Proxy Support For Chocolatey

Installing Chocolatey behind a proxy server

When trying to install Chocolatey behind a proxy server, you may be faced with errors like

Get Response returned: (407) Proxy Authentication Required

or

The underlying connection was closed: Could not establish trust relationship for the SSL / TLS secure channel.

Steps to help address this:

  1. Copy the install.ps1 file locally.
  2. Open a PowerShell command line.
  3. Set the following environment variables - $env:chocolateyProxyLocation (with proxyserver:proxyport), $env:chocolateyProxyUser (if it is a domain account, ensure you have the appropriate domain prefix for the account, e.g. AD\UserName or UserName), and $env:chocolateyProxyPassword with your password.
  4. With that same shell open where the environment variables are set, run the downloaded script to install Chocolatey.

In PowerShell, it looks like this:

$env:chocolateyProxyLocation = 'https://local/proxy/server'
#$env:chocolateyProxyUser = 'username'
#$env:chocolateyProxyPassword = 'password'
# install script

NOTE: This will only work with the installation methods that call https://chocolatey.org/install.ps1 (or use a similar script, like Puppet/Chef scripts do) as part of the install.

Troubleshooting Installation

You've tried everything and Chocolatey still won't install from https://chocolatey.org -

The underlying connection was closed: Could not establish trust relationship for the SSL / TLS secure channel.

It could also be that your trusted root certificates are missing or not up to date (Windows 2012 does not install root certificates by default). You will need to download and install the following certificates into your LocalMachine's Trusted Root Certification Authorities certificate store.

To access chocolatey.org:

To access packages.chocolatey.org:

System Proxy Settings

Chocolatey by default already supports system set proxy servers

image

NOTE: Unfortunately proxy bypass lists may not be available when using this method. We recommend explicit proxy settings.

Existing Proxy Environment Variables

Starting with Chocolatey v0.10.4, Chocolatey will automatically pick up the following environment variables if they are already set:

Explicit Proxy Settings

Chocolatey has explicit proxy support starting with 0.9.9.9.

You can simply configure 1 up to 5 settings and Chocolatey will use a proxy server. proxy is required and is the location and port of the proxy server. The values for user/password are only used for credentials when both are present.

choco config set proxy <locationandport>
choco config set proxyUser <username> #optional
choco config set proxyPassword <passwordThatGetsEncryptedInFile> # optional
choco config set proxyBypassList "'<bypasslist, comma separated>'" # optional, Chocolatey v0.10.4 required
choco config set proxyBypassOnLocal true # optional, Chocolatey v0.10.4 required

Example

Running the following commands in 0.9.9.9:

choco config set proxy http://localhost:8888
choco config set proxyUser bob
choco config set proxyPassword 123Sup#rSecur3
choco config set proxyBypassList "'http://localhost,http://this.location/'" #0.10.4 required
choco config set proxyBypassOnLocal true #0.10.4 required

Results in the following items being added to the config file:
image

Explicit Proxy Settings at Runtime

Starting in 0.10.4, you can pass proxy information at runtime with each command. See https://github.com/chocolatey/choco/issues/1173

--proxy="'value'" --proxy-user="'<user>'" --proxy-password="'<pwd>'" --proxy-bypass-list="'<comma separated, list>'" --proxy-bypass-on-local

What to do if my proxy is socks?

It may just work. It hasn't been validated yet.