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When it looks dirty or looks like it's lacking oil. I have cleaned mine twice since I've had it. Both times it was because it looked like it needed oil, not because it was that dirty. The pink will start to fade as it needs to be oiled. Be careful not to over oil - though - gets messy. A little goes a long way.
I reoil mine about every 1000 miles as it starts to look dry (SE Breather really sits out in the sun). I usually only clean it every other time or every 3rd time depending on how dirty it looks.
Really dependant upon how much riding you're doing and how nasty it is. Just visually inspect. If it looks nasty, or you seem to be getting some popping, clean it. That's how I know mine is a little dirty.
Also, I keep a 2nd cleaned and oiled filter handy so I don't interrupt my riding. Swap out the dirty one for a clean one.
I do mine once a year. Usually in the fall before layup. I have done it more often and not much dirt comes out. The SE blue paper one would last me 2 years.
__________________ 06 FXDLI
Many thanks to our people in uniform for it is their courage and sacrifice that makes our nation great.
I don't let mine get too dirty or too dry.As said the filter looks gray when it dries out,you'll notice it more towards the front where the wind hits. It's really easy to do,buy the kit and read the instructs. let it dry really well and add the spray oil to the top. I let mine sit an hour and the oil seaps thurally into the filter media.
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'08 vivid fatbob,
BUB7 2/1,
A/N big sucker,pcV,
dually switchblades, grips shifter and B-Pedal
SB solo seat for cruzin
Jackyl's 2"+Spacerjim's2"
If you're running an open filter like the one in my sig pic you will need to clean and re-oil it every two days or more often if you want it to be pink.....
In other words, I just gave up and clean it when I change the oil.
K&N on my Dyna... cleaning info needed.
06 FXDLI 
