Why Platform Freelancers Struggle With the Colombian Digital Nomad Visa

This is the Colombian Digital Nomad Visa case I could not win.

The applicant was a freelance web designer who had been working through Upwork for years. Real skills. Real projects. Real income. Good reviews. Money arriving in the bank every month from work performed online for clients outside Colombia.

On paper, this looked like exactly the kind of person the Digital Nomad Visa was created for.

A genuine remote worker.

But Colombian immigration did not see it that way.

The client had real platform income

This was back in 2022, during the early days of the Colombian Digital Nomad Visa under the new rules. My client had been studying in Colombia and wanted to stay legally while continuing the same freelance work they had already been doing for years.

The work was legitimate. The income was consistent. The services were provided online. The clients were outside Colombia. There was no Colombian employment relationship and no intention to work for a Colombian company.

We prepared the application with the documents available: passport, bank statements, migration records, proof of studies, Upwork evidence and the platform’s Certificate of Earnings.

The Certificate of Earnings proved the income. It proved the platform activity. It showed that the work was real.

But it did not solve the problem immigration cared about.

The problem was not income. It was relationship evidence

Immigration came back with a requerimiento asking for letters from employers or clients confirming the work relationship and remuneration.

That is where the case became difficult.

Upwork is not a normal employer. It is a platform. It connects freelancers and clients, manages parts of the relationship, processes payments and provides a digital record of the work. But it does not usually give freelancers a personalised immigration letter confirming a traditional employment relationship.

The individual clients are often short term. Some hire you for one project. Some disappear when the work is finished. Some are individuals. Some are small businesses. Some do not want to issue formal letters for immigration purposes. Some do not even understand why they are being asked.

That does not mean the freelancer did not work.

It means the evidence immigration wanted did not reflect how platform work actually operates.

The work was real. The income was real. The platform was real. But the available documents were platform evidence, while immigration was asking for relationship evidence.

That is the gap.

Why platform work does not fit neatly

The Colombian Digital Nomad Visa is supposed to cover remote workers, independent workers and digital entrepreneurs. In theory, that should include many people working through platforms.

But the way the visa is assessed still feels very traditional.

The officer wants to understand who you work for, who pays you, what the relationship is, how much you earn and whether the work is genuinely remote and foreign sourced.

That is easy when the applicant has a foreign employer. It is also easier when the applicant has one or two stable foreign clients who can provide contracts and letters.

It becomes much harder when the applicant works through a platform.

A platform freelancer may not have one employer. They may not have one stable client. They may not have a conventional contract outside the platform terms. They may not receive payslips. They may not be able to ask past clients for notarised or formal letters.

And yet they may still be exactly what they say they are: a remote worker earning foreign income online.

What we argued

We explained how platform based freelancing works. We explained that Upwork is a digital marketplace, not a traditional employer. We explained that the applicant’s work history, income and client reviews showed real economic activity.

We also explained why the requested client letters were not realistic in this model. The platform substitutes much of the traditional client relationship. The work exists, but the paperwork does not look like the paperwork an immigration officer expects from a company employee or long term contractor.

The officer did not accept that explanation.

They still wanted client letters.

Formal relationship evidence for a work model that does not naturally produce it.

The hard choice

At that point, we had two options.

We could keep pushing with documents we did not have and risk a formal denial, or we could step back before the case became worse for the client’s immigration history.

I recommended stepping back.

A denial can stay on the applicant’s record and make future applications harder. In this case, keeping the record as clean as possible gave the client better options than forcing a weak file through to a negative decision.

It was the right strategic decision, but it was still frustrating.

Because the problem was not that the applicant was fake.

The problem was that the system did not know how to read the file.

Why this case still bothers me

Since then, I have handled more complex Digital Nomad Visa cases. I have dealt with unusual work arrangements, difficult documentation, company owners, remote employees, foreign contractors and non traditional professional profiles.

Many of those cases succeeded.

This one did not.

And it still bothers me because the applicant was exactly the kind of person people imagine when they hear “digital nomad”: someone with portable skills, international clients, remote income and no intention of entering the Colombian labour market.

But the visa system did not only ask whether the work was real.

It asked whether the work could be proven in a format the officer was comfortable accepting.

That is a very different question.

This is not only an Upwork problem

The same issue can arise with other platforms.

A language teacher working through an online teaching platform may face a similar problem. The teacher may be giving real lessons, earning real income and working entirely online for students outside Colombia.

But if the platform will not provide a formal letter, and the students are not direct long term clients who can issue proper documentation, the same grey area appears.

Who is the foreign company?

Is it the platform?

Are the students the clients?

Is the platform only an intermediary?

What document proves the relationship?

What document proves remuneration?

These are not always easy questions, and the visa platform does not give much room for nuance.

That is why I do not treat platform cases as simple checklist applications.

Is there a way to build a stronger platform case?

Possibly. But it has to be honest.

The strategy should not be to pretend the applicant is an employee if they are not. It should not be to invent a traditional client relationship if the platform model does not work that way.

The better strategy is to explain the platform relationship clearly.

For some platforms, the strongest argument may be that the applicant provides independent remote services through a foreign digital platform, under that platform’s terms, and receives remuneration through that platform.

That argument is stronger if the platform can provide a letter confirming the applicant’s active status, role, payment structure and remote work arrangement.

If the platform will not provide a letter, then the file needs to work harder. Platform terms, tutor or freelancer agreements, payment reports, transaction history, profile evidence, reviews, completed jobs, tax records, invoices where available and bank deposits all need to tell one coherent story.

But I want to be very clear: these documents may improve the case, but they do not guarantee approval.

The key issue remains whether the officer accepts platform based work as satisfying the visa requirement.

If you work through a platform, read this before applying

If most of your income comes from Upwork, Fiverr, a teaching platform or a similar digital marketplace, you need to understand the risk before applying.

The issue is not whether your work is real.

The issue is whether your work can be documented in the way Colombian immigration expects.

A Certificate of Earnings may prove income. A platform profile may prove activity. Reviews may prove credibility. Bank statements may prove payment.

But immigration may still ask for relationship evidence: who you work for, under what arrangement and with what remuneration.

That is where platform cases can break down.

I wish I could say I now have a clean formula for these applications.

I do not.

For remote employees, company owners, structured freelance businesses and contractors with stable foreign clients, the Digital Nomad Visa can work very well. For pure platform based freelancers, especially Upwork based applicants, I remain cautious.

Not because the work is not real.

Because the Colombian visa system still seems more comfortable with traditional work relationships than platform based work.

That is the warning.

The lesson from this case

This case taught me that a Digital Nomad Visa application is not just about qualifying on paper.

It is about translating your work into a form the visa authority can understand and accept.

For platform workers, that translation is often the hardest part.

If you work through a platform and want to apply for the Colombian Digital Nomad Visa, do not treat it as a simple checklist application. Before you apply, the real question is not only whether you earn enough.

The real question is whether your work model can be explained and documented in a way the authority is likely to accept.

If you are unsure, talk to me before you apply. I will give you an honest assessment of whether your file is strong enough, whether the platform evidence can be developed into a credible case, or whether applying now may create more risk than opportunity.