District Court Judge Colleen Kollar-Kotelly ordered Microsoft into intense settlement talks with the US Department of Justice (DOJ) and the 18 state attorneys general in September.
Kollar-Kotelly had set a deadline of 12 October for both sides to work out an agreement on their own or bring in a mediator to help steer to a settlement in the next three weeks
With the passing of the first deadline, most legal and industry experts say there is little chance that the two sides will reach a consensus.
Microsoft would not comment on whether any progress in the ongoing settlement talks would be announced or on the status or content of any talks currently under way.
Microsoft and the government plaintiffs will meet Kollar-Kotelly on 12 October to update the court on the settlement efforts. The two sides are also expected to offer names of potential mediators to take over the discussions, or the court will appoint one.
Ernest Gellhorn, an antitrust professor at George Mason University Law School said there was little chance for the case to end out of court. "It could happen, but it would be a surprise," he said.
Gellhorn noted that the two sides have already tried a similar settlement effort with no luck. In April 2000, before District Court Judge Thomas Penfield Jackson delivered his original ruling that Microsoft had illegally used its monopoly of the operating system to hurt competitors in other markets, the case was sent into negotiations. After five months of protracted talks, no deal emerged.
Microsoft has now exhausted most of its remaining avenues of appeal. The US Supreme Court announced on 9 October that it had rejected the company's request for a review, offering no accompanying opinion.
If a settlement is still incomplete by the November deadline, Kollar-Kotelly has ordered that the case be sent back to trial, where she will devise a remedy to impose on Microsoft.