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In your Jira for Outlook settings you can change the automatic upload of your attachments

If you create a new issue with attachments, all attachments referring to that issue, will automatically be uploaded. However, you can make adjustments to your attachments i.e. you can delete one or more if you do not need them.

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If you do not click on any attachment, all documents will automatically be uploaded.

uploaded attachments

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deleting attachment

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Deleting an attachment looks like this. You click on the document you wish to delete and the blue hook disappears. This attachment will not be uploaded in your Jira issue.

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