No, you can't have mulitple emails assocaited with one id. Logging in 3 times would work but is a pain and probably misses the point that (I think) you would like to have all email sent from nominated accounts to be associated with a common JIRA account?
I did a similar thing with LDAP for JEMH a long time ago that did an LDAP lookup and chose a user based on whichever of the possibile addresses matched a known JIRA user, but its currently unimplemented. I guess youd need a pluggable extension to be able to customize. How many users are you talking about 1, 10,1000?
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