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I’ve heard all sorts of horror stories about Vista and Win7 not supporting a bunch of older stuff, notably early versions the productivity software we use. Thankfully, it hasn’t been that bad, though I’ve got a bunch of Win95 and 98-era games that I don’t hold out much hope for.

Here’s everything I’ve found so far (for Win7 64-bit):

Current, free/open source software (should all be strictly up to date, and none of them have given any trouble):
Adobe Reader 9.3.0
Firefox 3.6
FreeCiv 2.1.11
FreeCol 0.9.1
OpenOffice 3.2.0
OpenTTD 1.0.0-RC1 (has a 64-bit executable)
QuickTime 7.6.5
SeaMonkey (nee Mozilla) 2.0.3
TeamSpeak 3.0.0-beta16
Thunderbird 3.0.3 (I just upgraded from the 2.x series, a lot of changes)
VASL 4.8.1
Vassal 3.1.13

Productivity Software: (the truly important stuff)
CorelDraw 8 – Installed fine. Need to test, and try updating. – Update: Went crash-happy fairly quickly and started crashing on launch. Now updated to X4.
Dreamweaver 8 – Installed and runs fine.
PhotoShop 5.5 – Installed fine. Have had one hiccup, looks like the system was just being slow.

Games: Organized by year of release….
1996
Age of Sail – Will not install *1
Command & Conquer Gold – Will not install *1,3
Command & Conquer: Red Alert – Will not install *1,3
Star General – Will not install *1,5
1997
East Front – Installed and runs fine (!!)
Heroes of Might and Magic Compendium (I & II+expansion) – Will not install *1
Imperialism – Will not install *1,2
Panzer General II – Will not install *1,2
Total Annihilation – Installed and runs fine – However, the two expansions refuse to install *1
1998
Jeff Wayne’s War of the Worlds – Installed. Game only works a lowest resolution (640×480) – otherwise it crashes when it changes modes. And it did crash once during play.
People’s General – Installed, has graphics problem where map does not display, only controls *4
Warlords III: Darklord Rising – Will not install *1,5
1999
Heroes of Might and Magic III – Installed and runs fine. Though it did advise I needed NT 4 SP 2.
Imperialism II – Installed and runs fine.
SimCity 3000 – Installed and runs fine.
2000
Starfleet Command II – Installed. Will not accept keyboard input for entering CD-key. (USB issue?)
2001
Europa Universalis II – Windows 7 warned of compatibility problems. Need to check on latest patch.
2002
Master of Orion 3 – Installed. Seems to run fine, Win7 was worried that it didn’t install correctly.
2005
Civilization IV – Win7 warned of compatibility problems. Installed, ran fine, and then I used the in-game patching service, whereupon it died. I need to reinstall without patching and try it out.
2008
World of Warcraft: The Burning Crusade – Had trouble with initial patching the first time, but a uninstall/reinstall sorted it out. Runs fine.

(This list will be updated with more titles for a while yet.)
1 cannot start or run due to incompatibility with 64-bit versions of Windows.
2 Error: Didn’t work: Result:216
3 The program, INSTALL.EXE could not be found
4 Win2K had this issue
5 Hitting ‘Install’ on the autorun menu causes it to go away, and never do anything again. No error is presented.