Jeff Clark is dressed as if he’s just come home from work — a yellow button-down shirt with the sleeves scrunched up, a pen in the front pocket. His hair looks boyish, a contrast to the decidedly grown-up nature of his task.

He’s bent over his laptop, his glasses partially down his nose, anticipating the next move like a soldier planning for battle. Reapplying for unemployment benefits is a type of combat. Every two weeks he must struggle with Florida’s convoluted online system to confirm that he’s still unemployed.

The screen finally indicates that he’s done, and that his request has been received. He glances at the clock. It only took 1 hour and 15 minutes. Not bad. Each time, he gets better at avoiding the obstacles.

“This has gone relatively smoothly,” Clark, 62, says to me from the kitchen bar of his Safety Harbor home.

That anyone would describe wasting that much time in a positive way confirms so much about what is wrong with Florida’s unemployment system. We’ve read stories about how hard people had to work just to sign up for benefits. The state had the worst rate in the country for processing unemployment claims, based on U.S. Department of Labor data. Only the delusional could say Florida handled the process well.

But the drudgery doesn’t end once they receive the sought-after employment benefits. Clark and tens of thousands of others must reclaim benefits every two weeks. The website routinely cuts out as they fill out the online forms, the instructions often don’t make sense, and applicants are told that their claims have pending issues, with no further explanation.

Clark would prefer to spend his time doing almost anything else, but he knows that if he doesn’t navigate the website every two weeks, the money he needs will stop coming. He’s willing to plod through a self-described “nightmare” to get it.

***

Clark’s Florida story is similar to many others. He and his partner bought a house in Safety Harbor in 2006, where they lived as part-time snowbirds for 10 years, seeking refuge from the cold of their New York country home. When Clark lost his job in 2016, they moved here full-time.

Clark tells me he designed kitchens for Lowe’s Home Improvement, but wanted to try something smaller. He landed with a mom-and-pop renovation company based out of Largo.

Then the coronavirus hit.

Business was already tight, the owners told him. “We know we’ll never survive this,” they said.

Two weeks into the crisis and Clark went from employed to unemployed.

When he first tried to log into the unemployment system, he quickly got kicked out. He logged in again and the same thing happened. Around he went. Log in — booted out. Make a little progress — booted out. He was tempted to give up many times,

Finally, Clark read somewhere about logging in around 2 a.m., when most people are tucked safely in bed. He dutifully set his alarm. But everybody else had the same idea. The website was still jammed.

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On April 5, Clark went old-school: He sent a paper application by certified mail. Ten days later, he learned it had arrived.

About two more weeks passed, and Clark still hadn’t heard anything. The state finally told him he had to verify three of his former employers. Two of them he recognized, but one was in California. He’d never worked there.

“I thought, ‘Oh, this is going to take another month,‘” he said. “And then it actually resolved itself pretty quickly.”

Around May 1, almost six weeks after he first tried to apply, the site told him he was approved. Nine days later, he received a paper check for $600, the weekly amount the federal government kicked in to help workers affected by the crisis.

The state’s payment came out to $225 a week, less than the maximum of $275. Clark thought he was owed more, based on his salary and how long he had worked, but he was too worn down to officially dispute the payout.

Clark doesn’t back down from challenges. He’s the guy who writes letters to the head of a company when they don’t do the right thing. But he was happy to be receiving some money and wanted to be done with it all.

Okay, you win, he thought, unaware of the battle ahead.

***

Clark’s shoulders tense up and his eyes squint as he logs into the system for his two-week renewal.

“You can feel the blood pressure and the pulse rising,” he says.

Every two weeks, Clark wonders if a small mistake will mean the difference between getting $825 or nothing at all.

We eye the clock. It’s 11:29 a.m. Neither of us know how long this could take. I left my afternoon open in anticipation of hours sitting in front of the computer screen. Clark has no choice but to do the same. Once, when he went to renew, the system jolted him out multiple times, claiming a connection failure. There was no issue on his end, Clark said. His WiFi was working fine.

The first screen indicates that he has a spot in the waiting room, but there’s no indication of how many applicants are ahead of him. Clark doesn’t dare wander away. He must watch the screen, for he only gets 10 minutes to log in once he gets to the front of the line.

A little man runs across the screen, resembling the logo of AOL’s Instant Messenger, a relic of a bygone era. It’s an example of how the whole system feels — a few years too old and way too unwieldy, especially given that the state spent $77 million to buy the system in 2013 and $110 million to fix it in recent weeks.

Clark takes almost 20 minutes to get out of the waiting room. The site begins by asking him to verify his address and how he wants to receive his money — direct deposit, debit card or some other way. Sounds easy, right?

But it gets progressively harder. The website indicates that the Department of Economic Opportunity has suspended the requirement to provide work search contacts, where applicants have to show that they have applied to five jobs a week to qualify for benefits. In good times, the requirement ensures that someone on unemployment is making active strides to find work. But with the coronavirus — and a double digit unemployment rate — there aren’t nearly enough jobs to go around. Suspending the requirement makes sense, but the application system acts like the requirement is still in effect.

Sitting with Clark, I watch him make a few more clicks, and sure enough he arrives at a page that indicates he must provide five work search contacts or prove that he visited a CareerSource center, which help people find jobs.

Weeks ago, the contradiction had him shaking his head. He raced around trying to find the addresses for the websites where he applied for jobs. Now, he knows the drill. But he wonders if the confusing instructions would deter some people from claiming benefits.

Eventually, Clark gets to a page that asks if he is unemployed as a result of COVID-19. Answering yes is theoretically enough to override the work search questions from the earlier page. But like so much with this system, it’s not clear.

Before Clark can confirm that the coronavirus caused his layoff, the screen drops. Secure connection failed, it reads.

Within a minute, he is able to log back in. Eventually the system says there are pending issues with his application, but doesn’t offer any other details. A day later, he gets his direct deposit.

“The thing that drives me crazy,” he says at the end of it all, “are the hoops you have to jump through that just don’t seem necessary.”

In a follow-up interview, Clark tells me he is in talks for a seasonal position with Home Depot. He’s finally learned how to navigate the arduous benefits system, but he might not have to do it again.

He won’t miss it.