<P> Following their reunion, Bobby explains Dick Roman's endgame for humanity; cure humanity of all its diseases before herding them as livestock for the Leviathans to feed on . In the midst of his explanation, the brothers receive an email from a dead Frank Devereaux, who informs them that his hard drive, in Roman's possession at his headquarters, is currently being cybernetically attacked and will lead to their new aliases and safe houses being compromised . While Bobby attempts to convince the Winchesters to send in his flask, the brothers are concerned his hatred for Roman will compromise the operation and leave him out . The hacker responsible of cracking Devereaux's hard drive, Charlene Bradbury, witnesses a Leviathan eating and cloning her boss and is quickly able to be recruited to help the brothers against the Leviathans . While the operation is successful--wiping the hard drive, hacking Roman's email account and intercepting an important package--Charlene is unable to escape the building in time . Bobby, having snuck his flask into her bag, cracks the doors and begins to attack the Leviathans, breaking Charlene's arm in the process, leading to a concerned discussion between the brothers as to Bobby's self - control . Bobby later returns after having to recharge for a while and describes himself as "stronger than ever ." Bobby becomes increasingly frustrated in "There Will Be Blood", which only feeds his fast - growing rage and turns him more into a vengeful spirit, culminating in his possession of a maid, whom he uses to go seek vengeance on Dick . In the seventh season finale, "Survival of the Fittest," Sam tries to stop him, but Bobby is no longer completely in control of himself and nearly strangles Sam to death . Realizing what he is doing, he regains control and leaves the maid's body . Now knowing the danger of him losing control again, Bobby requests that Sam and Dean burn his flask . They reluctantly do so, causing his ghost to disappear . </P> <P> Bobby next appears in eighth season episode "Taxi Driver," in which Sam and Dean learn from rogue Reaper Ajay that instead of going to Heaven when his flask was burned, Bobby was taken to Hell on Crowley's orders . Needing to rescue an innocent soul and release it into Heaven to complete the second trial to close the Gates of Hell, Sam travels into Hell and finds Bobby who initially believes he is a demon as he is being tormented by demons pretending to be Sam and Dean all the time, but Sam convinces him with personal information only he and Dean know . The two escape into Purgatory, but find the Reaper that Ajay is missing (having been questioned and killed by Crowley). With the help of Dean's vampiric friend Benny, Sam returns to Earth with Bobby's soul, but when Bobby goes to ascend to Heaven, he is trapped by Crowley, who wants to take him back to Hell to punish him for the "damage" he has done to demons in his hunting career . However, the angel Naomi intervenes, drives Crowley off, and allows Bobby to ascend to his rightful place in Heaven, thus completing the second trial . </P> <P> When Sam is in a coma and dying in the ninth season premiere "I Think I'm Gonna Like It Here", his subconscious desire to give up and die manifests in the form of Bobby . "Bobby" takes Sam away from the Impala and talks to him about moving on being a good thing and something he should do before taking him to a house in the woods where he says what Sam needs is . The part of Sam's mind that wants to live promptly manifests as Dean and kills "Bobby" to try to convince Sam one last time to live, but Sam decides to go with "Bobby's" advice . </P> <P> During the tenth season episode "Inside Man", Bobby is relaxing in Heaven when Sam and Castiel contact him through a séance to help break Metatron out of Heaven's prison . Though he feels himself to be rusty, Bobby agrees and escapes his Heaven, releasing all the other Bobby Singer's to create a distraction . Bobby gets Castiel into Heaven and helps him free Metatron before returning to his own Heaven . He leaves a note with Castiel for Sam, telling him not to stop searching for a cure for the Mark of Cain but to stop lying to Dean about it . He also states that helping again was the most fun he had in Heaven and he will accept any punishment for his actions . After returning to his Heaven, Bobby looks at a picture of him, Sam and Dean at his old salvage yard as Hannah and a few other angels come after him for punishment . </P>

How many times does bobby die in supernatural