Xerox is working with bankers at Jefferies to prepare a new bond issue, which would refinance a bridge loan the investment bank provided to fund the company’s recent repurchase of its own stock from Carl Icahn, according to 9fin sources.

The exact timing of the bond offering is yet to be determined, but the deal could potentially be launched before the end of October, the sources said. The company is expected to issue around $555m of bonds, the same size as the bridge loan.

Xerox’s stock currently trades at $14.19 per share for a market cap of $2.23bn. The company is holding a webcast on 24 October to discuss its third quarter earnings.

By replacing the Jefferies bridge loan with bonds, which are expected to be offered to a large group of institutional investors, Xerox would fully turn the page on the Carl Icahn chapter of its long history.

The veteran investor took a stake in the printing company back in 2015. He worked the typical shareholder activism playbook, urging the company to explore strategic alternatives and demanding to sit on its board. In 2018, Xerox split into two separate entities — one focused on hardware, the other on services — and gave Icahn three board seats. Then things got messy.

Five years and many lawsuits later, following a legal battle over the company’s leadership and a failed takeover bid for computer hardware giant HP, it’s Icahn who finds himself under pressure from investors. His company Icahn Enterprises has been targeted by short-selling firm Hindenburg Research, which earlier this year accused the company of a “ponzi-like” structure in which proceeds from new share issuances are used to fund dividends to existing shareholders.

Icahn’s problems have mounted over recent months. In the weeks following Hindenburg’s report, he admitted to the FT that he was wrong to take huge bets that financial markets would crash, and in July he was forced to restructure a multi-billion dollar personal loan provided by a group of investment banks and backed by his holdings of Icahn Enterprises stock.

A successful Xerox bond issue would also shift some risk from Jefferies’ bridge book. The investment bank was named in Hindenburg’s original report in May, in which the short-seller argued that consistent buy recommendations from Jefferies’ sell-side research team helped prop up the Icahn Enterprises stock price.

It’s unusual for an investment bank to underwrite such a large loan for a single share buyback. Icahn is one of a small handful of high-profile clients that command enough influence to receive this kind of treatment, said a source familiar with the situation.

Headquartered in Connecticut, Xerox is a relatively familiar name in the high yield market. It has multiple bonds in its capital structure, including 5% notes that mature in 2025. Those notes currently trade at 93.8 for a yield-to-worst of 8.766%.

Xerox declined to comment for this article. A spokesperson for Moelis, which advised Xerox on its repurchase of stock from Icahn, responded to our inquires but did not provide comment. The media team at Jefferies did not respond to an email requesting comment.