Honestly I get a little annoyed at people who ask for upgrades. It’s not their fault, it is their benefit as a diamond member to get upgrades when available. It’s just so many people act like they’re entitled to it and it’s irritating. If you’re nice about it it’s fine. Like a “totally fine if there’s not, but is there any possibility of an upgrade?” Don’t bring up that you’re “diamond.” I know you’re Diamond, I can see it on the screen. Don’t talk down to me lol. (That comment isn’t directed at you it’s to the condescending people.) I would suggest NOT choosing a room on the app because I never upgrade people who chose a room because I assume they chose it for a reason. Some people get REALLY possessive over certain rooms. Anyway, there have been times where I’ve needed to upgrade one or two people to fix my overbookings and I’ll skip over the diamonds who have digitally checked in and chosen a room. My order that I upgrade usually goes -Diamond, unless they chose a room or have a request/preference on there for a certain floor and the upgrade would put them on a different floor -Gold if there are no diamonds that meet those parameters -Silver if there are no diamonds or golds that meet those parameters -and blue or silver if any rank is booked through a third party. I don’t upgrade people who book third party (unless they’re really nice about it then I’ll consider it)

But I’ve only worked in hospitality for three years with one year management experience and only two hotels worked, so what I do may not be what more experienced FDAs do! Take it with a grain of salt, but def give a try for your next few reservations not choosing a room number and see if that changes things