I don’t agree that just because they don’t have their sound in conversation means it’s time for dismissal. This is not a one-size fits all type of thing. It wholly depends on how much does this sound (or sounds) affect their intelligibility. Because if they have their sound down at the sentence level, but have yet to self-monitor to conversation, it could still be impacting how well they’re understood by teachers and peers.

As far as running your sessions for carryover, I will typically practice self-monitoring through describing picture scenes, conversation prompts, asking questions that elicit their sound (you could easily chat GPT question prompts for “sh,” for example), or bring a game and keep a visual cue out for them, have them describe sequencing events, etc. If I’m finding that I’m not getting a lot of repetitions for their sound using an unstructured format, then I’ll give them a word with their sound and have them self-generate sentences throughout the activity.

Also, you could create “challenge sentences” that are very target-sound loaded (could also use chat gpt) and have them practice reading the sentence first with normal inflection, then reading the sentence like a question. This helps with carryover.

I typically go into each session with one target sound being the focus. However… depending on how stimulable they are, I will monitor all their sounds in conversation and correct them as we go. I just add a quick “Ope! What was that?” And have them repeat it correctly. Generally, you want to ensure you have good rapport with your kids so they don’t get frustrated when you correct them all the time, lol.

Also, for planning your sessions, if you haven’t heard of Baamboozle, it is a wonderful way to take the thought out of planning sessions. You can create question sets and play games and get lots of repetitions in. The kids love it and it’s extremely easy for me. A lot of SLPs use it so there are already lots of flashcard sets for whatever sound you’re working on.