There are too many outdated instructions online. This place is meant to contain the most up-to-date instructions for running Age of Empires 2 DE on macOS (with multiplayer support).

You need MacOS Big Sur 11.1 or greater.

• Install Crossover (requires a paid license but there's a free trial)
• Create a new Windows 10 bottle in Crossover
• Install Steam
• Open steam and install AOE2:DE
• In the bottle, install "DXVK (Builtin)"
• In the bottle, install "DirectX for modern games"
• In the bottle settings, enable DXVK
• In the bottle settings, optionally enable "High resolution" to enable Retina display resolution
• Download the patched ucrtbase.dll here
• In the Crossover bottle, click "Open C: drive" and navigate to C:/Windows/System32
• Put the ucrtbase.dll file you downloaded in that folder (overwrite the existing file)
• Open the Wine configuration panel: in "Libraries" add concrt140.dll and ucrtbase. They should show up as native, builtin in the list.
• In Steam, optionally set AOE2:DE launch parameters to SKIPINTRO

Feel free to send pull requests to update this guide.

Someone on reddit wrote a guide on how to play aoe 2 de on mac os without needing crossover. https://www.reddit.com/r/aoe2/comments/150t2v1/aoe_2_de_fix_on_mac_using_wineskin_winery/

Copy pasted here just in case

Here's a quick guide on how to get it running (should work on Intel and Apple silicon Macs):

• Start by installing Homebrew (https://brew.sh/) by opening terminal and typing the following:

/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

Install Wineskin Winery (https://github.com/Gcenx/WineskinServer) by typing the following in terminal:

brew install --cask --no-quarantine gcenx/wine/wineskin

• Open the Wineskin Winery app that should appear with the rest of your apps in your Applications folder.

• Make sure you have the latest wrapper (currently 2.9.1.9 or higher) and install the latest engine (currently WS11WineCX64Bit22.1.1-8 or higher).

• Click on the “Create New Blank Wrapper” button at the bottom. I named my wrapper “Steam” since it’ll be used for all my steam games. Wineskin Winery will create a new wrapper that will appear in “/Macintosh HD/Users/[YOUR USER NAME]/Applications/Wineskin/” folder (not the same Applications folder that has all your applications).

• If Wineskin Winery freezes and becomes unresponsive, just give it some time. If it doesn’t fix itself in 5 minutes, then just kill it by holding the cmd option esc keys to get the force quit menu and kill the unresponsive process. Usually, the wrapper will be created successfully, so go ahead and use it directly.

• Open Finder and navigate to “/Macintosh HD/Users/[YOUR USER NAME]/Applications/Wineskin/”.

• Right-click on the new Steam wrapper and click on “Show Package Contents”.

• Click on the Wineskin app in there. This will be how you control the wrapper's settings.

• You can click on “Install Software” if you have a .exe file, but in the case of Steam, it’s better to install it through Winetricks as explained in the next steps.

• Click on “Winetricks”. -It might take some time to load, so be patient :)

• Search for Steam and install it with vcrun2019 or vcrun2022. It may take some time, so be patient. -Wait until it’s done installing and it should work afterwards! Just close the winetricks page and launch the wrapper directly like you’d do with any other app.