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Canvas assignments
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Can a students submit/upload more than one document for a single assignment without the second one replacing the first one? I need two different documents from each student for one assignment.
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Yes (at least in some cases). What they do is upload the first file and then click "+ Add Another File". Once they have uploaded all of their files, then they click "Submit Assignment".
See the How do I submit an online assignment lesson in the Canvas Student Guide. It looks like you can have multiple uploads, but only one text entry, website URL, or media recording.
If you're using the Google Assignments or Office 365 options, you can select multiple items.