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Free as in ... HTTPS certificates? [Obtaining and configuring a free HTTPS certificate for an Azure Web App with a custom domain]
Wednesday, May 18th 2016

Providing secure access to all Internet content - not just that for banking and buying - is quickly becoming the norm. Although setting up a web site has been fairly easy for years, enabling HTTPS for that site was more challenging. The Let's Encrypt project is trying to improve things for everyone - by making certificates free and easier to use, they enable more sites to offer secure access.

Let's Encrypt is notable for (at least) two achievements. The first is lowering the cost for anyone to obtain a certificate - you can't beat free! The second is simplifying the steps to enable HTTPS on a server. Thus far, Let's Encrypt has focused their efforts on Linux systems, so the process for Windows servers hasn't changed much. Further complicating things, many sites nowadays are hosted by services like Azure or CloudFlare, which makes validating ownership more difficult.

As someone who is in the process of migrating content from a virtual machine with a custom domain to an Azure Web App, I've been looking for an easy way to make use of Let's Encrypt certificates. A bit of searching turned up some helpful resources:

Nothing was exactly what I wanted, so I came up with the following approach based on tweaks to the first two articles above. The Let's Encrypt tool runs on Linux, so I use that platform exclusively. Everything can be done in a terminal window, so it's easily scripted. There is no need to open a firewall or use another machine; everything can be done in one place. And by taking advantage of the nifty ability to boot from a Live CD, the technique is easy to apply even if you don't have a Linux box handy.

  1. Boot an Ubuntu 16.04 Live CD
  2. Run "Software & Updates" and enable the "universe" repository
  3. sudo apt install letsencrypt
  4. sudo apt install git
  5. git config --global ""
  6. git config --global "User Name"
  7. git clone
    • Be sure /.well-known/acme-challenge/web.config exits and is configured to allow extension-less files:
            <mimeMap fileExtension="" mimeType="text/plain"/>
  8. sudo letsencrypt certonly --manual --domain --domain --email --agree-tos --text
    • Note: Include the --test-cert option when trying things out
  9. Repeat for each domain:
    1. nano verification-file and paste the provided content
    2. git add verification-file
    3. git commit -m "Add verification file."
    4. git push
    5. Allow Let's Encrypt to verify ownership by fetching the verification file
  10. sudo openssl pkcs12 -export -inkey /etc/letsencrypt/live/ -in /etc/letsencrypt/live/ -out fullchain.pfx -passout pass:your-password
  11. Follow the steps to Configure a custom domain name in Azure App Service using fullchain.pfx
  12. Enjoy browsing your site securely!
Tags: Technical Web
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