Happened at my workplace. An phishing email went out to test how likely people were to click the link.
Anyone who clicked the link had to take phishing training. Anyone who forwarded it to our internal "hey this is a phishing email" service also had to take training... because the internal service would automatically click the link.
Have you checked for compatibility with the programs that are crashing? Before you go through the effort of installing everything, it's worth checking if anyone else got it to work: https://appdb.winehq.org/
As for upgrading, that would depend on the distro you're running. What do you use?