A bit late but I've had 2 old steel bikes that had this problem after removing the original headset cups (flared headtube after removing). Not really sure why but they were both bikes that were not cared for and sitting in a garage for 20 years+
See if the original cups fit or if they're too loose now too. If the head tube is really flared you can use a shim on the new cups, that's what I did and never had any problems.
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