I want to reflect on the effects that automation can have on your daily life as a developer, after I came to think of the shift I have been through the last couple of years when it comes to deployments and habits and automation surrounding deployments. I dawned on me the other day, that deployments are now completely a non-event for me, and has been so for quite some time. I just don’t think about it anymore. In stark contrast to the extremely tired meme #nodeployfriday circulating on twitter. How did that happen?

Some context: I work in a team developing and maintaining about 20ish web applications. The team is small and fairly autonomous, at least when it comes to technical matters. My efforts into automating deployments and builds started around 2015-2016 at my previous employer (very similar in team size and technical stack) and the basis was a kind of semi-automated deploys but with few safeguards and the feelings involved in deployments where mixed. Deployments were talked about a lot, coordinated with several people and was a medium sized deal. Not huge, but definitely not small either. And the rule was don’t deploy on fridays (which is huge culture smell, maybe worth a whole post in itself). And deploys had to monitored.

The end goal was of course to be able to cut down on lead times for putting code into production, with side goals of making it less of a pain to deploy, fewer failed deployments and fewer nervous faces when doing deployments.

Steps to safer deployments

There are several steps you can take to make your deployments more automated and safer, depending on the context you are in. Adding more unit and integration tests to the code, considering using feature toggles for new functionality, thinking carefully about the way the team communicates about the code (pair programming, code reviews, mob programming etc), using smoketests and possibly integration tests and performance tests before advancing the deploy from one stage to another and so on. Also, trying to deploy smaller chunks at a time contributes to safer deployments and can give you positive spiral effects. Deploying often (as you do with small changesets) is painful when deployment is a manual process. This leads to automation of the deployment process, which makes it easier to deploy, so you do it more often etc. etc.

In our case we made use of integrated healthchecks in the applications (checked by the orchestration platform) and smoketests built into the deployment pipelines. The effects are that 1) the new version does not start when healthcheck fails (first gate) and if smoketests fail (second gate) deployments halts and is rolled back. If this is enough for you, depends on the context and the apps involved. First we automated the build of the apps and not the deployment. The deployment was manual, with only healthchecks when doing deployment. This made deploys much less of a worry, but still very much a topic of conversation. It took quite some time before everybody was comfortable with deploying on fridays (rule now was that you could deploy anytime, but be prepared to clean up afterwards if something went wrong). Gradually, deployments were not talked about anymore, but the decision to deploy was still a conscious one. The habit settled nicely, but I felt that we where missing out on some benefits in terms of automation.

Going the Distance

This was the case when I switched employers and got the opportunity to start anew with more experience. My goal was to be able to deploy apps (at least some) directly to production on push to master. The apps in question here varied a lot in terms of importance, quality and scope. The discussion now became: “How much, and what, do we need to do in order to make this app deploy directly to production?”. That is profoundly different conversation to have, rather than “how often should we deploy” or “can we deploy on friday?”. A related question that can crop up in cases like this, is “how do we communicate changelogs to sales/marketing/users/whoever?”. This is not a topic you should skip! It’s important to get this right, but it’s also worth asking some questions about who uses the information in the changelogs and for what? But, automating the changelog is also possible via commits or other means.

So, automating deploys to production: how to achieve it? First try to determine if this is at all wanted in your context. Web development can more or less always achieve this, but there are a lot of other types of software where the work involved may not match the perceived benefit. This is an important question. But let’s say you want to go that way, here are some tips:

  • Take small steps
  • Make build and deploy errors discoverable (build status to dashboard, slack etc)
  • Make errors clear and understandable
  • make the log clear to read (see previous point)
  • Use version control for your build pipelines and infrastructure
  • add tests to important parts first
  • add health checks
  • add smoketests
  • make deployments visible in dashboard with application metrics

Start with auto-deploy to test environment, build out unit tests, integration tests and other tests as needed. Gain confidence in the application and deploymentes. Measure how often builds and deploys to that env fails, if possible display it on a graph that everybody can see. Start deploying automatically to staging environment og pre-production depending on what you have. Gain more confidence - rince and repeat. Gain confidence also in the build and deployment infrastructure itself. If it fails you, improve it.

This confidence builds slowly. Let it accrue over time, don’t force it. Especially let team members not interested or unexperienced in the tao of deploys take part, improve and use it. This is important, since when deploys are automatic, nobody (and everybody) will have to take action when something goes wrong.

As deployments are made increasinly more automatic, they just fade from your mind and if you’re not paying attention to this you might not realize it. The chatter about deploys disappear from the workplace and things just happen. The point of being able to see the deploys marked on metric graphs (see my post on deploy overlays) is important when deploys are automatic, to be able to catch when a deploy introduces some weird behaviour in an application.

For me, the end result of this is a more relaxed work situation where changes flow from development to production. No deployment anxiety, no periods where deployment isn’t allowed and we can spend our time focusing on other things rather than talk about deployments. I like it this way.

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02 August 2019