When text is displayed vertically in crosstab and 'Stretch with Overflow' is selected, the text will not stretch
Rotated text does not stretch. It was not supposed to. One reason is that in JR, everything grows and stretches downwards, and never sideways.
You could argue that the crosstabs indeed grow sideways, but they they are very special.
If it was for simple elements such as text to grow sideways, we would need to complicate the rendering engine a lot, in order to allow elements to move sideways when pushed by expanding rotated texts.
You could log this as a feature request, but I don't see it solved soon, so you might be better of by simply making the vertical text fields wider or use a smaller font size, if you know the text does not fit on one line.
I hope this helps.
Thanks for your response and help, Teodor!
It would be a nice feature and changed the category accordingly.