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I am currently playing a Rogue who is the party's 'healer'.

I put that in quotes because he's taken a background of Back Alley Doctor, meaning he has the Risky Surgery feat which says:

Your surgery can bring a patient back from the brink of death, but might push them over the edge. When you Treat Wounds, you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds. If you do, you gain a +2 circumstance bonus to your Medicine check to Treat Wounds, and if you roll a success, you get a critical success instead.

We're only 1st level right now, but when I reach 2nd level, I'm considering taking the Assurance feat, which says:

Even in the worst circumstances, you can perform basic tasks. Choose a skill you’re trained in. You can forgo rolling a skill check for that skill to instead receive a result of 10 + your proficiency bonus (do not apply any other bonuses, penalties, or modifiers).

At 2nd level, assuming I improve my Medicine to Expert, my bonus for medicine checks would 4 (for Expert) + 2 (level) + 3 (Wisdom) = +9.

Given that a successful Treat Wounds check only requires me to pass a DC15 check, it seems that by using Assurance I can always guarantee myself a success since my result would default to 19. Could I combine this with Risky Surgery's benefit which stipulates that a regular success becomes a critical success?

Additionally, is it correct to assume that I can't get Risky Surgery's +2 bonus since Assurance bars any other bonuses?

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    \$\begingroup\$ I updated your answer to correct your Assurance calculation - you don't add ability modifiers to your Assurance result. This was just tangential to your question (seemingly) so it seemed okay to fix. If you like to ask it as a separate question or roll back or change the edit, feel free to do so. I just didn't want someone to pick up an invalid assumption from the question. \$\endgroup\$
    – ESCE
    Aug 31, 2023 at 18:46
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    \$\begingroup\$ @ESCE I see what you did, but I'm going to rollback because brandon's answer addresses my erroneous assumption. My own inexperience with the system led me to make that assumption, so I'd rather keep it in. \$\endgroup\$ Aug 31, 2023 at 21:41

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You can Combine Them

Nothing in either ability prevents this combo (though it's worth noting that the damage happens before healing), however you're correct that you wouldn't get the +2 from Risky Surgery with Assurance preventing any modifiers from applying. Further, you also don't add your ability modifier to the skill using Assurance.

So with your example you'd only add your +6 proficiency bonus at level 2 as an expert, still enough to automatically succeed and therefore critically succeed as long as you're using the trained DC of 15 rather than the expert DC of 20, though you wouldn't be able to automatically critically succeed at the expert check until level 6 with a +10 proficiency bonus.

Rolling for the expert DC at level 2 would instead give a +11 modifier, 60% to heal 4d8+10-1d8 (avg. 23.5) with 40% to deal 1d8 damage instead of the guaranteed 4d8-1d8 (avg 13.5), which is fairly fitting for the idea of Assurance allowing you to reliably get something without reaching your maximum.

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    \$\begingroup\$ Personally, I would bold the part about not getting Wisdom to the check since that's kind of counterintuitive for new players (who are most likely to need to see this Q/A) \$\endgroup\$
    – Ifusaso
    Aug 31, 2023 at 18:27
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    \$\begingroup\$ It should be noted that its (Current HP-1d8)+(4d8+10). Order of operations is important in this calculation. You risk killing your patient outright before the healing effect. "...you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds" \$\endgroup\$ Sep 1, 2023 at 3:37
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    \$\begingroup\$ It's even still risky if 1d8 won't kill them since success->critical success only adds 2d8. 2d8-1d8 is negative ~11% of the time \$\endgroup\$
    – Lunin
    Sep 1, 2023 at 18:03
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    \$\begingroup\$ You can't Risky Surgery on Battle Medicine.... \$\endgroup\$
    – Ifusaso
    Sep 1, 2023 at 23:54
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    \$\begingroup\$ The only 'risks' to Risky Surgery are rolling higher on the d8 than the 2d8, or rolling a crit without the Feat and losing d8 compared to what you would have healed. You'll never kill anyone (not a PC anyway, possibly an NPC if your GM is sadistic) because they will immediately be healed after taking damage. \$\endgroup\$
    – Ifusaso
    Sep 1, 2023 at 23:56
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You Cannot

Assurance states that:

Even in the worst circumstances, you can perform basic tasks. Choose a skill you’re trained in. You can forgo rolling a skill check for that skill to instead receive a result of 10 + your proficiency bonus (do not apply any other bonuses, penalties, or modifiers).

While risky surgery states that:

Your surgery can bring a patient back from the brink of death, but might push them over the edge. When you Treat Wounds, you can deal 1d8 slashing damage to your patient just before applying the effects of Treat Wounds. If you do, you gain a +2 circumstance bonus to your Medicine check to Treat Wounds, and if you roll a success, you get a critical success instead.

When you use assurance you can't roll a success for risky surgery, because you forgo that roll. Instead, you receive a result (10 + 6, for a 2nd level Expert), which against a DC 15 means you receive a success that risky surgery can't improve.

As you've already noted, risky surgery's +2 circumstance bonus is also useless with assurance, so risky surgery grants no benefit when combined with assurance.

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    \$\begingroup\$ I strongly suspect that this is a case where the rules aren't intended to be taken quite that literally \$\endgroup\$
    – Ifusaso
    Sep 6, 2023 at 14:46
  • \$\begingroup\$ Yeah you're probably right, and with that literal of a ruling you also run into the idea that you get a success rather than roll a success in the typical case. If they're distinct then that line doesn't make much sense. \$\endgroup\$
    – brandon
    Sep 6, 2023 at 19:41

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