Ruby Proxy Rubygems Ironruby

How to Update `Ruby Gems` Behind a Proxy (ISA-NTLM)

If you are a Ruby developer, you know how essential Ruby Gems are for enhancing your applications and speeding up your development process. However, working behind a corporate proxy—especially one operating in NTLM mode, like Microsoft ISA server—can complicate matters. You might find it particularly frustrating if you want to install or update your Ruby Gems but are unsure how to navigate proxy settings.

In this blog post, we will discuss a straightforward solution to update Ruby Gems from behind a proxy, focusing on the use of environment variables.

Understanding the Problem

When your development machine is behind a proxy server that enforces NTLM authentication, direct connections to the RubyGems repository might be blocked. This limitation often leaves developers stuck, unable to download the essential gems they need for their projects. The additional challenge posed by situations where legacy tools like rubysspi might not work further complicates the situation.

You may find yourself asking:

How can I easily handle these proxy settings?
Is there a method to configure this without excessive hassle?

Let’s dive into the solution!

Solution: Configuring the HTTP Proxy

The simplest way to update Ruby Gems when behind a proxy is to set the HTTP_PROXY environment variable on your machine. Doing this will provide the required authentication for accessing external resources through your corporate firewall.

Steps to Set Up the Proxy

Create a Batch File
You can create a simple batch file (.bat) to set up your proxy credentials and make the process easier. Here is what the contents of the batch file should look like:
```
SET HTTP_PROXY=http://%USER%:%PASSWORD%@%SERVER%:%PORT%
```
Replace %USER%, %PASSWORD%, %SERVER%, and %PORT% with your actual proxy username, password, proxy server name, and port number.
Example Configuration
If your username is wolfbyte, your password is secret, and your proxy server is named pigsy that runs on port 8080, then your batch file would include the following line:
```
SET HTTP_PROXY=http://wolfbyte:secret@pigsy:8080
```
Running the Batch File
Before you attempt to update Ruby Gems, run your batch file in the command prompt to ensure that the HTTP_PROXY variable is set correctly.

Important Considerations

Security Concerns: One potential downside is that your password will be stored in plain text within the command session. While this might be manageable for personal or local use, always consider security best practices when handling sensitive information.
Testing the Configuration: After setting the HTTP_PROXY variable, you can verify its effectiveness by running a command to update or install a gem. If configured correctly, the command should pass through the proxy without issues.

Conclusion

Updating Ruby Gems while working behind a Microsoft ISA server in NTLM mode may appear daunting, but configuring the HTTP proxy environment variable streamlines the process considerably. This method eliminates the need for complex configurations or additional gems that may not work as expected.

By following the steps outlined above, you should be able to efficiently manage your gems and keep your development work flowing smoothly. Remember always to keep security in mind when handling proxy credentials.