"Board Cutout (Multi-Layer) Region (0 hole(s)) Multi-Layer"
It looks like you've defined [what you thought was] the board outline, with a cutout region instead.
A board cutout is a Region object, tagged as board cutout and placed on Multi-Layer (the layer is forced when the option is enabled).
The proper way to define board outline is to draw it on a layer (typically Mech 1 or Keep-Out), and D
, S
, D
(Design, Board Shape, Define from Selected Objects). Draw a contiguous non-overlapping path to avoid confusion or errors (a non-contiguous path will usually cause the "create from primitive external edges" dialog, and may not give the result desired).
The board outline is, I think, an object internally, a closed polyline much like a Region, but not selectable as such (or, not normally so). (As of AD14 or so, it used to be editable as such; this was dropped in favor of the redraw mechanism.)
In summary: board outline is positive space, which creates the board area as such. Board cutouts subtract from that outline, creating negative space within the board area. Board cutouts aren't meaningful outside the board boundary (you can't subtract from nothing).
Polygon placement with respect to board outline, doesn't matter; pouring is determined by clearance rules, including to board edge/outline and Keep-Out objects. Normally it's drawn similar to board outline for convenience.
Also check on board planning mode (press 1
) to make sure a solid board region of the intended stackup (D
, K
/ Design, Board Stackup) is present.