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From the Mail Queue page in Jira, you can switch over to the Error Queue and click Resend error queue to have Jira try and re-process those emails.
If debugging is enabled for Outgoing mail, info about these messages will be written to the outgoing-mail log file.
Based on the specific error you're seeing in the outgoing log, you can try to troubleshoot further!
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Mail Log:Jira Administration: Applications > Email Requests
https://support.yamnet.com/secure/admin/SDMailInfo.jspa
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