Kremlin forces appear to be badly losing their latest war, but it isn't in Syria or Ukraine.

It's in cyberspace, where Russia's communications watchdog Roskomnadzor this week began trying to block the popular messaging app Telegram because its encoded services are allegedly “terrorist friendly.” Since the app has consistently refused to hand over its encryption keys to law enforcement, it has been a target of official ire for at least three years.

But Roskomnadzor appears to have brought a sledge hammer to a knife fight, and so far its efforts to hit Telegram have created massive collateral damage among business and official websites. Meanwhile millions of Russians – including Kremlin officials and State Duma deputies – continue to use the service despite the ban, according to business news agency RBK.

It's not just about privacy, an issue that does not seem to be as important to Russians as it is for many in the West. Part of Telegram's popularity is that its news channels have become a major information source for Russians. Even Kremlin spokesman Dmitry Peskov used to regularly announce his upcoming briefings on Telegram because it was the most reliable medium. Both Kremlin loyalists and opponents have used it as a primary method for getting their messages out. It is also a way for Russian officials to anonymously leak information to the public.

Analysts say that while the Russian government may want to crack down on the country's freewheeling internet culture, exemplified by Telegram and its iconoclastic Russian founder, it has not equipped agencies like Roskomnadzor to do that, and it may well be an impossible task.

“Roskomnadzor is not only failing to achieve its goals, it is attracting more Russian users to Telegram,” says Alexey Kovalev, an independent media expert. “In fact it's a complete mess. How is it that a country that's accused of launching sophisticated cyber-campaigns around the world can't seem to do anything effectively in that department on its own home turf?”

Pavel Golovkin/AP People walk past paper airplanes that protesters threw in front of the Federal Security Service building in Lubyanskaya Square in Moscow, April 16, 2018. Russia's communications watchdog said Monday it has begun enforcing a nationwide ban for the popular messaging app Telegram.

Pavel Durov and the Kremlin

The Russian government has succeeded at blocking web networks before, most notably LinkedIn. The communications watchdog is now threatening to shut down Facebook, with its 25 million Russian users, by the end of the year. But in Telegram, it may have met its match.

Telegram has 14 million users in Russia, and 200 million worldwide. Its founder is Pavel Durov, often called the Russian Mark Zuckerburg, who has very deep pockets, immense tech-savvy, and a huge grudge against the Kremlin. Four years ago Mr. Durov was compelled to relinquish his stake in his own brainchild, VKontakte, Russia's most popular social network. The controlling stake was grabbed by Kremlin-friendly tycoon Alisher Usmanov.

There has been similar pressure to make Durov, who no longer lives in Russia, step away from Telegram. Once again one of Mr. Usmanov's social media projects, a messaging service called Tam-Tam, is being talked up as patriotic Russian replacement for it.

“Everyone sees through this hypocritical talk about Telegram being used by terrorists. Clearly the only reason for this is Pavel Durov's defiance of the Kremlin,” says Mr. Kovalev. “What we're seeing is a complete collapse of the state's credibility.”

Roskomnadzor has blocked plenty of websites in the past under Russia's draconian anti-extremism laws as well as a 2014 law that requires all internet services active in Russia to store their data on servers that are physically located inside the country. When LinkedIn failed to comply, the watchdog sent out letters to Russia's 4,500 Internet Service Providers, ordering them to restrict access to the site.

Last year the State Duma also legislated a ban on virtual private network (VPN) services that allow internet users to mask their own identities. That didn't work. According to Russian internet giant Yandex, the use of VPNs by Russians has spiked since the banning of Telegram.

“Over the last 5 years Roskomnadzor has blocked around 100,000 IP addresses, but what they have been doing over the past few days represents a giant leap,” says Alexander Kalinin, an expert on cyberdefense with IB Group in Russia. “If they do find a way to block Telegram they might do the same with other messenger services.”

Digital whack-a-mole

But blocking Telegram's IP address didn't do the trick, because Durov rapidly shifted to the cloud services of Amazon and Google, where millions of IP addresses could be used. Trying to shut down Telegram in a vast game of digital whack-a-mole, Roskomnadzor wreaked internet havoc among legitimate Russian websites that use the same services. Two days into the battle, Durov tweeted that the Russian government had blocked 15 million IP addresses without landing a punch on Telegram.

Within the last two days, Russia blocked over 15 million IP addresses in attempts to ban Telegram on its territory. Regardless, Telegram remained available for the majority of Russia’s residents #digitalresistance https://t.co/2syVbVzXPg — Pavel Durov (@durov) April 17, 2018

That may not last. Roskomnadzor is trying to convince internet giants Google and Amazon to drop Telegram from their app stores, and may well succeed. Crushing Telegram in Russia in some fashion similar to China's Great Firewall is possible, but will take a long and extensive effort to achieve, says Andrei Kolesnikov, a former communications official and veteran Russian cyber-expert.

“It all depends on the price they are willing to pay to create a controlled national cyberspace,” he says. “In China it's possible, but they don't do it by blocking IP addresses as Roskomnadzor is doing. In China they block the whole pattern. But this is a very expensive exercise” requiring vast resources and sustained effort, he says.

“In China the number of outbound links is limited, basically only three operators control all traffic. In Russia there are more than 1,000. So, Russia, in terms of internet architecture – the number of cross connections – is one of the most resilient internet countries in the world....

“What Roskomnadzor is doing now is basically playing a big game of cyber-Russian Roulette. They are creating a lot of collateral damage, and at some point they are going to hit some critical function at home or abroad and cause real trouble,” he says.

The trouble with Telegram

The power play against Telegram may be part of a larger battle to force internet giants like Facebook, Google, and Twitter to comply with the Russian law requiring them to store data on Russian servers. Kovalev thinks it may prove effective.

“Facebook cares more about its profits than its users; this is apparent from everything we are seeing,” he says. “It seems to be bargaining for terms [with the Russian government] now, and may cave to some of the demands. The same will likely happen with the others. They are profit-driven commercial companies, and Russia is a big market.”

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Not so with Telegram, which is a non-profit service, with a stubborn, idealistic, and anti-Kremlin genius at the helm.

“It's hard to predict how this is going to end,” says Mr. Kolesnikov. “This could go on a long time, and get very messy, because it doesn't look like either side is willing to back down.”