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Hello, first things first, I am not a computer guy, I just wanna play some old games on my Mac. That being said, I'll try my best to be as helpful as I can be. I hope I posted this in the right place. Below are all the specs, after the debug output I'll go into detail regarding my problem.

Mac version: macOS Mojave 10.14.5

Playonmac version: 4.3.4

graphics: Intel HD Graphics 5000 1536 MB

debug output:

 

] - Running wine- winepath -u C:\\users\\Drew\\Desktop (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c)

000b:fixme:winediag:start_process Wine Staging 4.0-rc4 is a testing version containing experimental patches.

000b:fixme:winediag:start_process Please mention your exact version when filing bug reports on winehq.org.

dbus[18396]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

/Users/Drew/Library/PlayOnMac//wineprefix/civ4/dosdevices/c:/users/Drew/Desktop

[07/06/19 16:03:47] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[19626]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:03:51] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 16:03:56] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 16:04:27] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[20194]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:04:53] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[20392]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:05:18] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[20555]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:11:43] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[21421]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:37:28] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[21826]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:43:03] - Running wine- winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)

000b:fixme:winediag:start_process Wine Staging 4.0-rc4 is a testing version containing experimental patches.

000b:fixme:winediag:start_process Please mention your exact version when filing bug reports on winehq.org.

dbus[22416]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:43:55] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[22551]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 16:48:13] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[22803]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 17:11:52] - Running wine- winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)

000b:fixme:winediag:start_process Wine Staging 4.0-rc4 is a testing version containing experimental patches.

000b:fixme:winediag:start_process Please mention your exact version when filing bug reports on winehq.org.

dbus[23408]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 17:14:40] - Running wine- winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)

000b:fixme:winediag:start_process Wine Staging 4.0-rc4 is a testing version containing experimental patches.

000b:fixme:winediag:start_process Please mention your exact version when filing bug reports on winehq.org.

dbus[23572]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 17:15:01] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[23706]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/06/19 17:16:38] - Running wine-2.13-staging Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 17:19:39] - Running wine-2.13-staging winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)

[07/06/19 17:20:35] - Running wine-2.13-staging winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)

err:process:__wine_kernel_init boot event wait timed out

[07/06/19 17:21:45] - Running wine-2.13-staging winecfg (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)

err:process:__wine_kernel_init boot event wait timed out

[07/06/19 17:23:31] - Running wine-2.13-staging Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

err:process:__wine_kernel_init boot event wait timed out

[07/06/19 17:24:09] - Running wine-2.13-staging Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 17:24:28] - Running wine-2.13-staging Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 17:24:58] - Running wine-2.13-staging Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 17:25:00] - Running wine-2.13-staging Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

[07/06/19 17:25:49] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[26515]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

wine: configuration in '/Users/Drew/Library/PlayOnMac//wineprefix/civ4' has been updated.

[07/07/19 09:20:01] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[27941]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/07/19 09:21:00] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[28510]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/07/19 09:21:25] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

000b:fixme:winediag:start_process Wine Staging 4.0-rc4 is a testing version containing experimental patches.

000b:fixme:winediag:start_process Please mention your exact version when filing bug reports on winehq.org.

dbus[28714]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

0009:fixme:thread:create_user_shared_data_thread Creating user shared data update thread.

0009:fixme:service:SERV_QueryServiceObjectSecurity 0x16c190 4 0x16c3d8 0 0x32f0d0 - semi-stub

0009:fixme:service:SERV_QueryServiceObjectSecurity 0x16c190 4 0x16c3d8 28 0x32f0d0 - semi-stub

0009:fixme:service:SetServiceObjectSecurity 0x16c190 4 0x32f04c

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

[07/07/19 09:35:21] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

dbus[28956]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

[07/07/19 09:39:45] - Running wine- Civilization4.exe (Working directory : /Users/Drew/Library/PlayOnMac/wineprefix/civ4/drive_c/Program Files/Firaxis Games/Sid Meier's Civilization 4)

000b:fixme:winediag:start_process Wine Staging 4.0-rc4 is a testing version containing experimental patches.

000b:fixme:winediag:start_process Please mention your exact version when filing bug reports on winehq.org.

dbus[29171]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!

0009:fixme:thread:create_user_shared_data_thread Creating user shared data update thread.

0009:fixme:service:SERV_QueryServiceObjectSecurity 0x16c190 4 0x16c3d8 0 0x32f0d0 - semi-stub

0009:fixme:service:SERV_QueryServiceObjectSecurity 0x16c190 4 0x16c3d8 28 0x32f0d0 - semi-stub

0009:fixme:service:SetServiceObjectSecurity 0x16c190 4 0x32f04c

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

0009:fixme:ntdll:NtQuerySystemInformation returning fake driver list

 

Ok, so I have an old PC CD-ROM of Civlization IV, with the 2 discs for installation. I was able to successfully install the game on PlayOnMac, I have a desktop shortcut and it shows up in PlayOnMac as an app that I can run. So when I go to run it, I have Disc 1 in my cd drive, and I click on the application button in PlayOnMac and I click run. When I click run, the game window pops up and I get this error message:

https://drive.google.com/file/d/1qdwe4T7obSXobPnvHdb1qdnLBT08XqlD/view?usp=sharing

 

Then, on PlayOnMac, I get this error message: 

https://drive.google.com/file/d/1nWoQoEUlojGEEUscdHmumkv_gNEsjm1r/view?usp=sharing

 

Does anyone have any ideas on how to help me actually play the game?

"Please insert the correct CD-ROM, select OK and restart application" : it might be the DRM (anti copy protection) that block you.

Perhaps clicking the bluelink below the text message, will give interresting details.

That's an interesting thought about the DRM, I don't suppose there's anyway around that?

 

I did click the blue link, it just takes me to 2k's homepage, nothign helpful.

This seems to confirm the issue (About NoCD).

 

If you have a lot more time to spend (and to learn), you may read : 'Manual installations' on our wiki.

Thank you for your help, wouldn't hurt to do a deep dive to figure this out