There are two weird windows cases that might be not be of much value but quite interesting. I have specs.
1) LFN on Windows 3.1 This actually can happen (Winver=3.1, Dosver=7.0). This should be supported LFN on Windows 2000, XP I have verified, the DOS 7 LFN interface works on 2000 and XP Perhaps this should be made to work on wine nt4 mode.
2) Win 3.1 running PE executables Fundamentally weird, but I have specs (OH, and the files required to do this were released by Microsoft for free redistribution)
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