Some advice I got a long time ago that worked for me:
Ditch the rubber gasket, and use LOTS of silicone instead.
Not just on the face, but inside, on the threads, for a deep seal where bulkhead goes through the acrylic.
Those gaskets are not the best quality. They do degrade and harden over time, and things can burrow into rubber.
More importantly, if you move the bulkhead during tightening, or you over tighten, that rubber gasket
can deform away from the pipe, and not seal correctly.
+1 on not over-tightening, regardless of method.