Developer - Database Tinkerer - IT Manager

Hints: Deploying an HTTPS-enabled, Elastic Beanstalk, Python/Pyramid application

Posted: 2017-04-25

Over the last few weeks, I have been learning the best way to deploy a HTTPS-enabled application through trial and error. Three possible options are through the AWS Certificate Manager (ACM), Let's Encrypt, and using your own CA issued certificate. There might be others, but these are the methods I tried. In this article I will go over each and what ended up working for me.

As a general rule, I try to take the path of least resistance. If a method requires learning something I don't immediately know, and it looks like it will take more than a few seconds to understand, I move on to the next best prospective option. Of course if I exhaust every path then I will go back and learn the tech needed. In this example, that technology ended up being .ebextension files and EB CLI, but in hindsight I don't think I needed EB CLI.

We'll be going over

  • AWS Certificate Manager
  • Let's Encrypt
  • Bring your own certificate (BYOC)
  • The option that did work

AWS Certificate Manager

This is by far the easiest to use. It can be used through the web console and is pretty intuitive. However, it is too simplistic and that means you might not be able to use it, or you'll have to adapt your project around it. Below I list out the benefits and drawbacks that I noticed.


  • Easy to use.
  • Quick to get started.
  • Little knowledge needed to deploy an HTTPS app.


  • Terminates HTTPS at the load balancer.
  • Can't be used with single instance deployments

The benefits speak for themselves. I actually had an Elastic Beanstalk instance up and running with this approach very quickly. However, I ran into an issue. Since the HTTPS requests were terminated at a load balancer my app was creating HTTP links. One of my requirements was no HTTP. Everything would be redirected to HTTPS.

This approach started to become more involved, and the rigidness of ACM made me look else where. I could have made my application serve up every link as an HTTPS one, but that felt like I was avoiding the real problem. Also, there were a few posts I found sporadically that mentioned that ACM didn't work with single instance environments. All of these reasons made me think that this probably wasn't going to work out, at least easily.

Let's Encrypt

This option sounded awesome. They seem to have a large community backing them up, documentation is every where, and it was free! However, there wasn't any documentation by AWS, and since I had a very vague understanding of HTTPS at the start of this I didn't know how to apply the existing documentation very easily.

What I found was that an HTTP server was needed by the Let's Encrypt script to establish trust, and I wasn't comfortable playing with my existing server as it was working just fine. I did try to get it working with another test instance, but I kept running into issues. All I wanted was the certificate. To make things more complicated the certificates only lasted a few months. This means that many people recommended setting up a cron job to renew the certificate monthly.

These points all created too much resistance for me, and I decided I'd try the next option.

Bring Your Own Certificate (BYOC)

The traditional way to implement HTTPS is to create a private key and a certificate signing request (CSR), submit it to a cerficate authority (CA), and get a certificate and chain bundle in return. The private key, certificate, and chain can then be added to the server, and once the web server is configured, HTTPS requests can be properly handled.

The benefits here are

  • Plenty of documentation for many combinations, even for python on AWS Elastic Beanstalk, in the the official documentation.
  • Options to verify who you are.
  • Relatively cheap. It only cost me $10 a year for a single domain. I've spent more money on more questionable things.
  • Best option to get a basic understanding of how HTTPS works


  • Have to pay some money.
  • Verification could be tougher than ACM.
  • Have to go through another third party for the certificate.
  • It can be finicky to set up on AWS if you don't know what you're doing, but it was the easiest of the three for me.

Between learning how HTTPS works and the vast amount of documentation this this yielded the best results for me.

The Option that Worked for me

At this point it should be clear that I went with BYOC. I went with a single domain certificate to keep things simple. However, it took me time to figure out the proper way to get AWS to do what I wanted. At first I thought that I wasn't going to be able to use the web console to do this as it seems to lacks the ability to customize certain configurations that are need to implement HTTPS properly, but I'll need to test more to confirm this.

I will note that some reading is required at this point. There are plenty of resources out there on HTTPS to get understanding of SSL (and why it isn't used anymore), TLS, and the various things that go into making HTTPS happen. You could probably get away with skimming the material, but I would strongly recommend learning it if you are securing an application where privacy is needed. If the application you are deploying has a login then read up on it.

Get the Certificate

I used an existing instance to generate the certificate signing request (CSR). I followed the instructions on Namecheap.. My instance uses Apache, and their instructions worked out great. Basically, all I had to do was

openssl req -new -newkey rsa:2048 -nodes -keyout server.key -out server.csr

and then follow the prompts. The important bit is the Common Name. It has to be the domain that you are securing.

Once this bit is done save both the server.key and the server.csr. You will need them both later. To confirm the files, you can inspect them with the text editor of your choice. The server key will contain a header that says something like "-----BEGIN RSA PRIVATE KEY-----", and the CSR will say "-----BEGIN CERTIFICATE REQUEST----."

Then go to your certificate authority (CA) of choice and submit your CSR. I bought a PositiveSSL certificate from Comodo through Namecheap. The first step is to submit the CSR which can be done by either pasting the text into the submission form or upload. Then Comodo will require that you use one of three methods to validate who you are. The options are email, hosting a verification doc, or creating a CNAME record.

Once validated they will email you the certificate and a bundle file. Both are needed for proper certificate deployment.

Deploying the Cerficate and Supporting Artifacts

There is no way of getting around it. You need to use configuration files. An .ebextension file was the easiest way for me to get AWS to import and configure HTTPS. I also used EB CLI To make environment deployments easier


This approach forced me to learn EB CLI which is a very powerful tool compared to AWS's web console. In my past articles, I described how python is broken with AWS. I think it is possible to add in a working python build using EB CLI by installing a python build that properly supports pip, but that is an topic for another article.

At this point AWS has some great documentation. This will take you 95% of the way. However, it doesn't explain how to store your certificate securely. For that you have to read a doc on storing private keys.

Another missing point is that their httpd config will not get you an "A+"" from Qualys SSL Labs. To do that you'll need a better SSL configuration for httpd. For that I took some of the statements from Spencer Jones' blog post. He was setting up an instance to use Let's Encrypt, and his directives cleared up most of, but not all, the complaints from SSL Labs. The final issue I ran into was that I was not including the complete certificate chain. This is where the bundle from the CA comes into play. That needs to be deployed just like the certificate and private key. It is invoked by httpd with the following configuration line.

SSLCACertificateFile "/etc/pki/tls/certs/"

Obviously, I cheated a bit by referencing all of the docs I used, but to be fair, knowing the proper order to read them in is half, if not most, of the battle. In my case, I think I would have done the following if I knew all of this in the beginning:

  • Create a CSR and private key via openssl.
  • Using said CSR (not the private key) obtain certificate and bundle from CA of your choice.
  • Add a new httpd configuration file to my project under a newly created .ebextension directory.
  • Upload the certificate, private key, and bundle to S3. Make sure they NOT publicly accessible.
  • Create a new single instance environment within AWS to host your app.

Once deployed your app should now be able to handle HTTPS traffic.

A Note on Load Balancing

Brandon Schwartz (twitter: @electraphant') had pointed out the AWS documentation needed to get HTTPS working on a load balancer via passthrough.

Basically, they instruct you to setup your application to handle HTTPS requests and then add a rule to the security group to allow inbound traffic on port 443. I haven't tried it out myself, but it looks fairly easy. I'd also like to think that you can skip the first step if your single instance application is working with https.

Things I might be forgetting

This was a tough trial and error process for me. I kept trying different things until I got it working. That said, I might be forgetting some things:

  • Enabling HTTPS traffic (port 443).
  • Correctly enabling S3 access.
  • Setting up Route53 so that it points to a URL instead of an IP that could change. I might even be wrong here.

As a final reminder, this was written as a set of hints. Your scenario might be different. You might be using nginx instead of apache, you might need to use a load balacer, your CA might supply different files, you might be using a wildcard certificate, and etc. As time goes on I'll refine this article so that it is more explicit. If you need help with your case feel free to reach out to me on twitter, and I'll try my best to guide you.

Last Update: 2017-08-05


This site/blog/soapbox is where I intend to post stuff that I feel might help someone even if the only someone is me. For now I only plan to post how-tos and maybe an occasional response to some new tool or workflow.

The site is still being tweaked, so please be patient. As time goes on I will add new features.

In real life, I am a IT manager who started as a PeopleSoft consultant out of college, but then stumbled into Python via PHP (funny story). Since I learned quite a bit about databases in my Peoplesoft days I kept it up by making sure the databases behind the apps I maintained stayed healthy. I eventually landed at BenefitPlan Manager where I am trying to make things a little better each day.