A family of Microsoft word processing software products for creating web, email, and print documents.
I share your frustration Matthew! I too have been having similar repeatable problems with Word, and have not been able to find out how to get someone at Microsoft look at it seriously.
My problem is that Word indexes and ToCs are reporting incorrect page numbers — but only when the document uses an OpenType CFF font (Adobe Garamond Pro, Minion Pro). If I change the document to an OpenType TT font like Times New Roman or Segoe UI, the rebuilt index and ToC reports correct page numbers. (See my detailed Office TechCenter post here.)
I think that feedback I received about this problem on an Adobe support forum (here) may be related to the problem we are both encountering:
Adobe Garamond Pro and Minion Pro are both OpenType CFF font families. Times New Roman and Segoe are both OpenType TrueType font families.
The primary difference between the OpenType CFF and OpenType TrueType fonts is the outlines and hinting technology used by the font.
OpenType CFF uses the same Bezier curve and hinting mechanism used by the original Type 1 fonts used in the original PostScript printers and use a coordinate system based on 1000.
OpenType TrueType uses the quadratic curves and programmatic hinting mechanism used by TrueType fonts, using a coordinate system based on 2048.
I am wondering whether Word is doing something that assumes that 2048 value (it shouldn't) for font character widths being based on. It is crazy enough to actually be the issue and about the only thing that I can think of that just might be the root of the problem.
This seems to fit the behavior we are seeing, and certainly suggests a bug. I do hope that a Microsoft Office technical person sees this thread so it can be investigated and resolved quickly.
(If it will help, I can provide a document that exhibits this problem so it can be examined.)