How to thread a bobbin
Are you pushing the bobbin presser against the bobbin (Pg 14, Step 4, Part 3 bottom of page). Usually, pressing that bar and locking it against the bobbin will activate the bobbin winding mechanism. (Make sure the bobbin is seated all the way down in the bobbin holder.)
As the bobbin winds and fills with thread, it pushes that bar out. When the thread reaches a certain level in the bobbin, the bar is pushed out and releases, stopping the bobbin winding mechanism.
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I have the same problem with my Kenmore. It is an old machine, but sews just fine, lately can't get the bobbin filled. I had to fill the bobbin by hand
Bobbin won't fill
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