From the new lessons learned bucket the question is how much time and money should you spend keeping your projects up to date?
I’ve been managing a project for about 10 years or so and treating it like an appliance. As in toaster. Plug it in, put in the bread, flip the switch and wait for the ding. The problem is that even the most mundane devices wear out. In this case I moved one component to a server behind an SSL wall and some haproxy bits that require some sort of SNI capability from the client. Unfortunately the existing wget and curl do not support SNI and so I need to upgrade. However the base OS has been EOL for years and so the various repos have been shut down.
Now that’s EOL.
So I tried to build the projects from source. hahaha. Either the source was also behind an SNI firewall or I was missing other elements that simply would not install. At this point upgrading the systems could be a major undertaking… But before you go crazy about service contracts and the like… the customer is nearly 4-5 years behind in payments.