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What I’m wondering is if there was ever a time where Darth Vader ever had to go undercover, and took off the distinctive black armoured portions of his suit, so that he was just wearing the life support elements? Maybe he’d be trying to pass himself off as an old war veteran or something.

Answers based on Legends or Canon would be fine, though Canon would be preferable.

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    He doesn't strike me as an 'undercover' sorta guy. – Valorum Jan 11 at 21:33
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    @Valorum As Anakin Skywalker, he was known for his unconventional and daring tactics, which is why he was called “the Hero Without Fear”. Also, I know for a fact that he and Ahsoka Tano once went undercover as a slaver and his slavegirl, so it’s not something that he’s inexperienced with. – nick012000 Jan 11 at 22:18
  • I doubt this would happen, but I'd love to watch it – DJ Spicy Deluxe Jan 12 at 0:08
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    Vader does admit in 'Thrawn Alliances' that his armor makes him pretty much instantly recognizable, and when he felt any need for stealth, the furthest that extended was his freighter from the Clone Wars, 'The Twilight', which was derelict on the outside but was actually equipped with the best of everything. Other than that, I dont think he gives a dead womp rat if goes in disguise or not. – EwokSniper Jan 12 at 1:20
  • He'd probably do fine, just as long as nobody showed a 'lack of faith' in his disguise ... – Sean Condon Jan 12 at 15:01
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I'd strongly suspect the answer is NO.

Although I can't quote canon specifically to the contrary, there is, I think, enough circumstantial evidence to the contrary:

  • In Episode VI, Vader/Anakin says "Luke, help me take this mask off." Luke replies: "But you'll die." Anakin's reply of "nothing can stop that now" indicates that he would die either way.
  • In Episode III, we see Anakin fried to a crisp and missing most of his limbs. The armour not only holds him together but apparently acts as a respirator. Though you'd think a galaxy spanning KIII civilisation could synthesise a couple lungs for their new dark lord!
  • In Episode IIIb we see that Vader requires special medical baths. Presumably because he can't take his armour off.

If he dìd take off his armour, he'd still have to wear entirely concealing clothing to cover up the scarred head & face, the mechanical arm, the mechanical hand and the two mechanical legs. He'd appear as out of place as a Secret Service agent trying to act natural! And as for the "life support elements", the helmet itself seems to be integral with the life support system. The scene in III where the upper half of the helmet is placed clearly shows that the lower half of the helmet is some kind respiratory apparatus the removal of which will cause his death.

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