SAN FRANCISCO — Yahoo is making amends for years of blundering with one smart move: an early investment in China’s Alibaba Group that has turned into a multibillion-dollar boon.

The latest windfall will be delivered with Alibaba’s record-setting IPO completed Thursday, which is expected raise up to $25 billion for the e-commerce company and its early backers. The company’s shares will begin trading for the first time today on the New York Stock Exchange.

Yahoo is in line to make anywhere from $8.3 billion to $9.5 billion from the initial public offering, depending on whether investment bankers exercise their right to buy additional stock in the deal. The payoff supplements the $7.6 billion jackpot that Yahoo collected two years ago after selling another chunk of its Alibaba holdings and reworked a licensing agreement with the Chinese company.

Even if Yahoo ends up selling its maximum allotment of 140 million shares in the IPO, the Sunnyvale, Calif., company will still retain a roughly 16 percent stake in Alibaba Group Ltd. worth another $26 billion to $27 billion.

Not a bad return, considering Yahoo acquired its Alibaba stake for $1 billion in 2005 in a deal engineered by company co-founder Jerry Yang and former CEO Terry Semel.

The Alibaba investment has helped ease the pain of Yahoo’s struggles in Internet advertising, the heart of its business. Yahoo’s annual revenue has slipped from a peak of $7.2 billion to projected $4.5 billion this year, a decline of nearly 40 percent.

The downturn has occurred even as advertisers steadily shift more of their budgets to the Internet and mobile devices, but most of that money is flowing to Yahoo rivals such as Google and Facebook — companies that have built more compelling digital services.