If you turn the handwheel by hand is it stiff?
SOURCE: Kenmore Sewing Machine model # c877.15
I have an old Kenmore and here are the directions from my manual: 1. Draw thread from spool through bobbin winder tension discs. 2. Wind thread around an empty bobbin several times. 3. Place bobbin onto bobbin winder shaft with thread coming from rear of bobbin. Push bobbin winder latch against bobbin until it clicks. 4. Release clutch by turning clutch knob toward you. Start machine.
SOURCE: kenmore 12 stitch sewing machine-wont sew
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SOURCE: instructions for theading a Sears Kenmore Sewing machine model 158.14000
all machines thread the same. TTN tension,take up, needle.
Beginning
with the spool, guide the thread through the thread guides to the
tension assembly. Pull the thread through the tension assembly and test
it to make sure the tension is working correctly.
(To do this
test,adjust your tension setting to normal or medium or 5 or something
in the middle. Raise the presser foot and pull the thread through the
tension. It should pull easily!! Lower the presser foot and pull the
thread. It should pull noticeably harder.) If it passes this test,
continue up through the take up lever,then down through the thread
guides to the needle. Make sure your needle is fully inserted and
turned the correct way.( If you load your bobbin case from the left
side,the needle rule is normally FLAT to the RIGHT is RIGHT. There are
some exceptions. If you have a newer style drop in bobbin or your
bobbin case loads in the front then the rule is FLAT to the BACK.
To wind the bobbin, guide the thread around the thread guide on
the left top of your machine, then to the bobbin winder. Wind the thread around the bobbin several times, place the bobbin on top of the bobbin winder, push it against the wheel and press the foot pedal. It should stop winding when the bobbin is full or you take your foot off the control
Sewman7
SOURCE: Sears Kenmore Sewing Machine Model 385. 1254180 Bobbin Won't Wind
The winding sound is the rubber O-ring against the spinning pulley (back
of hand wheel) - do not let this continue, it will wear out the O-ring.
I had the same problem and I found the shaft bushing of the winder dry and needed lubed. Use oil or spray lithium grease and it should work fine. Spin the bobbin shaft by hand (not the hand wheel) to get it freed up after oiling.
You can oil from the top and should take off the side case to clean the excess oil from the O-ring. The shaft bushing is a tight fit and any dry oil will get sticky and prevent winding.
SOURCE: Manual for older kenmore sewing machine
Manual Here: http://www.managemylife.com/mmh/lis_pdf/OWNM/1006108L.pdf
insert winder as in fig. check the thread direction
on figure hold and insert bobbins on shuttle race assymble. 
follow the red thread on figure.138 views
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