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Vicious mockery requires you to "see the target" within range (60 feet) and the target must "hear you".

Message has a range of 120 feet, does not require line of sight, and the target "hears the message" as a whisper.

Here are some things that may help this combo:

  1. The Spell Sniper feat (PHB) doubles the range of spell attacks
  2. A 3rd level sorcerer with Metamagic or having the Metamagic Adept feat (TCoE) gives access to Subtle spell (PHB) allowing the spell to be cast without any somatic or verbal components.

I am trying to be an "Insult Sniper" by being stealthy to hide and be covert with this attack.

  1. Under what conditions will this combo - vicious mockery and message - work?
  2. What could be done to avoid revealing your position to the target?

Posted as a separate question here: Can I cast spells requiring pointing at the target by looking in a mirror?

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    \$\begingroup\$ This seems well-focused. I'm not even sure why people consider slosing it, so a comment that goes into that would be insightful — from review. \$\endgroup\$
    – Akixkisu
    Jan 9 at 15:29
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Most of these features don't work as you describe, but you could still get 120 ft out of Vicious Mockery with metamagic

Specifically, spell sniper cannot apply to Vicious Mockery because you don't make an attack roll:

You have learned techniques to enhance your attacks with certain kinds of spells, gaining the following benefits:

  • When you cast a spell that requires you to make an attack roll, the spell's range is doubled.
  • Your ranged spell attacks ignore half cover and three-quarters cover. You learn one cantrip that requires an attack roll. Choose the cantrip from the bard, cleric, druid, sorcerer, warlock, or wizard spell list. Your spellcasting ability for this cantrip depends on the spell list you chose from: Charisma for bard, sorcerer, and warlock; Wisdom for cleric or druid; or Intelligence for wizard.

There's also no way to combine two spells. Both are actions and there's no mechanic to combine the spells even when cast the same turn. Even using metamagic to quicken one of them, they can't interact and affect each other.

You can still get 120 ft out of Vicious Mockery by using distant spell to double the range, but you cannot combine that with other metamagic options.

Vicious Mockery, then moving and hiding may be a better option

Either by using quicken spell metamagic + the hide action or mulitclassing into rouge to get a cunning action to hide may give the effect you want, just with a little more hit and run.

Blink may also give you a similar effect you want

Assuming you always roll an 11 or higher for blink, you will always end up on the Ethereal Plane and out of direct combat. The effect of this will be you blink into existence long enough to insult a target then disappear before anyone knows what happens.

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Under what conditions will this combo - vicious mockery and message - work?

None. Just because Message does not require line of sight does not remove this requirement from any other spell you cast. You might find a way to actually remove direct sight requirements from other spells with mid to late game divination items or magic, but they will explicitely say so.

What could be done to avoid revealing your position to the target?

Remain hidden? The requirement is that you need to see them, not the other way round. You could peep through a hole in the wall or be crouching in a bush at night, or be one of many people in a crowd. Anything that would be considered hiding should still be in effect when you cast the spell, especially with "Subtle spell".

Does a hidden creature that casts a spell reveal its position?

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