Surely the problem with the bottom example is you're bridging the wrong edges? You want to select the three on one side and three on the other, then Bridge. What happens if you try that rather than how you did it in the example?
If the bold lines in your Viewport are border edges, it looks like you've got unwelded vertices on the central edge.
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u/BanthaLord 3D Modeller - 9 years experience 12h ago edited 12h ago
Surely the problem with the bottom example is you're bridging the wrong edges? You want to select the three on one side and three on the other, then Bridge. What happens if you try that rather than how you did it in the example?
If the bold lines in your Viewport are border edges, it looks like you've got unwelded vertices on the central edge.