Rangers have been knocked out of the Europa League qualifiers after a 1-1 draw with Jagiellonia Bialystok handed the Polish side a 3-2 aggregate victory.
The defeat at Ibrox means manager Derek McInnes is still searching for his first win, with his team failing to secure a victory in their opening four matches of the season.
The Glasgow club will now drop into the Europa Conference League qualifiers, where they will face Czech side Jablonec.
Before the match, McInnes warned that the club were "playing with fire" due to a lack of defensive cover. An injury to Tuur Rommens left Rangers without a recognised left-sided defender.
McInnes deployed a back three of Manny Fernandez, Dujon Sterling and Olwethu Makhanya, with Djeidi Gassama and Daisuke Yokota as wing-backs. Lawrence Shankland, the newly appointed captain, was restored to the starting line-up after a substitute appearance in the first leg.
Early lead
Jagiellonia found early joy down the flanks, particularly past Gassama on their right. The visitors almost opened the scoring on 14 minutes when a slick move cut Rangers open and Jesus Imaz hit the post with only goalkeeper Ivor Pandur to beat.
Rangers took the lead four minutes later. Yokota, operating from the right wing, helped force a Video Assistant Referee review. A handball by former Celtic defender Yuki Kobayashi was penalised, and Shankland clipped the penalty down the middle.
The goal levelled the tie at 2-2 on aggregate. Dan Neil, one of nine new summer signings, helped Rangers win the ball high up the pitch from midfield. Thelo Aasgaard sent a low shot just wide on 35 minutes.
At the other end, Nik Prelec missed a chance for the visitors seven minutes before half-time, skewing a shot wide from a Rodrigo Conceicao cross.
McInnes reverted to a back four at the break, replacing Aasgaard with Ross McCrorie.
Boos at Ibrox
Jagiellonia, wearing red and yellow kits that led a radio pundit to note "they kind of look like Partick Thistle a little bit", found their equaliser on 65 minutes.
Andrea Klynge crossed to the back post, where Prelec headed past Pandur to make it 3-2 on aggregate.
McInnes substituted Nico Raskin shortly after the goal. Substitute Bojan Miovski headed just wide with a couple of minutes left to play, while Ryan Naderi also featured as Rangers failed to find a breakthrough.
At the final whistle, Rangers players slumped to their knees before awkwardly circling the pitch to applaud the remaining supporters. They were met with boos and torrents of abuse from the stands.
The toxic atmosphere carried echoes of Russell Martin's defeat against Club Brugge last season, though the Belgian side offered a higher calibre of Champions League opposition.
The result follows a home defeat to Hibernian last weekend. Rangers next face St Mirren in a League Cup tie on Sunday.
