Do you have to hold the bobbin winder down in order to get it to wind? If so, then the washers around the bobbin winder screw either need replaced or turned around on your Singer Featherweight 221 or 222
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Singer Featherweight 221 222 Repair Video Tutorial - Handwheel
If your Featherweight Bobbin Winder seems loose and floppy then it might just need to have the cupped washer turned around. Replacements can be found
Washer, Cupped for Bobbin Winder
New Bobbin Winder Assembly, Fits:, Singer:, 221 Featherweight, 222 Featherweight, Replaces Original Part Numbers:, 45929, 45859, Includes:, Friction
Bobbin Winder Assembly (New) For Singer 221 & 222 Featherweight
Singer Featherweight 221 and 222K Sewing Machine Parts – Tagged
A Concise History and Timeline of the Featherweight Bobbin Winder
The Bobbin Winder is supposed to wind the thread onto the bobbin smooth and even - with the thread flowing side-to-side as it winds. If your Bobbin is
Bobbin Winder Tension Bracket
Bobbin Winder Servicing on the Singer Featherweight 221 222 – The
Bobbin Winder Servicing on the Singer Featherweight 221 222 – The
Singer Featherweight 221 and 222K Sewing Machine Parts – Tagged