Boasting EFL experience with Barnet, Dagenham & Redbridge, Portsmouth and Coventry, the 27-year-old arrives to bolster the goalkeeping options at Huish Park.
A free agent since departing the Sky Blues in the summer, O’Brien was part of the side under Mark Robins that won immediate promotion back to League One in the Play-Off Final at Wembley in 2018.
Signed by Portsmouth as a youngster following trials at the likes of Manchester United and Arsenal, the former England Under-19 international was an unused substitute for Pompey in the Premier League before gaining a first taste of senior football on loan at Eastbourne Borough.
Various stints in the top four flights of English football have followed, with the stopper now arriving in Somerset from the Midlands.
O’Brien will wear the number 27 shirt at Huish Park and is available for Tuesday night’s meeting with Sutton United in the National League.