Down in the basement - Out on the dock
I'm only talking about the show.
The Angel's Flight escape plan began after Eleanor led June to the basement where Lawrence stored boxes of "Red Center dossiers". They contained identities and locations of Handmaid's children. There was another very important meeting in that basement.
Kid's futures are chosen for them. Who should do the choosing? Should it be the State? June was one of many folks who made the escape decision, from the bartender, maids, marthas (especially Beth and Sienna), and handmaids down to a specific individual who loved each kid.
What is Angel's Flight without the flight, hopeless and cancelled. The truck plan was doomed from the start. Lawrence knew it. One of my favorite THT scenes is in one of my favorite episodes, s3ep11 "Liars". June met in the basement with the rebel leader marthas. Even after June passed their pressure test, two of them tried to hide their disappointment that the boss gave the plane knowledge to June. One of the leaders of the rebellion made that decision for the kids.
I'm cynical about rebel leader June manipulating undercover asset Daisy, but she has a war to win. She doesn't think, for instance, about a few temporarily traumatized Angel's Flight kids and she shouldn't. Daisy has become unreliable and could be captured. Her knowledge is valuable to both sides. On the dock, June is testing the asset. Is the possible reward still worth the risk? June has a plan. Rita and others know about it. Should June pull Daisy and use her information to further the plan with another asset?
The dock meeting is like the basement meeting. In the basement, the resistance leader martha tested and helped June. On the dock, resistance leader June tested and helped Daisy. It was dangerous to keep the honey truck on the dock after it dropped the escapees. June kept the truck waiting because, from before the meeting, she was hoping to be able to send Daisy back in.
As far as June not learning about the effect of Gilead on individuals or not understanding the consequences of her decisions, she has faced the future of Hannah returning but not being her daughter. On the dock she says,
"I might never get my daughter Hannah back, but I will die fighting so that she can experience freedom as a woman, as a human being."
Even after learning that Daisy is close to Hannah, June is still going to pull her out, "I'm not gonna risk another one. I'm not gonna let you die." She doesn't reverse her decision until Daisy defies her and says, "Its my turn now. I might fail. I might even die. But its my choice."
"They don't know they need saving." Before the meeting, Daisy only wanted to save Becka and herself. After the meeting, she knows she needs to save all the girls.
Something about the dock scene bothered me until this rewatch. Right before June returns to the boat, she turns to Daisy and puts her hand to her open mouth in an exaggerated manner. I couldn't figure it out ... until thinking about the exchange above, I finally noticed that immediately afterward Daisy mirrors the the open mouth gesture. Is it symbolically a sharing of the burden?
I first thought that June took a pill and it foreshadowed her death. I believe it is burden sharing, but it could still foreshadow her death. Jesus and his disciples shared bread at the Last Supper. Is this a last meeting of June and Daisy?