Trump and his favorite fundraising platform both face donor problems

• Donald Trump's preferred digital fundraising operation is under scrutiny during the crucial 2024 presidential election.
• New emails give a window into the struggles some small-dollar donors are having with WinRed.
• Small-dollar donations to Trump's campaign in 2023 were a fraction of what he raised from small-dollar donors in 2019, both years during which he was campaigning for president the year before an election.

Every so often, Matthew Hurtt receives concerning emails. The subject lines are each slightly different: "Stop charging my account," "Urgent!" and "Donation not approved," but the people who send them all want the same thing: to halt the Republican political contribution platform WinRed from making any more automatic, recurring withdrawals from their accounts.

Hurtt is chairman of the Virginia-based Arlington County Republican Committee and says he's reviewed a "few dozen" of these types of emails since the 2020 election. When WinRed processes a contribution to a Republican campaign, the charge shows up on the donor's credit card or bank statement as a payment to "WINRED www.GOP.com, Arlington VA," according to a statement provided by Hurtt and reviewed by CNBC.

As a result, people often mistakenly believe their money went to the Arlington County Republican Party, he said.

"Cancel account and stop billing my credit card," Oklahoma resident Samie Elliot wrote in a January email that landed in Hurtt's inbox. She later explained to him that neither she nor her husband, who are both retired, recalled ever signing up for recurring monthly political donations and that these charges have been occurring for at least a year.

Federal Election Commission records, however, paint a very different picture of the Elliots.