Valve seals came off guides suddenly??

[96flhpi]

Short version - started to get some oil spotting on the rear plug, pulled both heads and 3 of the 4 oil seals came off the valve guides and are sitting right under the top collar.  Any idea what may cause that to happen suddenly?  Heads have been fine for about 4 years.  Wondering if it's just something that happens or is something behind it - kinda weird that 3 seals would let go in the same 3 week period.  I was running too much advance for about 75 miles don't know if it'd cause that.

Long version - '82 FLH with points conversion, tuned it up about a 3 weeks ago.  Old plugs looked great - no evidence of oil whatsoever.  I usually static time it to TDC as that gets me ever so slightly too advanced (only pings on very steep hills) and I retard it a touch until pinging goes away.  This time I bought one of those thingies to hold the points cam at advance and timed it to 35 degrees adv and that still put me at too much - only pinged very slightly on hills and it took me about 75 miles to decide I wasn't just imagining things. 

When I pulled the plugs to set timing the way I always have there was oil on about 1/4 the insulator of the rear, not totally fouled, running fine, no weird noises.  I marked a new plug so I could see the spotting was coming from the intake valve, figured seal gone bad, try to make it through the season.  That was about 2 weeks ago, like I said no noises running great  Yesterday, it starts loading up at just off idle.  I don't think they're related but figure while I wait for parts to clean/rebuild the carb (Keihin CV) I may as well see whats up with the head and that's what leads me here. 

Thanks as always for any advice as to what to check or if I can just have new seals installed.

[Don D]

Not a lot of information to take a stab at this. If the guides are the right size to fit the seals they are usually fine. The K-lines are lower profile than most and being metal to metal stay put a little better.

[96flhpi]

Thanks for reply HD Street.  Unfortunately I only know how to take stuff off and bring it in to a shop, can't rebuild this stuff myself so I have no idea what seals, guides, etc. are in there.  Like I said just find it weird it would be fine for years and then suddenly 3 of 4 loosen, but at the same time I don't want a shop to tell me I need new guides or whatever when really all I need is to replace the seals.

[wfolarry]

Did a set of Evo heads last week that had original seals. Pulled them off with my fingers.
Sometimes it just happens.
I use loctite on the K Line seals to keep them on.
They're taking the heads apart to replace the seals so it's easy to check the valve to guide fit while they're apart.
Maybe all you'll need are new seals.

[Don D]

I like the loctite idea.

[96flhpi]

Thanks WFO, I'll ask for the K-lines and for Loctite when I bring them into the shop.

[Hillside Motorcycle]

Did a set of Evo heads last week that had original seals. Pulled them off with my fingers.
Sometimes it just happens.
I use loctite on the K Line seals to keep them on.
They're taking the heads apart to replace the seals so it's easy to check the valve to guide fit while they're apart.
Maybe all you'll need are new seals.

We use Loctite on the K-Lines too.

[Buglet]

    Being using KW seals with no problem even on Pans.

[RTMike]

Hope there good shop close by to help you out,they can check for guide wear and install new ones and a valve job if needed.
I prefer Kibble white or Goodson seals but if Kline are needed ,green stud and Bering mount loctite is the answer.Thts my two bits for the day.

[Racepres]

Hope there good shop close by to help you out,they can check for guide wear and install new ones and a valve job if needed.
I prefer Kibble white or Goodson seals but if Kline are needed ,green stud and Bering mount loctite is the answer.Thts my two bits for the day.

Guaranteed to need a Valve job if you put Guides in it... No Way Around it...

[96flhpi]

Machinist at local shop I took them to yesterday said rare but not unheard of, and unless he finds the stem/guide fit is really sloppy or some other issue he can just install new seals with some Loctite.

Thanks to everyone who replied.