Okay, the last couple of months I've had an intermittent issue. Not necessarily looking for a solution, but maybe a helping hand on what things I could look at as potential fixes/replacements. (Okay, I guess that IS a solution.)

This is a 2016 Heritage.
Bike rides just fine. Sometimes when I go to enable the cruise control, it will turn on (orange light), but not engage (green light). When it does not engage (which is not always), about a minute or two later the red light (equivalent of a "check engine" light, I'm guessing?) will turn on. It might go away later on it's own, and always does if I restart the bike.

There have been a couple of times (but I just haven't ridden much lately - work and freezing weather), where the red light will come on even if I don't engage the cruise control. And sometimes the cruise controls works fine, and the red light doesn't come on.

Any thoughts to lead me in the right direction?

 

Since it sometimes sets a check engine light, check your codes... you should have a historic code in nothing else... that can lead you in the right direction...

Codes aside, cruise control issues, along with erratic speedo and/or turn signals not self-cancelling, can be caused by the VSS (vehicle speed sensor). It can be dirty or failing...

It's on the transmission case. You could pull it out and see if it has a bunch of "fuzz" (metal like filings) on it. Clean it off, reinstall it, and see if the problem goes away.

But codes are your best bet to start with...

 

You have a bad switch pack. The red light is a security light that has to do with can bus wiring. If cruise engages and then goes off and intermittent then I can almost guarantee it’s the switch pack.

 

The red light is different than your CEL. The red light is the same indicator as your security system light and will most times indicate an electrical or wiring issue instead of a mechanical failure which you would get from your CEL. The best option is to go into diag mode and check whatever codes are showing shown. Without seeing the switch housing on a 16, I am going to assume it's the same as my 21. To go into diag mode, hold your trip button and switch the bike to run. On your ODO it'll say diag and then you can switch through the different systems, emc, BCM, Speedo etc.

Harley Trouble Codes (fuelmotousa.com)

 

So, solved! Checked the codes, came up with:
BCM 62262 (Front brake switch stuck)
ABS C1094 (Front brake switch always on)

Watched a YouTube video on how to check codes. Got that. Determined it was these errors. Tested, and sure enough, first brake use and the light stayed on.

Watched another video on how to maybe solve it. I disassembled the housing around the switches at the front brake. Compressed air to clean out as much dirt as I could. A little bit of (highly evaporative) contact cleaner. Followed up with some WD-40 silicone. Brake no longer sticks!

Y'all saved me money on hitting up a shop!

 

Since my last post here (Mar 6, 2023), the fix had only been temporary. Turns out that something was goofy, and had rubbed the insulation of the wire pair, causing it to basically short out. I looked at it a few times but it was basically too delicate for me to mess with, possibly soldering onto a tiny circuit board. Knowing what the problem was, I would avoid using the front brake. Totally annoying. Yes, you don't need it, but it sure is nice. Now, if I needed it for a quick stop, I definitely used it. But I'd have to flick, flick, flick the front brake lever to maybe get it unstuck / unshorted again so that my brake light actually lit up when hitting the rear brake.

Finally (about 3 months ago) I broke down and went to a Harley shop to have it replaced. Probably the last time I'll go to HD for work, though, they really pissed me off. They were done in about 50 minutes. I look at the bill to take to the register and it shows 1.5 hours. I went back to the service advisor and said "y'all had this less than an hour". He says "that's the book rate" and went back to whatever he was doing. THIS is why people hate the dealerships. The work was fine and it's nice to have my front brake back again...

 

Flat rate is the norm
if it had taken 2 hours, you would have paid 1.5
Did you ask for an estimate ?

 

No, didn't ask for an estimate. That was my mistake. I just figured "they just swap it out", so.. honestly the 1.5 hours isn't bad. To me it was more of the principal.

 

It is a finicky job, you have to dig the original switch out of the material it is encased in, I did mine, same symptoms, I couldn't do it in 1.5 hours first time round, once you had done a couple it would be quicker I suppose.