As a WMG subpage, all spoilers are unmarked as per policy. You Have Been Warned.
The Games
The trilogy happens After the End
The lush scenery in the first game has an abandoned nature to it, especially the city. Then there are the anteater-like creatures and the warring race isolated in the cave in Nevermore 3. "The Learning" and "Sentient 6" are connected somehow
"The Learning" is about a computer that achieves consciousness, and begins attempting to emulate human behavior (or as it calls them, "flesh machines"). By the end, it begins to enact a sequence, which will eradicate humanity. "Sentient 6" is about a prototype of a sentient computer, which longs to become more than a machine (the lyrics implying that the machine wants to learn to dream, just like the machine in "The Learning" learned), and when it fails at that, it activates a sequence to eradicate humanity... Unless Nevermore wanted to write songs about two separate machines that both become conscious and decide to eradicate humanity, it seems a little too obvious that those two songs are connected. For added effect, they even played "The Learning" followed immediately by "Sentient 6" on the Year Of The Voyager album.The Webcomic
Ada was a peasant/servant when she was alive
This is a fairly popular theory, with a decent amount of evidence.- Ada acts Wicked Pretentious, including mispronouncing "fancy" words and calling herself a lady while acting like a whiny brat.
- Her chosen last meal when she was alive would have been caviar, a famously expensive delicacy. When she actually tries to eat it, she finds that she absolutely loathes caviar, leading Prospero to question why she would want caviar if she'd never eaten it.
- She attaches herself to people she sees as fancy or posh like Annabel and Prospero, always putting herself in a subservient role.
- Ada's literary namesake (from "Tamerlane") is a peasant girl.
How Ada will find her Spectre
A flashback will reveal Ada, like her Tamerlane counterpart, was a peasant desired by a man of higher birth. Specifically, she was a servant in a Secret Relationship with the nobleman she worked for. Ada was enamoured with her lover's promises to marry her, but always suffered insecurities that she was too lowly to be more than a dirty little secret. She died believing the nobleman had been stringing her along from the start, only for the flashback to reveal the truth: Her lover professed the depth of his feelings as she passed. The epiphany that she was loved, and for just who she was, is the confidence boost Ada needs to unleash her Spectre.- Jossed. Her flashback right before she unlocks her Spectre shows her being absolutely heartbroken at her lover giving her a fatal axe wound to the chest, where he told her she "made things complicated." Her Spectre is unlocked by Prospero rejecting her.
Lenore pulled a Sweet Polly Oliver in order to marry Annabel Lee
When Montressor and Lenore go into her memories, they see past Lenore cut her hair short before setting her room on fire. According to this theory, Lenore was Faking the Dead in order to reintroduce herself in a male persona and offer herself as a suitor to Annabel.- Confirmed. She pretends to be her own cousin, "Leo" Vandernacht.
The Deans came from a Literal Split Personality
Specifically, Merry and Mourn are the optimistic and pessimistic sides of one person. Possible reasons for the split are the original voluntarily split himself in two to better tag team the students, or a yet-to-be-seen Greater-Scope Villain forcibly caused the split to trap him in the academy.The Deans originate from The Tell-Tale Heart
Their creepy white eyes invoke the Old Man's "Evil Eye" from the story.Pluto isn't a real person
He's a cat who wished to become human. This is why his Spectre is a mix of feral beast and domesticated pet.Ada's Spectre will be based on The Fair Folk
Plenty of folklore depicts fairies as souls of the dead, not that Spectres are limited to standard ghosts. Ada could level up from petty mind games to effectively messing with her enemies with fairy-themed powers.- Confirmed, she's a banshee.
The Raven is Theo
Like his sister, he tried to circumvent the one second chance per class rule. He failed, and the penalty was to lose his human form and memories.Lenore and Annabel Lee died in a Murder-Suicide
Driven to desperation by her impending wedding, Annabel killed Lenore and herself to escape. This will cause their relationship to fracture once Lenore remembers. Alternatively, Annabel was about to go through with it before Lenore talked her down, only for a surprise third party to murder them.Annabel's killer was the man her father chose to marry her
He caught her planning to run away with Lenore, or maybe just talking about her, and killed her in a fit of rage.The academy staff are enchanted dolls
As Poppet and Dolly's names imply. The broken doll found in the off-limits wing is the missing maid.