Gibraltar is the world capital of the online gaming industry and boasts a booming financial services sector.
But ahead of the start of formal Brexit negotiation talks, the two key industries face an uncertain future.
Already the unpredictable consequences of the divorce deal between London and Brussels is creating confusion.
Peter Howitt, chief executive of the Gibraltar Betting & Gaming Association, said: “The European Court is trying to do two things, on the one hand they are saying Gibraltar doesn’t have separate European rights so is part of the UK, one member state.
“But in the Brexit process we see there is the idea that you could do a deal with the UK and Europe that would not necessarily involve Gibraltar.
“The biggest concern in Gibraltar really relates to the border with Spain, obviously we have a huge number of cross-border workers.”
The gaming industry is responsible for more than 10% of all jobs on the island.
But other countries such as Malta appear ready to benefit from any lost business.
While the EU-focused financial industry may need to reinvent itself and turn towards the UK market.
Adrian Hogg, chairman of Gibraltar Founds & Investment Association, said: “The financial services passport allows us to passport services around EU as if it were one nation.
“It is not black and white, there’s always grey in the middle. Yes, we may lose EU, but we would gain from elsewhere.
“We would gain from our clients in the UK, who would be less EU facing, we would gain from our clients in Switzerland, we would gain from our clients in Asia and America as well. I think after the referendum people generally shocked with the outcome and I think that now people have got over and they are looking for the opportunity that will arise”.
Companies have been lured to the island by its low tax rates and unfettered access to the EU.
Although it looks set to lose its selling point, authorities in Gibraltar are keen to look at new doors that could open from new trade deals.
Joseph Garcia, Deputy Chief Minister Of Gibraltar, said: “They have told us already that they will guarantee whatever access we have to the UK market.
“In addition we’ve been told whatever new trade deals the UK will do, once it left the EU, with other countries in the Commonwealth or the United States, whatever trade deals they will do, UK will include Gibraltar as part of those trade deals.”