Just a quick note, the OllyDbg UDD file remembers the size of Outpost2.exe. It will discard the UDD file and rescan the EXE if it finds the EXE size has changed.
I bring this up because recent updates caused the size of Outpost2.exe to change:
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r1100 | leeor_net | 2016-10-17 04:23:26 +0800 (Mon, 17 Oct 2016) | 3 lines
- Updated version strings throughout the Outpost2 executable and DLL addons.
- Added NetHelper to OP2 package.
- Updated OP2 executable icon to include a much more modern game icon.
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Backdating the exe to before this change confirms that OllyDbg is able to load and process the UDD file as expected.
Considering the UDD file contains years of reversing information, we'll probably want a way to work around this. This might mean updating the UDD file to match with the updated EXE file, or being aware of this issue and making updates to the EXE in a way that doesn't change the size.
If I had to guess, I'd say the icon update is probably what caused the size change. Can someone confirm the cause? If it is the icon change, is there a way to update the icon and maintain the same size? This might not be possible if the new icon is higher resolution.