(CNN) — In the fall of 2018, Hunter Biden received a rapid succession of emails from his accountant — all about his taxes.

“You’re late,” Bill Morgan told his client in October, noting that Biden had missed an already extended deadline of October 15.

“Your 2017 tax returns have yet to be filed,” the accountant reminded Biden two weeks later.

“You need to file 2017 so we can try to work out a payment schedule,” he added the next day.

Morgan also noted in that email that Hunter Biden’s aide had sent him a copy of a 2015 Internal Revenue Service notice. “They want $158,000,” the accountant wrote. “IRS has notified the State Department and they will not renew your passport until this is resolved.”

Welcome to the dysfunctional world of Hunter Biden’s finances. While the general topic of the president’s son’s financial woes has been widely reported, the details surrounding his earlier presentations may offer a glimpse into some of the areas federal investigators are delving into as part of an ongoing investigation. about possible tax violations and other crimes approaching a critical juncture. Prosecutors, the sources say, could make a decision soon on whether to bring criminal charges against the president’s son.

Hunter Biden’s legal danger has been exploited by Republicans seeking to accuse his father, President Joe Biden, of being an accessory to his alleged wrongdoing. Republicans hope, if they regain control of the House of Representatives, to investigate the Biden family through committees they will control.

Biden has denied any wrongdoing and has said he has cooperated with investigators. Her father is not implicated in the ongoing federal investigation, according to sources briefed on the matter.

CNN hired a cyberforensics expert to help authenticate a cache of emails related to Hunter Biden’s finances that were posted online by a former Trump White House aide and allegedly traced to a laptop that turned up at a repair shop. from Del.

The information from the laptop has fueled countless stories about Biden’s drug abuse, alleged sexual indiscretions and financial woes, many of which CNN — and other media outlets — have been unable to verify. Hunter Biden has not commented directly on the authenticity of the emails or the stories they are based on. He told CBS News last year that he didn’t know if that laptop was his.

Jake Williams, a former National Security Agency agent who analyzed the emails for CNN, said he was able to authenticate a subset of the emails because they contained verified signatures within their metadata that showed they had not been modified. Only emails that he authenticated are cited in this report.

Williams, who previously reviewed laptop data for The Washington Post, said most of the emails she reviewed for CNN could not be verified because they lacked the technical data needed for the validation process, among other reasons.

CNN’s review of emails showed that Hunter Biden struggled with fiscal problems for years and that at times his accountant seemed lost to keep track of the flow of the president’s son’s money. In an email, his accountant raised a question about a $550,000 receipt, asking whether it should be recorded as a loan or income from Burisma, the Ukrainian energy company on whose board Biden served. No response from Biden is shown in that email chain.

Biden received up to $50,000 a month for serving on Burisma’s board from 2014 to 2019, according to a Republican-led Senate report on his business activities.

Despite that generous income, Biden’s debts piled up, even as he received repeated warnings from his bank, his accountant and others.

“Insufficient funds,” read an automated Wells Fargo email Biden received in December 2018 that said one of his accounts was $1,700 short of a Porsche payment. Other bank alerts that year warned that Biden’s checking account had a “low balance” and that one of his credit cards had exceeded its “preset amount” of $65,000.

Attempts to charge another credit card were repeatedly declined due to insufficient funds, multiple emails in 2018 and 2019 show.

“I’m trying to figure out what to do with the bills,” Biden’s then-assistant emailed him on Dec. 28, 2018. She listed a number of payments Hunter Biden owed, including health insurance, a car payment and his salary.

“Pay for the health care. Pay for the Porsche,” Biden responded, though he said she should pay herself half the salary she said she was owed. Biden also complained that someone else was still receiving a portion of what she said Burisma owed her personally. “So there’s not much income these days,” she told him.

By March 2019, Hunter Biden’s bills, debts and back taxes totaled more than half a million dollars, according to another email from his assistant.

“Please let me know if there is a new plan to pay these bills,” his assistant wrote in that message, noting that he still owed about $370,000 in taxes and $120,000 in other bank debt.

Biden’s aide did not respond to multiple requests for comment.

Hunter Biden’s attorney, Chris Clark, said his client has now “paid in full” his IRS tax debts. Clark added that 2018 and 2019 were tough times for Biden, who struggled with alcohol and drug addiction after his brother Beau’s death. It’s unclear how far back prosecutors may be looking into Biden’s tax problems, which the emails say date back to 2015 and continued into 2019.

“He is current on his tax obligations and is committed to remaining so as he continues his recovery from addiction,” Clark said.

During some of the same months that Biden’s accountant messaged him about taxes owed, Biden made large cash withdrawals, emails show. He withdrew about $4,800 from ATMs in about two weeks in October 2018, for example.

Hunter Biden’s ex-wife, Kathleen Buhle, wrote a recent book recounting the couple’s financial struggles when they married. “More than once my debit card was declined at a store. I had to call Hunter to transfer money to my account,” she wrote in her book published earlier this year. “Hunter and I drove nice cars and had a nice house, but we were going fast on that hamster wheel and barely keeping up.”

In 2018, Buhle wrote to Morgan, the accountant, who has since died, seeking advice about an IRS tax lien based on an unpaid $112,805 bill.

Buhle said she was “at a loss” and asked Morgan to “please advise.”

In his own book, “Beautiful Things,” published last year, Hunter Biden wrote candidly about his addictions. He told NPR that he wrote the book to give hope to others who have struggled with substance abuse. He shared that the paychecks he received for being on the board of the Ukrainian natural gas company Burisma provided him with cash for crack.

“But because of that crazy, bad ending, the board pay morphed into some kind of fun, wicked money,” Biden wrote. “I was haunted by spending recklessly, dangerously, destructively. Humiliatingly. And I did.”

And he kept mending himself, “both figuratively and literally,” he wrote. “I still have a lot of work to do with myself, with my addiction and cleaning up the remnants of my past.”

CNN’s Katelyn Polantz and Jeff Winter contributed to this report.

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