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I've tried to ward them off the bribery route and hinting at how much that could backfire, but they're incredibly intent on getting a guard to go instead of themselves. I'm still allowing them by miracle of lucky dice rolls that it could work, but it seems the chances of getting caught is super high.

Then if/when Sabo does find out, does it basically make the Trickery option of this mission impossible? She's not going to fall for a duped document again after the first attempt.

Hey, long time lurker and first time post.

My players ran into Sabo a little too early and now she knows what they look like and their alignments. They were able to make a forged document but can't hand it to her themselves. They're thinking in bribing a dottari guard to hand the documents. I'm trying to figure out what the actual chances of this working were and what the rolls needed be?

Diplomacy to make the guard helpful.
Diplomacy again to make the guard risk his job on this request.
His bluff against Sabo's Sense Motive.

I imagine if Sabo starts grilling him on questions like "Sho is your officer? Who has requested this?" the guard would start breaking down and he would be immediately caught.