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Used to do this in .NET for personal projects then got pulled into various dotnet projects that had their own approaches. But it was really nice. What I had hoped to eventually achieve is being able to hotswap the library somehow so I can have a server with zero downtime for updates, but never found the time to do so. I would assume I would do it via a microservice type of architecture instead.

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You can just do this with nginx or whatever you have in front (IIS if you're into Microsoft stuff I guess?). Run service at port xxx1, this is your "live" port. When you wanna upgrade, launch service to port xxx2, do graceful reload of config, swap the ports around so "live" port now points to right service, graceful reload of config again and done!

I should have added I was not doing a web service.

So what kind of service were you doing? As far as I know, nginx and others can handle more things than just http.

IIS makes me want to explode and then die

In .NET for plugin management there are unloadable assemblies so you can dynamically load and unload e.g. plugins at runtime. However, it requires care, has caveats and the industry generally gravitates to other techniques for zero-downtime and/or rolling deployments where the replicas (nodes) are at first drained, then shut down, and replaced one by one or in groups but never in a way where there are none to serve the requests.

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