Selfhosted
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You are right. Either you are using docker very wrong, or docker is not meant for this use case.
You say "getting ubuntu server to fetch it's updated behind proxy". You shouldn't be updating Ubuntu from inside of docker. Instead, the system should be somewhat immutable. You should configure the version you want to use as part of the Docker file.
Same with python and keys. You likely want to install python dependencies in the Dockerfile, so that you can install them once and it becomes bundled into the container image. Then you don't need to use pip behind the proxy.
I'm not much into new year resolutions, but I think I'll make a conscious effort to learn Docker in the coming months. Any suggestions for good guides for someone coming from VM end will be appreciated.
I learn by twiddling knobs and such and inspecting results, so having come from a tall stack of KVM machines to docker, this helped me become effective with a project I needed to get running quickly: https://training.play-with-docker.com/
You basically log into a remote system which has docker configured, and go through their guide to see what command is needed per action, and also indirectly gets you to grok the conceptual difference between a VM and a container.
Jump straight to the first tutorial: https://training.play-with-docker.com/ops-s1-hello/
Thank you for these links, they look just right. Most tutorials I come across these days are videos. Maybe they are easier to make. These tutorials that allow you to tinker at your own pace seem better to me. Will you mind if I reach out to you over DM if I get stuck at something while learning and am not able to find the right answer easily?
Sure, that's ok. Thanks for asking.
The networking send to be where documentation for both docker and podman seem to be a bit slim, just a heads up.