I got Jellyfin up and running, it’s 10/10. I love this thing, and it reinvigorated my love for watching movies. So I decided to tackle all the other services I wanted, starting with Paperless-ngx…

What a nightmare. It doesn’t have a Windows install so I made an Ubuntu VM. Don’t get me started on Ubuntu. I just spent about 12hrs trying to get Portainer to cooperate and had to give up. I tried just installing Paperless the “normal way” and had to give up on that too.

My point: if you’re getting started selfhosting you have to embrace and accept the self-inflicted punishment. Good luck everybody, I don’t know if I can keep choosing to get disappointed.

Edit: good news! Almost everything I wanted to do is covered by Jellyfin which can be done in Windows.

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155 points

I know linux isn’t for everyone, but self hosting on windows is self-inflicted punishment. It’s just not the right platform. Sure it’s doable, but it’s death by a thousand papercuts.

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30 points

also Ubuntu will add more complexity to things, Debian will cover most of what you need.

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7 points

I wish I knew this before I started.

But my headless Ubuntu is working now, so I am not changing it.

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9 points

Don’t rush it. You will have plenty of opportunities to change into Debian when your Ubuntu stops working.

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3 points

Be me whose server is on Ubuntu 18.04 and needs upgrading to get Bluetooth into home assistant 😭

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1 point

For what it’s worth, I usually install Ubuntu Server instead of Debian because it comes with a few more things out-of-the-box that I would install anyway. I have several installations of 22.04 that have been upgraded since 16.04 and they work no problem. (I also have a few Debian installations working similarly well.)

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1 point

I made my jump from Ubuntu Server to Debian when I containerized everything onto a single proxmox machine.

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0 points

How so?

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Took maybe 5 minutes total to install paperless-ngx in docker on a Debian vm. No hassles, no headaches.

The problem is trying to install tools built for Linux on Windows.

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-12 points

You’re better than me

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20 points
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2 points
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I’ve got Docker up and running, but getting anything to work within Docker or getting a machine to access the services that it says are running is a different story

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-7 points

TECHNICALLY (yes, I’m fun at parties) you need 3 commands, as you also need to do an “apt update” after adding the repo. But we can chain commands of course. Do chained commands count as one? We could debate that for hours. Like why I prefer vi.

My point? None really, just having fun.

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9 points

Windows is just not ready for this stuff. Most of this stuff is built for Linux. Linux is THE server OS. And windows is painful for developers too, so there’s less solutions for it.

You’ll be a lot better off with Linux for self hosting.

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