If a recent flurry of opposition from Microsoft, Amazon, Yahoo, the U.S. register of copyrights and the governments of Germany and France, to name just a few, was not a clear enough indicator of disaster for the historic proposed settlement between Google and book publishers and authors, the 32-page brief filed late Friday by the U.S. Department of Justice, seems almost certain to derail the agreement, at least as currently constructed.

“The breadth of the proposed settlement—especially the forward-looking business arrangements it seeks to create—raises significant legal concerns,” wrote the Justice lawyers, including William Cavanaugh of the antitrust division and John Clopper, a Southern District assistant U.S. attorney. “This court should reject the proposed settlement in its current form and encourage the parties to continue negotiations to modify it so as to comply with [class action law] and the copyright and antitrust laws.”