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Its like using someone elses computer or using a computer that you either trust or own to connect to the internet on your behalf, said Mallory Knodel, chief technology officer at the Center for Democracy and Technology, noting VPNs are generally used by companies to keep internal business assets private when employees work remotely and as a way to get around content filters.

A diverse and large combination of existing VPN providers, newly created VPNs, and those already in use in Cuba could form a stealthy ecosystem and help sustain internet connections as some would be inevitably blocked.

It's unclear when the Biden administration will approve a VPN system strategy. A senior administration official told POLITICO they are discussing providing wireless LTE communications with private-sector providers and continue to explore various options, including stratospheric balloons. The official said the Departments of State, Commerce, Treasury and the Federal Communications Commission have been directed to develop the required rules, licenses and authorizations.

Sen. Bob Menendez (D-N.J.), chair of the Senate Foreign Relations Committee and one of several Cuban American leaders Biden met with last week, supports using VPNs.

Chairman Menendez believes this is one of the most effective ways for people on the island to access and share information outside of the regimes control and, as such, has been working through numerous channels to support those efforts, said Juan Pachn, spokesperson for Menendez.

The biggest obstacle is the Cuban regime's ability to shut down the internet island-wide or in specific regions anytime.

I think more help, bringing in more access to different VPNs [and] faster communication will be appreciated. But that won't solve the issue completely because the main problem is that, once the government turns off the internet, people have no access to the VPN servers so they can't use a VPN either, said Salvi Pascual, executive director of Apretaste!, a social networking app that expands internet capabilities, web services, and privacy for Cubans.

Even if the regime chose not to shut down service, there would likely be a cat-and-mouse game between Cuban internet authorities and VPN servers.

But because most of the internet traffic would be political, itd be easier for Cuban authorities to track their target, said Jon Callas, director of technology projects at the Electronic Frontier Foundation. With there being an economic embargo, there is no commercial traffic. So, it's all political traffic; so that's part of why it makes it easy for the Cuban government to shut these down.

In place since the 1960s, the U.S. embargo prevents most American companies from conducting business in Cuba.

According to the 2021 Inclusive Internet Index, a tool commissioned by Facebook and developed by The Economist Intelligence Unit that measures internet access and affordability across the globe, approximately 31 percent of Cuban households have internet access, ranking 83rd in availability of 120 countries.

Both Knodel and Callas said a VPN strategy could succeed in the short-term, with Knodel noting longer-term success would be dependent on Cubans being able to make informed choices about how they want to use the internet and what they want to use it for.

Pascual said that VPNs are far from foreign to Cubans.

People in Cuba are already using VPNs," said Pascual, who thinks the issue boils down to the American political will and building infrastructure on the island that the Cuban government does not control pitching construction of a cell tower on the Guantanamo Bay Naval Base and suggesting the U.S. embassy share its Wi-Fi, which will be easy to spread all through Havana through the internal network.

It is hard but I think the main issue right now is political will, he said.

Callas said a VPN strategy is extraordinarily well-intentioned, but overly simplistic.

While a VPN essentially creates a network connection that no one can see the content of, they can still see that you're doing it and that would mean that the Cuban government could likely know what the start point and what the end point is of the VPN, he said, noting that the technology would work better when paired with political and economic strategies. Technical solutions for political and economic problems are always imperfect.

When working with Cubans, or others facing similar restrictions, who are unfamiliar with VPNs, its important to do trainings with them using trusted community outlets and refrain from politicizing the tool, said Dragana Kaurin, founder and executive director of Localization Lab, a global nonprofit that makes open source technology, including VPNs, accessible in underserved regions through collaboration with local developers and organizations.

When we frame technologies like this, as tools of democracy when we politicize technologies in this way, we, as developers of these tools, exclude the people who don't line up with the entire ideology, she said.

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Could VPNs help Cubans access the internet under the regimes nose? - POLITICO