The so-called "soft play" period that began Thursday was to shake out bugs before the anticipated statewide launch of online betting next Tuesday. And for Brennen there were plenty of bugs that needed shaking.
One of the main culprits in his - and other gamblers' - initial encounter with legal Internet gambling was the sophisticated technology designed to ensure that gamblers are actually within New Jersey's borders. In several cases, it appeared to have worked too well.
It was a possible scenario detailed by The Associated Press in a weekend story quoting online gambling officials who said they moved their "online fences" away from the state's borders to ensure players from other states couldn't get online to gamble. The result was no-play zones that far exceeded the narrow strips foreseen by online technology experts last week.
It was not immediately clear why the technology locked out users who were 10 to 15 miles from the border.
"It's frustrating knowing you're in the jurisdiction and you can't get anywhere," said Brennen, who vowed not to give up.
The 33-year-old unemployed bartender from Ventnor began his quest to bet online in a seat near the men's room at a McDonald's in Atlantic City, the shining Boardwalk casinos glittering in the background. He kept getting security messages from different gambling web sites saying they either didn't know where he was, or didn't believe he was in New Jersey.
So he got in his car and drove 5 miles inland and 5 miles north to a highway rest stop, where he still had difficulty getting online with the gambling sites. Back into the car again, he drove another 10 miles west, to a chain restaurant. Surely, he thought this was far enough inland to let him connect.
Wrong. The Borgata Hotel Casino & Spa and five sites run by Caesars Entertainment didn't believe he was in New Jersey. Others let him register to gamble but insisted on more proof of residency that he couldn't immediately provide, like a utility bill.
In addition to the Borgata, the casinos that participated in the rollout were: the Tropicana Casino and Resort; Trump Plaza Hotel and Casino; the Trump Taj Mahal Casino Resort; Bally's Atlantic City and Caesars Atlantic City, along with the Golden Nugget.
The casinos, approved by the New Jersey Division of Gaming Enforcement, collectively offered 14 websites where customers can - eventually - make real-money bets.
Tina Gonzalez, of Ocean Township, in Monmouth County, tried to set up an account with the Borgata but wound up in a 40-minute call-center purgatory, then set up an account with Caesars and watched her computer crash.
"I made a small deposit, but when I tried to play they said I wasn't in New Jersey," she said. "I'm afraid that when they try to do this statewide on the 26th it's going to be mayhem."
She used the Twitter hash tag #softlaunchfromhell to describe her experience.
Others also took to social media to air their own grievances, including a man in western Monmouth County who was locked out by location technology that also didn't believe he was in the state, when he was a good 10 to 15 miles away from the border.
Joe Lupo, senior vice president of the Borgata, said the casino never intended to go online Thursday, and said it was still testing its systems.
The Tropicana set up an interview for a reporter with one of its customers Thursday, then canceled it, saying it hadn't yet gotten the go-ahead from its information technology partners to launch the system.
The test period was established to determine whether technology designed to ensure all gamblers are in New Jersey and at least 21 years old works correctly. The test also will evaluate electronic payment technology and the integrity and functionality of the casino games.
Online betting will mark the biggest expansion of gambling in New Jersey since casino gambling began in 1978.
Brennen, who played online poker years ago when its legality was murkier, expected to be patient with the new technology.
"The Borgata has always run top-notch since the day it opened, so I'm sure they'll be fine," he said. "When you're about to do something again you haven't been able to for years, you can wait a little longer."