Как убеждавате член на семейството да надстрои една стара (и вероятно компрометирана) система?

The situation I face is a family member whose position is the following:

I do not want to update something that works because updates may break something. Look at our old computer that runs Windows 98. I have been using it every day for everything for 15 years now and it works without any problem, even though there is absolutely no anti-virus or anything.

Using the same reasoning, he strongly resisted installing any updates or service packs on his other computer running Windows XP, and now that XP is dead, I cannot even imagine how he will react to the choice of either:

• Buying several copies of Windows 7 for his computers for serious money, or
• Switching to Linux and basically relearning how to use computers from scratch

What facts can I use to convince them that it is bad if the computer is infected with malware, even if they do not notice anything wrong?

The best and least refutable argument is, that if you have nothing else to protect, you have your reputation.

If your account starts sending virus spam, you have to answer to everyone in your address book.

If the FBI starts asking why your PC engaged in a coordinated DDOS attack on a bank’s website (because you got enrolled in the Zeus botnet), you have to let them sift through all your personal artifacts to (hopefully) prove you are not a cyber-criminal suitable for imprisonment for 30+ years. Or worse yet, someone used your computer as a proxy for downloading child pornography, stealing and selling credit card data, or selling drugs on the Silk Road.

Everyone has their reputation (and potentially their freedom) to protect. Emphasizing that is one of the more effective ways to teach people (patching) religion. Just an investigation on some of these topics is enough to show up in background checks, which can follow you the rest of your life.

The best way to explain to non-technical people is via an analogy, and this is analogous to keeping information in a shoebox on your open windowsill. It depends on your behavior whether or not the information in the shoebox is worth taking, or whether anyone will end up taking it, but the fact remains that anyone that has a half a mind to do so easily can.