Couple things,
OEM seals
Check tech manual as to which way the seal is orientated (spring up, or down). They are not always the same.
With seal removed, check the sump and see if there is a small hole, in the seal's cavity, which supplies oil to the seal. If so, the seal cannot be inserted enough to block the hole. If no hole, there's usually a lip to limit depth.
If using a pipe, etc., make sure it's diameter matches the outside edge of the seal only. Most people won't have a socket deep enough to clear the length of the crank.
As stated, make sure the seal's edge, at the crank, does not roll.
I've had very good luck with doing this with the engine still mounted. Best of luck.