"Isn't the inside of the filter the dirty side?"
All pleated filters flow from outside to inside. There's a support structure inside the pleated media that keeps it from collapsing. I've seen water filters hooked up backwards, the media just blows outwards and pretty much stops any flow, it can rupture too.
The "bolt" holding our bike filter housings on has a pressure relief valve inside. The cross holes near the bolt head are outside of the filter, past its outer end plate. A really dirty filter gets clogged up increasing the pressure needed to force oil through it. At some pressure the piston inside the bolt will push in against the internal spring, uncovering a second set of cross holes opening inside the filter letting "dirty" oil bypass the filter. Not good but better than not having any oil get through to the engine.