UK legislation to remove Britain from the European Union should not proceed, according to MSPs.
Holyrood voted by 90 to 34 for a motion from the Scottish Government saying the European Union (Notification of Withdrawal) Bill should not proceed.
It came after a heated debate in the Scottish Parliament, in which Brexit Minister Mike Russell warned Theresa May's plans for a hard Brexit will lead to a "hard Britain".
While the Supreme Court has already ruled the UK Government does not need to consult the devolved administrations before it starts the formal process of leaving the EU, Russell insisted the debate in Edinburgh was ''more than symbolic''.
The SNP joined together with most Labour MSPs, the Greens and the Liberal Democrats to vote against the triggering of Article 50.
Tory MSPs, however, voted against the motion, along with three Labour rebels - Elaine Smith, Neil Findlay and Richard Leonard.
Former Scottish Government cabinet secretary Alex Neil, who previously revealed he voted to leave the EU in the 2016 referendum, has not yet returned to Parliament after undergoing a heart procedure.
With 62% of Scots voting Remain in the referendum, SNP ministers are seeking some way of keeping Scotland in the single market.
First Minister Nicola Sturgeon and others have warned time is running out for the UK Government to reach an agreement which could prevent a second referendum on Scottish independence.
After the vote at Holyrood, Russell said: "Scotland's national Parliament has today sent a clear message to the rest of the UK and Europe - we oppose a catastrophic hard Brexit that dumps Scotland outside of the single market against its wishes.
"The Prime Minister promised Scotland would be 'fully engaged' in agreeing a common UK approach to triggering Article 50. We have taken those promises at face value and developed constructive, detailed compromise proposals showing how we can keep our place in the single market, which is around eight times bigger than the UK's alone.
"Yet so far the UK Government has offered nothing - not a single compromise in return, or even a view on our proposals.
"We do not yet know when Article 50 will be triggered, and have not been given any information about how the UK Government will seek our involvement. The promise of a 'UK agreement' on its content looks to be an empty one.
"Today's vote is therefore a key test of whether Scotland's voice is being listened to and whether our wishes can be accommodated within the UK process.
"There is still time for the UK Government to recognise the existence and importance of devolution, the views of this Parliament and the clear, democratically expressed voice of the people of this country - but that time is running out."
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