It is just I toggled the checkbutton in the UI logic. Should this change propagate automatically into the search logic?

I'm not sure I understand you? If you set "always wrap search" preference and apply/ok the preferences dialog then yeah it should "propagate" to the search logic so searches always wrap.

Should it not be on by default?

So why not just open an issue to change that? 😁

For reference the wrap option was split from a combined option here as a result of the discussion in the Geany ML thread which basically makes the decision to keep it off as it was before, since there is no good reason for either provided, and since there are no statistics on what would be preferred. So you need to provide some better justification than personal preference to change it, see the ML thread.

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