She is first seen in Entry 27, passes by Jay, walking in the other direction, while he is exiting the hotel.
She asks Jay what does he have on his chest (refering to the chest camera) in Entry 28. We learn her name, and she states that Jay's name sounds familiar but she can't remeber from where. Jay's camera picks up strange noises coming from her room at night.
In Entry 30, Jay and Jessica talk again. His camera has strage distortion arround her. She says she's in a hotel because she got kicked out. Later at night, Jay hears strange noises from next door again, and knocks her door. She opens the door, seemingly sleepy, and says she doesn't know what Jay is talking about.
During Entry 31, Jay knocks her door to ask her about local parks. She seems to be in a bad mood, which is inconcistent with her easy going personality she seemed to have in the previous entries. She calls out Jay's inconcistent story for being in a hotel room.
In Entry 32, she's the one who comes to talk to Jay. She is visibly upset, notes again Jay's constant change of excuse to be in the hotel, and demands for explanations. Jay tells her he will explain everything, but he needs time to get it all straight in his head. She agreeds to return to her room, seemingly calmed, and Jay tells her to leave the door open.
Entry 33 takes place inmediatly after the previous entry. Jay goes to her room, only to find it empty. Masky's appearence shortly after makes some people believe he has something to do with her dissapearance; either way, her fate is unknown. This is the last time she has been seen, the next appearances being chronologicaly before this one.
Entry 44 Alex calls her and leaves her a message saying to "disregard his last message because he got in touch with Amy". This proves to be some relation between Amy and Jessica, and it's safe to assume this is the same Jessica of the hotel because Jay also thinks this.
In Entry 47, we learn that Jay got Jessica's number from Alex. Later, Jay calls her, and she says that Alex told her he had found Amy. Jay tells her not to trust him, not to answer her phone if he called her again, and that they will talk again. In hindsight, Jay realizes it's his fault that Jessica got involved in the first place.
During Entry 50, after Alex's and Jay's walk in the woods, the former says to bring Jessica next time, which leads to the events of Entry 52: Jessica and Jay follow Alex through the forest, she without really understand why or what is happening, he with suspition towards Alex's purposes (even telling her to stay behind him in case of anything happened). Alex lures them to a cabin in the middle of the woods, in which he shouts at Jay and points at them with a gun, visibly shaken. Masky appears from behind Alex, without him noticing, and attacks him. During the struggle, Jay and Jessica get away. They arrange to meet in a hotel, which obviously is the hotel from entries 27-33. They get two rooms, next to the other. That night, Jay wakes up to the screams of Jessica. Runs to her door, and knocks on the door while shouting her to open. The Operator appears, and seemingly Jay attacks him, or it sucks Jay towards him. Jay appears on the floor, inconcious. Jessica's screams are no longer heard. The clip ends and Jay assumes that Entry 27 was the next morning. This entry confirms Jessica as Amy's roommate.
During Entry 76 we see Jessica again as the Masked Man, followed by the Hooded Man, carries her in to Rosswood Park forest. There she encounters both Alex and the Operator. The Operator takes her away. This entry is speculated to take place around Entry 33 and it is argued whether she has passed on or not.
Her fate in Entry 86 is described by Alex as dead. But in Entry 87 she is shown to be alive and well.