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 Relative newbie here, I came to this thread from a search on the Primal client for "outbox", very helpful thread for getting my head around what outbox is and is not. (Their search is fast but you have to wade through a lot of mastodon stuff sometimes.)

Just to make sure I’m getting it, if I’m replying to your note but you don’t follow me, and we have no relays in common, then you won’t see my reply? But if Person X replies to my reply, and you happen to be following Person X, then outbox should direct your client to fetch my note along with Person X's reply? That is to say they should both show up for you roughly at once, as long as the relevant relays are up?  
 No, if you reply to my note I always see you, since following the Outbox basic schema you are writing in my read relays. This is true even if you reply to someone I replied to, since replies usually include all the references up to the root.

The problem arises if someone you don't follow post in a sub-thread you are not participating, in this case you will not see that note using the plain Outbox model.

But, as nostr:nprofile1qqsrhuxx8l9ex335q7he0f09aej04zpazpl0ne2cgukyawd24mayt8gprfmhxue69uhhq7tjv9kkjepwve5kzar2v9nzucm0d5hszxmhwden5te0wfjkccte9emk2um5v4exucn5vvhxxmmd9uq3xamnwvaz7tmhda6zuat50phjummwv5hsx7c9z9 pointed out, Outbox model is not a set of predefined rules, it's a paradigm, clients should creatively search other solutions to improve discoverability.
For example a client could try to rebuild sub-thread using (recent) interactions by your social graph. 
 Ah, got it now, thanks Daniele. Sounds like an exciting problem.

Could clients potentially do some work on the posting side too? For example when posting a reply there’s a checkbox marked “non-follower friendly” or something to that meaning, and if you tick that then when you write it’ll perform some opt-in action that’ll make life easier for the clients of lurkers and other non-followers to connect the dots and surface your reply when they browse the thread? 

Or a popup for the same, with options for "always", "never" and "ask every time" that can be adjusted later in settings. Other words push some responsibility to the posting side, make the math easier on the deducing side.

If yes I’m guessing there'd also be many thread-joiners who would be more than happy for their replies to be less visible to lurkers and other non-followers, glad to be given the choice but would choose the opposite: opt out, purposely keep things so thread-group clients can easily sniff out the reply but non-follower clients, even those doing their best to follow the traditional outbox paradigm, will have a hard time sniffing it out (as you say is the case now). Becomes like a feature, not a shortcoming.

Also if yes then I wonder what such an opt-in action at time of posting might be?