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Insanity.exe opens up with a gameplay where the player controls Tails in an aircraft and avoid the walls as platforms. If the player fails, an image of Tails.exe appears along with a loud scream from The Maze. The player can continue again. If the player progresses enough, Tails will meet an evil clone of himself, Tails.exe, and an image of Tails.exe appears. Then, Insanity.exe delves into the aftermath of the previous two games, where Sonic is depicted as selfish and harmful, believing that anyone who crosses his path deserves suffering from his wrath. As a consequence of his actions, Sonic's fate becomes sealed by his own self-centered nature, leading him to become isolated from his friends, especially his close companion Tails. Throughout the game, Tails seeks to fix Sonic's wrongdoings. However, in the end, Sonic's deep-rooted fear ends up betraying him. The presentation ends with "But the story hasn't ended there."

The game starts in Final Hope, designated as Act 9, where the player assumes control of Sonic in a desolate and monochromatic world. Movement is executed using the arrow keys, while jumping and sprinting are executed with the X and shift keys, respectively—an ironic choice considering these controls are used in those of previous games. At the game's outset, a message appears, expressing Sonic's sense of familiarity with the surroundings and is driven to find a means of escape from this eerie place.

Throughout the world, the player encounters simple obstacles such as platforms that collapse upon touch, leading to spikes. Soon, Robotnik makes an appearance, reminding Sonic that they are being pursued by Zalgo, who has taken control of Tails' body. It is revealed that the Tails they are facing is, in fact, a clone, while the real Tails remains elsewhere. As the game progresses, Sonic eventually falls from the terrain and is met by the malevolent version of Tails, impeding his path.

Continuing onward, the player encounters a text that reads "You Can't Run," accompanied by visible static on the screen and images of the evil Tails, along with eerie laughter. Upon reaching Tails, contact is interrupted by a black screen, which then transitions to another screen similar to that of BEN Drowned creepypasta. The screen features a blue dot with text declaring, "So.. now you know my true identity. You're on my world now... I am the Hivemind..."

After the screen ends, the gameplay resumes with Sonic appearing in a level characterized by glitchy blocks and rings. Upon reaching the midway point, a sudden interruption occurs, cutting to a frame where Tails emerges behind the player. Simultaneously, loud white noises accompany Tails' unsettling message: "Having fun, [DESKTOP NAME]? I hope so. I hope you enjoyed watching all those sealed fates. You know what was going to happen to them, although you did more than just watch. You took control of them. Led them to me. You are as responsible for their deaths as I am [DESKTOP NAME]."

Continuing the gameplay, the player eventually reaches a dead end, with a conspicuous hole that appears. If the player falls into this hole, the perspective shifts to another character, Tails. Tails spawns in the same bloodied terrain and reflects on the events, stating, "Eggman used my body to summon that devil." As Tails continues running, mysterious GameMaker texts manifest, including Sonic saying "cough W-What are you?" and unnamed figure proclaiming: "I AM GOD" and "YOUR SOUL IS MINE."

Tails assumes Sonic is in danger and catches up to find both a clone of Tails and Sonic standing behind a wall of spikes. The player must make a choice on which figure to push through the spikes, trying to discern the identity of the unnamed figure. If the player chooses to push Tails towards the spikes, Sonic will express gratitude, saying, "I'm glad you got rid of that insolent fool, friend." Tails, puzzled by Sonic's altered demeanor, questions, "Hmm... I guess... why are you talking like that, Sonic?" To which Sonic responds nonchalantly, "Oh.. It's nothing..." and then suggests, "Let's just get out of this creepy place, shall we?" Tails agrees, saying, "Yeah, right." Following Tails' remark, a brief scene cuts in where Sonic's eyes open to reveal black eyes and red pupils, suggesting that Zalgo may be controlling Sonic's clone. An interruption occurs, displaying the image of Sonic.exe, and simultaneously, another image automatically opens in the browser, leading to the application closing. The browser then proceeds to install a copy of MY5TCrimson's version of Sonic.exe.

If the player chooses to push Sonic through the spikes, a momentary freeze occurs, and a black screen reminiscent of the BEN Drowned creepypasta appears. The screen displays the text, "You shouldn't have done that. Don't like playing by the rules?" Followed by an image of Sonic.exe grinning with the text "DIE NOW!" After this interruption, the gameplay shifts to a style similar to that of Sunshine.exe. Now, the player controls both Tails and Sonic, who must run forward to escape the approaching darkness. Along the way, they must navigate through various obstacles, utilize springs for jumping, and collect gray rings. The level includes traps in the form of high walls, chasms, and collapsing platforms. In the background, a flashing image of Tails.exe appears with the text "I AM GOD," accompanied by the music used in the end of Nec1's version of the Suicide Mouse creepypasta. Additionally, there is Portuguese text that reads "MANO CADURIK ESTEVE AQUI, HUEHUE BR!" which translates to "MANO CADURIK WAS HERE HUEHUE BR!" An easter egg can also be found, where Suicide Mouse stands idle below the platform at the start of the level.

If either of the characters falls or gets caught up by the darkness, an image of Tails.exe, particularly the one used in the start of the gameplay, appears with a loud scream used in The Maze. Towards the very end, the playable characters will encounter Doctor Ivo "Eggman" Robotnik. A brief dialogue takes place, during which the Exe version of Tails, who is revealed to be Tails Doll inside, makes an appearance. Soon after, Sonic and Tails leave, leaving Robotnik alone with the doll. Robotnik ponders, "What can I do with this doll to get rid of Sonic? I'll just take it and see what I can do." The game concludes with a "THE END" screen, featuring a glowing red Tails Doll. A question mark then appears on the "THE END" text, and the game closes.