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Switching ecosystem is dicey but moving from Mac OS to Windows isn't so much an ecosystem switch though.

Here's my blog post addressing that myth: http://www.kentran.net/2015/10/how-macnix-users-can-stay-pro...

Please have a look at MSYS2. It's far, far easier to use than cygwin and even has `pacman` as a package manager

I have used MSYS2 but decided to come back to Cygwin.

1. Commands in MSYS2, while fast in its shell, are slower than Cygwin's commands when run in PowerShell. 2. MSYS2 can't be installed via Chocolatey. It's because MSYS2 owners are against Chocolatey (insane!). Which makes it harder to automate the replication of my environment across machines. 3. Cygwin does has package managers. I use Cyg-Get, which is also available via Chocolatey.

>Commands in MSYS2, while fast in its shell, are slower than Cygwin's commands when run in PowerShell

The only bugs related to this are to do with slow LDAP/AD lookups - can you elaborate?

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