Originally Posted by elusive1

1. I pull out the Hilton App and show them the availability, adding there must be an error, please check with the manager. (85% success )
2. If they claim it is at their discretion, I get HHonors on the line, lets see what the rule actually is.
3. If that does not work, I request an appointment with the properties actual GM in the morning, hoping he/she can explain to me why this Diamond isn't getting the upgrade he is entitled to, as there is space available. I have never had an unsuccessful result if I managed to meet the GM. Would not help for the 1st night, but fixes things going forward as well as usually gets me a super room for the stay.

The trickier issue is if the next level up is sold out, but other levels are available. IMO, if we all did this, the issue would cease.

Color me self-entitled!