The 20 or so civilians, some of them quite elderly, make their way gingerly across the blown-up bridge that leads to government-controlled territory.
More importantly, it will give them access to medicine, money and cheaper provisions.
"When you're 56 of course it's hard, but we have to climb because we need money," Lena Vasilivna tells me after scaling the informal border on her return journey.
Credit cards, banks and ATMs don't function at all in the rebel-held east.
People are cut off from all the services the Ukrainian state would usually provide, such as pensions and benefits.
The government made an official announcement in November, but locals say the funds dried up months before that.
The conflict between the Ukrainian government and pro-Russian separatist rebels has claimed more than 6,334 lives since it erupted 13 months ago, according to conservative estimates from UN relief officials.
The Ukrainian government of Petro Poroshenko puts the death toll above 8,600, including nearly 7,000 civilians.
The war, which holds enormous geopolitical importance for Russia and Europe, grew out of protests by pro-Russian separatists, which escalated after Russia's annexation of Ukraine's southeastern peninsula of Crimea.
Russia's move followed the February 2014 revolution that overthrew pro-Moscow president Viktor Yanukovych.
Separatists took control of parts of the Donetsk and Luhansk regions and set up the self-proclaimed "Donetsk People's Republic" (DPR) and "Luhansk People’s Republic" (LPR) in April.
Kiev and NATO say the rebels are backed by Moscow, which Russia denies.
The war’s frontline has become Ukraine’s de facto Berlin Wall, splitting the country east and west, dividing the two populations – sometimes members of the same family even – into haves and have-nots.
An untold number of civilians cross the frontline every month to get money and supplies from the west.
They can't afford to stay there and rent apartments, especially with no means of employment, so they return east with whatever they can carry.
Vasilivna lives in the small village of Nikolaevka, seven kilometers from the bridge.
When fighting intensified in February, she slept on the floor in the corridor, hoping the extra walls would provide greater protection if a shell hit.
Once a month, she makes her way like hundreds of others across the bridge to the town of Stanytsia Luhanska to pick up her mother's medication for high blood pressure and her pension from the post office.
In government-controlled territory, Vasilivna has access to cheaper goods.
At home, she would pay $5.65 for one kilo of pork fat.
Across the bridge, she can get it for $2.11.
A box of teabags costs 70 cents on the western side versus $1.65 on the east.
She has to stop at three checkpoints and is never sure she'll be allowed to pass.
Sometimes, the guards say she cannot go through for security reasons.
Other times, she is denied passage but given no explanation.
Even when she does make it, difficult trade-offs have to be made:
"If we buy medicine, we can't afford to buy some food," she explains.
Who is helping?
Most of the estimated 1.2 million Ukrainians in need of assistance in rebel-held Ukraine can't keep crossing to and fro like Vasilivna to make ends meet.
Many have no income at all and are reliant on whatever aid comes their way.
According to an extensive assessment of humanitarian needs conducted by the NGO Forum in Ukraine in March, of the more than 670,000 people who urgently needed food aid, almost 90 percent were in rebel-held areas.
International aid agencies are struggling to fill the void left by the Ukrainian government, which cannot access the rebel-held east, and by the separatists, who are trying to build their own quasi-state with limited means.
It is an impossible task, especially as February's truce is a ceasefire in name only.
"There's a huge population that we will never be able to cover," Loïc Jaeger, deputy head of mission for Médecins Sans Frontières (MSF) in Ukraine, tells me.
A limited number of aid convoys do cross quite regularly from the west, but they can't access certain areas, especially villages in lawless Luhansk region far from crossing points, down minor roads.
Some help is provided by the Russian government, but it isn’t clear how widespread or regular this assistance is.
Aid agencies are also hampered by a Ukrainian government policy, introduced in January, requiring people who travel from government-controlled areas into rebel-held territory to formally apply for permission first.
Daniel Bunnskog, the International Committee of the Red Cross (ICRC) representative in Luhansk, says this bureaucracy means dozens of trucks have been left languishing for days at Ukrainian checkpoints waiting for the correct passes.
"It doesn't seem to be a unified system where everybody has the same opinion of what's supposed to happen when you come with your passes and trucks," he says.
"It makes the timely delivery of the assistance very difficult."
The policy has limited the amount of aid the UN's World Food Programme (WFP) can deliver in rebel territory.
WFP reports officer Ryan Mcdonagh says figuring out how to get past the checkpoints has become a daily struggle because the process is so inconsistent and unreliable.
"It's really important to get food in now… you have areas that have been cut off for months," he tells me.
"At the same time that we’re trying to get in as much food as possible to some of these (rebel-held) areas, this administrative hurdle becomes an increasingly more burdensome challenge."
Many people in the rebel-held part of Luhansk region have to rely on soup kitchens run by separatists.
Apart from MSF and ICRC, few international aid organisations have a consistent presence here, where the humanitarian crisis is worst.
"There are very few humanitarian actors to fill the gap which actually exists between needs and what is available," Bunnskog says.
"The main provider of assistance is (the) so-called LPR government… mainly through the (assistance) it receives from the Russian side."
Impossible security situation
Even in Donetsk, a city of one million people before the war that is significantly better resourced than most, hundreds of people still seek food and medicine every day.
When I visit in early spring, the majority of shops are closed down, but there are still markets and grocery stores open.
This is also true for the rebel stronghold of Luhansk city, where most businesses are boarded up yet some supermarkets remain well-stocked.
As I drive north or west from Luhansk city or north from Donetsk, however, a different story quickly emerges: the scale of the destruction increases dramatically as I enter the heavily shelled areas close to the frontline.
The conditions I find are appalling in many towns and villages.
But the security situation is calmer than it was, especially during the bouts of intense fighting that marked the long, hard winter.
Access to rebel-held areas has significantly improved since a second ceasefire agreement was struck in February, allowing more aid convoys to make their way in (the first, in September, collapsed almost immediately).
But the fighting has not stopped.
Both sides blame each other for truce violations and mortar and grenade attacks are still reported regularly.
The Ukrainian government accuses the rebels of continuing to use heavy weapons that should have been withdrawn under the peace deal.
At least nine fatalities were reported just on Wednesday, most of them civilians.
The security situation is particularly dicey in Luhansk region, where an increasing number of assassinations of rebel commanders in recent months has been interpreted by Kiev as a sign of growing divisions between rival separatist factions.
Control of towns and checkpoints in the rebel-held part of Luhansk region are nominally split between the separatist LPR "government" and a group of Ukrainian Cossacks – famed for their traditional role in defending the borders of the Russian empire.
But some frontline towns, like Pervomaisk, have witnessed bitter internal power struggles.
In January, the Cossack mayor was shot dead, while a local warlord allied to another group of Cossacks, Alexander Bednov, known by his nickname "Batman," was killed along with six bodyguards when an anti-tank missile blew up his armoured car.
Natalia Stupina, who heads LPR’s humanitarian operations, insists there has been no problem working with the Cossacks and says she would welcome more international agencies into the area.
"Certainly, for the sake of people," she tells me.
But in reality, even if LPR officials allow aid convoys in, they cannot guarantee them safe passage through the rebel-held part of the region.
"When you don’t have a clear vision of who is where and who (you) should talk to to get access to Luhansk, you might not want to take the risk to come here," says Bunnskog.
The dangers for international aid organisations operating in this environment are extreme.
At the end of April, rebels raided the offices of the International Rescue Committee in Donetsk for alleged "spying," expelling five foreign nationals and taking two Americans hostage for nine days.
In October, a Swiss ICRC worker was killed when a shell landed near his office in Donetsk.
"You cross several checkpoints, and checkpoints along the frontline are often places where you have quite a lot of tension," says Bunnskog.
"When you have convoys of 10, 12, 14 huge trucks going through these areas and being checked… sometimes (for) hours, you're basically exposing your teams to a high risk."
'No hope for my life'
On an overcast and cold March morning, rebels standing next to empty trenches at the checkpoint for Pervomaisk say it is a "closed" town and outsiders have to get special registration to enter.
I am only allowed in with an escort.
Boxes with MSF's logo on them are stacked at the entrance of a municipal building.
Dozens of people have lined up nearby to register for free bread.
The streets tell a tale of destruction: shell holes in the road; wires dangling down from broken telegraph poles; row after row of bombed-out apartment blocks – plastic sheets flapping violently in the wind, failing to cover glassless windows.
Inside one building, I find 78-year-old local resident Anna Reshedko.
Aside from her high blood pressure, she needs medication for a long-term heart condition.
Even if Pervomaisk's badly damaged and under-resourced main hospital had what she needed, it is several miles away and too far for her to reach; she can only walk for 30 minutes a day.
So she spends her time sitting in her unheated apartment with a coat covering the legs she can barely stand on.
Cold air streams in from a bedroom window broken during the shelling.
At one point in the winter, she says the inside temperature fell to just four degrees Celsius (39 F).
Reshedko keeps her bathtub full because the water normally comes in just once a week.
At times, she has gone weeks without running water.
Once, she sat next to a window and cried out to passersby to get her food and water because she couldn’t walk out of her apartment.
"When the cars with the aid came here, I couldn't go there," she says.
"Everybody (got) the aid and I couldn't."
She rarely uses her electric heating blanket because she is scared it might stop working when she really needs it.
Reshedko worked as a nurse for 40 years but has not received her pension in 10 months.
A pink beret conceals her partly bald head, the result of stress after her husband and mother died two months apart, 20 years ago.
She has no family left.
"There is no hope for my life," she says.
Indiscriminate shelling, including in residential areas, cut off some towns from any international aid until after the second ceasefire.
Nowhere was fought over more fiercely than the strategic town of Debaltseve, a vital rail and road junction that Ukrainian forces finally relinquished control of on 18 February after a long siege, at a heavy cost of both men and weaponry.
Freight cars now litter the ditches on the way into town.
At the checkpoint to enter, burnt-out military vehicles lie still like monuments behind the fighters who check documents and question those who come in.
In the town centre on this bright and sunny day, rebels hand out boxes of food aid from the back of a truck.
But only a few streets away, Oleg, who doesn’t want his last name used, emerges from the dark, damp underground shelter where he lived for six weeks with his wife and young son.
Sleeping in a tiny room covered with carpets to keep the heat in, they created a makeshift kitchen next door to store jars of homemade preservatives stockpiled in preparation for the war.
They are happy to return upstairs to their apartment despite the lack of electricity and running water.
But Oleg, 45, fears their relief might only be fleeting.
"Any moment they can start (to) fire here (again)," he tells me.
Only a fraction of Debaltseve's 25,000 original inhabitants remain in the town, which is largely destroyed.
Nearby Zorynsk, with a pre-war population of 7,500, is a ghost town.
Only 20 kilometers (12 miles) from the frontline, it was also heavily shelled in February.
But it did not have the same strategic value as Debaltseve so it garnered less attention.
On one street, pieces of wood are scattered across a lawn.
Those few beams are all that is left of an entire house.
It would be impossible to tell had it not been for another badly shelled house next door.
One or two vendors still ply their wares in the town's market, but most of the rusty stalls are all shut up.
At the market entrance is 83-year-old Anna Vasiliyevna, wearing her roommate's old dress and selling cigarettes.
She works from 5am to 5pm, earning 25 cents a day.
For lunch she has a piece of bread and an onion.
Sometimes, she gets a bowl of soup from a kitchen run by the local separatist authorities.
While it means she can survive, she still goes hungry in a conflict she says is worse than the first one she had to live through 70 years ago: World War II.
Vasiliyevna went without heating this winter in her damaged apartment.
She stopped getting her pension in July and could no longer pay for gas, which increased in price, as did bread:
“ I can’t afford the food if I pay the bills....It would be better if I died in my flat.”
While the better summer weather will make it is easier for civilians and aid agencies to move around, it will also improve conditions for fighting.
"Every indication has suggested this is a lull before the storm in so far as the fighting is concerned," says WFP's Mcdonagh, who expects the number of people requiring food aid to double if agencies can't get enough provisions across the frontline.
The violence has already intensified through April and May, with both sides reporting causalities and accusing each other of shelling.
A report this week appears to confirm statements from US officials that Russia has built up more troops on the border than at any time since October, and a NATO commander has warned that he believes the rebels are taking advantage of the ceasefire to prepare for a new offensive.
Restrictions have been placed on residents crossing from rebel-held Luhansk to government-controlled territory.
At least those who can still move between the warring sides of eastern Ukraine get some respite.
Many others can't.
While the summer may bring more fighting, the winter will almost certainly bring further misery.
Analysts see no end to a cycle of conflict that could be frozen for years.
For those trapped on Ukraine's frontline, like Anna Reshedko in Pervomaisk, there is little to no hope:
"We don’t know what will happen tomorrow and I don't even want to think about [it] because the war is not over", she says.
"I'm going to die because there's nobody to help."