Special Actions in Combat

If a player does something tactically clever that requires an action and an attribute check to succeed, the reward of success should be at least somewhat more than a single Advantage (or Disadvantage) roll applied against a single target. I might choose to allow someone else an attack of opportunity (with advantage), apply the Advantage or Disadvantage to two targets or allow the player to make a single weapon attack as a possible reward.

I encourage player creativity, so feel free to attempt task not specifically covered by the rules. I’ll use the guidelines from p193 (Improving and Action) and p195 (Contests in Combat). In general this follows the rules for Grapple and Shove - sacrifice one of your weapon attacks when you take the Attack action to contest your Strength (Athletics) against the target's Strength (Athletics) or Dexterity (Acrobatics).

These “optional” actions from the DMG (p271-272) provide some examples of what I’ll allow: Return to House Rules
 * Disarm - Make an attack roll contested by the target’s Athletics or Dexterity to make them drop whatever they’re holding. You have disadvantage if they are holding the item with two or more hands. They have advantage on the check if they are larger, or disadvantage if they are smaller.
 * Overrun - Force your way through an occupied square with a contested Athletics check as an action or bonus action. You have advantage if you’re larger than the target or disadvantage if smaller.
 * Shove Aside - With Disadvantage on your shove attempt, you can move the target to the side rather than away (5ft).
 * Tumble - Move through an occupied space with a contested Acrobatics check.