Here are some pics of what im talking about

 

See this thread, your bypass adapter is very similar to my oil pressure adapter. I left the oring in place and had leaks, ended up having to use an annealed copper crush washer between the factory sensor, and block to get a good seal.


To me, it seems insane to bleed off oil pressure before it it reach the block. We already have issues with oil pressure and snapping cranks.

 

To me, it seems insane to bleed off oil pressure before it it reach the block. We already have issues with oil pressure and snapping cranks.

Indeed. I bought a Filtakleen unit way back but never installed it for the very reason. To OP: I have posted this in other threads, but since this one is specifically on the Insane Diesel Bypass rig (a seemingly great one BTW) I'll post again.

Context- I reached out to Cummins way back in 2019 to ask about using the Fleetguard LF9028 combo filter on our 5.0 engines. He said he saw no reason why that filter would be a problem, but his last two sentences really caught my eye!
I quote directly below for folks reading this to ponder:

"We generally advise against stand-alone bypass filters on the lighter duty engines mostly due to the fact that there’s not much extra capacity for the oil pumps in those engines.

With combo filters (LF9028 for example), this isn’t the case since you’re not robbing any oil flow from the engine (all the flow goes through the single filter and is sent downstream to the bearings, pistons, turbo, etc.)"

 

I'm thinking to have the rubber o ring on before tightening everything back up to the correct torque.

 

Keep the O Ring on is my opinion along with properly torquing everything correctly to eliminate leaks.