7 On Your Side started investigating and it's unclear exactly how many people are affected, but now legislators and the state's top cop are probing for answers.
"A lot of anger, a lot of frustration," said Samantha Gobler, a single mom.
"It's the most aggravating thing," said Max McGuire, an Empire Blue Cross customer.
Max McGuire and Samantha Gobler are both in healthcare purgatory.
She's been trying since October to get insurance through the Affordable Care Act. The marketplace website shuttled her to Empire Blue Cross.
"Dealing with Empire has been a nightmare," Gobler said.
Fighting over the phone with New York State's largest insurer's become a routine part of the single mom's day.
"She couldn't answer if you've paid for insurance or not?" 7 On Your Side's Nina Pineda asked.
"No," Gobler said.
"She couldn't answer if you're covered?" Pineda asked.
"No," Gobler said.
"She couldn't send out your cards?" Pineda asked.
"No," Gobler replied.
Out in Northport, Max is maxed out of patience, the hypertension and diabetes patient was shocked after a recent visit to his doctor's office.
He had no coverage, even though he thought he enrolled over and over.
"You paid three times?" Pineda asked.
"I paid four," McGuire said, "You're sitting on the phone for an hour and half with somebody who says, 'I don't know what to tell you, you're paying isn't here."
"I do not think they've been responsible as a company," State Senator Liz Krueger said.
State Senator Liz Krueger wants to find out if any laws have been broken and is asking for the Attorney General to investigate after getting an earful from constituents with Empire enrollment issues.
In this letter 7 On Your Side obtained, the Attorney General tells the CEO of the insurance giant, people with chronic condition and needing emergency care were left with "a gap in coverage that can be devastating."
"The scary thing is what if you didn't get the healthcare you needed because you couldn't pay out of pocket and the insurance wasn't there," Krueger said.
But after 7 On Your Side got involved there were results.
"I got a wonderful call from Blue cross blue shield," McGuire said.
Max got a letter stating his coverage began January 10th, and the same day, Samantha's doctor said both she and her daughter are insured.
"Thanks to 7 On Your Side for making it happen, we're one of the lucky ones," Gobler said.
An Empire spokesperson acknowledged the numerous enrollment problems but said they've made "significant progress" in "resolving outstanding issues" and extended call center hours and just shipped out 15,000 ID cards.
For those who've had problems, or haven't paid, they've extended the deadline to pay to the 31st. Coverage will be retroactive to the 1st of the year.