Not *always*, but usually, eventually.
Here's my experience. I bought a 1993 M900 Monster new, and it turned out to have the weak studs. At 19K miles (about a year and a half of ownership), a stud broke on the vertical cylinder, and I had it replaced. This was in early 1995. The larger scope of the problem was not known to us at that time, so we just thought it was a fluke, and just replaced that one. Just a couple of months later, at 22K miles, one of the studs on the horizontal cylinder broke. By this time we had heard of the problem, and Ducati had made improved studs available, so I told the mechanic to replace all of them with the improved studs.
Here we had a communication breakdown; I thought he had gone then and replaced all the studs on both cylinders, but he only did all the studs on that horizontal cylinder. So I went on my merry way, thinking I was done with the issue, but still having 3 of the original studs in the vertical cylinder, plus the one that was replaced at 19K miles (but was replaced with a new one of the same weak design). Had I known this, I would at least have had them all replaced when I had the piston rings done at 122K miles.
Quite a few years later, in late 2011, the bike developed a base gasket leak on the vertical cylinder. So I took it in to get that fixed, and was surprised to be told that I still had the old weak studs in that cylinder, and that they were stretching and about to break, which is why I got the base gasket leak. At that point, I had 198K miles on the bike. I thanked the old studs graciously for lasting 18 years on that cylinder, and for letting me know before they broke, and then ruthlessly had them all pulled out and redone with the better studs.
So I would not say that they will *always* break, but that there’s a good chance of it, and of course the more miles, the more likely.
PhilB