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I've tested this on my Win9x build, so far so good, everything works okay. I can test out hibernation functionality if you wish.
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Okay, so setting MSVCRT to XP Compatible (NT5) allowed it to fully work, which means that somehow msvcrt is broken on non-SSE2 CPU from v3.0i upwards
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What's really weird about this is that it works great on VMware with both HFSLIP and 2011 ISOs, but not on my Pentium III. This behavior started with v3.0i and is persistent until v3.1a.
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I'm getting random crashes in Windows Explorer with v31 and v31a, it happens upon traversal of two directories, when it crashes to an error explorer.exe has generated errors. Not sure it someone else also gets this, this was installed on a clean HFSLIPped Win2k installation.
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I've wasted a massive amount of time trying to get VBox 4.x to work, but to no avail. Removing the OS check with Orca causes a premature fail of the setup program. The last version I was able to install with either Orca of FCWIN2K is 2.1.4.
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The latest version of youtube-dl works fine, as well as the Youtube-DLG frontend after replacing its FFmpeg with a build by CoRoNe. Also, the latest version of MPC-HC (1.9.7) works fine when using the Vista version of msvcrt.dll. Both were tested with Extended Kernel v30f and unofficial VC++ runtimes by BWC (2010 through 2019).
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Everything Search Engine (voidtools.com) version 1.4.1.969 (latest as of the writing of the post) works on Windows 2000, despite claiming support only for XP and newer. Tested on Win2000 Pro SP5.1, haven't tried vanilla 2K.