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We learn very quickly that the headmaster's study has paintings of all former headmasters and headmistresses on the wall. Eventually we learn that they can travel to at least one other painting of themselves. When Dumbledore died, it seemed like his portrait magically appeared on the wall. (Although I recall reading that Harry put Snape's picture up himself, can anyone reconcile those?)

Is there just one other painting of each headmaster that they can visit? I get the idea this is the case or else there would be empty frames of headmaster paintings all over, as it seems they can only be in one frame at a time.

If it is just the pair, how does the second come to be? Does it just magically appear like Dumbledore's portrait did after he died? Where might it appear? There wasn't a second of Dumbledore mentioned when his main picture appeared after he died, but iirc the OoP ended up with the other end of him.

If it's multiple, how are they linked? An enchantment? How close do they have to be in appearance? Could any magical child paint a stick figure of Albus Dumbledore and have their mommy make it a connection to the Headmaster's study? (It is things like that that make me think it must be just the two, tied portraits.)

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How portraits appear

J.K.Rowling explained that portraits normally appeared in a magical way:

Q: All the paintings we have seen at Hogwarts are of dead people. They seem to be living through their portraits. How is this so? If there was a painting of Harry’s parents, would he be able to obtain advice from them?

JKR: That is a very good question. They are all of dead people; they are not as fully realised as ghosts, as you have probably noticed. The place where you see them really talk is in Dumbledore’s office, primarily; the idea is that the previous headmasters and headmistresses leave behind a faint imprint of themselves. They leave their aura, almost, in the office and they can give some counsel to the present occupant, but it is not like being a ghost. They repeat catchphrases, almost. The portrait of Sirius’ mother is not a very 3D personality; she is not very fully realised. She repeats catchphrases that she had when she was alive. If Harry had a portrait of his parents it would not help him a great deal. If he could meet them as ghosts, that would be a much more meaningful interaction, but as Nick explained at the end of Phoenix—I am straying into dangerous territory, but I think you probably know what he explained—there are some people who would not come back as ghosts because they are unafraid, or less afraid, of death.

--J K Rowling at the Edinburgh Book Festival, 15 August 2004.

Her later explanation about the Snape's portrait was not so detailed:

Laura Trego: Was the absence of snapes portrait in the headmasters office in the last scene innocent or deliberate

J.K. Rowling: It was deliberate. Snape had effectively abandoned his post before dying, so he had not merited inclusion in these august circles.

J.K. Rowling: However, I like to think that Harry would be instrumental in ensuring that Snape's portrait would appear there in due course.

--J.K. Rowling and the Live Chat, Bloomsbury.com, July 30, 2007 (2.00-3.00pm BST).

My theory is that a powerful wizard could have probably reinforced the imprints that Snape left behind, attaching them to a hand-drawn portrait or even magically creating the drawing. They could also create and animate the portrait artificially, using the same magical technique as Professor McGonagall in the first book (when she tranfigured magical chess figures to make them alive).

Multiple portraits

At least in two cases, the portraits appeared in two places:

  • Professor Phineas Nigellus Black: Hogwarts Headmaster's office and Grimmauld Place.
  • Professor Dilys Derwent: Hogwarts Headmaster's office and St Mungo's hospital.

We can note that all of these buildings are magically powerful and both persons were strongly linked to these places.

Other instances of their portraits might exist somewhere, but we don't know this for sure. Professor Dilys Derwent could also have an ancient mansion with her portrait in it, who knows.

I am pretty sure that all of the portraits appear 'automatically' and are magically linked without any need to perform an incantation manually.

How it works

There might be two or more portraits, but the person is unique. When it moves to another portrait, it disappears from the current one.

Obviously, the person would look the same if you catch him or her on any of the portraits.

Visiting neighbours

Apart from ability to move between their own portraits, they can move to the neighbouring portraits, at least at Hogwarts & at the Ministry of Magic. Right after the incident with Arthur Weasley:

But Dumbledore stood up, so quickly it made Harry jump, and addressed one of the old portraits hanging very near the ceiling. 'Everard?' he said sharply. 'And you too, Dilys!' [...] 'Everard, you will need to raise the alarm, make sure he is found by the right people -'

Both nodded and moved sideways out of their frames, but instead of emerging in neighbouring pictures (as usually happened at Hogwarts) neither reappeared.

And at the Ministry:

He doesn’t look good, he’s covered in blood, I ran along to Elfrida Cragg’s portrait to get a good view as they left. --Harry Potter and the Order of Phoenix, chapter 22

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    More to the point, shortly after the passage you quoted: "'Everard and Dilys were two of Hogwarts' most celebrated Heads,' Dumbledore said ... 'Their renown was such that both have portraits hanging in other important Wizarding institutions. As they are free to move between their own portraits..." Seems clear that they can travel between all of their portraits.
    – Joe White
    Commented Jan 18, 2012 at 2:32
  • How does the second to last quote show that they can move to neighboring portraits in Hogwarts?
    – Alex
    Commented Apr 10, 2019 at 22:15
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In the Order of the Phoenix, mention is made that Dumbledore sent various popular headmasters to visit several of their photos in the Ministry to determine what happened to Author Weasley. I'm therefore certain that the paintings can travel from painting to painting.

The moving photographs are done by developing the film in some kind of a special potion, so I would assume the painting is made with a special kind of paint. Many of the paintings travel, but usually from neighbor to neighbor, and not to other paintings of themselves. I'm sure there must be a better explaination somewhere, but...

Perhaps there is only one "intellegent" painting, but the other ones just go do mindless things? I'm not quite sure what the explanation is, but there are definitely more paintings than one that the people can travel to.

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    There is a difference between a "painting" and a "photo" in the Potterverse. Living people can appear in photographs, but the images are mindless and mute; they simply mime what the person was doing (or trying to do) when the picture was taken. Paintings such as the ones in the headmaster's office have an imprint of the person's real personality, and there is only one person regardless of the number of paintings of the person exist. Painting-selves can converse, and can visit their other portraits, and can visit other paintings in one of those locations (it's not clear exactly how this works).
    – KeithS
    Commented Nov 30, 2011 at 22:39
  • @KeithS '(it's not clear exactly how this works)' It's magic of course! Though it's a wonderful thing for world builders it of course does have limits... But I would hazard to say that here that's exactly it: magic. It's as if the two paintings are portals that allows transporting the subject between where ever the two portraits are. As a world builder that's how I would look at it but maybe Rowling has another idea and certainly other people would have additional ideas.
    – Pryftan
    Commented Oct 26, 2017 at 18:16

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