I just tried dosbox-x. With the dos startfile of privateer2 I get this error:
Missing or invalid 386fx driver
DOD/4GW error (2001): exception 0Bh (segment not present) at 160:00000019
etc

when I try the patched exe I just get the message: this is a Windows95 executable
but it should play win95 file per default or is there some settings I have to change?

I tried both gog was my standard method of starting, but i tried bosbox directly too. I am in contact with gog support and sent them dxdiag files. they had some tips like update drivers and start in compability mode, etc but that didn't help. But since it isn't working with dosbox directly too, I'm not sure if they caused the problem.

Sounds suspiciously like the conf file is wrong and needs a higher ram xms/ems configuration modified.

386fx driver... i believe DosBox-x is suppose to support Glide, but that dll needs to be present too in with the game folder. Can't recall if it has it by default or not.

edit: Says that Privateer 2 is a dos game... but Deluxe is a windows version.

So it might be patched to run directly rather than through dosbox? Don't know, i'll install my version from 2016 and see what it has/says.

edit2: Threw in a DosBox-X and was able to run it directly without any changes, including the minimal dll drivers.

So... not sure what's going on for you.

Mind you i DID manually start the program with the appropriate flag(s) via cygwin; But making your own shortcut to use it should work too.

So for trying the dosbox-x. copy the appropriate files to the DOSBOX folder

Create-shortcut on dosbox-x.exe

Edit the shortcut, to show (likely) "{GAMEPATH}\DOSBOX\dosbox-x.exe" -conf "..\dosbox_privateer2.conf" -conf "..\dosbox_privateer2_single.conf" -noconsole -c exit

Then it will likely run.. Though i wasn't running it with dosbox_privateer2.conf, only the single. Meh we'll figure it out.

when i start the patched exe without any changes for compability it says I have to run install.exe
when I start it in compability-mode for Win95 windows changes the settings to WinXP and wants me to test that. After that it says i had to run install.exe

I'll try editing the shortcut too and let you know my results.

its working!
First I discovered that I was able to start the game via the windows menu (right-click on dark.exe, run with dosbox-x). But the game crashed when I started talking to the barkeeper (triggers video). Interestingly I still can not start the game by opening dosbox and starting it there.
Then I started writing this post and therefore tried some settings again including configuring the soundsettings of the game (autofind, no sound and back to autofind again). But now..... TADDDDDAAAAAAA:-)
Thanks for all the help and your efforts!

You're the second person in a few months who has had trouble with dosbox games...the first person just went on an insane rant about how much GOG sucked, glad you managed to find a solution.

Old games required running a setup program after installing, before running the main game executable - to set up the sound card, etc. It's easy to forget when nowadays everything is plug and play.

Yay *Cheers!*

So it was sound settings? Most curious. Sounds in DOS was always manually configured, but usually was Port 220 IRQ 5 DMA 1; Port 330 MIDI using Soundblaster/SB Pro... that's pretty much was the standard.
Usually after install, setup is automatically launched before going to the game.

Or in cases like Lemmings and games with tons of video sound support, a batch file would ask you which video card and sound card, then launch the appropriate version of the game.

But as the other programs including setup usually aren't part of the shortcuts, people would easily get lost too.