I've lost two bearing buddies off the same axle on the last two times I've towed my boat respectively. Is this an indication of something else wrong other than they might not have been set correctly?

thanx

Depends is it a Loadright if so common problem with the plastic ones.If they are metal might be getting hot from either brakes dragging or bearing going south.
If they are the plastic ones just get metal caps drill a hole and put a grease fitting in them works great.

Could be heat expansion (from a bearing going bad or too much grease). Also make sure they are installed evenly, tap them on with a rubber mallet or use a piece of wood (lay a 2X4 across and hit with a hammer).

Take them off and throw them away. Put air tights on and you will have no more problems. No grease slinging!

It's a Road Master, I don't drive more than one mile each way. Been tapping them in with a rubber mallet. Maybe too much grease? Never heard that before, I usually pack them pretty good, so maybe that's it.

Too much grease!!!

Agreed. The problem with bearing buddies is that people tend to overgrease them. When the hub heats up the grease expands and either pushes out the seal or pops off the cap.

Try putting some red thredlocker on them.

I had that same issue before and was from a hairline crack in the hub.

The last set of buddies I bought were a Brand Called Red eye. As you pump them up a little indicator pops out. When it is red, they have enough grease in them. Tells you when they are full. Jeff Wurl