Jester David
Hero
As the DM, I ask for the type of check, the player doesn't say "I make a Deception roll", they describe what they're doing and I decide what flavour of Charisma check is required.
If the player asks to have disadvantage on that roll... sure, why not? Have disadvantage. And if it's an a very inconvenient place in the story, I'll even award Inspiration.
If the player asks to have disadvantage on that roll... sure, why not? Have disadvantage. And if it's an a very inconvenient place in the story, I'll even award Inspiration.