Warning: Contains SPOILERS for The Handmaid's Tale season 4, episode 6, "Vows," and from The Testaments.
June Osborne has finally made it to Canada in The Handmaid's Tale, but will she stay there or end up returning to Gilead? While The Handmaid's Tale has long explored June's struggle within Gilead, there's also been a struggle within herself. June has either tried or had the opportunity to leave on a few occasions; on some, she has been captured, but on others she has decided not to go. Tethered to Gilead by the love she has for her daughter, Hannah, and for the need to lead the rebellion against the totalitarian regime, it's often seemed unclear whether or not she would ever make it out.
Well, make it out she has. The ending to The Handmaid's Tale season 4, episode 5, "Chicago," saw Moira finding June in the titular city, following an aerial attack. The implication there was that Moira would at least attempt to take June back to Canada, though whether she'd go willingly or not was another matter. In the end, thanks to some convincing from Moira, June does get on the boat to Canada - and then after another bout of doubt, eventually decides to stay. Combined with the Gilead port authorities checking the boat, it's a nervy ride to see whether June will make it, but in the end she does get to Canada and takes her first steps into freedom.
It begs the question, then, of what comes next and, of what freedom looks like for a person who has defined themselves by fighting back against Gilead? For now, it may be enough for June to simply be in Canada. She can, at least briefly, rest, recuperate, and reconnect with Luke, Moira, Nichole, Emily, and Rita, finally regaining the sense of family and friendship that has been lost to her for so many years. But this is The Handmaid's Tale and this is June, and so there'll be a need for a lot of action to come, both from herself and, once they realize what has happened, the Canadian authorities, given she is public enemy #1 in Gilead and threatens the delicate nature of their relationship with the regime. June could well be used to testify and give evidence against Gilead, but may also find herself at least wanting to go back.
The trailers for The Handmaid's Tale season 4 show what looks like June in a courtroom, demanding "justice." It would make sense, then, if June is brought in as a key witness in the trial of Serena and Fred Waterford, since she has more than almost anyone to be used against them. Similarly, June can give a lot of evidence against Gilead as a whole, which Canada may use to put pressure on its leaders. At the same time, since Canada may fear repercussions for harboring June, a wanted fugitive in Canada, then another agreement may need to be reached. Serena Joy's pregnancy is a key aspect of season 4 yet to be fully explored, but it could be what cements her and Fred's return to Gilead; since it means she can have children, then she could perhaps return in a new role that would allow her and Fred to somewhat resume their old lives and status, in exchange for June's safety in Canada.
With this, though, is the question of June's daughter, Hannah. June being in Canada means she can reunite with one of her children, but her entire experience in Gilead has been driven by the quest to find, protect, and rescue her firstborn child. It's what has stopped her from leaving before, and what almost does so again here. If June believes she has a chance of rescuing Hannah, then she absolutely would do whatever necessary to do so, even if it meant returning to Gilead and risking her newfound sense of freedom. Even that itself isn't wholly accurate because, given what June has suffered, the fact she can't return to what she once knew as home for as long as Gilead rules, the ongoing fight to take it down and save all those oppressed, and the plight of Hannah, this is only a step towards freedom, not the real deal.
Another clue may be found in The Testaments, Margaret Atwood's sequel book. That story picked-up 15-years after the end of the first novel (which The Handmaid's Tale has continued on past and then some, since its ending aligned with the season 1 finale), and while June is not a key player, she is referenced. She's been living in Canada, working against Gilead from outside; she becomes an agent of Mayday, and is under triple protection at their unit in Canada. That could feasibly still happen even if she returns to Gilead again, but it may hint that June never does leave Canada, and that Hannah will remain in Gilead for a long time to come.