A $5.8 Billion Test
Software companies used to find it easy to borrow money. Not anymore.
Lenders have spent 2026 worrying that artificial intelligence will make some older software businesses worth less.
New AI tools can do parts of the work those businesses sell. So lenders are not sure how durable their profits will be.
That worry has made them picky about who gets a loan. Gainwell Technologies is about to find out just how picky.
Refinancing means swapping old debt for new debt, usually to buy time before payments come due. The plan wipes out all of Gainwell's current borrowing.
As part of that plan, the company began marketing a loan to a business already carrying heavy debt, a type of financing known as a leveraged loan.
The maturity is five years, a person with knowledge of the matter said. The source asked not to be named because they were not authorized to speak publicly.
Why Software Debt Got Pricier
Software companies are getting a colder shoulder from lenders than the rest of the leveraged-loan market. The gap is the biggest in years.
Get the free Always Be Buying eBook and learn the simple system for building wealth on any income
When these companies come looking for money, investors demand better terms. Proofpoint Inc. showed what that looks like.
In late July, the Thoma Bravo-owned company had to rework its $4.3 billion financing and hand lenders major concessions because of anxiety about AI-driven disruption.
A concession is simply a better deal for the lender, like a higher interest rate or extra protections if things go wrong.
That same anxiety has pushed many private-equity-owned software firms to pay more and borrow for less time.
Shorter maturities mean the borrowed money comes due sooner, which puts more pressure on the company to perform. Gainwell's deal shows the pattern.
Gainwell is marketing the first-lien loan with an interest margin of up to 4.75 percentage points above a benchmark. The offering price is 98 cents per dollar, so buyers get the debt for less than its face value, which adds to their return.
What This Deal Tells Us
Gainwell is not borrowing from a position of strength, at least on paper.
Moody's and S&P both give the company a triple-C rating, a credit score that counts among the weakest for leveraged borrowers.
Even so, S&P moved Friday to put Gainwell under review for a possible upgrade. The agency said the refinancing "will address significant approaching maturities and improve liquidity."
A lender call is set for Monday. The loan's final size has not been decided.
Last week, Bloomberg News reported Gainwell was in talks to refinance nearly $5.7 billion in debt, so the plan that emerged Friday is a bit bigger.
The transaction is not meant to raise fresh money for growth; it exists to replace old loans and buy breathing room. That makes investor demand a pure test of confidence in Gainwell's cash flow and its ability to withstand AI-related disruption.
Why should you care if you are not a lender? Software is one of the industries most exposed to the artificial-intelligence shift. That shift is deciding which companies can borrow money, on what terms, and at what price.
If the biggest software debt deal of 2026 clears easily, it suggests lenders have made peace with AI. If Gainwell has to give more ground, the fear is not going away.
Either way, the cost of borrowing eventually reaches your portfolio. Companies paying more to borrow have less left over for growth, hiring, and the profits that turn into investment returns.
Download the free Always Be Buying eBook and start putting your money to work today
