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Attempting to play Star Trek Online. Installation via the PlayOnMac installer seemed to go fine, launcher updated game files, but when I try to launch, I get the following Windows error message: 

Unsupported DirectX Version

Support for the Video Card you are using has ended. You will be unable to play using this Video Card. Please upgrade your Video Card to one that supports DirectX Hardware Feature Level 10.0 or higher; See your Video Card manufacturer's documentation for information on DirectX Hardware Feature Level support. 

Not experienced with PlayOnMac, so I'm sure whether this is a Wine issue or an issue with the Mac's underlying video card (late 2014 27" iMac Core i5 with AMD Radeon R9 M295X 4 GB video card) or how to troubleshoot. 

Any advice?

EDIT: If it helps, this appears to be an issue a number of native Windows users had 2 years ago tied to the Windows 10 Creator Update: 

https://www.reddit.com/r/sto/comments/7ik4hc/graphics_card_issue/

 

Aangepast door DoctorOddfellow

Do you use this script to install the game ?:  https://www.playonlinux.com/en/app-2491-Star_Trek_Online.html

Aangepast door Dadu042

 

No, I selected "Star Trek Online" from "Install A Program" in the PlayOnMac app interface. 

 

Aangepast door DoctorOddfellow

Ok, so it's the same script. I looked at, but I can't help.

Note: POL/POM v4 has poor support for DirectX > v9.

Aangepast door Dadu042

I have it working using Wine 3.17, late 2012 IMac, High Sierra, NVIDIA GeForce GT 650M 512 MB. At the STO log-in screen, choose Option, check Safe Mode, then log in. More recent versions of Wine give me the the unsupported DirectX alert. I also have to reset the graphics once I'm in the game.

I can confirm 3.17 does load the game with the safe mode option.