How are replies handled for existing issues?

If an issue has been created from a particular email from Outlook, are replies to this email automatically added as comments?

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No, they won't be added as comments automatically, you need to add them manually. But we are going to improve this step to pre-select the related issue.

Depends on your use case, but to automatically add comments you can also leverage built-in features of JIRA as explained here: https://confluence.atlassian.com/display/JIRA/Creating+Issues+and+Comments+from+Email or use plugins like JEMH: https://marketplace.atlassian.com/plugins/com.javahollic.jira.jemh-ui

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