Always, sometimes pack them with too much grease and have issues with "hydraulic lock" when trying to press them in as it tries to force the excess out of the grease nipple hole. then fit the nipple and grease again.
There is always one or two cups that are dry when it is removed despite regular greasing and the others look nearly new and are full of the stuff.
I grease everything on any reassembly unless there is a valid reason not to. Have a nice selection from standard copper grease to some old fashioned axle grease that is like tar and will never come off!
OK - it is not through lack of trying then!
Are they drilled properly? It almost sounds like a grease passage issue, grease guns can generate excellent pressure and should be able to push grease through OK but it doesn't sound like this is happening!
Do you do a lot of off-roading ?
My conclusion is that due to the grease nipple angle it does not equally distribute the grease and it will burst a seal on the easy access cups before fully filling the more difficult ones. Because they get changed regularly they press out easily and I can now swat one over in about 20 min including removal and refit of the prop shaft it is just annoying.
When you fit them are you packing them with extra grease and pumping in some extra with a grease gun? Sounds simply like a lube issue.
A good quality grease is worth while, I have an original can of moly slip that I use a very small amount of for assembly of things, then use normal grease, it makes a marked difference, I have been using it on bearings and in engines (little dab under valve caps, rockers etc.) and all sorts my entire life and some of the stuff I built up with it years ago is still going strong and bearings look brand new etc. I am not suggesting you go to this extent but good grease and plenty of it should work a treat.
The cost of Moly Grease is very similar to standard LM grease.
Do you do a lot of off-roading ?
I have 2 Defenders, the one for church I never change UJ's and the one that get's hammered in the muddy stuff quite regulary !