I'm trying to make a click pen mechanism, where a piece in the center of the cylinder in 1 spin locks in place, and in another spin it slides into one of the slots.
I need to cut out part of a cylinder with the 2 other objects. Thing is when I try to do it, only 1 object successfully cuts the cylinder, and the other object either does nothing or cuts only 1/4 of the cylinder... And what's weird is the 2nd object is just a duplicate of the first one. I removed all doubles from all objects and the cylinder, recalculated normals, applied rotation and scale, tried flipping normals, still no progress...
This is working Boolean cut with first object
This is the part where it just doesn't work or works weird/half way (with the second object). It's the duplicate of the first object and some why it doesn't work and I don't understand why...
Edit: Forgot to mention, I also tried joining/merging both objects together and removing dupes, still doesn't solve the problem sadly:

I would be very happy for help! Thank you in advance!
I also checked other threads and non of them had an answer for my specific problem.
Anyways, I got to a solution but this question got closed so I couldn't answer it. Here's how I did it: I couldn't really find a specific "right" way to fix the problem. But I used lemon's suggestions. What I did is I set both booleans to "Carve" instead of "B-Mesh" which did cut most of what I needed, just left some faces and added some edges in the middle of faces and and random vertices. After I applied the booleans I just manually deleted all the edges and random vertices and the left-over faces and remade the faces that needed to be remade. I hope this answer helps anyone in the future! Thank you lemon!

But isn't "Removing Duplicates" supposed to remove also the duplicate faces? I mean there can't be 2 faces between 4 vertices... From what I know of course... – I'mJustANewbie Jul 24 '19 at 15:00