He served under Captain Raymus Antilles on the Tantive IV in 0 BBY. When that vessel was captured over Tatooine, he was taken prisoner by stormtroopers and sent to the glitterstim mines of Kessel. There, he managed to hijack a starship, along with a group of other droids.
Squeaky could not pilot a ship, so he programmed the auto-pilot to do terrain-following mode for a few miles, then flee. He was not aware of how uneven Kessel's terrain was, and was as a result surprised to find his escape route took his group on a wild ride through Kessel's twisting canyons. After the escaped droids left the planet and dispersed through the galaxy, the incident was immortalized throughout the galaxy as the "Runaway Droid Ride."
Eventually, the intelligence he displayed on Kessel led to his being manumitted, allowing him to live his life without a master or a restraining bolt. Eventually, he joined the Alliance to Restore the Republic, where he became an X-wing ground control officer, and a waiter at the Downtime cantina. Later, he became the quartermaster for Wraith Squadron.
Squeaky was a bad-tempered droid, with Wedge Antilles noting that he was more verbally abusive than any other droid he had met. He was known to insult customers at the Downtime, and argue incessantly with Chewbacca when he accompanied him on missions.