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Wineskin install and modding guide (play Oblivion on a Mac!)


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Yes, it's possible to install and mod Oblivion on a Mac! This guide will show you how, using Wineskin, a GUI interface for Wine. Wine is a free, powerful run environment for Windows software that translates Windows instructions to instructions other operating systems, like Mac or Linux, can understand, without the kludginess and memory bloat of emulation. This isn't a mod list, but it uncovers some pitfalls and solutions I discovered when trying to install certain tools and mods in Wineskin.
This guide is Mac-focused since I'm a Mac user, but I imagine it should be useful to Linux users as well. I'll try to keep this guide as noob-friendly as possible, as I'm basically a noob myself. So if you already understand what a given section is talking about, feel free to skip.
Lastly, for those of you tempted to leave "why not just get a real gaming computer" type comments: Some of us like Macs, and like games, and we're fine with it. There is no reason for you not to be fine with it as well. Please be fine with it. Those who feel the need to express how they're not fine with it will probably be tolerated but sneered at.
Okay, let's begin:
0.) How do Wineskin and Wine actually work?

As mentioned, Wine translates Windows-specific instructions so whichever operating system you are using can use it. It is not running Windows, so it is a lot faster and slicker than Windows emulators or virtual machines.
When you install an application using Wine, you first create what Wine calls a bottle or wrapper (I'll use both terms interchangeably). A bottle is like a self-contained part of your computer that has everything the application needs to run. I think of it like a ship in a bottle; a miniature universe that’s separate from the rest of the world, but that those of us in the world can still look at. A Wine bottle is similarly self-contained but can interact with the rest of your computer.
One important thing about this to understand is that while on a PC you’d only need one version of a particular set of libraries, like DirectX let’s say, to run all the games that need it, for Wine you need a different installation of these libraries in every bottle that requires it. So if you have ten bottles for ten different games that require DirectX, that’s ten different installs of DirectX, one for each bottle. That seems really weird and pointless until you realize how essential this self-containedness is to how Wine bottles operate. Something like DirectX can’t run on a Mac, so if you were going to make it universally accessible, you’d have to rely on something like emulation, and the whole point of Wine is to avoid emulation. It really is the smoothest way to run Windows apps on non-Windows systems.
Wineskin is a popular GUI interface for Wine, meaning you can use it like a typical application, without typing commands into Terminal. You can create new Wineskin bottles with a program called Wineskin Winery, or you can download premade bottles using Porting Kit (see next section). Once you have such a bottle, you right-click and select “Show Package Contents.” This will allow you to see everything inside the bottle; the bottle is in fact a package, which is basically like a folder that works like a file if you double-click it.
One thing you’ll see inside the bottle is the actual Wineskin app. Yes, every bottle made using Wineskin Winery has it’s own version of Wineskin inside. This is what actually lets you install software. Usually it’s just a matter of clicking the “Install Software” button and picking the installer exe from your Downloads folder. This should suffice for the GOG version of Oblivion. With Steam it’s a little more involved. See the next section.

0a.) Advanced features in Wineskin.
This in an IMPORTANT section! Read this section if you see something in the guide that you don’t know how to do in Wineskin. If something in this guide confuses you, it may be because you didn’t read this section!

For all these, right-click your Oblivion bottle, “Show Package Contents,” open Wineskin, and select “Advanced.”
  • Custom EXE Creator: For creating exe shortcuts for mod managers and other tools. Select the Tools tab, then Custom EXE Creator. Click Browse to find the EXE inside your bottle you wish to create a shortcut for. Make sure to name the app, then click “Save.” Your custom exe should appear in the root of your bottle. Just double click to run it.
  • Winetricks: Useful for installing libraries and such, among other things. Select the Tools tab, then Winetricks. Search for the library or other dependency you wish to install. Click the little triangle to open the dlls folder, then check the library you want to install. Click the Run button and wait for the installation to complete. It should say something like “Winetricks complete!” in the lower panel once it’s done.
  • Config Utility: Needed to override certain libraries to get mods like ENB, ENBoost, and MoreHeap to run. Select the Tools tab, then Config Utility. Select the Libraries tab and use the “New override for library” panel to search.
  • Uninstaller: For uninstalling programs and libraries inside the bottle, and also the best way to see what programs and libraries have been installed. Go to Tools, then Uninstaller. Just select what you want to uninstall and click “Remove.”
  • Change Engine: We’ll need this to update to a 64-bit engine, necessary for installing larger mods. New engines go in the /Library/Application Support/Wineskin/Engines folder of your Mac. Go to Tools, then Change Engine Used, then just pick the engine from the drop-down menu.
  • Change the Windows EXE: Go to Configuration and look at the top text panel. For the Steam version, this should be /Program Files/Steam/steam.exe . For GOG, once you have OBSE installed, it should be /GOG Games/Oblivion/obse_loader.exe .
  • EXE flags: Go to Configuration and look at the text panel near the top. This is where you can type the code to bypass the Steam app when opening the Steam version of Oblivion (see “1a.) Setup for the Steam version” below).

1.) Installing Oblivion on a Mac

This guide assumes you've purchased a legal copy of Oblivion: Digital Deluxe Game of the Year Edition from either Steam or GOG. You can purchase Steam games for PC games on the Mac version of Steam, and you can download purchased Windows games from GOG just as easily as Mac games. We’ll be using Porting Kit, a nice front end for downloading and managing premade bottles, put together by PaultheTall.
  • Download Porting Kit.
  • Open Porting Kit and navigate to the Library tab, then select Server.
  • Search for Oblivion, right-click, and select “Download.” Pick either the GOG or Steam version to download.
  • Now navigate to the Library > Local tab. Right-click and select “Find Wrapper,” then move the bottle to wherever you want.
  • If you want to change the game’s icon, highlight the bottle and hit Command-I. Copy your preferred icon to the clipboard, then select the icon in the Get Info panel and hit Command-V to paste.
  • To install the GOG version, right-click the bottle and select “Show Package Contents.” Open Wineskin, click “Install Software,” and pick the GOG installer you’ve downloaded to install.
  • To install the Steam version, double-click the bottle to run it and log into Steam. Go to Library and select “The Elder Scrolls IV: Oblivion” and click the Install button to download. See the next section for additional tips for making the Steam version run smoothly.
  • Oblivion should now run. To make installing mods a bit easier, do the following: “Show Package Contents,” then navigate to your Oblivion folder (for Steam, it’s drive_c/Program Files/Steam/steamapps/common/Oblivion) and make an alias of your Oblivion folder (right-click, “Make Alias”). Then put the alias in the root of your Oblivion bottle (what you see when you first click “Show Package Contents”).

1a.) Setup for the Steam version

â¨Here are some things to do in Steam once you’ve download the Steam version of Oblivion to keep the actually Steam app as unobtrusive as possible.
  • Open your wrapper to launch Steam. Under the Steam menu, select “Settings,” then select “In-Game.” Uncheck “Enable the Steam Overlay” and click “Okay.”
  • Under the Steam menu, select “Go Offline” then click “Restart in Offline Mode.”
  • Open Wineskin and click “Advanced.” Add the line “ -applaunch 900883” to the EXE Flags (or if you happen to have the non “Digital Deluxe” version, “ -applaunch 22330.” This will launch Oblivion without opening Steam at all. If you need to open Steam inside your wrapper for some reason, just delete this line in Wineskin.
  • Steam will often try to download and install updates before launching. It appears to be a bug in Steam, and I haven’t found a good way of getting around it.

You should now be able to open Oblivion just by double-clicking the bottle you made like any other application.
1b.) The Oblivion ini file

 

 

  • To generate the Oblivion.ini file, just open and quit Oblivion. It can be found in the /Documents/My Games/Oblivion/ folder of your Mac.
  • Make an alias and put it in your Oblivion folder. Do NOT rename it to Oblivion.ini, as it will confuse BOSS.
  • Now is a good time to make some common tweaks to the .ini. Open the Oblivion.ini alias. I recommend turning off the Intro and Main Menu movies, and turning off bBorderRegionsEnabled. See here.

 

 

2.) Install TES Mod Manager, OBSE and BOSS

To mod Oblivion, you pretty much need a mod manager. I recommend TES Mod Manager (TESMM) for most mods, as it’s very user friendly (It’s the newer version of a program called “Oblivion Mod Manager (OBMM). Anything that works with OBMM should work with TESMM as well). We’ll also install Wrye Bash (see next section), another mod manager that can do some things TESMM can’t. To use TESMM we need to be sure to install the required .NET 4.5 framework in our bottle and to update to a 64-bit Wineskin engine so we can install larger mods.
  • Open Wineskin. Use the uninstaller to uninstall Mono (a sort of Wine version of .NET that will conflict with the .NET framework we actually need).
  • Use winetricks to install .NET 4.5.
  • Download the latest Vanilla 64-bit Wineskin engine and put it the /Library/Application Support/Wineskin/Engines folder of your Mac.
  • Now download the TESMM installer. Open Wineskin and click Install Software to run the TESMM installer exe. Use Wineskin to create a custom exe.
  • Open TESMM installer. Choose Oblivion and define the game path if need. Click the “Install OBSE” text in the bottom-left to download Oblivion Script Extender (OBSE, necessary for very many mods).
  • If you have the GOG version, download the “latest loader” for OBSE and put it in your Oblivion folder, overwriting the existing loader. Set the Windows EXE in Wineskin to /GOG Games/Oblivion/obse_loader.exe .
  • Download the BOSS installer. BOSS (“Better Oblivion Script Sorter”) is essential for making sure your Oblivion mods load in the proper order.
  • Open Wineskin and install BOSS in your Oblivion wrapper. The default location is fine.
  • Open TESMM. There should be an “Auto sort using BOSS” button. Try clicking on it: if an error occurs, open Oblivion and close it, then try again.

3.) Install Wrye Bash

Another mod manager that’s a little less user-friendly than TESMM, but with more features such as the ability to create a bashed patch (see section "7. Installing Other Mods" below). Some mods can only be installed with Wrye Bash.
  • Download the Wrye Bash installer.
  • Open Wineskin and install Wrye Bash in your wrapper. Install the Standalone version. This installer will automatically download the C++ library Wrye Bash requires.
  • Ignore the warning about installing in Program Files that comes up with the Steam version.
  • Uncheck “Start Menu Shortcuts,” click “Install,” click “Next,” uncheck “View Readme,” close.
  • Create a custom EXE in Wineskin. The Wrye Bash app should be in a folder called “Mopy” in your Oblivion folder.
  • Make an alias of the Bash Installer folder (drive_c/Program Files/Steam/steamapps/common/Oblivion Mods/Bash Installers) and put it in your Oblivion folder.
  • Note, after Wrye Bash is nearly done rebuilding the bashed patch, it displays some info in HTML. If your wrapper doesn’t have a way to interpret HTML, Wrye Bash will crash, and the bashed patch will fail to rebuild. Your Oblivion wrapper should include Gecko (a sort of Wine version of Explorer), but if it doesn’t (use Uninstaller in Wineskin to see if it’s there), you may need to install Internet Explorer 8 using Wine Tricks.

4.) 4gb patch/Large Address Aware (LAA)

Oblivion was designed to only use less than 2gb of RAM, which can create problems for heavily modded games. We can make Oblivion “Large Address Aware,” which doubles the amount of memory it can use. You need at least 4gb of memory and a 64-bit OS to see any benefit, but most Macs meet these qualifications. I’ve read the GOG version of Oblivion is already Large Address Aware, but I haven’t tested it yet.
Daniel’s 4gb patch is the most popular solution at NexusMods to making programs LAA, but it doesn’t work in Wineskin. Luckily, there’s an alternative that does.
  • Download the program “Large Address Aware.” Unpack the archive and put it in your Oblivion folder.
  • Create a Custom EXE and call it LAA.
  • Open your Oblivion folder and make copies of Oblivion.exe, OblivionLauncher.exe, and obse_loader.exe (select, right-click, “Duplicate”) as a backup.
  • Open LAA and click the “…” button. Select the Oblivion.exe and click “Okay.”
  • Check the Large Address Aware Flag box, then click Save. If it’s already checked, leave it checked! It means it’s already LAA (possibly because you have the GOG version).
  • Repeat for OblivionLauncher.exe and obse_loader.exe. Alternatively, choose Intermediate Mode to edit these files all at once.

5.) ENB/ENBoost

ENB is a graphics boost, and ENBoost is a related performance booster. Unfortunately they can’t both be run in Oblivion. I’ll focus on ENBoost since that what I use, but this guide should help with installing ENB as well. The trick to getting these programs to work in Wineskin is to make sure you have the proper libraries installed and that you have the proper overrides for these libraries enabled in Wineskin.
  • Download ENBoost for Oblivion. Also, download these ini files.
  • Open Wineskin in your wrapper.
  • Run Winetricks and search and install the d3dx9_43 libraries.
  • Run Config Utility and navigate to the Libraries tab.
  • Search for d3d9 in the “New override for library” menu and click Add.
  • Make sure the override is set to “native, builtin.” Click Edit to change if needed.
  • Do the same for d3dx9_26, d3dx9_40, and d3dx9_43.
  • Click “Apply,” then “OK” to close.
  • Unpack the enbseries_oblivion_v0259enboost archive and open the folder. Open the WrapperVersion folder.
  • Move enbhost.exe and d3d9.dll files to your main Oblivion folder.
  • Unpack the ENBoost 1_0-45266-259 archive and open the folder. Open to the folders that best match your graphics card and OS. For me it was AMD > 64bitOS.
  • Move the enblocal.ini file to your main Oblivion folder.
  • Open enblocal.ini. I recommend changing ReservedMemorySizeMB to 512.
  • Change VideoMemorySizeMB. Formula: VRAM + Memory in MB - 2048. Max value is 10240. Check About This Mac for values. 1 GB = 1024 MB. Save and close.
  • Alternative formula (for ≥ 8gb RAM): VRAM + shared video memory - 350. Shared memory is probably 1536 (i.e. 1.5 gb). See here to find out for sure.
  • When you launch Oblivion, you should see a message in the upper left saying that ENBoost is loading. If not, then ENBoost is not working right. A possible solution is to run Winetricks to make sure all the required libraries are installed (d3d9, d3dx9_26, d3dx9_40, and d3dx9_43) and set to “native, builtin” in Config Utility.

6.) MoreHeap

MoreHeap is a performance boosting mod that works by changing how Oblivion manages memory. Like with ENBoost, we need to make sure that the proper overrides are enabled, though in this case we have just one library to worry about.
  • Download MoreHeap.
  • Unpack the installer. Move the Version.dll file to your main Oblivion folder.
  • Open Wineskin in your wrapper.
  • Run Config Utility. Navigate to the Libraries tab.
  • Search for Version.dll in the “New override for library:” menu and click Add.
  • Make sure the override is set to “native, builtin.” Click Edit to change if needed.
  • Click “Apply,” then “OK” to close.
  • Run Oblivion, then close to generate the MoreHeap.ini and MoreHeap.log files in your main Oblivion folder. Exit Oblivion.
  • Open the MoreHeap.ini file. I recommend changing both DefaultHeapSize values to 768. Save and close.

7.) Installing other mods
IMPORTANT! Unlike Windows, Mac OS does not automatically merge the contents of two folders when you drag one folder to a location with another folder of the same name. Instead, the first will overwrite the second, or you get two folders with the same name. This is important when manually installing mods. For example, the instructions for installing Oblivion Stutter Remover say to “Simply drag the Data folder from the zip to your Oblivion folder.” Don’t do this! It will overwrite your Data folder and delete any mods it contains. Instead, you have to open the unzipped folder and open all the nested folders (/Data/OBSE/Plugins/) until you get to the two files you need. Then navigate to your /Oblivion/Data/OBSE/Plugins/ folder and move the two files there.
Again, this goes for any manually installed mods. With most mods you’ll use a mod manager like TESMM or Wrye Bash. Here are general instructions for doing so. Some mods have more specific instructions, and you should follow those instead.

To install mods in TESMM:
  • Put the mod archive in your Oblivion folder.
  • Open TESMM. Click “Import.”
  • Select your mod archive and click “Okay.”
  • It doesn’t usually matter whether you import info from Nexus or not, but I usually let it try (you can automate this behavior in “Settings”).
  • Type the name of the patch if needed. I uncheck the “include version in file name” box. If it’s a very large mod, you may need to check the “OMod v 2” box or the install will fail.
  • Click “create OMod and wait.”
  • Click the mod when it appears in the right pane, then click “Activate.”
  • If there’s an Install Wizard, go through the steps.
  • Check any .esp or .esm files that appear in the left pane.
  • Run BOSS to sort the load order. If BOSS doesn’t recognize a mod, sort in manually in TESMM according to the mod’s instructions.
To install mods in Wrye Bash:
  • Put the mod archive in the Bash Installers folder (if you followed the steps in “3.) Install Wrye Bash,” you should have an alias in your Oblivion folder.
  • Click the Installers tab, click “Okay,” and wait.
  • Right-click the archive and click “Install” (or if available, “Wizard”).
  • Follow the steps in the Wizard, if there is one, and check any available options you’d like in Wrye Bash.
  • Click “Install.”
  • Click the “Mods” tab to turn on any new .esp or .esm files.
  • Quit and open TESMM and run BOSS to sort the load order. If BOSS doesn’t recognize a mod, sort in manually in TESMM according to the mod’s instructions.
BSA Redirection/Archive Invalidation: This step is needed for mods that replace textures and meshes, so Oblivion knows to use the new resources.
  • Open TESMM. Click “Utilities” and select “Archive Invalidation.”
  • Make sure “BSA redirection” is selected. Click “Update now.”
Rebuild the Bashed Patch: This step is needed for mods that add things like new items and other “objects” to Oblivion, so that they are distributed in the world as they should be.
  • Open Wrye Bash. Scroll down until you find the Bashed Patch.
  • Right-click and select “Rebuild Patch.”
  • You can click “Okay” or “Skip” for the “Deactivate These Mods” dialog, but be sure to leave everything check. “Okay” will merge the patches into the Bashed Patch, while “Skip” will keep them unmerged.
  • Click “Build Patch” and wait.
  • A dialog will appear to summarize the rebuild. Click “Okay.”
  • If Wrye Bash crashes before this last step, it is because your wrapper doesn’t have a way for Wrye Bash to read HTML and render this dialog. See section “3.) Install Wrye Bash.”

8.) Installing other tools (TES4Edit, TES4LL, TESLODGen, etc.)

 

 

 

You may come across these tools as requirements for other mods not featured in this guide.

  • If there’s an installer, use Wineskin to install. If it’s just an exe file or manual install, put the file or files somewhere in drive_c of your Oblivion wrapper.
  • Create a Custom EXE in Wineskin. In the case of TES4LL, check the “Use Start.exe” option and pick one of the batch files.

 

 

9.) Recommended Mods

There are loads of mods that are frequently recommended, but that I haven’t tried yet.

 

 

Edit: Added link to Wineskin engines in the TESMM section.
Edited by 1Mac
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  • 7 months later...

Thank you for writing up such a detailed guide! I am having an issue with a step in the process that I fear may be preventing me from moving further along in the process:

 

Step 2.

I keep getting a Fatal Error message when opening TESMM. The error message states, "An unhandled exception occurred. Extra information should have been saved to 'C:\users\username\My Documents\tmm_crashdump.txt' in the application's base directory. Error message: Object reference not set to an instance of an object."

 

I was able to successfully install - I think - the OBSE loader, as it shows to running in the bottom left corner of the screen within TESMM.

 

I am unable to close the TESMM application w/o receiving the same Fatal Error message. The only way I can get out is Force Quit.

 

 

I happened to stumble upon the PS Now free 7 day subscription when I saw they added Oblivion, and it was just an awesome trip down nostalgia lane. Since I am not going to be spending $20 a month to play Oblivion on console, I thought I would try and see if I can get the game to work on my Mac. The game loads, but I was wanting to get the recommended mods installed prior to playing, as I would very much like to continue to get some Oblivion play time. However, I am much a noob when it comes to mods and such as having never played around with them before.

 

Any help you can provide is very much appreciated. Thank you!

 

Brent

Edited by bnew1013
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  • 1 month later...

This is a late response, but better late than never, I hope. Tesmm requires dotnet, so you need to install it using Winetricks. I actually never use Tesmm anymore. Wrye Bash has a bit of a learning curve, but it’s a much better mod manager that’s much easier to install than Tesmm. You can find BAIN versions of nearly any mod you’ll need, including DarNified UI, so you never need to install an OMOD ever again.

 

I’d like to update this guide some time with an up-to-date wrapper, but it may be some time.

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  • 3 months later...
  • 2 months later...
  • 6 months later...

Having trouble with OBSE and the GOG version of Oblivion.

 

In character creation, my character is forced to have dark black skin/scales/fur. This doesn't happen in the vanilla launcher.

 

Also, it seems like none of my mods installed through Wyre Bash and TESMM link up with OBSE. These mods are active through the vanilla launcher.

 

Do you have any suggestions?

Edited by HarveyBirdmanJD
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For the black skin issue, you need to create an override for d3dx9_27.dll. Do this with the Config Utility In Wineskin. You may need to download this file via Winetricks first.

 

I’m not sure what you mean by mods linking up with OBSE.

 

Fyi this guide needs some updating. For one I don’t use TESMM anymore and use Wyre Bash exclusively. For another I don’t use the wrapper from Paul the Tall, instead making my own using Unofficial Wineskin, found here: https://portingteam.com/topic/11037-unofficial-wineskin-project/

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