Why doesn't my Xbox One repeat videos in the Play to Option?

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Windows Central Question

My Xbox one Doesn't repeat videos in the Play To option

When I used to use the Play To option from my PC to my Xbox one, It used to play down the list of videos I have on a list I create but now all It does is play one video (MP4 Files) from the list and just stops.

I'm unable to fix this and I called Microsoft and there weren't able to help either.

I was wondering if anyone here can clear this up for me? Been having the biggest headache for the past couple of weeks with this.

Thanks!,

Sunny.