An internal application I’m currently working on communicates with an LDAP server to authenticate users. It uses the OmniAuth Gem for that. I recently updated the app to Rails 6 and after some minor tweaks, everything worked fine on my local Docker container. Jubilating, I merged the changes into master . Tiny robots swarmed round, building the Docker image and running tests on GitLab CI. After checking that all tests are green, they pushed the Docker image they had built to production. And suddenly, logging in didn’t work anymore. In the logs, OmniAuth told me that it could not talk to the LDAP server.

We use the same LDAP server both locally and in production. Assuming the bug was caused by my update to Rails 6, I wasted hours debugging OmniAuth and Rails 6. But why did this only occur in production? Locally, I could still log in and out as usual. Finally I thought: Maybe, just maybe, Docker was doing something different on my machine. I ran docker-compose build but still could not reproduce the bug locally. Then I ran docker-compose build --pull to update my base image and finally: The bug occurred locally.

So I tried to contact the LDAP server from the Docker container with openssl s_client -connect $SERVER . OpenSSL could not negotiate a cypher. Why was that happening? The LDAP server is pretty old and only supports TLS 1.1. The Docker base image I used is based on Debian, and starting with Debian 10, they decided to only communicate via TLS 1.2 and newer. So I finally found the bug. But how could I have prevented this from happening?

I asked my colleagues for help and learned that a Docker tag (like 2.6.3 in my case) is more like a Git branch than a Git tag. Using 2.6.3 as my tag only means that I get some version of Debian with some version of Ruby 2.6.3. Including the version of Debian in my tag ( ruby:2.6.3-stretch ) would have prevented the update from Debian 9 (Codename “stretch”) to Debian 10 (Codename “buster”). So after changing the base image to ruby:2.6.3-stretch , logging in worked again in production. As soon as the LDAP server is updated, I can change it to ruby:2.6.3-buster .

Encoded in my label I now have the minor version of Ruby and the major version of Debian. This will not prevent all breaking changes, though (for example, the authors could decide to not install some APT package they did before). To improve that, I could take this further:

I could use Debian as my base image and install all required software (including Ruby) myself. I could publish my own base image based on Debian and then use that as my base image.

I decided against both solutions, as installing a specific version of Ruby is traditionally not exactly a pleasure . For now, I will stick with ruby:2.6.3-stretch and hope that there will be no breaking changes on that tag.

This problem reminded me that we always need to get familiar with the semantics of versioning in an ecosystem we’re not familiar with. In the case of a Docker image, we need to make sure we understand what the tag of my image describes. Putting the version of each installed dependency into the label could get cumbersome pretty quickly. An alternative way of publishing the Ruby image would be to publish a ruby2.6.3 image and use the tags for semantic versioning (with an OS update being a breaking change).

Thanks to Joachim Praetorius, Lars Hupel, Martin Kühl, Niko Will, Michael Schürig, Martin Eigenbrodt and Bascht for their help and advice.