Connector will not go to the edge of a shape

[Croc]

wapperdude,
Transformations such as regrouping or dragging shape-master-shape change a lot. Therefore, you can indirectly get the desired effect, but not understand the true reason.
Suppose the original shape could be created in the early version of Visio and when playing Visio used the conversion "Compatible mode". And after your transformations, the shape will be perceived as created in the later version and processed using other algorithms. (This is just an assumption).

[wapperdude]

Hi Croc...
I agree, neither of the approaches I suggested identify the underlying cause.  That's why I called them work-arounds.

I tend to agree with Vojo, this is not an overly complex shape.  The fact that either work-around provides a solution seems to support that fact.  Making a guess, I'd say both the good and bad shapes came from the same source and were built under identical conditions (same Visio version, same PC, etc).  Thus, by guess and inference, I think compatibility may be ruled out.  My suspicion is the shape has a corruption and both work-arounds eliminate the corruption.  But, it's just a guess.