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Authorities in Iran are expanding their reach in their efforts to enforce compliance with the country’s strict hijab law by pushing popular start-up companies to police their younger, tech-savvy employees.

In recent weeks, the operations of at least three web-based companies — the DigiKala online retailer, the Azki.com insurance company, and the Taaghche book app — have been shut down. In each case, the closures came after the emergence of photographs showing female employees without the mandatory head scarf.

The images had reportedly been posted on employees’ personal social-media accounts, not by the companies themselves. But that did not prevent the authorities from going after the start-ups that until recently had been touted for their successful, cutting-edge business models.

The pressure on such firms comes after Culture and Islamic Guidance Minister Mohammad Mehdi Esmaili said on July 27 that action would be taken against start-up companies if their employees failed to comply with the Chastity and Hijab Law.

But observers say Tehran is playing a dangerous game that threatens to further alienate the younger generation and potentially make entrepreneurs and foreign investors think twice about bringing modern businesses to the Islamic republic.

The start-ups that have come under scrutiny vary in their organization, with some being private, some semi-private, and some having strong ties to the government either directly or indirectly, Amir Rashidi, the New-York-based director of Internet security and digital rights at the Miaan Group, told RFE/RL.

But they all share common traits and differ from the old way of doing business in Iran, in that they employ young, educated people to deliver services to younger customers using modern technology.

“The kind of culture that exists [at the companies] is usually not the kind of culture that could represent the culture of the Iranian government,” Rashidi said. “Because this is the new generation. These are the techie people. These are the most connected population of Iranians, who are connected to the outside world because of the Internet, because of the job that they do, who have more opportunity to be in touch with [people] outside the country.”

In the wake of months of street protests that broke out last year against the Islamic dress code and the clerical establishment, hard-liners have sought to strengthen the Chastity and Hijab Law. According to new draft legislation presented by parliament late last month, fines of up to $720 can be levied against women who defy the law, along with prison sentences of up to three years.

The revision of the law was prompted by the protests that began following the death of 22-year-old Mahsa Amini after she was arrested for an alleged hijab violation, and has been described by prominent members of the clerical establishment as necessary to preserve the Islamic republic’s fundamental values.

Amid a crackdown on the antiestablishment protests that resulted in at least 500 deaths since September, the authorities have disrupted Internet access multiple times and have gone after individuals who used social media to show support for the demonstrations by posting pictures of themselves without head scarves.

Prominent female celebrities and athletes have been among those targeted, including three film and television actresses who were sentenced last month and diagnosed as having personality disorders after they were photographed without their hijabs.

On July 23, the pressure on start-ups began with the suspension of DigiKala’s business. And just a day before parliament published the text of the new Chastity and Hijab bill, and hours after Esmaili’s warning to start-ups, a legal case was filed on July 27 against the book retailer Taaghche, along with similar actions against Azki.com.

The shutdown of the companies had an immediate effect, with customers expressing dismay at being cut off from purchasing books, products, and services online, and business associations warning that the action would harm efforts to develop the business sector.

Since then, Azki.com and Taaghche have been allowed to resume operations after releasing public commitments that they and their employees would adhere to the Chastity and Hijab Law.

The situation at DigiKala, often described as Iran’s Amazon online retailer, remains unclear.

On August 2, a post on the company’s website said that the “violation” depicted in a photograph posted on the personal site of one of its employees “was not approved by the company’s management.” DigiKala, the statement continued, “always considers itself obligated to comply with all national laws” and the company hoped that by being allowed to resume operations it “can play a more substantial role in better serving the people and economy of the Islamic republic.”

Then, within hours, the statement was inexplicably removed, and the company’s offices remain sealed and its business suspended.

In its effort to exert control over the start-ups, which have been lauded as examples of Iran’s ability to successfully launch modern companies on its own despite the hurdle of international sanctions, Tehran is essentially forcing them to police their own employees.

But the approach has been met with warnings by the Association of Emerging Businesses of Iran, which following Azki.com’s closure said that such suspensions presented a “big and crisis-causing obstacle” to the development of the private sector.

Rashidi expressed skepticism that “using people against people” would work, both at the societal and business level.

He says that in the absence of digital rights and the recent emphasis on compliance with the Chastity and Hijab Law, the government will be able to catch offenders more easily and to fine and even arrest them. But in the end, he said, “it’s going to create more tension and challenges.”

And outside investors and partners of Iranian companies are likely to take note as well, Rashidi said.

“Some of these companies have investors from outside Iran,” he said. “And this definitely will affect those companies, because they don’t want to be seen internationally as a supporter of censorship.”