Arsenal had both David Luiz and Bernd Leno sent off as their seven-game unbeaten run came to a screeching halt at Wolves.
For a sizeable chunk of the first half at Molineux, Arsenal would have been forgiven for thinking an eighth game without defeat was fait accompli.
Mikel Arteta's side bossed the opening stages, and thought they'd taken the lead inside ten minutes when Bukayo Saka's strike nestled inside Rui Patricio's net. However, it was ruled off by VAR for an offside in the build-up.
Arsenal took a deserved lead on 32-minutes courtesy of a fine individual effort from Nicholas Pepe.
But things diverted steeply downhill for the visitors in first-half injury time. David Luiz was shown a straight red card after he appeared to clip Willian Jose from behind with the Brazilian bearing down on goal.
Ruben Neves tucked the resulting penalty beyond Leno to give parity to the barely deserving hosts.
Four minutes after the restart there was no denying Wolves their lead. Joao Moutinho's long-range drive flew into the corner beyond the reach of Leno to make it 2-1.
Arsenal appeared deflated and were reduced to half-chances from that point on. And with 18-minutes to go their task became an impossible one.
Leno handled outside the box, and was given a straight red by referee Craig Pawson.
Pedro Neto squandered a clearcut chance to make it 3-1 shortly after, but a weak shot was gathered cleanly by Alex Runarsson.
A win would have seen Arsenal move above neighbours Tottenham into sixth in the table - instead they end the night tenth. While any lingering worries regarding Wolves' safety have eased with the three points.
Arteta voiced his frustration with the Luiz red card after the game, saying, "If there is any contact it's him [Willian Jose] with David.
"I don't know if they have a different angle to what they have or you have.
"Those big decisions are like that but it's nothing I can change at the moment.
"It was a big decision and they can justify if they got it right then I put my hands up and apologise.
"The only thing I'm saying is I'm sitting here and I cannot see any contact and it's really frustrating because it's a big moment in the game."