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Let me start with when I think what caused the issue. I installed highway crash bars. I had to remove the pedals on each side, because the highway bar goes in between the frame and the pedals.
I removed the shift pedal and carefully placed it on the ground on a towel. I assume something got messed up with the adjustment.
Ever since I have a very difficult time shifting into second. It takes me 4 to 5 attempts of full force shifting before if finally goes into second. After the bike warms up it might only take 2 attempts. Or maybe at that point I am warned up, lol.

I have a 2016 Scout Sixty with a heel toe shifter. I exclusively use the heel shifter to shift up, cause it's easier for me. I am kind of short.
 

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Just put highway bars on my Scout last Saturday, no problems encountered. I also have heel toe shifter.

I wondered if the slight offset of the shift rod might cause a change, so I was glad it didn’t.

You want might want to make sure the shift rod end pivots aren’t binding. Maybe add some (synthetic all-purpose or marine) grease on those. Make sure they are clean first.

And give the engine side lever a look. It should be at a right angle/perpendicular to the rod.
 

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Discussion Starter #3
Just put highway bars on my Scout last Saturday, no problems encountered. I also have heel toe shifter.

I wondered if the slight offset of the shift rod might cause a change, so I was glad it didn’t.

You want might want to make sure the shift rod end pivots aren’t binding. Maybe add some (synthetic all-purpose or marine) grease on those. Make sure they are clean first.

And give the engine side lever a look. It should be at a right angle/perpendicular to the rod.
Thank you. I will check that out. I've been looking up install videos etc. and it does not look as if the rod really plays much of a role in the shifting, yet more to the pedal adjustment. So, it should've not been anything I did. Just weird.
 

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YW
I didn’t need to make an adjustment, but since you’re looking over everything else you could check your handlebar clutch lever+cable too while you’re at it.

The only thing I encountered as a possible problem was the brake side highway bar going tight up against the brake line.
I almost loosened the retaining bolt on the brake line under there but eventually didn’t need to.
Maybe you somehow pushed or pulled the clutch cable when doing that side. Just a thought.
 
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