I can tell you why you get that particular result. A Section Close bar line will be used as the landing point for a later Master Repeat Close. If you add additional endings to your last Special Ending, you will see that the repeat is actually performed, but it starts at the Section Close.
!NoteWorthyComposerClip(2.5,Single)
|Clef|Type:Treble
|TimeSig|Signature:2/4
|Note|Dur:Half|Pos:-1
|Bar
|Ending|Endings:1
|Note|Dur:Half|Pos:0
|Bar|Style:MasterRepeatClose
|Ending|Endings:2
|Note|Dur:Half|Pos:1
|Ending|Endings:7
|Bar|Style:SectionClose
|Ending|Endings:2,3,4
|Note|Dur:Half|Pos:2
|Bar|Style:MasterRepeatClose
!NoteWorthyComposerClip-End