I've read through this thread and the Fitzmaurice link. Let me summarize the salient points as I understand them, and y'all let me know if I misstep.
1) Using a 100W head within its limits (not clipping) into a cab that can handle 1000W won't damage the cab. This seems obvious -- it's like running a 1000W head with the volume turned down.
2) If you push a 100W head into hard (square wave or something approaching it) clipping, attempting to get more out of it than it can reasonably give, you might actually be getting more like 200W of output from it. Your 1000W cab should still be safe (even if it sounds like crap), but you might well blow or fry a cab that can only safely handle 150W, with the 200-ish Watts you're getting from your 100W-rated head. (To say nothing of what prolonged use like this might do to your head.)
3) In the above case of the clipped 100W head (putting out 200-ish watts) and the 150W cab, you'd be better off with with a 200W head run near, but not at, its clean-power-potential, putting 150 Watts into the 150W cab.
4) "Underpowering" is a term that's used inconsistently. You can't damage a speaker component by giving it "too little power," but if you use an amp that can't give you enough clean juice for the job at hand, push it to clipping, and in the process of clipping it generate more power than your speakers can safely handle, whether thermally or mechanically, then, yes, you could bust something. (If the clipped output is still below what your speakers can handle, though, it'll just sound bad -- without hurting them.) You could, under the right circumstances, then, get into trouble using an "underpowered amp" (even though "too little power" is NOT what's damaging your speakers). I think some of the confusion stems from that.
5) A square (fully clipped) wave has a lot of high-frequency content -- if too much gets to your tweeter, it could be damaged (because of too much power to the tweeter), even if the rest of the speaker components are okay. (You could run into a similar problem with an envelope filter used at extreme settings, too, right?)
6) A square wave's average power = its peak power. More average power = more heat generated than with a "musical" wave of the same peak power (where its average power is lower -- think of plucking or slapping notes on your bass). If the average power/heat generated is more than your speakers can handle, then, trouble. Otherwise, simply bad sound.
7) Thermal power handling is thermal power handling. Mechanical is influenced by your cabs, not just the drivers in them.
Am I missing anything? This is for my own understanding as much as anything. A year ago, I thought I NEEDED at least a 1000W head for my 1000W rated cab, both to use it to its potential (now I think actually putting 1000W into it would be a bad idea) and to avoid damaging it through clipping.