Something i feel like doesn't get touched upon: Henry is aware he's a fictional character. This was confirmed by Dogman himself on several occasions.
But there's a catch: Unlike other self-aware characters, Henry actively hides this from the player, as he knows we would try to stop him.
He makes it sound like his 'ultimate goal' is removing the shackles of mortality from humankind to foul the player, who doesn't know he's self-aware and could fully buy it. But that's not his end goal.
Major hints towards this:
"Once enough souls are collected, i will have a substantial number of souls to produce the machine that i have hoped to build from day one. A machine that can sucessfully take an adult male from our realm to another, and back again. Soon, i aim to no longer be in this realm at all." - Tape 5 (JOY4)
Henry talks about gathering souls to build a machine to escape Dayshift at Freddy's, however he words his goals in such a way that you could interpret "ascending to another realm" as him surpassing his own mortality, but that's actually just a small step on his plan: First, he finds a way to become immortal so that he has unlimited time living, THEN he starts researching ways to enter the real world (in this case, through a machine).
DSAF 3 Legacy ending - through the entire route, Henry slowly strips away the player's control over Jack. The explanation for this is that Miller has a passive aura (his influence, HIS LEGACY) that can corrupt people all while he's still in the void, which you can with see with Legacy Jack:
In dsaf 1, Dave convinces him to join him. At this point Jack just wants to mess around with him while having some fun to boot. He's like "Yeah we can do that, why not". He's not evil (yet), he just wants to goof around.
In dsaf 2, Henry's influence starts seeping in: Legacy gets more and more malicious as the route goes on BUT there's still a small fragment of his humanity in him: Dave mentions that Jack looks genuinely sad after Peter's speech, showing that it affected him and maybe even led him to reflect on his actions, showing that Legacy isn't an near emotionless monster (...yet...).
By the end of Dsaf 3, Miller's influence has degraded Jack to merely a vessel, with no free-will nor conscience (we, the player, are Jack's conscience since he doesn't have a soul. Gonna elaborate more on that in a minute); He straight up BLOCKS US from choosing a dialogue option that could ruin his plans; At this point, Henry has more control over the player character than we do, and that leads up to the most symbolical moment of Henry's self awareness:
At the end of the route, once Henry has full control of Jacktrap, the first thing he does is cut ALL contact with the player and make himself untraceable. He does this by crashing the game and deleting the save file, but he's still somewhere in your device, secretly researching a way out through his vessel while you are literally unable to find him. We can't find or control Jack, they're both just... Gone.
Worth mentioning that hes also immortal so he has all the time in the world to accomplish his goal and no oposition. HE WON.
This poster that can appear on the Flipside.
"This universe is critically misunderstood" - tape 1 (JOY1)
Aware that the universe doesn't restrict itself solely to the game.
"My influence... the culmination of my being... I leaked into your world. Go ahead, let me DIE. I'll be back. I always COME BACK!" - DSAF 3 Good Ending
"your world" refers to irl, he's saying that the evil that exists and can harm real people is part of him.
After someone asked on reddit about what happens after the Dsaf 3 Evil ending, Dogman himself replied "Henry probably does some DDLC type-shit and tries to become real" (i couldn't find the comment itself but i swear it was real i'm not going insane).
Henry would NEVER directly aknowledge us as that would give himself away; he knows we are seeing every single one of his moments, hearing every single conversation, so he leaves a red herring (making it seem like his ultimate goal is immortality) to throw us off.
He sees us as this looming threat to his plans that is always there and must not be undestimated, not even when things are under his control.
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