Warning: Contains SPOILERS for The Handmaid's Tale season 4, episode 5, "Chicago."
The ending of The Handmaid's Tale season 4, episode 5 delivers a surprising twist that could shake-up the future of the show, with June being caught in aerial attacks on Chicago before being rescued by Moira. The Handmaid's Tale season 4 has continued June's attempts to push back against Gilead, but she's had to take flight more than she's been able to fight. That reaches a dramatic endpoint in season 4, episode 5, "Chicago," which sees June and Janine caught in a brutal attack upon the episode's eponymous city.
Making matters worse is that the attack is launched by none other than Nick, aka Commander Blaine, who is given no choice thanks but to give the strikes the go-ahead thanks to the scheming of Commander Lawrence. While Nick does try to buy some time to get the forces (and, he hopes, June) out of Chicago, it's not enough. As June and Janine chart course to find another group who may offer a chance to join the rebellion, they're caught in the bombings. Janine's fate is left unclear at the end of The Handmaid's Tale season 4, episode 5, but June is found by a familiar face: Moira.
For anyone who didn't watch the trailer for The Handmaid's Tale season 4, this likely comes as a big twist, which it's certainly designed to be and feels like. There was little indication that Moira and June's paths would be crossing so soon, but with Chicago at the heart of the resistance and those in Canada trying to keep tabs on June's whereabouts - perhaps tipped off by Nick himself - then there is logic to her being found. With the old friends finally reunited, the question is what comes next? Moira finding June offers her a real opportunity to escape from Gilead and get to Canada, but will she take it, and if so, for how long?
The Handmaid's Tale season 4 trailer hinted that June does indeed go to Canada, including a shot of her looking much more smartly dressed and demanding "justice." This could be June giving evidence against Gilead, helping to take it down from the outside, rather than the inside. But even if she does make it Canada, things there won't be easy. June has, in her mission, caused a lot of consequences, and changed a lot of lives. Moira herself has shown anger at June for her actions, and while there'll undoubtedly be happiness at being reunited, there'll also be hard work and tough conversations. That's before factoring in June's status: she is public enemy #1 in Gilead, and if Canada takes her in, then it would escalate tensions further, meaning that there's a great risk for everyone involved.
Combined with that is the idea that June may not want to stay in Canada. June has had a lot of chances to escape before, but has always either been captured or decided to stay, and the key part of that is Hannah. That situation hasn't changed, and it's hard to imagine June willingly leaving her daughter behind in order to stay in Canada, even if she can do more to to work against Gilead from across the border than within it. June has long been reckless and willing to put her own life and that of others in danger, and that could well continue going forward, despite Moira finding her in The Handmaid's Tale season 4, episode 5. It would hardly be surprising if June returns to Gilead in order to try and find Hannah, while she also has a lot of unresolved issues with Nick - he's unlikely to escape Gilead himself anytime soon, but there's much more story to explore there, further necessitating her return.
The ending of The Handmaid's Tale season 4, episode 5 also leaves a big question over Janine's fate. It seems unlikely that she will be dead, given her body isn't shown, but there's also no hint of whether she makes it to Chicago. It's possible she does get out too, or that they can't find her body and have to leave her behind - but if the latter, that's only another tether to Gilead for June. The ending suggests that she will be taken into Canada, but with The Handmaid's Tale renewed for season 5 (and likely more beyond), then there'll be a lot more twists to this story.