> I don’t agree that it’s “shady” but you can already tell that it would negatively affect conversion to directly inform people of what they’re doing, rather than waiting for them to do it and then automatically upgrading them.

"shady" is an understatement, not an overstatement.

"If we auto-upgrade, there will be people who miss it or will be too apathetic or procrastinating to fix it, therefore better conversion rates" is on the bad side of "shady".