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i got frustrated with the saddle bag bolts on the boulevard too..so came in to look up some info. i tried different suggestions i seen here sitting on bike, etc, but this worked for me. put front bolts on first...the back i spent over an hour trying to get the bolt in. i finally just pulled up on rear fender lightly with my hand and the bolt went in like a knife through butter. took it out and tried again before i signed up and posted. might save someone an hour of frustration. l
Thanks so much to you and the OP (CajunCountry), I got stuck when I pulled out both bolts on one side to install my back rest. I came on here and found exactly what I needed. I first used your advice to push the metal at the back of the fender up a little and pushed the front bolt in and then the back bolt (also had to push that metal piece up).

The other side, I did it as CajunCountry said with the front bolt first and then the back bolt, one at a time.
 

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I'll keep these in mind if I ever need to replace the stock bags that hold a lot and keep the rain out with gee whiz bags that don't do either.
 
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