Quite hard to tell exactly what is going on from just a screenshot but possible issues could be: Shapes are Dynamic and not up to date, check Shape>Global Dynamic Parameters or Design Status; the PGND shape is Static, rather than Dynamic and won't be updated to connect the Vias, change the Shape Type to Dynamic could help; you are using Negative Artwork and Dynamic Shapes and the Shapes need to be updated to reflect the connectivity change. Dynamic Shapes and positive artwork would be the recommended approach to Shapes, Shape updating of "Smooth", or "Rough", would ensure that Shape to object connectivity gets updated "as you go"
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