Click Accounting > Expenses > Update Filter to show status your expenses is in (Approved/Accepted, Approved/Not Accepted, Not Approved/Not Accepted)
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If your Expense has been Approve/Accepted, you will need to Unapprove the Expense in order to make an Edit. If your Expense is in one of the other categories you will skip this step of unaccepting.
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Change your filter to Approved/Not Accepted or Not Approved/Not Accepted, then click Edit next to the Expense where you need to load a file or replace an existing file.
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If a file already exists, you will click the trash can icon to remove the existing file. Then Click the Drag & Drop box to browse for your file.

Once you've uploaded your new file, click Save and Approve. Then from the list of Expenses > click the ellipse icon > Accept to finalize the Expense.