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In The Goblet Of Fire Sirius is coming to Hogsmeade to stay closer to Harry. He is having a rough time there living in a cave without food and any necessities.

Sirius was wearing ragged gray robes; the same ones he had been wearing when he had left Azkaban. His black hair was longer than it had been when he had appeared in the fire, and it was untidy and matted once more. He looked very thin...

"I've been living off rats mostly. Can't steal too much food from Hogsmeade; I'd draw attention to myself."

But later we find out that Dumbledore not only knew Sirius was struggling there, he actually helped him to find the place to stay.

"You are not Sirius's only correspondent," said Dumbledore. "I have also been in contact with him ever since he left Hogwarts last year. It was I who suggested the mountainside cave as the safest place for him to stay. "

I believe from the context it's safe to assume he means the cave in Hogsmeade.

Why did he let Sirius starve and wear his old rags knowing he could't just go and get even as much as a toothbrush? Hasn't Sirius ever asked for at least food while they were in touch for months?

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Note that the time frame between Sirius' escape and this meeting is very short. In that time, Sirius is still on the run from the entire ministry. The world cup taking place means a very large number of wizards are present in the country (some of whom at least would know his face). Good clothes are of no real consequence to someone who is not expecting to be seen by other people. As to why Dumbledore did not provide anything, the books give no explanation but here is my reasoning-

  1. It is too small a matter for Dumbledore to fret much about.
  2. Sirius is highly self-dependent and would not have asked for food anyway.
  3. We do not know if Dumbledore met Sirius, only that he corresponded (probably via the Floo Network or owl, in which case he can't provide food for long term).
  4. He cannot send anyone to the cave specifically to provide food for Sirius.
  5. There was no way Dumbledore could have sent enough food for what was possibly months of stay.
  6. This was during the the 4th year, Dumbledore was too busy: quarreling with the Ministry about the disappearances, organizing the Triwizard, running Hogwarts etc. Why would he devote time to send food to a grown wizard who was anyway successfully on the run for more than a year from the whole ministry? He expected Sirius to take care of himself.
  7. To Dumbledore, actual safety was more important than comfort- he didn't make Harry or Snape's life a bed of roses anyway. He expected hardships/losses in the war (he even took into stride the effect of the horcrux ring on his hand & planned his own death).
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    I believe your reasoning is the best we can get from the books, though I still feel it's out of character for Dumbledore. 1,6,7. Danger of starving or freezing to death is no small matter and though Dumbledore does not tend to provide any luxuries, he looks like a man who respects human dignity. Mind that he was among those who helped to accuse Sirius in the first place, so in a way he is responsible for Sirius' miserable life. 2. Sirius asked Harry for help and very willingly indeed. 3,4. If Harry could provide Sirius with food, Dumbledore would surely find a way. I can think of several. – Shana Tar Sep 26 '18 at 7:28
  • Oh, and don't forget Sirius had to steal from people. I do not think Dubledore was Ok with stealing. – Shana Tar Sep 26 '18 at 7:36
  • @ShanaTar Sirius wouldn't have to steal from people if he got necessities from Dumbledore. – ElmoVanKielmo Sep 26 '18 at 10:00
  • @ElmoVanKielmo Well, that's the point, isn't it? He apparently haven't got anything from Dumbledore – Shana Tar Sep 26 '18 at 10:04
  • @ShanaTar I was referring to your "Oh, and don't forget Sirius had to steal from people. I do not think Dubledore was Ok with stealing." There's a circular dependency in your reasoning. Sirius had to steal because he didn't get help (i.e. from Dumbledore) - so you can't use stealing as an argument against helping him. If Dumbledore wasn't ok with stealing, he should exactly offer help in order to prevent this. – ElmoVanKielmo Sep 26 '18 at 10:31
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The ministry was looking for Sirius and it was too much of a risk for Dumbledore to try and send supplies. The ministry had been watching Dumbledore for a while and he would've gotten framed for helping Sirius escape. Plus yes Dumbledore helped Sirius with finding a place to hide but he had a lot of other important things to worry about like keeping the kids at Hogwarts safe and looking after Harry knowing that Voldemort was after him. I'm sure he wanted to do more for Sirius but doing anything more would put him and the kids at risk.

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