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[[Azazel]] was able to move freely between Hell and Earth, and [[Alastair]] appeared to be able too, as well as [[Crowley]]. [[Castiel]], and other [[angels]] have been able to enter and return, though at a cost as entering Hell for angels can be very dangerous.
In the rare instance that a human [[soul]] is able to escape from Hell, unless there is divine intervention, a damned soul cannot gain entry into [[Heaven]]. There have been only three known exceptions to the rule: [[Dean Winchester]], who was sent to Hell after his [[crossroads]] [[deal]] came up, but upon being killed by the [[hunter]] duo of [[Walt and Roy]], Dean was allowed entry into Heaven in order for the angel [[Joshua]] to pass along a message from [[God]] to the Winchesters. After [[Bobby Singer]] was killed by the [[Leviathan]] [[Dick Roman]], Crowley ensured through the use of the rogue [[reaper]] [[Ajay]], that Bobby would end up in Hell. Bobby was later rescued by [[Sam Winchester]] for the second [[trial]] to close to Gates of Hell, which required that "An innocent soul has to be rescued from Hell and delivered unto Heaven", which allowed Bobby entry
into Heaven. For years it was unknown what became of [[John Winchester]] after his escape from Hell, after the second death of [[Mary Winchester]], [[Castiel]] confirmed that John was in Heaven with Mary, telling Sam and Dean that Mary was with "John, and there's no sorrow. There's no guilt. Just joy."
As Sam attempted to contact Lucifer without opening the Cage, harrowing Hell with Crowley and Rowena, Rowena was able to perform a ritual from to ''[[Book of the Damned]]'' to pull Lucifer's essence from the Cage without opening it, summoning him into a warded holding cell in Limbo.
After God opens every door in Hell, the Cage is opened as well,
potentially allowing Michael to escape.
[[File:DamnedSoulsReleased.png|thumb|right|350px|[[Chuck]] unleashes damned [[soul]]s from Hell.]]
After [[Chuck]] declared it "the End" of Sam and Dean's story, he opens a crack in the earth unleashing the souls of the damned onto earth. The demon [[Belphegor]]
revels to Dean that while in Hell, every single door "sprang open all at once", the sky cracked and all the souls, an estimated 2-3 billion escaped to earth. God released all of the souls and demons by opening [[Portal|the Rupture]], a giant tear in the ground of a cemetery in Harlan, Kansas leading into Hell itself. The Rupture was later closed by Rowena, Sam and Dean with the ''Sanetur Acre Vulnus'' spell and Rowena sacrificed herself to send all of the souls and demons back.
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*[https://monicawoe.livejournal.com/24710.html 6x14 - thoughts about Helltime] by monicawoe (February 2011); [http://archive.today/2Bv7K archive link]*[https://samwinchestermeta.tumblr.com/post/130287109257/thornshrike-an-exercise-in-time-dilation An exercise in time dilation mathematics] by joonchi; thornshrike (November 2012); [https://web.archive.org/web/20171104084848/https://samwinchestermeta.tumblr.com/post/130287109257/thornshrike-an-exercise-in-time-dilation archive link]*[https://outpastthemoat.tumblr.com/post/39930485602 “That's efficiency:” A few thoughts on Crowley’s hell] by outpastthemoat (January 2013); [https://web.archive.org/web/20181205030956/http://outpastthemoat.tumblr.com/post/39930485602 archive link]*[https://spnmetaarchive-blog.tumblr.com/post/54813303566/we-get-the-hell-we-think-we-deserve We get the Hell we think we deserve] by nerdinessboundaries (April 2013); [http://archive.today/dHDGe archive link]*[https://fandomdebunker.tumblr.com/post/63573255978/ive-heard-people-say-that-sam-was-in-the-cage-for Ask: I’ve heard people say that Sam was in the cage for around 180 to 200 years. Can you tell me how accurate that is and then show me the math on that?] by fandomdebunker (October 2013); [https://web.archive.org/web/20150418055048/https://fandomdebunker.tumblr.com/post/63573255978/ive-heard-people-say-that-sam-was-in-the-cage-for archive link]*[https://larinah.tumblr.com/post/72881333749/sams-hell-is-reminiscent-of-how-mary-and-jess Four Hells - Sam’s, Dean’s, Crowley’s show for Cas, Bobby’s] by larinah (January 2014); [http://archive.today/eBfML archive link]*[https://semirahrose.tumblr.com/post/122755748633/i-accidentally-crushed-my-soul Short and Cruel Reflection on Cage!time vs. Earth!time] by semirahrose (June 2015); [https://web.archive.org/web/20200405023158/https://semirahrose.tumblr.com/post/122755748633/i-accidentally-crushed-my-soul archive link]*[https://ameliacareful.tumblr.com/post/131113536362/sam-dean-the-cage-and-memory Sam, Dean, The Cage, and Memory] by ameliacareful (October 2015); [https://web.archive.org/web/20200201230755/https://ameliacareful.tumblr.com/post/131113536362/sam-dean-the-cage-and-memory archive link]*[https://semirahrose.tumblr.com/post/173467717313/sam-was-tortured-for-around-200-years-at-least “...even ''if'' Sam’s estimation of his experience of Hell isn’t right and we just go with Dean’s, Sam was tortured in the Cage more than five times as long as he has been alive” (Untitled)] by semirahrose (April 2018); [https://web.archive.org/web/20200407011014/https://semirahrose.tumblr.com/post/173467717313/sam-was-tortured-for-around-200-years-at-least archive link]