After the Obama administration sanctioned SMP Bank — in which Mr. Rotenberg and his brother own a 76 percent stake — Russia’s Central Bank gave it a 10-year, $3 billion loan with a below-market interest rate, ostensibly to take over another struggling lender. When Italy seized $40 million of property Mr. Rotenberg owns there through offshore companies, including a luxury hotel in Rome and two villas in Sardinia, the lower house of Parliament quickly passed legislation allowing citizens whose property had been seized to seek compensation from the government. Though the tycoon has said he does not plan to take advantage of it, the bill was immediately called “the Rotenberg law.”

Whatever Mr. Rotenberg’s precise relationship to Enlightenment, his role as chairman offers the company the sort of protection — known as “krysha,” or roof — that ensures a favored status in the bureaucracy. The publishing house is not only well positioned to take advantage of the unified textbook mandate, but also another new directive that mandates that all textbook publishers offer electronic versions of their books by January 2015.

According to Mr. Konobeyev, smaller publishers like Titul are still waiting for the ministry’s electronic textbook guidelines. Enlightenment, however, is ready to go, according to Mr. Ivanov. The agreement the publisher signed with Microsoft in late September, to share research and development on a Windows-based tablet that could be provided to schools across the country, should only “strengthen our position in the market,” he said.

The question for Microsoft, as with many American companies doing business in Mr. Putin’s Russia, is whether the potential profits outweigh the risk. United States law forbids American companies from doing business with companies majority-owned or controlled by sanctioned people like Mr. Rotenberg.

His presence on the board, the opacity of the ownership structure and other elements of the sale should make an American company reluctant to do business with Enlightenment, said Katrina Carroll, a lawyer at WilmerHale who until last year was a senior officer in the Treasury Department’s office of terrorist financing and financial crimes. “I’d never advise a client of mine to go forward under these circumstances,” she said.

Last week, Microsoft decided to put off its plans, based on new information it had received from The Times.

“Microsoft signed a nonbinding agreement to provide, free of charge, to Prosveshcheniye, the same type of technical assistance that we provide at no cost to thousands of schools and publishers worldwide,” the company said in a statement. “Although we conducted due diligence in both Russia and the U.S. — including consulting the U.S. government and engaging respected international law firms — and have not found evidence that Prosveshcheniye is subject to U.S. or E.U. sanctions, we’ll follow up on the concerns by postponing work under the agreement and conducting an additional review.”