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Without any info about comp settings, framerates, cache and so on we can't really tell you much. This could be one of those 0.001 seconds things where comp framerate and footage don't align correctly.
Mylenium
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You are the end of the layer so will not be ale to see the mask, you can only see the mask when you have the playhead over a frame on the layer where the mask exists. If the playhead is at the out point of the layer, it is not on a frame so you cannot see the mask.
If you need to continue editing the mask you could switch on Time Remapping which will allow you to extend the layer to the duration of the other layer so you can contiue masking.