No shops are open, and the city has had no electricity, gas or water for three years.
Ukraine has attempted to deliver supplies but has not had success in recent months, and it is deemed too dangerous to risk leaving on foot along mined roads out of the city. The ceasefire is supposed to allow supplies to reach the city and enable its roads to be cleared of mines to allow people safe passage out.
One woman told the BBC she is in hospital recovering from two surgeries after stepping on a land mine.
“I don’t know how long I will have to spend there,” she said, worried about not being able to join Friday’s planned evacuation.
It is hard to make contact with people in Oleshky as communication is patchy and and many are reluctant to speak of the situation in fear of reprisals from the Russians, making it is difficult to verify reports the ceasefire is being implemented.
Many details on the evacuations plans are unclear, initially including how and where to register for it. Some people want to know if they can bring their pets. Others are questioning what future they will have if they opt to leave their homes.
While people are optimistic about leaving, there are also fears that Russia may not allow them to return to Ukraine, or examine their phones and online activity for signs of Ukrainian support, which could see them be taken away and tortured.
Someone who has been speaking to family in Oleshky said they fear shooting could restart during evacuations and Ukraine will somehow be blamed for not upholding the truce.
Last month, the Kremlin acknowledged that Oleshky faced “a critical situation” and “problems with supplies of food and medicine”, but added that “Russia’s military was working to resolve them” and blamed Kyiv.
In response to the situation, the White House said last week that Melania Trump had secured a ceasefire, with no details for how long it would last.
Russia’s defence ministry said on Telegram it had stopped firing toward the Ukrainian city of Kherson – across the river from Oleshky – at 04:00 Moscow time (01:00 GMT) in preparation for the humanitarian operation.
Ukraine’s parliament commissioner for human rights, Dmytro Lubinets, also confirmed in a social media post that the ceasefire had begun.
“As head of the Ukrainian negotiating team, I confirm that the Ukrainian side is honouring its commitments,” he wrote on Facebook.
The White House said in the statement last week that “non-military, civilian leaders from both countries will work together to visit Oleshky residents in their homes and determine the level of assistance they require”.
While the US first lady is relatively lower profile than some of her predecessors – and only occasionally seen at White House events – she has become involved in addressing humanitarian issues stemming from the Russia-Ukraine war.
In August 2025, she penned a letter to Russian President Vladimir Putin, telling him it was “time to protect children and future generations worldwide”.
While a truce is under way in Oleshky, elsewhere strikes continue.
On Monday evening, attacks on the Ukrainian capital Kyiv hit a university and a bridge, killing one person and injuring 14 others.
In Russia, one person was killed and six others were injured after a Ukrainian drone strike on Bryansk.
Additional reporting by Hafsa Khalil and Sareen Habeshian
