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I like trying different OSs, but I have yet to try a Illumos-based OS. Can I run all or most Linux Software, just by building from source?

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You should be able to built most Linux software by hand (except very linux-kernel specific software), but as there are Illumos-based distributions which include package manager, it should be way more easy to use them and install pre-built software packages from the corresponding repositories. Using distributions with GNU userspace enhances also the compatibility with Linux/GNU system.

Building packages by hand can take very long and could require high system resources - if you are only trying some OSs, you normally do not want to do this.

jofel
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    I briefly played with [DilOS](http://www.dilos.org/) recently. It seems to work reasonably well. It uses the Debian `apt-get` package system. The main worry I have with any of these forks is longevity. Which are flashes in the pan, and which will prevail, if any? – Warren Young Jun 26 '15 at 13:22
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    For instance, the [pkgsrc](https://www.pkgsrc.org/) team statistics for their [most recent release in April 2015](http://mail-index.netbsd.org/pkgsrc-users/2015/04/14/msg021358.html) showed they successfully built 13092 out of 15246 packages in their collection for the SmartOS distro of illumos. – alanc Jun 27 '15 at 21:21
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    @alanc Do those statistics provide any indication of how much time and effort went into building each package on SmartOS? In my experience, building Linux-developed packages on a Solaris-based OS often requires considerable effort. – Andrew Henle Jun 28 '15 at 18:01
  • @AndrewHenle - no they don't. Making these packages build is part of Jonathan's job, and he's been increasing the number every quarter, so I would not be surprised if there's been many hours of effort to get that far. I personally find that many of the more common & well maintained packages build out of the box, thanks to autoconf & similar tools, but I also maintain upstream software at X.Org and know it takes effort there to keep that working cross-platform. – alanc Jun 29 '15 at 03:21
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No; you can try to build the software, but it doesn't mean it'll be a success without source modifications. For example; building PHP 5.5 on OmniOS will fail at socket compatibility requiring patches to be a success; you can see my modifications here to make it work.

Also, Linux based OS's are GNU; Illumos based ones are CDDL (the leaders of illumos-gate based projects prefer CDDL over GNU); they do come with GNU software but it's not the default. You'll find that grep -F or certain find functionality doesn't work on Illumos OS's unless you use the /usr/gnu/bin version of the software.