Moscow's defence ministry released a video showing the new Tu-22M3 strategic bomber taking off with a MiG-31 fighter jet before the MiG releases the Kinzhal missile, which shoots a cone of flames behind it as it accelerates out of frame.
The exercise "worked out planning, preparing and joint operating of Kinzhal missile systems and Tu-22m3 long-range bombers", the ministry said.
Mounting the Kinzhal on the Tu-22M3 increases its range from 1,200 miles to over 1,800 miles, sources in the defence industry told the state-run TASS news agency.
The bomber will also be capable of carrying several of the missiles, which take their name from a type of double-edged dagger and are reportedly capable of travelling up to 10 times the speed of sound.
They can also carry a nuclear payload.
Russia's president, Mr Putin, has described the missile as an "ideal weapon". He claimed it flies at such a speed it was "invincible" to Nato's missile and air defence systems.
The missile has been tested at least 12 times, with the most recent trial taking place in July against a target nearly 500 miles away, CNBC reported.
The Russian military said a squadron armed with the missiles has been patrolling the Caspian Sea since April.
Although Mr Putin boasted about the Kinzhal and other weapons systems at an annual state address in March, the US defence secretary, James Mattis, has said the technology showed nothing which would change the Pentagon's perspective.
“I saw no change to the Russian military capability and each of these systems that he’s talking about that are still years away, I do not see them changing the military balance," he said.
"They do not impact any need on our side for a change in our deterrence posture.”
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