It looks like you may have an encrypted TIFF file and maybe no support for it in the libs. You could try converting to PNG format. I don't understand what you're doing with the box files -- why not just use a normal language mode instead of training? We need to see the image you're trying to process to tell what's going on.
D:\Little\Tesseract-OCR\build>tesseract A.tif ug.A.0.box nobatch box.train
Tesseract Open Source OCR Engine v3.02 with Leptonica
TIFFReadDirectory: Warning, TIFFstream: unknown field with tag 37724 (0x935c) en
countered.
TIFFReadDirectory: Warning, TIFFstream: unknown field with tag 37724 (0x935c) encountered.
TIFFReadDirectory: Warning, TIFFstream: unknown field with tag 37724 (0x935c) encountered.
Empty page!!
Empty page!!
--Sven