That's common on a RK IF you don't release the full pressure on your downshift. Downshift, lift toe off the lever, then downshift again. You might be suprised that that could be your only problem.

 

This sounds like you may be in need of a "third-gear adjustment." See your service manual, as it's something you can do yourself. I had to do it once on my '96 after experiencing the same shifting issues. I didn't measure like it said in the manual, but just eyeballed it. It needs to have equal slack fore and aft when in third gear, something you check when stationary, of course.

 

Hey Iclick, I've read a lot of your advice and usually it is spot on. But, without going to the manual, what the heck is a third gear adjustment? I've been riding HD since the mid 80s and have never heard of this! Thank you in advance for your answer
Mike

 

Clean and lube your shifter. Mine had lots of rust and old lube. Cleaned with a scotchbrite pad and a light coat of white molly marine lube,you won't believe the difference.

 

I no longer have my '96 service manual to refer to, but from memory it is an adjustment made on the left side of the tranny near where the shifter arm enters the case. You loosen a nut and adjust with a small Allen wrench, IIRC, where the shifter slack is equal fore and aft when in third gear. It's similar to the configuration of the clutch adjuster on the basket, only much smaller. I had to make this adjustment once on that bike when I couldn't engage certain gears. If there is too little slack toward the front it won't engage the lower gear readily, and vice versa. If anyone has a service manual for one of these bikes perhaps they could read up on it and post the step-by-step instructions, but I recall it being easy except for the access to that adjustment mechanism. I recall using a small (¼" or similar) open-end or box-end wrench and tied a string to it because I kept losing my grip on it. It was a PITA like most things you do on these bikes.

My '07 doesn't have this adjuster, or if it does I don't see it or any mention of it in the manual.