[4] The cancellation of the ambitious Kh-90 ramjet missile due to the INF Treaty in 1987 led to a renewed emphasis on improving on the Kh-55, in particular to achieve the <20 m accuracy required to hit infrastructure targets with conventional – as opposed to nuclear – warheads.

[17][19][20][21] Russian news agency TASS reported on 17 November 2016 that modernized Tu-95MS armed with Kh-55 and Kh-101 cruise missiles had launched airstrikes against targets in Syria.

[22][23] On 17 February 2017, Tu-95MS strategic bombers, flying from the Russian territory through the airspace of Iran and Iraq, attacked purported ISIL facilities near the Syrian city of Raqqa with the Kh-101 cruise missiles.

[24][better source needed] On 26 September 2017, Russia's Tu-95MS strategic bombers carried out further missile strikes with Kh-101 on ISIL and the Syrian branch of al-Qaeda (now known as Hayat Tahrir al-Sham) in the provinces of Idlib and Deir Ezzor.

"[26] Ukraine at War: Paving the Road from Survival to Victory,[27] a July 2022 study published by the UK Royal United Services Institute (RUSI) for Defense and Security Studies, disagreed, noting that "as far as Ukrainian military scientists can determine, this is actually quite rare", with RUSI instead attributing the high rate of downed missiles to Ukrainian interception.

On 6 March 2022, about eight Kh-101 cruise missiles launched by Tu-160 and Tu-95MS strategic bombers from over the Black Sea targeted the Havryshivka Vinnytsia International Airport.

[28] On 14 September 2022, Ukrainian MoD reported Russian forces used eight Kh-101 cruise missiles, probably from Tu-95MS bombers, to target various hydraulic structures in Kryvyi Rih.

[31] According to Defense Express, analysis of wreckage and debris from a Kh-101 shot down over Ukraine in March 2024 indicates that starting from early 2024, the size of the Kh-101 warhead was increased from 450kg to 800kg.

[37] The Russian Ministry of Foreign Affairs denied that Russia hit the hospital and claimed the destruction was caused by a Ukrainian air defense missile.