On the night of Sessions' disappearance, she told her roommate that she was going out alone for a power walk. Between 4:00 and 5:00 in the afternoon, she left her apartment on SW 35th Place. Sessions left her wallet, identification, and keys in her apartment. Sessions was wearing a white pullover sweatshirt with long sleeves and grey horizontal striping with "Aspen" printed on the front of the shirt's collar, red sweatpants, and tennis shoes. She was also wearing a two-tone silver and gold women's Rolex wrist watch and was carrying a black Sony Walkman. After five hours, when Sessions had still not returned, her roommate alerted Sessions' mother that her daughter was missing. The police did not initially handle the disappearance as a crime because a crime scene had not been found. There was no sign that Sessions had left her apartment's parking lot, nor were there any signs of a struggle. People who were in the area of Sessions' disappearance have stated that someone fitting Sessions' description was seen speaking to individuals sitting inside a vehicle. Eyewitnesses were uncertain as to whether the woman entered the vehicle, and authorities have never confirmed that the individual in question was Sessions.
Investigation
Michael Christopher Knickerbocker was considered to be a suspect involved in the disappearance of Sessions. While Knickerbocker was in prison serving five consecutive life sentences, he reportedly told his fellow inmates that he had murdered Sessions. He also said that he had chained Sessions to a tree, and discarded her body close to Fort Myers in the Caloosahatchee River, but because Knickerbocker was not living in Gainesville at the time of Sessions' disappearance, the feasibility of his involvement has been questioned. , police believed that now-deceased and convicted serial-killer Paul Eugene Rowles was responsible for Sessions' disappearance and murder. At the time that Sessions had disappeared, Rowles was working for a construction-related company near the path where Sessions had last been seen. Rowles also did not show up for work on the day that Sessions went missing. Rowles had kept an address book with information on the people he had murdered. For example, the book listed Linda Fida, known to be one of his victims, as the first woman that he had killed, and may also contain a cryptic reference to Elizabeth Foster. Notably the book contained a notation "#2 2/9/89 #2", which is believed by investigators to refer to Sessions' date of disappearance, and to identify her as Rowles' second victim. Sessions has been excluded from 150 unidentified decedents in the United States.
Finding Tiffany Sessions projects and aftermath
The FBI have said the search to find Sessions is the largest in Florida's history. Public efforts to find Sessions include the Charley Project, and the Tiffany Sessions Facebook Project Page. The Sessions family are offering a $25,000 reward for any information in the case. They have worked closely with the Alachua County Sheriff's Department and the Florida Department of Law Enforcement to find the remains of Tiffany or convict any suspects involved in this case. In 2013 a detective named Keven Allen said that he had made finding Sessions his number one case. As well, Tiffany's mother Hillary has written a book about her missing daughter called Where's My Tiffany?, that describes her joy of raising Tiffany, and her heartbreak about losing her.
