So I've recently developed a loud intermittent chirping/squeaking sound coming from the primary the last day or two.

With the engine off and rolling the bike back and forth in first gear produces the squeak, too.

I pulled the primary cover off...and everything seems as it should...but the squeak sounds like its coming from behind the inner primary cover behind the clutch basket.

I'm thinking the main drive bearing is shot...do these symptoms sound familiar to anyone here?

It's an 06 dyna, btw

 

Could just be the rear drive belt.

 

Don't think it's the rear drive...the squeak is present when the engine is running but stationary and in neutral.

 

Does it do it with clutch pulled in could be the IPB

 

Could be the inner primary bearing.... take your finger and feel behind the inner primary to see if you have an oil leak. Usually a bad bearing results in a bad seal that weeps primary fluid down the back side of the inner primary.

 

Been through that particular problem ... IPB replaced 10,000 km ago. Not the same symptom/sound at all.

It's a pronounced squeak that appears especially when I brake hard to a stop and will stay squeaking even in neutral standing still.

When I got home and shut the engine off, I rocked it back and forth in 1st gear and which also produced the squeak.

I'm 99.9 % sure it's the main bearing on the output shaft...I'm just checking to see if anyone else can confirm my suspicion before I take it in to a shop.

I had some tranny fluid drip down the back of the inner primary(I know its tranny cuz it's redline which is milky red)...

I was wishfully hoping it was coming out of the shifter shaft seal. now I fear the worst.

 

The IPB race may have walked into the main drive gear and is rubbing on the seal or as you are thinking the maindrive gear bearing may have taken a crap.