The time has come - after 10 years I decided to finally leave my old Windows 2008 server behind and accept the inevitable... That there was no way forward with the old machine.
Yes that sounds somewhat logical and no reasonable person would operate an Windows 2008 server these days. It was crazy what I partially had to do to run .NET 4 (or higher) on it. ASP.NET MVC 3? ASP.NET MVC 4? WebSockets?! All that stuff we take for granted (starting with basics like nice SEO friendly URLs) was actually hard work on the old machine. So what kept me running it for the past 10 years? The fear of migrating!
It turns out I simply had no time to take all the settings and websites into considerations. Multiple email inboxes and many many databases have been scattered on the old box. Needless to say that some of the webpages also did use the local HDD / root folder for storing things, e.g., media files like pictures or arbitrary downloads. I feared that a migration may be very riskful and challenging from a timing perspective.
Two weeks ago my hosting provider contacted me to give me another warning (not the first one). The operating system on my machine was heavily outdated (ah yes, not did I was not aware of it). However, one thing was different this time... they mentioned to grant me a grace period when going for a new server. Two weeks side-by-side operations.
I looked into my calendar. It turns out I had no plans for Saturday night. I looked into my server; some of the inboxes that I feared would be hard to migrate have been closed or abandoned. Some of the webpages should not be moved (well, I still keep the data, but no need to take the page live again). So yes - this is my chance!
Now 2 weekends later I can say that everything was migrated with close to zero downtime (5 minutes). The hardest part was the migration of the .de domain (even though it worked flawlessly on the outside it took a while until denic accepted the change - apparently having two more nameservers registered on the server itself leads to inconsistent results from their perspective, which is why I had to register these two DNS also on the DNS of the service provider).
Besides being fully up-to-date on the OS level, this new server gives me plenty of new capabilities and choices. Every page now has Let's Encrypt installed and used. The renewal is automatic (thank god). WebSockets are just working. The computing power is now better - my page is 30-40% faster for end users and has gained tremendously for administrative purposes.
I am not yet sure if this new server will survive 10 years, but independent of that I am quite happy and convinced for the moment.