A thread on the Orthodox doctrine of the so-called Aerial Tollhouses. I encourage you to read it if you are on the fence about the doctrine.

This thread originally by Render. Posting here in case he decides to leave.
This will be an attempt to EXPLAIN this doctrine, because its opponents often try to strawman it into something that sounds utterly absurd and easily dismissable to those who have not researched the issue in depth.
What the doctrine teaches is that when you die, angels appear to take your soul to heaven, while demons appear trying to drag your soul to hell. The demons accuse you of your sins as part of this process, while the angels defend you (see the below icon for an example).
This process generally occurs while the angels are trying to help you ascend to heaven, though very holy men ascend almost instantly, with few demons attacking them, while wicked men are simply immediately dragged to hell.
Please note that the demons are not “judging your souls in place of God” in the doctrine, as many people think. God is the only judge and Final Judge.
It’s very clear (as you will see below) that the demons merely take the role of a prosecutor, accusing your soul of sins, while the angels are your defender. But in the end, God alone is the impartial judge who decides your salvation.
This is the core of the doctrine. Anything else is merely an attempt to use figurative language to explain this doctrine. There are not literally custom booths in the sky where you have to pay a literal toll to demons to pass.
Even the tale of Theodora’s journey through the tollhouses, a roughly 10th century text, which is the source from which much of the language of tolls and custom houses is most used, makes it very clear that it is using figurative language...
...to describe what can only be understood spiritually. (Source: http://orthodoxinfo.com/death/theodora.aspx )
Metropolitan Hierotheos of Nafpaktos, a very highly regarded theologian-bishop in Greece, writes about this far better than I can at: http://orthodoxinfo.com/death/soul_taxing.aspx

The whole article is worth reading, but his conclusion sums it up.
This book is absolutely filled with citations on the tollhouses from Scripture, Church Fathers, liturgical services, contemporary saints, etc. It was endorsed by numerous bishops and prominent theologians in America...
...including the heads of the Antiochan, Russian, and Romanian Archdioceses of America and the former head of the OCA. I HIGHLY encourage you to read it if you truly want to understand the massive amount of historical support the doctrine has in Orthodoxy.
I cannot hope to provide even 1% of the citations St. Anthony’s provided on this subject, but I’m going to provide at least a few of them below to show that the tollhouses are not some sort of "gnosticism,” but have instead been a prominent view since ancient times.
I cannot hope to provide even 1% of the citations St. Anthony’s provided on this subject, but I’m going to provide at least a few of them below to show that the tollhouses are not some sort of "gnosticism,” but have instead been a prominent view since ancient times.
The idea that demons try to seize our souls when we die was present in the early Church. St. Justin Martyr wrote, around 160 AD, of this (source: https://www.newadvent.org/fathers/01287.htm)
But the very first clear depiction of the journey the soul takes through the air, and the role of the angels and demons in this process, can be found in the “Life of St. Anthony” by St. Athanasius the Great, written in the early 300s (source: https://www.newadvent.org/fathers/2811.htm)
As you can see from this source, St. Anthony and St. Athanasius very clearly taught that the demons try to hinder our ascension into heaven when we die by accusing us of sins. But if we have confessed and repented, we have nothing to fear from them.
But if we are sinful, the demons will successfully block our ascension, and drag us into hell.
Here is an example of this belief found in the writings of Saint John Chrysostom (From the late 300s or early 400s). As you can see, Saint John believed that angels would guide our souls to heaven, but...
...the “dreadful powers” of the demons would also try to demand our souls (source: http://www.tertullian.org/fathers/chrysostom_four_discourses_02_discourse2.htm)
Likewise, St. Cyril of Alexandria (early 400s) believed that Satan is owed a “debt” by us if we are sinful (hence the “toll” metaphor), and we must pay it off in this life by repenting (source: http://www.tertullian.org/fathers/cyril_on_luke_09_sermons_89_98.htm)
Here is an tale from the early days of the Church that expressly uses the language of “tollhouses” to describe the process of our ascension into heaven and accusation by the demons. Source is the “Prologue of Ohrid” compiled by St. Nikolai Velimirovich.
Here is a clear explanation of the doctrine of the tollhouses that can be found in the famous and universally renowned “Sayings of the Desert Fathers,” compiled sometime in the 400s.
And here is an example of a monk who, even before he died, was confronted by the demons accusing him of his sins. This can be found in the Seventh Step of the Ladder of Divine Ascent...
...an early 7th century text that is the most renowned monastic guide ever written in the history of the Church (source: http://www.prudencetrue.com/images/TheLadderofDivineAscent.pdf)
Here is an explanation of the doctrine found in the famous “Precious Pearl” traditionally thought a work of St. John of Damascus, though some scholars date it to the 11th century. Either way, it’s very old (source: https://archive.org/details/stjohndamasceneb00wood/page/199)
Here is a tale of a monk who died, saw the process of the soul ascending into heaven and being accused by the demons before being returned to life to tell the living of what happens to the soul after death.
Just as St. Bede, above, wrote of this, so too did St. Boniface, Apostle to the Germans, showing that this doctrine is not unique to the East, but also once existed in the Orthodox West (source: https://archive.org/details/cihm_84747/page/n102.)
Another Western source on this is the “Life of St. Columba,” a famous 6th century Western saint (source: https://sourcebooks.fordham.edu/basis/columba-e.asp).
Beyond the Church Fathers and lives of the saints, the doctrine of the tollhouses can be found in many of the liturgical services of the Church, such as one of the versions of the service of Compline (source: https://goarch.org/-/the-akathist-hymn-and-small-compline).
Probably the service that makes it most explicit is the “Prayer at the Departure of the Soul,” a monastic service performed immediately after a monk dies (source: https://archive.org/details/ServiceBookOfHolyOrthodoxChurchByHapgood/page/n397).
Likewise, many contemporary saints firmly believed in the doctrine. Here are quotes from two famous 19th century Russian saints, including the famous quote from St. Theophan the Recluse that...
“No matter how absurd the idea of toll-houses may seem to our ‘wise men’, they will not escape passing through them.”
Likewise, St. John of Shanghai and San Francisco, one of the most famous 20th century Orthodox saints, was an open and ardent proponent of the doctrine (he was the one who taught it to Fr. Seraphim Rose, in fact). Source is https://orthodox.net/articles/life-after-death-john-maximovitch.html.
St. Paisios, an incredibly famous late 20th century elder of Mt. Athos, also taught the doctrine (source: https://johnsanidopoulos.com/2017/01/saint-paisios-athonite-on-toll-houses.html).
Another mention found of demons leading a soul to hell after a person died and was judged by God. Source is St. Pope Gregory the Great's "Dialogues" c. 600 AD ( http://tertullian.org/fathers/gregory_01_dialogues_book1.htm#C12):
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