Can I retrieve and then stow away an item every turn without using up my Action?

Question

The context for this question is a Shadow Origin Sorcerer that tries to fight exclusively within the Darkness spell created by their Eyes of the Dark feature (a feature which permits the sorcerer to see through their own Darkness effect) to gain Advantage on their attack rolls during the fight. The problem, however, is that if the Darkness effect is present, it could negatively affect their allies, especially if they're spellcasters that become literally unable to cast their attack roll spells when they can't see their targets.

So the strategy I came up with to try to counteract this effect is to follow the following plan for combat:

1. Before the fight (or during the first round of combat), cast Darkness (using Eyes of the Dark, naturally) on a gemstone that the sorcerer keeps in their possession.
2. Stow the gemstone away into a pouch or their pocket, "shrouding" the Darkness effect.
3. When their turn arrives in combat, pull the gemstone out of their pocket, revealing the Darkness effect
4. Attack the enemy (a melee attack with a rapier), gaining advantage on their attack roll (because they can see the target, and the target can't see them).
5. Put the gemstone away, shrouding the Darkness effect again

The problem is that, by the strict rules of the Object Interaction rules, I don't believe this is possible, since retrieving and stowing away an item requires a full action, not just the Free Object Interaction permitted.

Is my understanding of the Object Interaction Rules, which is that it's not possible to execute this sequence of events in a single turn, correct? If it is, is there something else I could do to suppress the Darkness effect during my allies' turns?

Answer 1

You are correct. You cannot affect an item twice for free as part of your movement and/or action. In chapter 9 of the PHB (Under "Your Turn" then "Other Activity on Your Turn") it says specifically that you can interact with one item for free and if you want to interact with a second object, you need to use your action.

I don't have great suggestions for getting around this but I did have one... sub optimal idea. The darkness spell has a radius of 15ft. If you have a 30 movement you could simply move in 15ft then move back out 15ft after the attack. This also gives you some fudge room in that you could hold the stone in the front of your square or back of the square if your ranged friends need 5ft somewhere to get line of sight. When first engaging the enemy you have the stone out then put it away at the end of that turn before starting the engage/disengage dance. The reason this is sub-optimal is that they will get a reaction against you every turn but at least they'll be at disadvantage.

Answer 2

Before inventing a workaround, ask your DM

D&D 5e uses turn-based mechanics to resolve combat. However, "turn-based" doesn't mean all characters stay frozen during other character's turn. In fact, turns are simultaneous. There is a compromise between realism and simplicity — that's why special mechanics like opportunity attacks and other restrictions exist.

If your character pulls out a gemstone with Darkness and then stows the gemstone away — the rules ensure the Darkness will be applied the whole round, giving all the participants a window to react. That's why the "one object interaction per turn" restriction exists. This complies with the "turns are simultaneous" general principle.

Any loopholes, which allow you to (de)activate Darkness "on your turn only", might lead to unneeded debates with the DM. Ask the DM first. If you find a workaround for this restriction, this workaround might be vetoed by your DM.

Instead, you may try different tactics. Since you don't trigger attacks of opportunity being invisible, you are free to roam through the battlefield. Approach the enemy, attack it and then retreat, giving vision to your allies.