Oh, no doubt. The issue is that the tools don't appear to document their limitations and constraints, and there is often no way of knowing until you get bitten.
At least with OSS you can look at the code behind the program to work out how it calculates things like the bend radius.
I'm no engineer, so I had to look it up (Wikipedia was no help whatsoever on this occasion) but I located this page which gives the formula and an explanation:
"Calculating the correct flat pattern layout is crucial to getting a good quality finished part from your press brake. Yet, many CAD and CNC programmers have no idea how to calculate the required values. Years ago, the real experts created cheat sheets and tacked them to the wall. They only taught the new apprentice how to apply the results shown on the cheat sheet, not how to calculate the numbers. Well, now those experts have retired and it's time for a new generation to learn the right way to do the calculate the correct flat pattern layout."
http://www.sheetmetalguy.com/bend-allowance.htm
Now admittedly the guy does put the responsibility on the operator, but it appears CAD packages can indeed calculate this for you. So long as the right info was input into the program, the formula should be programmed correctly and the operator should be able to have confidence in the results!