Documentation for JIRA 5.0. Documentation for other versions of JIRA is available too. 
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Please follow the instructions in the general upgrading JIRA documentation.
JIRA 4.4.4 includes a dependency on atlassian-mail version 1.25 which is not 100% backward compatible with atlassian-mail 1.24 included in previous releases of JIRA.
JIRA 4.4.4 also ships with javamail 1.4.4, which we cannot guarantee is 100% compatible with javamail 1.4.1 (shipped with previous releases of JIRA).
Hence, there are two significant points to note as a result of these changes:
com.atlassian.mail.server.MailServer.getSession() method returns objects of the javax.mail.Session class rather than alt.javax.mail.Sessionmockobjects-j1.3-j2ee1.3.jar are no longer exported (i.e. made available) to Atlassian version 2 plugins. This jar is no longer distributed with JIRA.We believe that very few (if any) 3rd party plugins will be affected by the two changes mentioned above and that such plugins will be broken as a result of these changes.
com.atlassian.mail.server.MailServer.getSession()method, doing either of the following should be sufficient to get it working with JIRA 4.4.4:MailQueueItem.mockobjects-j1.3-j2ee1.3.jar (which is highly unlikely and could be considered questionable), we encourage you to either:jar with the plugin.According to the changelog for javamail (http://www.oracle.com/technetwork/java/javaee/changes-220864.txt), we believe that these changes should not negatively impact current plugins. On the contrary, many bug fixes and compatibility improvements in this new version of javamail should make existing JIRA mail handlers more robust.
JIRA 4.4.4 comes with substantial mail logging improvements and capabilities, which should be valuable to customers and support personnel troubleshooting problems related to incoming and outgoing mail.
Part of this feature work required the need to upgrade both the atlassian-mail and javamail libraries to the versions mentioned above. The anticipated small negative impact resulting from these upgraded libraries led us to believe that there was little or no business justification for supporting their older versions.
In addition to the above, please read the JIRA 4.4 Upgrade Notes and as well as the Important Version-Specific Upgrade Notes for the versions of JIRA you are skipping.