
and the shim hadn't sealed against the cannister where it had a slight kink in it:

I couldn't find any problems with the o-ring.
I've always used genuine filters and, never having given it any thought, have always fitted the new shim, o-ring and gasket that came with the filter. This has been going on for 100,000km and I've never had any problems.
Of course now that I've read up on it (http://www.largiader.com/tech/filters/canister.html) I find that the gasket is not only unnecessary but can cause the o-ring to not compress enough to do its job.
I'm still not sure exactly what happened but I'm guessing that because of the gasket there wasn't enough pressure on the shim to overcome the kink (they often arrive slightly bent), I don't know how the oil got around the o-ring, and I don't know why the gasket broke (I put grease on them before installing) but this one looks as if it was seated oddly. The right hand bit seems to have moved outwards. I guess hot, thin oil found the weak spots.
This filter etc has been there for about 5000km and I don't know how long it has been leaking. I've been blaming pushrod tube rubbers for the oil on the engine. I guess I should have looked more closely.
No damage done this time, but a possible trap for those who take a simple filter change too lightly.