Experts, correct me if I'm wrong, but the character limit
includes the entire path, not just the filename. If your folder
structure goes deep, then you are more likely to run afoul of the
255-character limit.
I encountered this myself a few years back. The way it played
out was like this: I created a topic in RH named
SomeReallyLongTopic.htm. It looked fine. However, when I next
opened RH, that topic showed as a broken link. Checking in Windows,
I saw that the filename had been truncated to SomeReallyLo.htm.
RoboHelp was looking for the original name, while Windows was
enforcing the character limit - not a compatible situation. As
expected, shortening the filenames solved the problem.
G