Users need to be motivated to upgrade. If their current software works sufficiently on the sites they care about, then they have no need to upgrade. If the sites themselves are enabling this behavior, by bending over backwards to work on with old browsers, then they are part of the “problem”.
I don’t like automatic updates and generally keep them disabled. Software upgrades tend to reduce functionality and instead force unnecessary UX redesigns on users, so I’d rather avoid them. I wish developers had the [EDIT: incentive] to release security patches independently from functionality changes, but few do that anymore, sadly.
It's been an age since I've worked in an agency, but back in the IE era, at least once a month a dev would ask to use a 'modern feature'. Something to support some a new piece of design from the design team, or save hours or days of dev, or remove the need for hacky 'fixes' that could be done cleanly with modern browser support.
So off to analytics they would go. "X thousand users are using IE8. We're converting at X%. Removing support for IE8 just means these people will shop elsewhere and we'll lose X thousand pounds a month. You need to support IE8."
Believe me, I wish it was as simple as saying developers are "part of the problem," because it would be an easy fix. But try selling that (without a huuuuge struggle!) to the person who holds the purse strings.
Sadly the new features usually only came on new sites. It's much easier to push it through when you're not cutting off an existing income stream.
I don’t like automatic updates and generally keep them disabled. Software upgrades tend to reduce functionality and instead force unnecessary UX redesigns on users, so I’d rather avoid them. I wish developers had the [EDIT: incentive] to release security patches independently from functionality changes, but few do that anymore, sadly.