Let’s be honest, if filing your taxes feels like a punishment, that’s because it is. 

Every June, millions of Kenyans log onto the KRA iTax portal hoping for a quick, responsible, citizen-like experience.

What we get instead is a digital assault course that tests patience, network stability, and emotional resilience.

The system crashes, hangs, throws error messages, logs you out, and demands passwords you last used during COVID. It’s like the system was designed not to work. 

And so, a simple task like filing a nil return, which should ideally take five minutes, becomes an hour-long spiritual battle.

Meanwhile, the deadline is non-negotiable. You miss it by a day, and KRA will slap you with a fine before the website can even reload.

So here’s the question: why is filing taxes harder than paying it? 

Tax in itself is not the enemy. Most Kenyans accept the principle. We get it, taxes build nations (or at least, they’re supposed to).

But the problem is in the experience. In 2024, why is KRA still running a platform that behaves like a clogged cybercafé in a blackout? 

Let’s not forget: this is the same Kenya that claims to be a tech hub, the so-called Silicon Savannah.

We have eCitizen, we can buy land online, book hotels in two taps, hail cabs, and run entire businesses on Instagram.

Yet somehow, the one thing that’s mandatory for every citizen – filing taxes – feels like a sabotage mission. Something doesn’t add up. 

The truth is, the system isn’t broken by accident. It’s just designed without empathy.

It’s built with the assumption that the average Kenyan is a tax expert, has stable Wi-Fi, knows what “PIN certificate” means, and can upload Excel spreadsheets without error.

There’s no human-centred design, no intuitive interface, no “Oops, we’re down but we’ll fix it!” message.

It’s cold. Mechanical. Bureaucratic. And it shows. 

Instead of being a bridge between the people and the government, KRA’s system feels like a firewall. It doesn’t invite compliance; it punishes effort. And the worst part? They know.

Every year, the same complaints come up.

Every year, Kenyans flood X with screenshots, memes, and cries for help. But nothing changes. 

Now imagine being a 24-year-old trying to do the right thing. You’re unemployed, but you still have to file. You click ‘Nil Return’, and the portal crashes.

You reload. It hangs. You enter your PIN, and it is rejected. You verify the details, and it says “session expired”.

You can’t build a tax culture by punishing honesty. You don’t encourage civic responsibility by making the process feel like an IQ test on a broken platform.

If anything, this just creates a generation that sees the system as hostile and avoids it altogether. That’s not how trust works. 

The irony, of course, is that KRA has all the technology to track digital transactions, mobile money, betting accounts, and even SMEs using online tills.

Yet when it’s time to build a user-friendly filing experience, they act like they’re out of budget.  

Also, let’s talk about customer support, or the lack of it. During peak filing days, calling KRA is like trying to contact a ghost. Emails go unanswered. Social media DMs vanish into thin air.

And if you decide to walk into a KRA office, you’re met with queues that stretch from the reception to the parking lot. That’s not service, that’s suffering. 

The writer is a digital marketer, brand strategist, and founder of the Pride of Kenya Awards, an initiative focused on youth empowerment and innovation