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Fair warning: if you haven't yet read Harry Potter and the Order of Phoenix, you may be spoiled.

As Hermione always said, it's impossible to penetrate Hogwarts' defenses. In Harry Potter and the Order of Phoenix, when Harry saw Mr. Weasley from Lord Voldemort's snake's eyes, Hermione told Harry that it's impossible to apparate into Hogwarts and Voldemort had no access to Harry. However, at the end of the book, Dumbledore sent Harry to Hogwarts using a Portkey. So why didn't Lord Voldemort use a Portkey to get into Hogwarts?

Edit: After Harry saw Mr. Weasley from Nagini's, Dumbledore sent Harry and the Weasleys out of Hogwarts using a Portkey.

Second edit:
as I said in comment, Dumbledore was in ministry of magic and he couldn't do any magic from there on Hogwarts protections.

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    Off the top of my head, I'd say that the Headmaster has the ability to selectively lift the prohibitions, as he did for their apparition training, but I have no canon proof... Waiting to see what Slitherincess has to say :) – K-H-W Feb 20 '12 at 5:41
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    @KeithHWeston That was my thought as well - similar to how he lifted the protective shields around Hogwarts so that you can't directly fly in when he saw the Dark Mark in HBP. – Dason Feb 20 '12 at 5:46
  • @Keith I thought that myself but dumbledore was at ministry of magic and he couldn't do magic on Hogwarts protections! – undone Feb 20 '12 at 6:01
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    None of the answers acceptably answer the Triwizard Cup portkey from and to inside Hogwarts grounds. – marcellothearcane Aug 22 '18 at 17:17
  • Highly related: scifi.stackexchange.com/questions/18248/… – Alex Jun 25 at 1:56
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I'm not sure it matters that Dumbledore was at the MoM, he was the headmaster.

What is mentioned in the question is that why couldn't Voldemort use a portkey at any time to enter the Hogwarts grounds. I think it is clear that magical protection prevented apparating into Hogwarts. From this we can presume that the restriction on using Portkeys is in place unless lifted by either the MoM or the headmaster.

The only time that a portkey is used to get into/out of hogwarts is when it was created by Dumbledore himself to send Harry and the Weasleys back to London. Clearly this was allowed as it was created by the Headmaster.

I don't think Voldemort would have been able to get into Hogwarts using a Portkey because of the aforementioned protection.

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    Technically when Dumbledore made the portkey he wasn't officially headmaster. – Dason Feb 20 '12 at 15:32
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    @Dason You're not wrong, but if you remember rightly, the school did not recognise that Umbridge was the headmistress, therefore we can assume that Hogwarts still recognised Dumbledore as the headmaster. – AlasdairCM Feb 20 '12 at 20:28
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    "The only time that a portkey is used to get into/out of hogwarts is when it was created by Dumbledore himself" Huh? Not sure where you get that idea. In GoF, Crouch Jr. had no problem making a Portkey to transport Harry and Cedric both away from the Hogwarts grounds and back in. Dumbledore certainly didn't authorize that. – Joe White Feb 26 '12 at 14:16
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    @JoeWhite Good point, I hadn't considered that. Not sure how that worked. – AlasdairCM Feb 27 '12 at 11:43
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    Not "the only time". What about the Tri-Wiz cup? – Möoz Feb 26 '14 at 21:40
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To use a computer security analogy, Hogwarts is protected by a magical firewall. A large part of that firewall was created by Dumbledore.

Therefore it is quite possible that there's a backdoor access (or root Headmaster level access) to send a Portkey to Hogwarts, but Voldie has no such access not being the headmaster.

Incidently, Rowling never said anything about Portkeys other than traveling using them to another country is illegal.

  • I'd say a backdoor in a firewall isn't what you want certainly without a perimeter network/DMZ (maybe involving a bastion host). Of course if it's temporary access one might say it's like port knocking with one time entry (instead of an OTP, one time password, say) but even then I'd say it's more complicated than just a firewall (or it should be anyway). I'm not trying to take away from your analogy btw; it's a good idea I just think it could be improved. I'd say it should require an actual action from the headmaster though as an added layer of defence (and security is a many-layered thing). – Pryftan Dec 10 '17 at 17:29
  • And yes I somewhat simplified this although one might argue I complicated your answer; but in my mind I am trying to complete it more. – Pryftan Dec 10 '17 at 17:29
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Who says he couldn't?

Consider the facts:

  • In Order of the Phoenix Dumbledore made a portkey from Hogwarts to Grimmauld Place and a portkey from the Ministry to Hogwarts, and there is no mention that he had to first remove any preventative enchantments in order for the portkeys to work.

  • In Goblet of Fire Barty Crouch Jr. created a portkey that took Harry out of the school grounds and later returned him to the school grounds. If there was some protective enchantment that prevented portkey travel to and from Hogwarts, it would seem to be unlikely that Crouch Jr. would have the ability to remove it.

  • When discussing how the other schools would arrive in Chapter Fifteen of Goblet of Fire Ron suggested portkeys and Apparition:

    "A Portkey?" Ron suggested. "Or they could Apparate – maybe you're allowed to do it under seventeen wherever they come from?"

    Hermione only objected to the Apparition suggestion, implying that it is possible to portkey into Hogwarts:

    "You can't Apparate inside the Hogwarts grounds, how often do I have to tell you?" said Hermione impatiently.

If we look carefully at what Hermione tells Harry when he thought Voldemort had transported him to London, we see that she says nothing to imply that Voldemort couldn't get into Hogwarts with a portkey:

“One day,” said Hermione, sounding thoroughly exasperated, “you’ll read Hogwarts, A History, and perhaps that will remind you that you can’t Apparate or Disapparate inside Hogwarts. Even Voldemort couldn’t just make you fly out of your dormitory, Harry.”

All she says is that Apparition is prevented and that Voldemort couldn't make Harry fly out of his dormitory.

Based on all the above, it would seem that Voldemort could have used a portkey to enter Hogwarts. However, in Chapter Twenty-Seven of Half-Blood Prince, Dumbledore seems to think that Hogwarts is impregnable:

"But you were saying... yes, you have managed to introduce Death Eaters into my school, which, I admit, I thought impossible.... How did you do it?"

Given that it is unlikely that Dumbledore simply overlooked portkeys, this might seem at face value to indicate that Voldemort would not have been able to enter Hogwarts via portkey. However, we can perhaps resolve this potential contradiction by suggesting that Dumbledore didn't mean that no form of entry into Hogwarts was possible; rather, he meant that he thought it impossible for Malfoy to bring Death Eaters in, which would at most tell us that he didn't think Malfoy capable of creating a portkey into Hogwarts.

So why didn't he?

If it is true that Voldemort could have entered Hogwarts via portkey we now have to explain why he didn't. The answer to this may be that he didn't need/want to:

  • Philosopher's Stone – he was already in Hogwarts on the back of Quirrel's head.
  • Chamber of Secrets – He was powerless and had no reason to enter Hogwarts.
  • Prisoner of Azkaban – He was powerless and had no reason to enter Hogwarts.
  • Goblet of Fire – The only reason for him to enter Hogwarts would be to kidnap Harry, and in Chapter Thirty-Three he says why he didn't do this:

    And then, the boy would return to Hogwarts, where he is under the crooked nose of that Muggle-loving fool from morning until night. So how could I take him?

    He did not say that he could not gain entry to Hogwarts; he merely said that Dumbledore would be watching Harry too closely for Voldemort to kidnap him.

  • Order of the Phoenix – As explained in Chapter Five, Voldemort was trying to keep his return a secret:

    “Because he doesn’t want to draw attention to himself at the moment,” said Sirius. “It would be dangerous for him. His comeback didn’t come off quite the way he wanted it to, you see. He messed it up.”

    “Or rather, you messed it up for him,” said Lupin with a satisfied smile.

    “How?” Harry asked perplexedly.

    “You weren’t supposed to survive!” said Sirius.

    “Nobody apart from his Death Eaters was supposed to know he’d come back. But you survived to bear witness.”

    The idea that Voldemort wouldn't venture into public, guarded places is reiterated in Chapter Thirty-Five:

    “Get it himself?” shrieked Bellatrix on a cackle of mad laughter. “The Dark Lord, walk into the Ministry of Magic, when they are so sweetly ignoring his return? The Dark Lord, reveal himself to the Aurors, when at the moment they are wasting their time on my dear cousin?”

    Additionally, at this point Voldemort wasn't really ready to confront Harry yet, as he still needed to hear the prophecy.

  • Half-Blood Prince – Voldemort had no particular need to enter Hogwarts. He had Malfoy assigned to kill Dumbledore, with Snape as a back-up. He could be pretty confident that Dumbledore would be dead soon, without him having to do anything. Venturing into Hogwarts would only have been an opportunity to get caught.

Additionally, Voldemort was always supposedly afraid of Dumbledore, which would add to his reluctance to enter Hogwarts. For instance, as Harry tells Slughorn in Chapter Four of Half-Blood Prince:

"I reckon the staff are safer than most people while Dumble-dore's headmaster; he's supposed to be the only one Voldemort ever feared, isn't he?" Harry went on.

And Slughorn more or less agreed:

Yes, it is true that He-Who-Must-Not-Be-Named has never sought a fight with Dumbledore," he muttered grudgingly.

Or as Ron said in Chapter Eleven of Half-Blood Prince:

"But Hogwarts is safer than their homes, bound to be! We've got Aurors, and all those extra protective spells, and we've got Dumbledore!"

Or has Hagrid said in Chapter Four of Philosopher's Stone:

One o' the only safe places left was Hogwarts. Reckon Dumbledore's the only one You-Know-Who was afraid of. Didn't dare try takin' the school, not jus' then, anyway.

So in conclusion we could say that Voldemort perhaps could have entered Hogwarts via portkey if he really wanted to, but he simply didn't consider it a purposeful endeavor.

1

The imposter Moody (Barty Crouch Jr.) also made a portkey to leave Hogwarts in book 4 so perhaps only the headmaster can make portkeys to enter Hogwarts, but a sufficiently powerful wizard could make a portkey to leave it?

  • Although it might be argued that a portkey can be made to enter by someone else since the portkey made by Barty returned to Hogwarts. Of course it might be implicit in that he didn't specify it isn't to return. Or then again maybe not if it's a loophole. I'd see it as a loophole but of course it's a loophole which saved Harry's life. Funny how things like that work... – Pryftan Dec 10 '17 at 18:00
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"Being the headmaster has its privileges". Dumbledore knew perfectly well how to undo some of the protections of the castle, and you can see this when he does it for the apparition lessons at the Great Hall or when he "enters at speed" with Harry from Hogsmeade.

The protective enchantments may have something personal, so only the headmaster would know how to deal with them. It's likely Dumbledore shared some of this knowledge with McGonagall and Snape, separately, but it is unlikely Snape shared this with Voldemort, so basically he had no way of knowing what to do to be able to get into Hogwarts, other than use a traditional, "legal" method, and that's why he couldn't just make a portkey.

Also, Dumbledore could make a portkey and undo the enchantments even if he wasn't at Hogwarts. Physical presence is not always a requirement for magic. For example, Mrs. Weasley's clock detects the presence and state of all the family members, and the Marauder's Map is used by Harry several times while he's in hiding (to see Ginny and others), far from the school.

As a side note, I always thought Fred and George secretly contacted Dumbledore so he could let them fly away when they escaped from Umbridge. Dumbledore, despite being busy hiding from the Ministry and working for the Order, must have accepted--probably cheerfully--this request and done something from a distance. Otherwise, their escape would be inconsistent with later events related to security.

  • Not sure about the Fred & George escape... The only time that it was mentioned that you couldn't fly into or out of Hogwarts on brooms was in HBP when additional protections were in force. – AlasdairCM Feb 21 '12 at 9:14
  • Maybe, but if there were protections before (like anti-apparition), there could have been protections so people could not fly to the grounds, in which case Fred and George must have done something. Since this is not mentioned in the books, it is just a personal interpretation, which, I must say, makes certain aspects of the story more enjoyable. – Janoma Feb 21 '12 at 13:06
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    In the first book, one of the elder Weasley brothers flies into the grounds to pick up the baby dragon. You're right that it's not specifically mentioned anywhere else. – AlasdairCM Feb 21 '12 at 13:43
  • Now that you mention Charlie and Norbert(a), we have to add that Sirius flies Buckbeack from Flitwick's office, Madame Maxime's huge carriage flies in and out of the grounds and six DA members fly thestrals from the Forbidden Forest to London, so it is possible that flying was actually allowed before HBP. – Janoma Feb 21 '12 at 14:59
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    Harry and Ron also fly into Hogwarts using a certain flying car. – Brendan Long Jun 25 '14 at 16:23

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