How to Install and Run .exe Files Using Wine on Apple Silicon Mac (M1/M2/M3/M4)

✅ Prerequisites

• Homebrew installed
  If not:

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

🧰 Step 1: Install Rosetta 2 (Required for Intel-based Wine)

softwareupdate --install-rosetta --agree-to-license

🍺 Step 2: Install Wine Stable via Homebrew

brew install --cask wine-stable

🛠 If you get errors like:

Error: It seems there is already a Binary at ‘/opt/homebrew/bin/…’

Then run:

rm -f /opt/homebrew/bin/{wine*,appdb,msidb,msiexec,notepad,regedit,taskmgr,uninstaller,winver,wordpad,regsvr32,cmd,control,start}

Then reinstall:

brew install --cask wine-stable

⚠️ Step 3: Allow Wine to Open (First Time Only)

When you run Wine for the first time, macOS might block it:

/Applications/Wine\ Stable.app/Contents/Resources/wine/bin/winecfg

❗ “Wine Stable” cannot be opened because the developer cannot be verified.

👣 Fix it:

• Open System Settings → Privacy & Security
• Scroll and click “Allow Anyway”
• Then run the command again

📦 Step 4: Install a .exe Software

Use this command to install (run the setup for) a Windows .exe file — for example SQLyog:

/Applications/Wine\ Stable.app/Contents/Resources/wine/bin/wine ~/Downloads/sqlyog/SQLyog.x86.exe

💡 This will open the installer window — just like on Windows. Follow the steps and install it in the default location.

📁 Step 5: Installed Files Location

Wine installs all Windows apps inside:

~/.wine/drive_c/Program Files (x86)/

For SQLyog, the .exe is here:

~/.wine/drive_c/Program Files (x86)/SQLyog/SQLyog.exe

🚀 Step 6: Run the Installed App Anytime

To open the installed app:

/Applications/Wine\ Stable.app/Contents/Resources/wine/bin/wine ~/.wine/drive_c/Program\ Files\ \(x86\)/SQLyog/SQLyog.exe

✅ You do NOT need to install it again every time you boot your Mac — the software stays installed under Wine.

🖥 Optional: Create a Launcher Script

If you want a shortcut:

nano ~/run-sqlyog.sh

Paste:

#!/bin/bash
/Applications/Wine\ Stable.app/Contents/Resources/wine/bin/wine ~/.wine/drive_c/Program\ Files\ \(x86\)/SQLyog/SQLyog.exe

Make it executable:

chmod +x ~/run-sqlyog.sh

Run it easily:

~/run-sqlyog.sh