to compensate for the compression ring
actually moving down.

Has this happened to anyone else? After riding it for a
while the problem goes away, but should one have to break in
a headset?

--
Phil, Squid-in-Training