Hey there @mwinn,
Can you let me know where you are sharing the file/folder from, ie. the website, mobile app or desktop app Dropbox folder? Also, after you’ve attempted to share, if you go back to the file/folder and click share again, you should see the email addresses of the recipients you've already shared with. Do you see the recipient's email there still?
If you want to enter a large number of email address at once, you can add multiple emails in the sharing window before clicking “Share” so you don’t need to add each recipient one by one.
Let me know what you find - Thanks!
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