Crestron Lutron Keypad Emulation

Hi,

We're currently working on a big Lutron & Crestron project and having an issue with the crestron emulating/controlling/triggering a button press on a physical keypad.

Keypad is setup as toggles with 1 button per circuit (each with cycle dim), button 1 on each keypad also has a double tap for a predefined scene and the last button on every keypad is a single action "room off"

Ive programmed the Crestron and have set the mode as PressHoldRelease.

When tapping the button via the Crestron the LED on the matching keypad button just flashes and does not toggle the circuit on. (Its like the Lutron believes/is acting like the button has been held?)
When the circuit is already on and you press+hold the button on the crestron then the applicable circuit does cycle dim.
Double tapping the button on the Crestron also just causes the LED on the keypad to flash and the lights don't toggle.

The single press "Room Off" does work from the Crestron.

Any thoughts?