I don't think the "obs settings / assume obs is in a session if date / time is within" is working, if I understand it correctly.

I have a session on 8/1 18:00 - 18:35 and the parameter above set at 2 and the "create new session" set to 4

Adding an obs at 18:35 prompts with default of "add to current session‚" as it should

Adding an obs at 18:36 prompts with default of "add to recent session‚" as it should

Adding an obs at 20:35 prompts with default of "add to recent session‚" as it should

Adding an obs at 20:36 prompts with default of "add to recent session‚" shouldn't it default to "start new session"?

Adding an obs at 22:35 prompts with default of "add to recent session‚" shouldn't it default to "start new session"?

Adding an obs at 22:36 automatically creates a new session as it should