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I just tried this out, and I do see some similar behavior when I first open Positron with a .qmd file in the source editor. Another way that I can get the outline to kick in is by making some change to the file (basically any change at all, it seems). Would you be willing to open this as a bug on the Quarto extension repo here: https://github.com/quarto-dev/quarto/issues

That is where this behavior comes from.

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Answer selected by davidjanmassgov
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