I have been thinking about updating itext from 2.1 7 to 5.0.1. It
sounds like a huge jump but in reality, there was only one version it
However, the 5.0.x update is not fully backward compatible. Here are
1- Instead of com.lowagie.text, the new itext uses the path
com.itexpdf.text. This is easy to fix on dependent packages:
- pdftk (I am a comaintainer. I already made a patch for this)
- tuxguitar (I am the maintainer)
I don't maintain the last two but I can patch them up if it is okay,
2- We used to ship itext with xml support. This part of the code was
not in the itext-2.1.7 tree but we had ported this over from a 1.x
release . I am not familiar with this part of the code and I was
told that this add-on was needed by maven. Is this still valid?
The issue is, itext-5.0.0+ dropped some other part of its code, which
our xml patch was depending on. In particular, the rtf support of
itext moved to a separate project 
Now we have a few options:
1- Package the new project separately. And move the xml patch to this package.
2- Drop rtf bits from our xml patch (I don't know if this is possible.
I didn't check. overholt?)
3- Don't update itext. Stick with 2.1.7 for now.
As I don't know what that xml patch does with maven, I hesitate
updating itext. By the way, why does maven not require itext?
Here is an initial attempt for the 5.0.1 update without xml support: 
Please share your ideas, potential problems, solutions, proposals etc.