Slobber Monster
First Post
With enough planning I think I can see ways to split this up into more rolls, so long as you change Diplomacy from a means to affect attitudes to a means to resolve proposed deals.
For your latter example, I might require separate checks for the forgery, disguise, and individual lies for background. If any of these is failed then backpedalling, ad-libbing and more lies are required to avoid blowing cover. Some cumulative circumstance penalities would still get applied to later attempts because the NPC suspects there's something a little "off" about the character. The final check to see if the PC can convince the diplomat to cooperate comes down to a single roll, but the road there is a little more interesting. Even then, subsequent rolls could be allowed if the PC ups the anti with bribes, blackmail, etc.
For your latter example, I might require separate checks for the forgery, disguise, and individual lies for background. If any of these is failed then backpedalling, ad-libbing and more lies are required to avoid blowing cover. Some cumulative circumstance penalities would still get applied to later attempts because the NPC suspects there's something a little "off" about the character. The final check to see if the PC can convince the diplomat to cooperate comes down to a single roll, but the road there is a little more interesting. Even then, subsequent rolls could be allowed if the PC ups the anti with bribes, blackmail, etc.