Setting up a new development machine without pressing Next a single time using Chocolately

· August 1, 2013

Up to now I have sadly not have time to look into Chocolatey. I know what it is but I haven’t played with it. As the time grew closer to set up a new development machine I thought I’d give it a run Chocolatey a run for it’s money.

Could my entire development environment be installed using a script? That is - from a bare-bones Windows installation could I run a script and get everything I needed in place.

This was a real challenge since I don’t know (nor want to learn) any powershell and consider myself to be a newbie Chocolatey user.

This post describes my journey.

Getting a virtual windows installation in place

I use OS X and VirtualBox to run virtual instances of windows. Creating a virtual image is simple enough in VirtualBox and then you can attach an .iso-file with the Windows installation.

The Windows 8.1 installation was pretty fast and within 30-40 minutes I had a bare-bones Windows installation in place.

Getting my stuff in place - local version

One of the really cool things about Chocolatey is that you can install it directly from the prompt (that’s cmd-prompt, no powershell stuff) with a command you just copy from their homepage:

When Chocolatey is installed you can start using it’s commands of which the most interesting is the “cinst” command. This is the command that installs a Chocolatey package for you. I ended up using “cinstm“that only does the install if the package isn’t installed before.

This means that it’s now only a matter of doing a long list of powershell (cinst is a powershell command) commands. Like this one for example that installs 7Zip:

There are four problems with this, at least for me:

  • I don’t like powershell
  • I don’t want to sit around issuing commands every other minute or hour (for big installs)
  • It’s not repeatable
  • I don’t know or remember the packages I want to have. Chocolatey has 1200 packages at the time of writing.

Let’s leave that last one and address the other issues first. I would like a file with these commands in and then just execute those commands. This can be done (thanks Calle for the tip) with this command:

And then my devApps.ps1 file just contains installation commands I want. Like this for example:

I could then merge the “get Chocolatey” -command with the “install dev apps”-command and have a single install.bat that I run to get this to run:

Getting my stuff in place - cloud version

If you start looking around in the Chocolatey package directory you’ll soon get too-much-apathy. There’s really no way to know what is in there without searching for it, which implies that you know what to search for. And what is good.

Over a number of installations and years we have all stacked up our own favorite tools and utilities that we like (and in some cases have a unhealthy relationship with).  

Now if there could only be a way to save my list of things that I like and usually install. This way I could share it with others and get tips, suggestions and maybe even inspire them.

But hey - there is such a way! I can store my devApps.ps1-file in the cloud, at for example.  There people could actually make pull requests and forks of my file to improve it.

So now I can only copy that file onto every new machine … no - wait. There’s a better way. Chocolatey used a cool little function called ((new-object net.webclient).DownloadString() in their install command. I can use that too and download my devApps.ps1 file from Github.

Like this:

A small gotcha for me was that you have to reference the RAW-version of the file. Of course, once you think about it since you don’t want to download the GitHub HTML-page. Of course - but I missed that the first time around.


This is so cool - I now have a installation script for all my development application that takes my machine from bare-bones Windows too fully installed development mode. Its repeatable (if I need to do this), it’s shareable (so I can get tips and suggestions and share with others), its automated (I don’t have to do next, next, next for hours) and I only one powershell command. Not too bad.

My installation scripts can be found, forked and improved here:


Right smack in the middle of my installation my virtual machine rebooted. I don’t really know why but that gave script-based installations time to really shine.

How did I recover from such a horrible thing as a machine reboot?

Simple - just ran the exact same script again. Since it’s using cinstm the script went through what was installed already and then continued where it ended… I had to rerun the command but that was all. Cool. Really cool!

Update 2

It worked… Kind of (see below)! It took me about 4 hours of letting the script run. Resharper and WebEssentials2012 failed but that was because of me. The script installed those add-ins to Visual Studio before Visual Studio itself. So I modified the script to run the Visual Studio installs first.

Also I failed. I forgot that for Visual Studio 2013 Preview you also need to install ”ASP.NET and Web Tools 2013 Refresh”. But that’s for a preview product so I felt that it didn’t count. Now did it?

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