Running *nix apps on Win10 “Anniversary update”: initial findings

Ever since Microsoft announced the “Bash on Windows” inclusion in the Anniversary update of Win10, I’ve been positively *itching* to try it out.  I spent *hours* in Git Bash, Cygwin and other workarounds inside Windows to get tools like Vagrant to work natively in Windows.

Spoiler: it never quite worked. [Aside: if anyone has any idea how to get rsync to work in Cygwin or similarly *without* the Bash shell on Windows, let’s talk.  That was the killer flaw.]

Deciphering the (hidden) installation of Bash

I downloaded the update first thing this morning and got it installed, turned on Developer Mode, then…got stumped by Hanselman’s article (above) on how exactly to get the shell/subsystem itself installed.  [Seems like something got mangled in translation, since “…and adding the Feature, run you bash and are prompted to get Ubuntu on Windows from Canonical via the Windows Store…” doesn’t make any grammatical sense, and searching the Windows Store for “ubuntu”, “bash” or “canonical” didn’t turn up anything useful.]

The Windows10 subreddit’s megathread today left incomplete instructions, and a rumour that this was only available on Win10 Pro (not Home).

Instead, it turns out that you have to navigate to legacy control panel to enable, after you’ve turned on Developer Mode (thanks MSDN Blogs):

Control Panel >> Programs >> Turn Windows features on or off, then check “Windows Subsystem for Linux (Beta)”.  Then reboot once again.


Then fire up CMD.EXE and type “bash” to initiate the installation of “Ubuntu on Windows”:


Now to use it!

Once installed, it’s got plenty of helpful hints built in (or else Ubuntu has gotten even easier than I remember), such as:


Npm, rpm, vagrant, git, ansible, virtualbox are similarly ‘hinted’.

Getting up-to-date software installed

Weirdly, Ansible 1.5.4 was installed, not from the 2.x version.  What gives?  OK, time to chase a rat through a rathole…

This article implies I could try to get a trusty-backport of ansible:

Does that mean the Ubuntu on Windows is effectively an old version of Ubuntu?  How can I even figure that out?

Running ‘apt-get –version’ indicates we have apt 1.0.1ubuntu2 for amb64 compiled on Jan 12 2016.  That seems relatively recent…

Running ‘apt-cache policy ansible’ gives me the following output:

mike@MIKE-WIN10-SSD:/etc/apt$ apt-cache policy ansible 
  Installed: 1.5.4+dfsg-1 
  Candidate: 1.5.4+dfsg-1 
  Version table: 
 *** 1.5.4+dfsg-1 0 
        500 trusty/universe amd64 Packages 
        100 /var/lib/dpkg/status

Looking at /etc/apt/sources.list, there’s only three listed by default:

mike@MIKE-WIN10-SSD:/etc/apt$ cat sources.list 
deb trusty main restricted universe multiverse 
deb trusty-updates main restricted universe multiverse 
deb trusty-security main restricted universe multiverse

So is there some reason why Ubuntu-on-Windows’ package manager (apt) doesn’t even list > 1.5.4 as an available installation?  ‘Cause I was previously running v2.2.0 of Ansible on native Ubuntu (just last month).

I *could* run from source in a subdirectory from my home directory – but I’m shamefully (blissfully?) unaware of the implications – are there common configuration files that might stomp on each other?  Is there common code stuffed in some dark location that is better left alone?

Or should I add the source repo mentioned here?  That seems the safest option, because then apt should manage the dependencies and not leave me with two installs of ansible (1.5.4 and 2.x).

Turns out the “Latest Releases via Apt (Ubuntu)” seems to have done well enough – now ‘ansible –version’ returns “ansible”, which appears to be latest according to

Deciphering hands-on install dependencies

Next I tried installing vagrant, which went OK, but then complained about an incomplete installation:

mike@MIKE-WIN10-SSD:/mnt/c/Users/Mike/VirtualBox VMs/BaseDebianServer$ vagrant up

VirtualBox is complaining that the installation is incomplete. Please run
`VBoxManage --version` to see the error message which should contain
instructions on how to fix this error. 

mike@MIKE-WIN10-SSD:/mnt/c/Users/Mike/VirtualBox VMs/BaseDebianServer$ VBoxManage --version 
WARNING: The character device /dev/vboxdrv does not exist. 
         Please install the virtualbox-dkms package and the appropriate 
         headers, most likely linux-headers-3.4.0+. 

         You will not be able to start VMs until this problem is fixed.

So, tried ‘sudo apt-get install linux-headers-3.4.0’ and it couldn’t find a match.  Tried ‘apt-cache search linux-headers’ and it came back with a wide array of options – 3.13, 3.16, 3.19, 4.2, 4.4 (many subversions and variants available).

Stopped me dead in my tracks – which one would be appropriate to the Ubuntu that ships as “Ubuntu for Windows” in the Win10 Anniversary Update?  Not that header files *should* interact with the operations of the OS, but on the off-chance that there’s some unexpected interaction, I’d rather be a little methodical than have to figure out how to wipe and reinstall.

Figuring out what is the equivalent “version of Ubuntu” that ships with this subsystem isn’t trivial:

  • According to /etc/issue, it’s “Ubuntu 14.04.4 LTS”.
  • What version of the Linux kernel comes with 14.04.4?
  • According to ‘uname -r’, it’s “3.4.0+”, which seems suspiciously under-specific.
  • According to /proc/version, its “Linux version 3.4.0-Microsoft ( (gcc version 4.7 (GCC) ) #1 SMP PREEMPT Wed Dec 31  14:42:53 PST 2014”.

That’s enough for one day – custom versions of the OS should make one ponder.  Tune in next time to see what kind of destruction I can wring out of my freshly-unix-ized Windows box.

P.S. Note to self: it’s cool to get an environment running; it’s even better for it to stay up to date.  This dude did a great job of documenting his process for keeping all the packages current.


3 thoughts on “Running *nix apps on Win10 “Anniversary update”: initial findings

  1. Hi Mike,

    I saw in your spoiler portion at the top that you’re trying to get rsync to work with Windows (I assume with Vagrant and Virtualbox since I followed your link from to find this page).

    I’ve also been poking around in this space. I have managed to successfully get vagrant-rsync working on Windows in combination with this project:

    They use/require the Babun shell on Windows in order to get rsync working properly. I’ve just installed Bash for Windows today because I was hoping to find a more elegant solution. From the WSL issues on Github and what you’ve written up here it seems like maybe Bash on Windows isn’t going to work for me yet I suppose.

    In my project I’m trying to get Windows to work well with some Docker images. But it seems like the native Docker client for Windows still doesn’t do very well with symlinks in a shared volume (because they’re using SMB). So I’ve been working at a Vagrant+Virtualbox+rsync+Docker setup.



    1. Thanks for reaching out David! I finally took the time to dig up my notes from that horribly frustrating experience with Windows+vagrant+virtualbox+rsync and publish them here. Please take a look at the error messages I encountered and let me know if you (a) saw something similar and (b) ever found a solution or workaround.

      I was pretty suspicious of the partial *nix implementation in the Cygwin Bash shell, and I’m thrilled to hear that *any* other shell would have made this work better. I haven’t yet explored the Bash on Ubuntu for Win10 approach, but I won’t be able to reproduce the same kind of setup since my bug implies I’ll have to try cbwin + the Windows versions of vagrant/virtualbox. If that works, so be it – at least I don’t have to dual-boot, and any bridge [i.e. cbwin] between Bash/Ubuntu/Win10’s shell and native Windows binaries is something we’ll probably need for the forseeable future anyway.

      I’d love to explore further what you’re doing and compare notes as we continue to pursue our respective approaches. Would you be interested in a little minor collab (or at least further documentation of what we’re using and how it’s been built)? I wouldn’t give up hope for Bash/Ubuntu/Win10 yet!

      Either way, I’ll probably dig into the cbwin + vagrant/Win + virtualbox/Win setup next week and will publish whatever I find out.


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