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Posted January 18, 2022
If I successfully parry an attack using my second attack as a fighter, and then use Swashbuckler to make an attack, does my counterattack have disadvantage?
Yes, but not because of Combat Expertise. While your counterattack is an attack, it's not an attack being made as part of the Combat Expertise technique, which is what imposes disadvantage on the second attack that is part of that technique. The additional attack granted by Swashbuckler is granted as a reaction, but its rules text specifies that the counterattack has disadvantage. The counterattack is not an attack granted by Combat Expertise.
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