A second successive loss and a performance shorn of quality and fight means the honeymoon period is very much over for Steve Burr.
Back-to-back wins in Burr's first two games in charge had raised spirts around the Swansway Chester Stadium but nobody will be under any illusions after this deflating defeat.
Welling were full value for the win, exploiting the hosts' defensive frailties and possessing far more energy and desire, and the Blues must do much better with testing trips to Macclesfield and Aldershot ahead.
Burr made two changes with Michael Kay and Matty Taylor - on loan from Forest Green Rovers - coming into the side and Kevin McIntyre pushing up to left midfield.
Wings' boss Jamie Day handed a debut to imposing England Under 18 striker Tobi Sho-Silva after he joined on loan from Championship side Charlton Athletic.
Welling were the better side in the opening 10 minutes with Harry Beautyman dragging an early chance just wide and the dangerous Ross Lafayette having a half-hearted penalty shout turned down.
McIntyre limped off holding his groin on 16 minutes and the visitors' took the lead thanks to some dreadful defending with the Blues reduced to 10 men. A hopeful pass from deep sailed beyond Ross Killock and George Horan, giving Harry Cornick all the time he needed to slot past John Danby.
Jamie Menagh replaced the injured McIntyre and Killock headed a John Rooney corner over as the home tried to inject some energy but even the simplest tasks seemed too tough for the below-par Blues.
Welling were playing with the benefit of a strong wind behind them and Joe Healy tested Danby from 16 yards but the conditions could not mask the hosts' underwhelming start.
It was hard to believe this was same group of players that had shown so much enthusiasm and passion in the wins over Barnet and Woking as possession was turned over far too easily and far too often
Things got even worse five minutes before the break as Danby dwelled on the ball and Sho-Silva dispossessed him before squaring to Ross Lafayette and the Wings' captain tapped home to put his side 2-0 up.
Referee Darren England did the home fans a favour when he blew the half time whistle, ending a 45 minutes that was best forgotten.
Burr will have no doubt had some harsh words for his side in the dressing room and sent his players out early for the second period.
Whatever he said seemed to make an impact with Kay curling wide from the edge of the box and Rooney having a shot blocked as the Blues created more in the first five minutes of the second half than they did in the entire first half.
But with a mountain already to climb, the summit got even further away on 53 minutes when Wings' winger Joe Healy smashed a low drive beyond the diving Danby and into the bottom corner to put the visitors three up.
Two minutes later the response that Burr and the home fans had been waiting for since going behind finally arrived. Menagh chipped towards Taylor, who controlled the ball on his chest before drilling past Lee Butcher to give Chester hope.
Top scorer Gareth Seddon came on for Reed having missed the last six games and the Blues began to show some desire and started to press, but worrying signs remained and the visitors never looked truly troubled.
Jarrett wasted the best chance of the second half, poking wide from eight yards out after Seddon had flicked on a Lewis Turner cross and that was about as close as the hosts got to a second goal.
Burr's side improved marginally and had more of the ball but struggled to find any fluency and can have no complaints about the end result as the Wings ran out comfortable and deserved winners and the miser was compounded when Killock saw red late on for his second booking.
Chester FC: Danby, Turner, Horan, Killock, Kay, Rooney, Jarrett, Miller (Bond 70), McIntyre (Menagh 17), Reed (Seddon 56), Taylor.
Subs: Fearon, Mahon.
Goal: Taylor 55.
Booked: Kay, Killock, Turner.
Sent off: Killock.
Welling United: Butcher, McLaren (Joe Obersteller 33), Hudson, Bergqvist, Jack Obersteller, Healy, Gallagher, Beautyman, Cornick (Guthrie 57), Lafayette, Sho-Silva (Ajala 63).
Subs: Turner, Wakefield.
Goals: Cornick 17, Lafayette 40, Healy 53.
Booked: Guthrie.
Referee: Darren England (South Yorkshire)
Attendance: 2,074.
