Having been handed the top three clubs in the Championship as his opening trio of games, Dougie Freedman, the new Bolton Wanderers manager, always knew his introduction to the job would be a testing one. So it proved as the Scot, from a seat in the main stand, saw his side surrender a lead to hosts enjoying their best run of form for almost a year. With the top two, Cardiff City and Leicester City, due at the Reebok Stadium, things don't promise to get easier.
Freedman has now suffered a second defeat here in the space of two months – Crystal Palace went down by the same scoreline in August.
However, things might have panned out differently had Lee Chung-Yong taken an arguably easier chance than the one with which he had just put the visitors ahead as half-time approached. A two-goal advantage could very easily have proved to be insurmountable.
As it was, all Bolton had to show for their efforts was the South Korean's chipped finish from 10 yards, the midfielder's first goal for 18 months, as the ball fell invitingly to him from Faris Haroun's mis-control, to show for their efforts.
It left them vulnerable to a stirring second-half comeback, one inspired by two predatory finishes from Scott McDonald, who has returned to the fold after settling his differences with Boro's manager Tony Mowbray.
The Australian, a substitute for the hamstrung Marvin Emnes, slid Middlesbrough level from close range midway hrough the second half when Bolton's goalkeeper Adam Bogdan diverted a shot from Ishmael Miller into his path.
The winner arrived with five minutes remaining, McDonald applying a deft glancing header to one of several inviting crosses from Emmanuel Ledesma, whose introduction at half-time proved significant.
"It's been a stop-start season for Scott," Mowbray said. "But the bottom line is that he's a very good player and the challenge for him now is to keep scoring."
Freedman, 38, took a back seat, albeit one of the more plush ones in the Riverside's directors' box, after his confirmation in the post 48 hours before kick-off left him little time to have any useful input for this fixture.
The way he was regularly scribbling in a notebook suggests he feels there are plenty of areas with room for improvement from a side sitting in the bottom half with only a single away victory all season after relegation in May.
Chris Eagles sent a 25-yard effort narrowly wide for Bolton, but it was Middlesbrough who carved out the clearer openings. Miller, an increasing influence as the contest wore on, was unlucky with a close-range header and an angled drive.
Bogdan also produced a fine save from Emnes after Faris Haroun dispossessed Tyrone Mears to release the Dutchman.
Lee scored against the run of play and should have made it two when he caught out Andre Bikey, but his shot sailed well over and Middlesbrough made the most of their escape to provide further evidence that they have every hope of emerging victorious from their imminent Capital One Cup trip to Sunderland.
Cardiff arrive in Lancashire on Saturday for Freedman's first home game in charge.
"Dougie's got a full week to train with the players and that gives him a chance to implement his ideas and do things his way," Jimmy Phillips, the caretaker manager, said.
"We had the chances to get the second goal to really put the pressure on Middlesbrough so it is disappointing.
"Dougie is inheriting a side that is playing with a lot of confidence, but the goals against column needs to be improved. We need to be stronger in defence."
Middlesbrough (4-4-2) Steele; Parnaby, Hines, Bikey, Friend; Reach (Ledesma, 46), Leadbitter, McEachran (Halliday, 87), Haroun; Emnes (McDonald, 23), Milller.
Bolton (4-4-1-1) Bogdan; Mears (Ngog, 88), Ricketts, Ream, Warnock; Lee, Spearing, M Davies (Pratley, 78), Petrov (Afobe, 65); Eagles; K Davies.
Referee Gary Sutton.
Man of the match McDonald (Middlesbrough).
Match rating 5/10.