Matias Saibene
Working progress
First, sorry for my bad English. I know that it is the lingua franca of this contemporary era, but nevertheless I find it difficult to write and translate and correct Google translate. Don't hesitate to correct me. What's more: I had to translate the PlayOnLinux options into English, so your experience with the PlayOnLinux interface may vary. Also, anything that isn't good in this tutorial let me know and I'll fix it.
This guide assumes that you know how to use your Linux distribution's package manager, including PPAs in the case of Debian, Ubuntu, and Linux Mint, etc. or pacman in the case of Arch Linux, Manjaro, etc.
Files you will need directx_Jun2010_redist.exe, Orbiter2016.zip, D3D9ClientR4.25-forOrbiter2016(r1446).zip
Before we start we are going to install Wine. On Debian-based distributions you can install it with the command
Bash:
sudo apt install wine playonlinux
Bash:
sudo pacman -Syu playonlinux
Now let's start with the tutorial:
Step 1: Launch PlayOnLinux and click Tools->Manage Wine Versions. Wait for the list of available Wine versions to load and once ready choose the Wine Versions (x86) tab, choose 7.11 and press the > button to start the installation. Then click Next. Note that this is independent of having previously installed Wine.

Step 2: Once Wine 7.11 is downloaded, close the window and in the PlayOnLinux window press + Install. Then click Install an unlisted program. Then Install program in a new virtual drive, click next, and then enter a name for the virtual drive, in our case Orbiter2016 without spaces and click Next.

Step 3: Now check the boxes Use another version of Wine, Configure Wine, and Install some libraries, and press next. Choose 7.11 and click Next. Then choose 32 bit Windows installation and click Next. Wait while the virtual drive is created.


Step 4: In Wine settings choose Windows 7 under Version to mimic and click OK. Then in the list of components check
- POL_Install d3dx9
- POL_Install directx9
- POL_Install vcrun2005
- POL_Install vcrun2008
- POL_Install vcrun2010
- POL_Install vcrun 2015
Click Next and wait meanwhile the selected components are being installed.

Step 5: In Select the installer file to run click Cancel and the window will close.
Now we are going to install directx_Jun2010_redist.exe and create the shortcuts for Orbiter.
Step 6: In the PlayOnLinux window, click Configure and choose Orbiter2016 from the list on the left, then click the Miscellaneous tab, then click Run an .exe file on this virtual drive.
Locate the directx_Jun2010_redist.exe file, double click it and continue the installation, indicating a folder to unzip the files. In my case inside the DXD9 folder inside the Desktop folder. Finally click Ok to start unzipping the files.

Step 7: Once finished, open the PlayOnLinux window and click Run an .exe file on this virtual drive again. Locate the DXSETUP.exe file that we saved to /home/username/Desktop/DXD9. And continue the installation like any Windows program. Do not close the PlayOnLinux window.

Now we are going to install Orbiter.
Step 8: In your file browser unzip the Orbiter2016.zip file. Copy and paste the folder that resulted from unzipping Orbiter2016.zip into /home/username/.PlayOnLinux/wineprefix/Orbiter2016/drive_c/
Step 9: In the PlayOnLinux Settings window click the General tab and then click Create a shortcut of this virtual drive. PlayOnLinux will scan the drive and once scanned select Orbiter_ng.exe then click Next and give the shortcut a name. In my case I'll name it Orbiter 2016. PlayOnLinux will rescan the drive and if you don't want to make a new shortcut select I don't want to create another shortcut and click Next. The window will close.

Step 10: Finally you will find the shortcut on PlayOnLinux and on your desktop, both equally functional. Open Orbiter with any of the shortcuts and click on Extra->Debugging options->Orbiter shutdown options and select Respawn Orbiter process to avoid problems when exiting the simulation.

You can now enjoy Orbiter on Linux (non-native, via Wine). If you wish, you can contribute to the @Gondos project by testing native Orbiter on Linux without Wine or PlayOnLinux.
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