Yes, its definitely a "feature". I have a special pair of angle pliers for pulling the drain plug and I discovered that a Ratio-Rite cup (for measuring 2-stroke oil in dirtbikes) can be positioned to sit steady on the serpentine belt so I don't even have to hold it (though I forgot about it and left one in there once and didn't find the melted remains for about 500 miles after I changed the oil, oopsie!).
My wife's 4.0 TJ Wrangler filter is mounted to the side of the engine case and there is absolutely no way to avoid a major spill all down the side of the engine and oil pan. One more thing to clean up, every freaking time!