Hilton HHonors - Always Gold

I have been Gold for years and have always qualified both with hotels stays and with $$$$ put on my American Express. A few years back I was Diamond for a year. Can anyone tell me why I never get targeted for the diamond upgrades? I see so may free upgrades to Gold, no offence to those who get them. But I pay for mine and I never get any breaks to become Diamond. What am I not doing?

Welcome to Flyertalk.

I think that the upgrade offers are to bring people back to the status they have had, not to bring people up to that status. Lapsing Diamonds get the offer to upgrade to Diamond for example.

Let me also welcome you to Flyertalk.

You can always email HHonors and request a Diamond challenge. Worst thing they can say is no.