Hi James,
Your first screen belongs to 3.x and they are transfer rules.
Second screen: when we change and activate any objects on your server above pop will prompt as per transport settings. Above pop belongs to transport request. so don't create or continue.
Try to check your transformations have any issues.
use program(t code - SE38) - RSTRAN_ROUT_RSFO_CHECK.
Later try to activate your transformations.You can go to your transformations, change mode, save and activate it. later you actiavte your dtp and try to execute it.
Or you can use program SE38 - RSDG_TRFN_ACTIVATE.
Transformations are below green mark and dtp is orange mark.
Thanks