The Handmaid’s Tale: Every time June almost escaped

If there’s one thing The Handmaid’s Tale does well besides keeping you in a state of mild emotional panic, it’s the art of the near-escape. And no one dances closer to freedom, only to pull back at the last moment, than June Osborne.

Over four intense seasons, she’s had more close calls than most action heroes, and yet, somehow, she keeps finding herself right back in the blood-red cloak, staring defiantly into the face of Gilead.

From the outside, it’s easy to wonder: why didn’t she just leave? The chances were there. The van, the plane, the train yard. Even a milk truck, for crying out loud. But The Handmaid’s Tale doesn’t work like a typical escape story. It’s not just about slipping past guards or cracking codes.

It’s about people, emotion, pain, and choices. And June’s choices, however frustrating they may seem, always make a certain kind of sense when you sit with them.

The Handmaid’s Tale: Why June’s escapes never quite worked

A van that led nowhere - The Handmaid's Tale Season 1’s cruel twist

Take the end of The Handmaid’s Tale season 1, for example. June is taken away in a van, unannounced, pulled from the Waterfords’ house with no real explanation. It looks like a rescue. It feels like an escape. But what waits on the other side is far from freedom.

Instead of safety, she lands in a fake training center where Handmaids are punished for breaking the rules. Gilead never makes things simple. That moment teaches us early on that hope in this world is often a trap, dressed up to look like a door.

A glimpse of freedom in the woods

Things shift in The Handmaid's Tale season 2 when June gets a real shot at escaping. With Nick’s help, she leaves the house, cuts out her tracker, and trades her red cloak for regular clothes. She slips out into the cold, heading into the woods. For a short while, it feels like she might actually pull it off.

She finds shelter, warms up, and even plays a music box while waiting for what’s next. But Gilead doesn’t let go that easily. She’s eventually caught and pulled back. The moment fades, and with it, her short-lived taste of freedom.

She gives the baby away - The big Season 2 finale decision

And then comes the finale of The Handmaid’s Tale season 2 - the moment people still bring up in arguments, on Reddit threads, in group chats.

June gets her baby out. She gets to the airport. There’s a getaway truck. There’s a plane. There’s a chance. But she doesn’t take it. She hands baby Nichole to Emily and stays behind.

Some viewers were furious. Others cried. June’s decision was about more than safety. Her older daughter, Hannah, was still trapped in Gilead. To her, leaving one child behind to save another felt impossible.

That moment wasn’t a failure. It was a sacrifice. It was also the beginning of a turning point in how she sees her role in all of this.

A fighter, not a fugitive

By The Handmaid’s Tale Season 3, June is no longer just trying to get out. She’s organizing from within. She’s meeting with resistance members, making moves, and taking bigger risks. At one point, she helps coordinate a plan involving trains — a proper escape route. She could have jumped on and vanished with the others.

But she doesn’t. Something inside her has changed. She’s not just running for her life anymore. She’s trying to take Gilead down from the inside. And as idealistic as that sounds, it’s also a heavy burden. The more she sacrifices her own freedom, the more determined - and at times, broken - she becomes.

The flight that lifted others - The Handmaid's Tale Season 3’s bittersweet ending

Still, she keeps pushing. The Handmaid’s Tale season 3 finale gives her the chance to pull off her biggest move yet, smuggling dozens of children onto a flight out of Gilead. And it works. The plane lifts off. People cheer. Some actually make it to Canada. But June doesn’t go with them.

She stays, bleeding and alone in the woods. She pulled off something incredible. But at what cost? This time, her reason for staying isn’t just about Hannah or guilt. It’s about the mission. She’s gone from survivor to symbol. And symbols don’t retire easily.

The milk truck nightmare, The Handmaid’s Tale season 4

The Handmaid’s Tale season 4 starts with one of the show’s most bizarre near-escapes. June and several Handmaids hide in a milk truck. It’s gross, it’s cold, it’s strangely tense. But it’s also a shot at freedom. Until it isn’t. They’re caught. Several women are killed. June is injured again.

It’s a brutal reminder that even with good timing and teamwork, the odds are always against you when the system is built to keep you trapped.

She finally crosses the border

Eventually, though, it happens. In The Handmaid’s Tale season 4, June crosses the border. She makes it to Canada. She’s out. She’s safe. Or at least, her body is. Because even then, June isn’t really free. Her mind is still inside the walls of Gilead. Her rage still burns. Her mission is unfinished.

The escape is real this time, but doesn’t feel like a victory. It feels like the end of one war and the beginning of another.

Why she stayed

The thing about June is that her reasons for staying weren’t just based on fear. She stayed for her daughters. She stayed for revenge. She stayed because she couldn’t stand the thought of walking away while others were still suffering. It wasn’t always logical, and it definitely wasn’t easy. But it was real.

What makes June such a compelling character is that she never takes the simple road. Even when the escape was a few feet away, she looked around and asked herself what it would mean to leave. Could she live with it? Could she call it freedom if she left people behind?

Each near-escape tells you something about her. About the world she’s stuck in. About how survival sometimes looks like a sacrifice. And how freedom, for some people, comes only after losing everything else.

Conclusion

At the end of The Handmaid’s Tale, June’s story isn’t just about running. It’s about staying. About standing. About choosing when to fight and when to flee. And every time she didn’t walk through that open door, she made it harder for herself, but also clearer to the audience that her journey was never going to be simple.