Return to Grace

Well, in simple terms, this achievement is tied to examining everything and making conversation with all AI, it's not just about Mum AI.
And, yes it starts from the very start of the game, it's hard to pinpoint the exact conversations (at least for me).
All I can suggest that you follow my video for the game and do everything I do for the Grace Ending, that is if you are up for another playthrough.

Good thing is that this game is short.

@Apostle92627 - Congrats!
Nothing new with downvotes. I just let it be, since nobody even speaks up why they downvote it :)

So my guess is you need to trust her to confide in her. Seems there's more to this achievement than just walking in the canyon. I tried a bunch of stuff so it's not an exact science. I finally got it to work by having as many conversations with Mom as I could by interacting with a bunch of stuff throughout all of the houses in the settlement area. I even fell off the shortcut beam on purpose because there's dialog from her there. Hope that helps anyone else. Let me know if I'm wrong and just got lucky

The only thing I changed in my last playthrough was I examined EVERYTHING so anything that said examine I did. I don't know if it matters though just mentioning what I did. I looked at everything in the Zen garden area, I picked the purple flower (not sure if it matters though) I fell on purpose on the first beam twice then went the safe route for the second beam and I also listened to all the wishes that are available until the hatch. I made sure to examine everything on the safe path too, from the hatch but i finally got the achievement for this.

I think the flowers are linked to this, I picked Red and didn't get it, will try purple and see if that works.

It's not the flowers I also picked red and got it on my first playthrough. I believe it must be linked to having enough conversations with Mom to trust her enough to talk about it, as I interacted with everything and got it no problem. On my second playthrough I only did what was necessary to progress and Adie wouldn't talk to Mom about her parents.

Flowers don't matter. I picked yellow and got it.

could it relate to not using jack to skip mom's hacks?

I think also make sure there are a few murals with text on it and some bricks to interact with in that snowy area. Mom responds to those.

I did not fell of the beam, but just interacted with everything, and it popped for me.

Edit: I played blind the first time and took it really slow. I listened to every bit of conversation. I replayed from the start last night and I think below is what is what got it for me. Maybe this helps, maybe it doesn't...

TL;DR: Take it slow and let all conversations play out to make sure there is time for all dialogue to happen.

In general, listening to mom at all times probably helps, but getting Mom's approval in chapter 3 seems like it is required for the achievement. Ignore Control and make sure to explore all rooms. Listen to all canisters you find, but you definitely do not have to listen to all canisters in the area as I missed several on my blind play and still got the achievement.

In chapter 4 when you get to the choice between the beam and the path, before doing anything, let all conversations play out (Allen, Pal, Mom), then head down the path and take it slow. Whenever a conversation began, I just let it play out before moving on. I didn't look at anything along way until the very end I looked at the rock formation. The whole time on the path I just took it slow and made sure to let each conversation finish. There seems to be certain trigger points to start the next bit of conversation and if you are still listening to previous bit it won't trigger and you'll never get to the point where you actually reveal something.

When I did 2nd full play for collectibles, rushing through the path area I only heard the first 3 bits of conversation that I'd heard when I was going slow so it never got to the point where you reveal something to Mom.

I had problem with this one, but i had save file just before shortcut beam, fall twice from it and then passed third time, opened all rooms without Jack's help and listened all canisters there, entered elevator, after that i just walked trough church explored few things around barricade, then climbed it, explored everything from there to the point where you get out in the snow, walked to the beam where Mom had some dialogue about me considering beam ,turned right, climbed down and followed snow path, interacted with 2 writings and stone mark, and just before first stone climb dialogue about some pilot started. There achievement popped.