Trump Envoys’ Moscow-Kyiv Trip Hits Security Hurdle as Witkoff and Kushner Prepare for Putin, Zelensky Talks
US President Donald Trump’s push for a Russia-Ukraine peace deal is facing a fresh complication: the safety of his two key envoys.
Special Envoy Steve Witkoff and Trump’s son-in-law Jared Kushner are expected to travel to Moscow and Kyiv this weekend for meetings aimed at keeping negotiations alive. But the plan has not been finalized, with Washington still seeking security commitments from both Russia and Ukraine, according to a source familiar with the situation cited by Reuters.
Reports from Russia’s state news agency TASS and US outlet Axios said the two envoys could visit Moscow on Saturday, September 5, before traveling to Kyiv on Sunday, September 6.
The trip would be significant because Witkoff and Kushner have previously traveled to Russia but have not yet held talks in Ukraine.
Why the trip is not yet certain
The main obstacle appears to be security.
The Reuters source said Washington wants assurances that the envoys will be protected while traveling between the two countries. According to the source, the US is seeking commitments from Ukraine not to strike Moscow during the envoys’ visit and from Russia not to attack Kyiv while they are there.
The concern comes as both sides have intensified long-range attacks.
Russia has launched repeated drone and missile strikes against Kyiv and other Ukrainian targets, while Ukraine has carried out increasingly deep drone attacks against Russian oil refineries, storage facilities and other infrastructure.
A Russian strike on Friday also hit the headquarters of Ukraine’s SBU security service in Kyiv, according to Ukrainian President Volodymyr Zelensky.
That attack underscored the difficulty of sending senior US negotiators into a city that has remained under sustained Russian aerial attack.
Kremlin spokesman Dmitry Peskov said Moscow would not announce the visit in advance, but indicated that Russia would provide information when the contacts take place.
Witkoff and Kushner could meet Putin first
If the reported schedule goes ahead, Witkoff and Kushner would meet Russian President Vladimir Putin in Moscow before heading to Kyiv for talks with Zelensky.
The sequence matters because the US team is attempting to engage both sides directly at a time when their positions remain far apart.
Putin said Thursday that there were still chances for a peace agreement, but he also maintained that Moscow and Kyiv must first reach an understanding between themselves.
Russia continues to demand major territorial concessions from Ukraine.
According to Reuters, Kremlin spokesman Peskov said Putin’s position that Ukraine should surrender the territory of four regions claimed by Russia and abandon its NATO ambitions remains “unshakeable.”
Ukraine has rejected those conditions, arguing that giving up territory under such terms would amount to surrender.
Russia currently controls roughly one-fifth of Ukraine, and the war has continued despite repeated US diplomatic efforts to move the two sides toward an agreement.
Ukraine is still under heavy Russian attack
The diplomatic push is unfolding against a worsening security backdrop.
CNN reported that Kyiv has faced near-continuous aerial attacks in recent days, with Russian strikes hitting buildings, warehouses and factories in and around the capital.
At least 53 people were killed and 134 injured in Kyiv city and the surrounding region between August 27 and the time of CNN’s report.
Russia has increasingly relied on large waves of drones and missiles, while Ukraine has responded with its own long-range attacks inside Russian territory.
Ukrainian strikes have targeted oil storage and refining facilities as well as commercial and industrial sites.
Zelensky has also warned about the dangers facing aircraft operating in Russian airspace. After those warnings, Putin accused Ukraine of making what he described as a threat of state terrorism.
The increasingly active air war makes the proposed diplomatic journey unusually complicated.
Zelensky has already confirmed talks are being planned
Despite the uncertainty, there have been several indications that the meetings are being arranged.
Zelensky said Thursday that tentative dates had been set for the US envoys to visit Ukraine. He said Witkoff and Kushner would arrive “in the coming days” and that he had spoken with both men earlier in the week.
The Ukrainian president also indicated that Kyiv would help ensure the safety of foreign diplomats during their visit.
TASS separately reported that the envoys were expected to travel to Moscow and Kyiv on September 5 and 6.
A Ukrainian lawmaker, Oleksiy Honcharenko, also said the expected schedule was Moscow on Saturday followed by Kyiv on Sunday.
However, Reuters’ reporting adds an important qualification: the itinerary remains subject to security arrangements.
That means the reported dates should not be treated as a finalized diplomatic schedule yet.
The bigger problem is still the peace deal
Even if the trip goes ahead without incident, the meetings are unlikely to produce an immediate end to the war.
The central disagreements between Moscow and Kyiv remain unresolved.
Russia wants Ukraine to make substantial territorial concessions and abandon its goal of joining NATO. Ukraine has repeatedly rejected those demands.
A source close to the Kremlin told Reuters that Putin remains focused on gaining additional territory and believes Russian forces could secure the remaining part of Donetsk by the end of the year.
Western military analysts cited by Reuters view that outcome as unlikely, pointing to Russia’s slow progress on the battlefield.
The gap between the two positions therefore remains enormous.
For Washington, the immediate goal of the Witkoff-Kushner trip may be less about announcing a final peace agreement and more about testing whether there is enough common ground to restart meaningful negotiations.
What makes the Moscow-Kyiv trip important
Witkoff and Kushner have become central figures in Trump’s attempts to broker an agreement between Russia and Ukraine.
They last visited Moscow in January, when they held lengthy talks with Putin at the Kremlin. Their expected visit to Kyiv would mark a new step in the US effort to engage directly with the Ukrainian side.
The timing is also notable.
The proposed meetings come while Russia and Ukraine are increasing attacks against each other, rather than observing a sustained ceasefire.
That creates a difficult contradiction for the US diplomatic effort: Washington is trying to move the two sides toward negotiations at the same moment that the battlefield and air war remain highly active.
The first test, therefore, may not be whether Witkoff and Kushner can persuade Putin and Zelensky to accept a peace framework.
It may simply be whether the two envoys can safely get from Moscow to Kyiv and hold the planned meetings.
For now, the weekend trip remains a reported plan rather than a confirmed final schedule. But if the security arrangements are completed, the Moscow-Kyiv journey could provide one of the clearest indications yet of how far Trump’s peace effort can move the two sides despite their deep differences.
