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I ride down into the 20s when there is no ice on the road. In the morning it was nearly impossible to shift out of first for about 1/2 a mile (which wasn't that bad since that's about the length of my gravel driveway). Was running Mobile One V-twin 20W-50. Switched to Rotella T6 5W-40 in the cold and the problem went away. Running T5 (15W-40) now that it's warm and don't notice an issue.
 
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'15 Vintage, same problem. So... I start bike and leave the garage in 2nd gear. Go 15-20 feet in 2nd, then stop while still in the driveway, then shift into 1st gear, and down the road I go's. No problem shifting 1st to 2nd, as long as I roll out that 1st 15-20 feet in 2nd.
 
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I also use a heel shifter, which gives you a lot more leverage on upshifts.
Word of caution when using that heel shifter. Since you have a lot more leverage there. It takes less force. I have seen my fair share of bent shift rods. What they all had in-common... heel shifters.

Bent shift rods = miss/short shifts = worn out clutch plates.
 
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I very briefly owned a 2017 roadmaster classic which I traded for a 2018 Roadmaster Icon Blue. On both of these bikes I have noticed that when I crank up in the morning it's very stiff trying to shift from 1st to 2nd gear. When the bike is warm I don't notice this issue.

Anyone else experience this? Am I overlooking something?

I typically will let the bike warm up for 2-3 minutes before heading out.

Thanks in advance
MY 15 RM same way especially if rolling on a downhill grade. I have 30k on it now & it’s still stiff if cold at warm up I’ve learned to have the RPM correct and acceleration or deceleration not loading the tranny. After I got this all down the bike shifts fine I also let the bike warm up longer before I ride.
 
Normal — just something to be aware of. I start my RM before I snag my helmet etc. Gives it just those couple of minutes to warm up. I gear up, and when I’m ready to roll I pull in the clutch, and do a quick downshift to first, back up to second with clutch in. Back to first and then I’m ready to roll. Easy peasy.
 
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I bought my Roadmaster in December and I've been riding it as much as possible since. I noticed the hard shift pretty quickly, and made note of the fact that it only happened in the first couple of miles... after that, no problem. So I started letting the bike idle while I'm putting on jacket, gloves, helmet, etc... haven't had a problem since. Reading through this thread has made me feel a little better about it. I was a worried that it might be an issue.
 
I very briefly owned a 2017 roadmaster classic which I traded for a 2018 Roadmaster Icon Blue. On both of these bikes I have noticed that when I crank up in the morning it's very stiff trying to shift from 1st to 2nd gear. When the bike is warm I don't notice this issue.

Anyone else experience this? Am I overlooking something?

I typically will let the bike warm up for 2-3 minutes before heading out.

Thanks in advance
Same thing and seems normal when cold. I went to the RM from a Goldwing. Goldwing was the same and even more pronounced.
 
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