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Keyword: Stealth Rulings
If you have a Stealthiness attached to Headstrong in his Alternate Mode, what happens? Does Brave trump the Stealth or vice versa?

The opponent can choose to attack any available target; they essentially cancel each other out.
Source: Wizards of the Coast (2019-02-11)    【Link to Ruling】
Tags: Stealth, Brave
What is Stealth?

Stealth is a new keyword ability that lets some characters strike from the shadows without fear
of reprisal. When choosing which enemy to attack, you must attack a character without stealth
if able.
Source: Wizards of the Coast (2019-03-01)    【Link to Ruling】
Tags: Stealth
If my opponent has one tapped character with stealth, and the rest of their creatures are
untapped, which character can I attack?


Stealth doesn’t override the rules for attacking tapped/untapped characters. Since the
tapped character is the only one that can be attacked, that’s where your attack is headed.
Source: Wizards of the Coast (2019-03-01)    【Link to Ruling】
Tags: Stealth
What happens if a character has brave and stealth?

Brave and stealth essentially cancel each other out. You must attack that character if able,
and you must attack other characters if able. This basically means you must attack a character
you can attack, the same as if those abilities weren’t there.
Source: Wizards of the Coast (2019-03-01)    【Link to Ruling】
Tags: Stealth
What happens if someone has Brave and Stealth at the same time, like if I played Hiding Spot on Blitzwing while he was in tank mode, do they cancel out, does the newer stays take effect?

They cancel each other out. An attacker is not able to fulfill both conditions, therefore the attacking player can choose a defender as normal.
Source: Wizards of the Coast (2019-08-23)    【Link to Ruling】
Tags: Brave, Stealth
If I have a Cassette in Bot Mode that is chosen as a defender but flip a Swerve does it fizzle the attack when the character flips to Cassette due to the Stealth on that side as long as another target is legal to attack? Or not, since it's already been chosen as the defender?

Once an attack is legally declared, the defender picking up Stealth wont matter.
Source: Wizards of the Coast (2019-11-09)    【Link to Ruling】
Tags: Swerve, Stealth