There are a lot of different Kenmore models. See link to the 385. https://www.manualslib.com/manual/150294/Kenmore-385.html
If not close enough comment with model number and someone here will likely locate.
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: Bobbin thread breaks
Make sure your bobbin thread is turning clockwise as it sits in the bobbin case. There is a screw on the outside of the bobbin case you can turn with your thumb slightly to adjust tension. If you dangle the case from the thread and give it a light ****, it should move down slightly when doing so-an indicator of good bobbin tension.
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: Bernina Bernette 65 sewing machine
Presumably neither of you has or knows how to adjust your bobbin tension so, I'm going to presume it's your hook. Make sure you are threading the machine coorectly then you'll need to remove your needle plate by removing the two screws, pull out your hook (this is the part your bobbin sits in) but make sure you note which way it sits inside your machine. Have a look at the plastic hook for any sharp edges or burs, you may need to replace your hook or try and gently sand (400grit) the plastic if possible. The key part of the hook is the small blunted point as this is what catched the loop of thread behind the needle. Please make sure that when you put your hook back in, that it is on the left side of that little guard sticking out on the lower right of your machine.
SOURCE: Manual for older kenmore sewing machine
Manual Here: http://www.managemylife.com/mmh/lis_pdf/OWNM/1006108L.pdf
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