Hmm. Not sure why I'm seeing this then. I have a 2020 iMac running Monterey and a 2017 iMac on Ventura and both exhibit this in Safari. I'll update the Wipr extension (with the Extras) and ads will start showing up even though it's enabled. Toggle it off and then back on again and it's good until the next update.
Are you guys quitting Safari before updating Wipr?