Arbroath found themselves a goal down on 49 minutes when an Eddie Malone free-kick was cleared to the edge of the box and the Warriors benefited from two mis-kicks.
Firstly Bryan Hodge’s wayward shot reached Sean Lynch and then his poorly struck effort flew high into the net, with Arbroath goalkeeper Scott Morrison posted missing.
Sheerin’s side rallied and Michael Travis’ deflected header from a Bobby Linn corner had them level on 64 minutes.
With 17 minutes left, Malone swung over a corner against the stiff wind and the ball travelled unchecked into the far corner of the net.
Stenhousemuir scored what proved to be the decisive goal six minutes later when substitute Errol Douglas ran through the middle of the Arbroath defence to round Morrison and slot the ball home.
Lee Erwin scored late on for Arbroath, but the Lichties were unable to find an equaliser.
Gayfield player-manager Sherrin said: “We are conceding far too many goals and there is no getting away from it. Whatever combination we try to stop us losing goals is not working at the moment.
“We responded well to losing a freak first goal but then gave away a goal directly from a corner. That gave Stenhousemuir a lift and made it more difficult.
“They started passing the ball about with some confidence and their substitute ran away from us at the third goal.
“Alan Cook’s shot in injury time that hits their goalkeeper and the post sums up how things are going. We have scored nine times against Stenhousemuir this season and not won.
Source: Lichties Mad