The first Azkaban Breakout happened in 1982, when Barty Crouch Junior and his dying mother were switched by his father and House Elf. While this escape went unnoticed for several years, it ended in tragedy for all involved. However, this cannot be called a Perfect Breakout because a prisoner still remained in Azkaban. Even worse, a guilty prisoner had been replaced by an innocent one.
The second Azkaban Breakout happened in 1993, when Sirius Black - who was only guilty of the crime of underestimating the person who framed him - took advantage of his unregistered Animagus form and left the island. He almost died in the attempt, but survived. However, this was not a Perfect Breakout because his disappearance was immediately noticed and he was on the run for the rest of his life.
The third Azkaban Breakout happened in 1995, when Voldemort broke out a dozen of his Death Eater lackeys. As with Mr Black's case, this was not a Perfect Breakout as it was noticed.
The fourth Azkaban Breakout was planned in 1999. In prison - and by no means innocent of the murder he was accused of - was Harry Potter. Attempting to remove him were his friends and associates from the Order of the Phoenix. They faced far more obstacles than any previous breakout, for two reasons. First, far more security precautions, such as 24 hour monitoring and magical signature detection, had been put in place by the efficient Minister Scrimgeour. Second, they did not want the world to know that Harry had escaped.
In short, friends of Harry Potter wanted to pull off the Perfect Azkaban Breakout.
This would, of course, be impossible.
8 September 1999
It had been two weeks since Rufus Scrimgeour had been dubbed by the worldwide media as The-Minister-Who-Sent-The-Boy-Who-Lived-To-Azkaban. He was not amused. It was not supposed to have worked out like this.
Why had the boy used the Unforgivables to deal with Lucius Malfoy? Why couldn't he have simply blown the blonde bigot's head off with a strong Reducto, or Scourgified his brains out, or Accioed his heart, or Banished his kidneys? All nice Light OWL-level spells that a lawyer could justify to a sympathetic Wizengamot, especially if the defendant pretended to show remorse. After all, several members of that robust body were delighted to see the last of the man who bribed and blackmailed and controlled their votes.
But no - the Boy-Who-Didnt-Think had cast the killing curse.
That was Big Bad Dark Arts. Never mind the fact that Malfoy was well into the second word of the same curse when the green light from Potter's wand hit him. Never mind the fact that Malfoy had just cast Avada Kedavra on the two youngest children of a respectable Ministry employee, who happened to also be his girlfriend and best mate.
In a huge public trial, the Boy-Who-Lived had voluntarily provided Pensieve memories of the three murders and admitted to the third, both without and with Veritaserum. There was no trace of Imperius, and the boy could throw that off in any case. Polyjuice impersonation had also been ruled out. That he had killed Malfoy was in no doubt; the question was how much he should be punished for it.
Personally, Rufus felt Potter had done the Ministry and Wizarding World a favour by eliminating the elder Malfoy, and had wasted a golden opportunity to experiment with castration curses before killing the man. Potter seemed to have similar sentiments, stating that "if the price of killing a bastard like Lucius Malfoy is spending the rest of my life in a cell, then the only thing I regret is not doing so earlier. Then my friends would still be alive."
Press coverage of the trial had been a nightmare, with news agencies all over the world in attendance. The best coverage came, surprisingly or unsurprisingly, from a local magazine.
The Quibbler had been steadily changing and gathering readers in the months prior to the trial, but its coverage of the event was what made it known as a legitimate news source.
Scrimgeour was a long time Quibbler reader. His name was not on the list of subscribers, however. Instead, a drinking buddy of his bought two copies, and sent him one. This friend, a respectable and well-travelled businessman who owned a couple of stores in Knockturn Alley, marked each article in Rufus' copy with a lucid comment that told him how to read the article. Comments included "true" or "I think this is false" or "ignore this" or "you don't need to know" or "you really don't want to know" or "Lovegood really is cuckoo about this" or, occasionally, "false".
Scrimgeour's favorite comment was "precisely false", which generally accompanied articles that said things like "Elves really are extinct and there is absolutely no truth to the rumour that they are living in peace in a different dimension".
The change in the Quibbler's style was coincidental with an event most upsetting to the Department of Mysteries. Their Number One potential recruit, who had been targeted since she was a sixth year, turned them down. Instead, Luna Lovegood took over her father's position as editor of the Quibbler. (He had then promptly embarked on a long-term expedition to find horned dinglebats and wailing whippersnappers in South America.) To the surprise of her former classmates, the odd Ravenclaw decided to take it mainstream and make it The paper of the young progressive elements of Magical Britain. This hugely expanded its subscriber base, particularly amongst those with Muggle connections and perspectives, and there was talk of making it a newspaper instead of a magazine.
Lovegood Junior had hired several columnists whose words would never decorate the pages of the Daily Prophet. One columnist was the "Newblood Witch", who used the words Oldblood and Newblood instead of Pureblood and Muggle-born. She revealed her actual name, in the interests of full disclosure (and credibility - though that cut both ways) after Malfoy's murder of her boyfriend and best female friend.
Hermione Granger's columns before the trials had pointed out several technicalities that, when combined, should have deemed Harry Potter subject to no jail time. Such as Malfoy's status as an escaped convict, the fact that the trial that put him in Azkaban in the first place should really have sentenced him to the Kiss instead of to a porous prison, the acceptability of using a spell on someone who has just used the same spell, and, most impressively, a long-forgotten law that allowed for family members to legally take revenge. Potter was argued to be family because he had - Gringotts confirmed it - been engaged to the youngest Weasley.
Fortunately for Scrimgeour, it had not required much politicking by his lackeys to persuade Wizengamot members not to let Potter off the hook completely.
The Newblood Witch's response to the three year sentence had been a column memorably entitled "The Law is a Flobberworm!"
After the sentence, Scrimgeour had visited Potter while the lad was in a Ministry holding cell awaiting transportation to Azkaban. There were well-buried and quite legitimate laws for the time honoured tradition of post-trial deal making. The boy was presented with the option of Go To Jail For Three Years or Cooperate With Us. The deal even included the option of being an honorary Auror, so that he could use Unforgivables in future.
However, Potter hadn't even considered the option of cooperation with the Ministry. The previous Minister's actions had completely alienated the boy, and Scrimgeour's own actions (bloody Shunpike!) had not helped. His advisors' understanding of the boy's psyche were off the mark completely, having been based on the now-known-to-be-ridiculous assumption that Mr Potter was a normal male teenager. The revised analysis, that he was a traumatized repressed angstsy attention-hating kid who hated bullies and had the Ministry only fractionally behind You-Know-Who on his List Of Big Bad Bullies, had come too late.
Oh well. At least Potter would be safe from Death Eaters and the like in Azkaban. Surely safer than he was currently - reports said that the boy had spent most of the two years since the demise of Albus Dumbledore disappearing on extended camping trips with his friends. With no adult supervisors, let alone Auror guards! Irresponsible brat.
Yes, it was a good thing he was under Ministry protection now.
Scrimgeour's Ministry had put in several measures to make sure that the prison was impenetrable. The additional measures were designed to stop all known previous escapes, and others they had thought of.
With the departure of the Dementors, the basic security measures - anti-Apparation, anti-Portkey and anti-House-Elf wards - had been strengthened.
Anti-Animagus wards were a different matter. They were clearly necessary - Shacklebolt had been spreading rumours that there was a rat animagus amongst the Death Eaters. (He claimed that it was Peter Pettigrew, but Scrimgeour would believe that when he saw it.) After all, recordings in the Department of Ministries when Potter and You-Know-Who had played Hide And Seek in the Department of Mysteries four years ago showed that Kingsley and Sirius were both members of Dumbledore's gang of elderly vigilantees.
However, the problem with anti-Animagus wards was that had not been invented yet. And probably never would be. Therefore, prisoners were tested every three months (every week in the case of allegedly powerful wizards like Potter) for Animagus ability. This would deal with unregistered Animagi, including people who somehow learnt the transformation while incarcerated. No cells had windows, and the ventilation and plumbing - in case any animagus form was small enough to escape through them - could be filled with paralysing gas at a moment's notice.
Each cell was monitored by remote Scrying - an excellent idea borrowed from Muggles - he had made a personal tour of Muggle prisons in London and Amsterdam under the guise of being part of a foreign delegation of Muggle crime enforcement officers. Potter's cell alone was always watched by at least two people in the remote scrying room at the Ministry, in addition to two guards at the door of his cell.
To prevent Polyjuice impersonation, particularly of the guards, all visitors to Azkaban had to drink a Potion that nullified the effects of any Polyjuice Potion they might have ingested.
The best new security measure was definitely magical signature detection. This was unique to each prisoner, so switches could not happen. All prisoners could be tracked, and if a signature disappeared from a cell for more than ten minutes, an alarm would sound.
There was absolutely no way to escape from Azkaban. Certainly not without everyone knowing about it.