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You mean the sealing ring on the bottom of the headset cover? If it's flapping around, it might bind up and cause a bit of drag, but probably not enough to notice. The loss of a good seal at the point seems to be a non-issue if you have cartridge bearings with their own seals, unless you spend a lot of time riding underwater.
gbj_tester
Witts
The rubbery bit that sits at the bottom of the spacers before they meet the frame on my steerer tube is a little bit pushed out / loose - is this a major problem?