The 20-year-old says he seemingly caught the virus twice within one month.
On December 27, Will received a text from NSW Health advising him he was positive.
"I had done RATs all through that time which came back negative, which was a bit confusing," Mr Benson told 9News.
The disability worker said he spent one week recovering, then resumed his normal routine once he'd completed isolation requirements and returned a negative rapid test.
"I was 100 per cent. Back to going to the gym full time, at work full time," Mr Benson said.
"It was back to normal life … when I took that negative RAT I was feeling 100 per cent."
Less than one month later, on January 30, Will became unwell again and was shocked when his rapid test returned a positive result, forcing him into round two of isolation.
"I contacted NSW Health and explained the situation to them and the lady on the other end of the phone unfortunately seemed just as confused as I did," Mr Benson said.
The double-positive stumped experts at the Hunter Medical Research Institute.
"It's unusual. Normally the protection you get from the infection is quite strong in the days and weeks ahead," Associate Professor Nathan Bartlett told 9News.
But the expert said reinfection was not out of the question, particularly with different variants circulating.
"The fact there's been a new onset of symptoms suggests it's a new infection," Associate Professor Bartlett said.
This case is proof of the importance of remaining vigilant, experts have warned, even if you've already had COVID-19.
Your COVID-19 questions answered
"You should be cautious if you do become symptomatic again in the couple weeks after the initial infection. You should get checked again," Associate Professor Bartlett said.
