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Hi Heather -
Is this happening for all of the assignments, or just a select few? There's a chance that something had availability dates associated with it, preventing access at certain times. The other thing is that something like a page or resource could be unpublished temporarily.
If it's a link to a graded assignment, Observers should be able to access it, just like students. Could you have your student check the item you're trying to see too?
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