I can't remember how this happened in the books, but in the Half-Blood Prince film's train scene, Draco's actions seem to make it very clear that he knew that Harry has an invisibility cloak. When did he learn of this?
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Probably in Azkaban, definitely in HBP; scifi.stackexchange.com/questions/85471/…– ValorumJul 10, 2021 at 20:06
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Back in Prisoner of Azkaban, there was a scene of Harry using his cloak to taunt Draco and his friends. It would make sense that Draco either saw Harry un-cloak or made a point of trying to understand exactly what happened. Either way, it's reasonable he knew of the cloak not long after that incident, and therefore well before Half-Blood Prince.– Anthony XJul 10, 2021 at 20:08
1 Answer
He was surprised to see Harry's disembodied head floating around in Harry Potter and the Prisoner of Azkaban. If he's got half a brain, he almost certainly worked out later that Harry was using an invisibility cloak, although there are other spells and charms that could achieve much the same effect.
Crabbe stumbled – and his huge, flat foot caught the hem of Harry’s Cloak. Harry felt a great tug, then the Cloak slid off his face.
For a split second, Malfoy stared at him.
‘AAARGH!’ he yelled, pointing at Harry’s head. Then he turned tail and ran, at breakneck speed, back down the hill, Crabbe and Goyle behind him.
Harry tugged the Cloak up again, but the damage was done.
We don't get proof positive until a couple of books later, in Harry Potter and the Half-Blood Prince.
‘Petrificus Totalus!’
Without warning, Malfoy pointed his wand at Harry, who was instantly paralysed. As though in slow motion, he toppled out of the luggage rack and fell, with an agonising, floor-shaking crash, at Malfoy’s feet, the Invisibility Cloak trapped beneath him, his whole body revealed with his legs still curled absurdly into the cramped kneeling position. He couldn’t move a muscle; he could only gaze up at Malfoy, who smiled broadly.
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4@Slytherincess - I remember going through the books quite closely when I was putting together my answer for How many people know that Harry owns an Invisibility Cloak?– ValorumJul 11, 2021 at 9:03
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The "when" part was probably after having a conversation with Snape about what he saw.– rtaftJul 11, 2021 at 22:08