Monday, 16 July 2018

Boxstarter and Chocolatey tips

Two big things happened earlier this year on the Chocolatey front. First off, Boxstarter (the tool created by Matt Wrock that allows you to script up full Windows installations including handling reboots) is now being managed by Chocolatey. still exists, but the source repository is now under the Chocolatey org on Github.

The second is that Microsoft are contributing Boxstarter scripts in a new Github repo –

If you’re looking to use Boxstarter to automate the software installation of your Windows machines, there’s a few tricks and traps worth knowing about.

Avoid MAXPATH errors

It’s worth understanding that Boxstarter embeds its own copy of Chocolatey and uses that rather than choco.exe. Due to some compatibility issues Boxstarter currently needs to embed an older version of Chocolatey. That particular version does have one known bug where the temp directory Chocolatey uses to download binaries goes one directory deeper each install. Not a problem in isolation, but when you’re installing a lot of packages all at once, you soon hit the old Windows MAXPATH limit.
A workaround is described in the bug report – essentially using the --cache-location argument to override where downloads are saved. The trick here is that you need to use this on all choco calls in your Boxstarter script – even for things like choco pin. Forget those and you still may experience the MAXPATH problem.

To make it easier, I add the following lines to the top of my Boxstarter scripts

New-Item -Path "$env:userprofile\AppData\Local\ChocoCache" -ItemType directory -Force | Out-Null
$common = "--cacheLocation=`"$env:userprofile\AppData\Local\ChocoCache`""

And then I can just append $common to each choco statement. eg.

cinst nodejs $common
cinst visualstudiocode $common 
choco pin add -n=visualstudiocode $common

Avoid unexpected reboots

Detecting and handling reboots is one of the great things about Boxstarter. You can read more in the docs, but one thing to keep in mind is it isn’t perfect. If a reboot is initiated without Boxstarter being aware of it, then it can’t do its thing to restart and continue.

One command I’ve found that can cause this is using Enable-WindowsOptionalFeature. If the feature you’re turning on needs a restart, then Boxstarter won’t resume afterwards. The workaround here is to leverage Chocolatey’s support for the windowsfeatures source. So instead of this

Enable-WindowsOptionalFeature -Online -FeatureName Microsoft-Hyper-V-All

Do this

choco install Microsoft-Hyper-V-All -source windowsfeatures $common


If you have a more intricate Boxstarter script, you may run into some problems that you need to diagnose. Don’t look in the usual Chocolatey.log as you won’t see anything there. Boxstarter logs all output to its own log, which by default ends up in $env:LocalAppData\Boxstarter\Boxstarter.log. This becomes even more useful when you consider that Boxstarter may automatically restart your machine multiple times, so having a persistent record of what happened is invaluable.
The other things you might want to make use of is Boxstarter-specific commands like Write-BoxstarterMessage (which writes to the log file as well as the console output) and Log-BoxstarterMessage (which just write to the log file)

Find out more about these and other logging commands by running help about_boxstarter_logging.

My scripts

I keep a few of my Boxstarter scripts at Feel free to have a look and borrow them if they look useful.

Find out more

If you’re really getting in to Chocolatey and Boxstarter, you might also be interested in Chocolatey Fest, a conference focusing on Windows automation being held San Francisco on October 8th.

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