To Use or Not to Use Cygwin

Yes, if you just want to use those neat Unix utilities, like grep, head, touch, tail, more, etc, and if you are patient enough to manage Cygwin installation. For anything beyond that, you should really consider Solaris x86 or Linux.

Cygwin installer is my worst install experience. After using Cygwin for years, I still find it confusing and tiresome to check/uncheck these little source/binary/remove icons.

I wouldn't run any serious apps, not even Apache Ant, from within a Cygwin shell. I don't need more dll mismatches, or path configuration problems. I don't want to duplicate all my environment variables (JAVA_HOME, ANT_HOME, MAVEN_HOME, CATALINA_HOME, JBOSS_HOME, SJSAS_HOME, etc) in both Windows Control Panel and .profile/.bash/.tcsh. I don't want to rewrite my convenience batch files to tcsh alias or bourne shell scripts.

I wouldn't build my projects using any part of Cywin. I wouldn't require team members to have Cygwin in their Windows box. Of course, I would never ask end users of my software to first install Cygwin, or some other Unix clone on Windows. If any software product have such requirement, I have doubt on its quality and maintainability.

If my development environment is Windows, I would hire a release engineer good at batch files, or even better, an Ant expert.

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