Chris Wilder was made to wait for his first win as Middlesbrough manager after Preston came from behind to win 2-1 at the Riverside Stadium.
Pressure looked to be mounting on Preston head coach Frankie McAvoy when Paddy McNair headed Boro in front in the 33rd minute.
But after a string of good saves from Preston's Daniel Iversen, McAvoy celebrated three points after two late goals inside four minutes.
Ched Evans, who played under Wilder at Sheffield United, headed Preston level 13 minutes from time before Emil Riis was gifted the winner soon after to prevent a third straight defeat.
Wilder had watched his new side record a point against Millwall four days earlier, but it is now five without a win for the Teessiders who were leapfrogged by Preston into 14th.
With goalscoring chances initially scarce, Middlesbrough were fortunate not to have conceded a penalty when Marcus Tavernier shoved Riis as he charged into the area.
Referee Andy Woolmer waved play on despite complaints from the visiting bench.
That proved a crucial decision too. Shortly after Tavernier whipped a beautiful ball across the face of goal that Duncan Watmore was inches away from getting on the end of, Middlesbrough went ahead.
Jonny Howson took over corner-taking duties from centre-back McNair and that move proved pivotal because the latter's thunderous header from the delivery crashed in off the underside of the bar.
Before the break Preston had a second penalty appeal waved away when Isaiah Jones slid in and Josh Earl fell to the floor, with white shirts surrounding the referee.
And with seconds remaining of the first half, Preston goalkeeper Iversen made a stunning save to prevent Watmore from making it two with a chip from 20 yards.
Overlapping centre-back Lee Peltier was next to go close early in the second half when he turned on to his right foot and curled an effort against the woodwork.
After that Preston had struggled to make an impression in the attacking third and it seemed a question of whether Middlesbrough would extend the lead.
McNair's curling free-kick from 25 yards forced a save from Iversen, who shortly after denied Onel Hernandez a goal too with his feet.
Iversen was then called into action to palm away a low drive from Andraz Sporar and those saves paved the way for the surprise turnaround.
Ben Whiteman sent over the corner in the 77th minute and Evans rose in a crowded area to head inside Luke Daniels' top left corner for his first of the season.
And after the referee waved away a handball claim when Tavernier's effort was blocked in the penalty area, Preston countered and were gifted the winner.
Sol Bamba's pass in his own box deflected off McNair and dropped to Riis. The Dane controlled before curling his eighth of the campaign beyond Daniels with nine minutes left to frustrate the Riverside crowd.
What the managers said...
Middlesbrough's Chris Wilder: "I thought Preston were the better side for the first 10. We got to grips with that. We got ourselves up in the game and for the amount of chances we have had we should have increased our lead. In the second half we were not so dominant, but there was nothing from the opposition that changed the flow. We were still in the ascendancy. What affected the game was our attitude towards it.
"For the period where we lost it we played like we were three or four up. We weren't, we were one up. If you are only one up then things can turn around. Even if we were three or four up I don't want to play like that. I thought we tried to force it, there were too many looking to be the star of the show, looking for the killer ball. The top and bottom of it is that we have lost a game we should have comfortably won. I want them to play with a certain amount of arrogance and confidence but there has to be something at the end of it."
Preston's Frankie McAvoy: "It was the players who delivered on the pitch. We started the game well, we
were brave. We had a couple of good shouts for penalty kicks in the first half, one in particular looks a stone-waller; the other I could see that given as well. We conceded from a corner kick again, we have worked hard on those, that's disappointing. In the main we defended well.
"That is now four wins in the last seven games. The biggest thing is the team spirit we have, it has always been there despite what other people think. The fans were magnificent as well. I am delighted we have won it."