Software⏱️ 3 min read📅 2026-06-15

How to Fix: Vagrant: SSL verification error behind corporate proxy

Vagrant SSL verification error behind corporate proxy issue resolved with adding custom CA certificate to trusted store.

Quick Answer: Add the corporate CA certificate to the local trusted store and update the Vagrant configuration to use the correct proxy settings.

📋 Table of Contents

  1. ⚠️ Common Causes
  2. 🔧 Proven Troubleshooting Steps
  3. ✨ Wrapping Up

Vagrant users who work behind corporate proxies may encounter an SSL verification error when trying to install plugins. This issue is frustrating as it prevents users fromaccessing certain plugins, hindering their ability to manage virtual machines efficiently.

In this guide, we will walk you through the steps to resolve the SSL verification error in Vagrant behind a corporate proxy.

⚠️ Common Causes

  • The primary reason for this error is that Vagrant cannot verify the SSL certificate of the RubyGems server due to the corporate proxy's SSL configuration. This is often caused by the proxy rejecting access to the configured plugin source or not responding correctly.
  • An alternative cause could be a mismatch between the local trusted store and the certificate used by the RubyGems server.

🔧 Proven Troubleshooting Steps

Configuring Vagrant to bypass SSL verification using environment variables

  1. Step 1: Set the HTTP and HTTPS proxy environment variables on your Windows 10 notebook using the following commands: set http_proxy=http://user:password@host:port and set https_proxy=http://user:password@host:port. This will allow Vagrant to bypass the SSL verification error.
  2. Step 2: Restart the Command Prompt or run the command `vagrant plugin install vagrant-proxyconf` again to test if the issue is resolved.
  3. Step 3: If the issue persists, proceed with method 2.

Adding the RubyGems server certificate to the local trusted store

  1. Step 1: Export the SSL certificate used by the RubyGems server from the corporate proxy's SSL configuration. You can do this using the following command: `openssl s_client -connect api.rubygems.org:443 -showcerts`. Copy the certificate contents and save it to a file.
  2. Step 2: Add the exported certificate to the local trusted store on your Windows 10 notebook. To do this, navigate to the `.../hashicorp/vagrant/embedded/cacert.pem` directory, right-click on the file, and select 'Install Certificate' from the context menu. Follow the prompts to complete the installation process.
  3. Step 3: Restart the Command Prompt or run the command `vagrant plugin install vagrant-proxyconf` again to test if the issue is resolved.

✨ Wrapping Up

To resolve the SSL verification error in Vagrant behind a corporate proxy, you can either configure Vagrant to bypass SSL verification using environment variables or add the RubyGems server certificate to the local trusted store. By following these steps, you should be able to successfully install plugins and manage your virtual machines without any issues.

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