I'll get started on Modoboa for mail...
🇳🇱
@stux I do not wish running your own mail server on my worst enemy... spam management is very hard to do well.
I use gmail strictly because they are so good at keeping spam out and it is next to impossible to get as good a result on a personal server.
@freemo I know, I know.. 
But I feel kinda desperate and don't know what to do anymore :(
For Gmail, do you use a free or paid/business account? I wonder if we can send from gmail with root domain?
@stux I dont know what your problem is or what your trying to do/solve.
I use a paid gmail for custom domains. I think the cost is 5$ a month. What do you mean by root domain? I use qoto.org for my gmail.
@freemo Well that's the issue.. It's something with DNs while that's all okay
Funny thing is.... I did had Google Business 2 days ago but switched to ProtonMail 
Only for incoming mail and not SMTP though but it seemed it fcked it all up somehow
Maybe a paid Gmail is indeed the best option
@stux I'd need to know a lot more about the problem to even begin to offer debugging advice let alone a solution. Just "its something to do with DNS" isnt much to go on.
I presume you are aware of MX records and how they can dictate mail routing regardless of the A/CNAME record and all the hbroad strokes.
@stux ok so none of what i suggested would be relevant. MX records are for incomming only... Why is it trying to send an email to such a weird address on its own internal domain though.. that seems odd.
@freemo Don't think so no 🤔
Isn't that sidekiq's doing? 
@freemo That the one I found the solution on indeed!
See medium article ;)
I checked and currently the file has no resolvers yet but im a but careful when messing with this
@stux Well they solved it by explicitly setting the DNS resolver to 8.8.8.8... you havent done this out of caution? What do you think that would break? I use 8.8.8.8 for all my servers, its the best dns resolver around IMO
@freemo Indeed
No sure, that's why I didn't change hahaha! 
Personally I dislike Google but i think you're right on this one
@stux Try 8.8.8.8, if it fixes the problem at least you know its your local resolver, at that point you can try finding a non-google resolver, or switch back to your old resolver once it updates.
@freemo I know, that's what i was thinking.. Since I added and now removed ProtonMail DNS but I'm not sure how that effected the Mailgun settings since it was on a sub domain and Proton on root.
That's why i was thinking maybe this is a solution?
https://medium.com/@ahmadb/fixing-dns-issues-in-ubuntu-18-04-lts-bd4f9ca56620