Ah-HA! GOT one! ;) Seriously, thank you and your company for confirming the issue and agreeing to fix it.
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So, I presume this is also what's causing "CheckComboBox.ItemSelectionChanged Event is not being Raised if (SelectedItemsOverride modified before drop-down has been opened)" (see my 5/1/17 2:22 pm comment)?
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So, I presume the workaround is to "Handle the (SelectedItemsOverride's Bound aka Source ObservableCollection Property's) Backing Variable's "CollectionChanged" Event"?