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Problem

"As a delegate of a calendar, when duplicating an old calendar entry, I'm unable to delete or change previous attachments. On my end, the attachments are deleted but once I send the new invite using the delegator's account, the attachments reappear."

Solution

This is a known Outlook web and desktop issue and has been reported to Microsoft. As a workaround:

1. Create a new meeting

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1. .
2. Copy and paste the relevant details from the old

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1. to the new meeting. Attach the updated files to the new meeting.
2. Cancel the old meeting, and send the new meeting invite. 

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