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In Order of the Phoenix, when Umbridge is headmistress of Hogwarts, she is carried off into the Forbidden Forest by the Centaur herd. Later, she's in the hospital wing mute, but reacts with agitation to the sound of clip-clopping.

Professor Umbridge left Hogwarts the day before the end of term. It seemed she had crept out of the hospital wing during dinnertime, evidently hoping to depart undetected, but unfortunately for her, she met Peeves on the way, who seized his last chance to do as Fred had instructed, and chased her gleefully from the premises whacking her alternately with a walking stick and a sock full of chalk.

Order of the Phoenix - page 755 - UK Hardcover - chapter 38, The Second War Begins

Did Umbridge technically abandon her post, even though it wasn't exactly in the way Snape did? By the end of the book, Dumbledore is back as headmaster; it's unclear to me what Umbridge's status became after she was taken by the centaurs and when her title would have changed back from Headmistress to Senior Undersecretary. Dumbledore kind of reappointed himself to the position of headmaster. Did Umbridge leave Hogwarts in good standing? Based on what is known from canon, would there be a portrait of Umbridge in the headmaster's office?

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    My personal opinion is that Umbridge was a usurper or pretender, and that Dumbledore remained Headmaster in exile (or perhaps a Rump Headmaster since he still controlled the physical castle). Therefore as with all pretenders she actually never held the post. – Mark Beadles May 8 '12 at 18:23
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    I'd agree with Mark Beadles on this. It's mentioned in the book that the Headmaster's office had sealed itself against her, so I don't think the castle itself ever recognised her as being Headmistress. I think it also raises the question of where exactly the portraits come from; the portrait of Dumbledore appears quite soon (within a matter of hours?) after his death in Half-Blood Prince, and there's no indication that anybody had put it there, and it seems like it would be a low priority anyway given that they'd just been attacked by Death Eaters. – Anthony Grist May 8 '12 at 18:38
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    @AnthonyGrist - this should be an answer, not a comment. Add a couple of quotes and it's a good one – DVK-on-Ahch-To May 8 '12 at 18:40
  • possible duplicate of Did all Headmasters get a portrait in Hogwarts? – AncientSwordRage May 8 '12 at 22:41
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This is going to be partly speculation on my part, so feel free not to accept as the final answer. However, there are a couple of things that lead me to think that Umbridge wouldn't have had a portrait in the Head's office.

The first is that while she's recognised by the Ministry of Magic as the Headmistress of Hogwarts, the castle itself (or, at the very least, the Head's office) doesn't appear to officially recognise her. Once Dumbledore has departed the Head's office seals itself off, and she's unable to re-enter it.

"... The Fat Friar told me -" he dropped his voice conspiratorially, so that Harry, Ron and Hermione had to lean closer to him to hear "- that Umbridge tried to get back into his office last night after they'd searched the castle and grounds for him. Couldn't get past the gargoyle. The Head's office has sealed itself against her." Ernie smirked. "Apparently she had a right little tantrum."

Order of the Phoenix - Chapter 28, Snape's Worst Memory

Then, in Half-Blood Prince:

In silence they ascended the moving spiral staircase and entered the circular office. ... In fact, it looked almost exactly as it had done when he and Dumbledore had left it mere hours previously ... And a new portrait had joined the ranks of the dead headmasters and headmistresses of Hogwarts: Dumbledore was slumbering in a golden frame over the desk...

Half-Blood Prince - Chapter 29, The Phoenix Lament

Given the events leading up to this - the school being attacked by Death Eaters and a teacher killing the Headmaster - and the timescale involved (probably less than two hours), I think it's unlikely that anybody took the trouble of moving a portrait of Dumbledore into the Head's office. I would guess, though can do no more than that, that the castle itself selects/creates the portraits of the headmasters and headmistresses.

If that is the case, and given that the castle didn't appear to recognise Umbridge as the Headmistress during her brief stint in the position, I doubt there'd be a portrait of her.

There is, also, the small matter of the portraits apparently only being dead headmasters and headmistresses. As of the events of the last book, Umbridge is still alive, so she definitely wouldn't have had a portrait at that point. It seems unlikely that, even after her death, she'd have received one.

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    harrypotter.wikia.com/wiki/Dolores_Umbridge Down under 'Imprisonment' "After Voldemort's final defeat by Harry Potter and the revolution of the Ministry of Magic by Kingsley Shacklebolt, Umbridge was arrested, tried and sent to Azkaban for her crimes against Muggle-borns, where she remained for the rest of her life." – Mike Ramirez May 9 '12 at 5:56
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    I had always assumed that the current headmaster of Hogwarts chose his or her successor (by naming them deputy head; that is in essence McGonagall’s function throughout the books). Whom the Ministry decides to name as ‘headmaster’ is quite irrelevant to the school, which has a kind of mind of its own, acted out through the actions of the current headmaster alone. – Janus Bahs Jacquet Apr 19 '15 at 10:24
  • See scifi.stackexchange.com/q/53547/4918 "In what interview does Rowling say Umbridge is sentenced to prison?" She probably didn't die. – b_jonas Oct 17 '17 at 10:19
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    You might want to add the extra detail from Pottermore about how the portraits are created. They're actually trained by the headmaster, not made by the castle. Umbridge probably never got round to making one. – The Dark Lord Oct 17 '17 at 21:56
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I believe she would not have. For one thing, she was an usurper and not viewed as a real headmistress. For another, Snape was not going to, Harry had to request it. She was so hated she wouldn’t get one ( the reason Snape nearly didn’t was because he was hated by the students.

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