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It shouldn't in principle be too difficult to arrange that PuTTY can be built for Win32s (an extension to Windows 3.1 to let you run 32-bit programs).
The last vaguely useful Win32s build I know of is from 1999 Nov 4, and even then the configuration dialog didn't work. The most recent attempt (2001 May 17) had a working config dialog, but crashed on starting a session, and as such doesn't really represent progress.
Compiler/linker support is required for a Win32s build. At the least,
the binary must have a .reloc section (symptom of its not
doing so is "Invalid format"). MSVC 4 (4.1 or earlier, not 4.2 or
later) can build for Win32s with /fixed:no, and
mingw32 appears to be able to
build with vile dlltool hacks, although I don't think there's suitable
startup code.
Increasing use of Windows' Unicode functions may spell doom for a Win32s port. Not sure.
Help here would be most welcome.
Audit trail for this wish.