Notepad++ on Mac

Notepad++ has no Mac build — but it runs beautifully through a translation layer, and so do most of the small Windows tools people miss. When to translate, and when a native swap is honestly better:

Most people buy Bourbon for the games. They stick around for a much more boring reason: three or four small Windows utilities they've used for fifteen years and have never found a Mac replacement they actually like.

These are good candidates. Small, self contained, no GPU needed, no phoning home to a license server.

The ones that work well

Bourbon ships a curated catalog that installs these from their official sources. The ones marked Recommended, meaning they install and launch cleanly:

• Notepad++, the editor people actually miss on macOS. Installer UI shows up as expected, just accept the defaults.
• PuTTY, small MSI installer. Network behavior can vary under Wine so test your own connections.
• WinMerge, lightweight diff tool and a good first thing to try if you just want to confirm your setup works.
• SumatraPDF, small native installer, solid document viewer smoke test.
• ImageGlass, lightweight image viewer. File associations might need setting up by hand.
• WinDirStat, disk usage visualizer.
• BleachBit, cleanup utility.

The ones to test first

These install fine, but their whole job involves talking to the outside world, which is where Wine gets less predictable.

• WinSCP, file transfer. Network tools vary with Wine's networking, so check it against your actual servers.
• ShareX and Greenshot, screen capture. Global hotkeys and system wide hooks are exactly the kind of thing that doesn't cross the boundary cleanly. Test before you rely on them.
• Everything, whose search index only covers the Wine prefix, and the NTFS service behavior it depends on isn't native here.

The honest caveat

For several of these, macOS already has a great native equivalent, and a native app beats a translated one every single time. Bourbon's catalog policy is blunt about it: anything with a real Mac build gets removed from the list entirely, because running a Mac app through Wine is just worse than installing the Mac version.

So this isn't "run all your Windows utilities on a Mac". It's that for the specific tools where the Windows version is the one you want and no Mac build exists, Bourbon installs them in a couple of clicks and keeps them working.