Dear Jmardy,
There is a small cup/depression at the entrance of the dipstick tube into the block. There is a small ridge on the dipstick to match the depression/cup in the block. There is a small O-ring that sits just below the ridge and into the depression. It has either disintegrated or been left off of most engines, in my experience.
Over the course of several engines, I found that, before I discovered the O-ring, RTV silicone doesn't work that well unless a large amount is used. If you clean up the dipstick and the cup/depression of residual silicone and place a commonplace O-ring with "just a dab" of silicone, then sealing is much better. FWIW.
Warmest regards, Chuck Engles