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After installing the corresponding server side of this add-on from the Atlassian Marketplace, two options are available in order to download the newest client version for Outlook To JIRA . 

Download Latest Outlook Add-on

Option 1: Full Package (All Dependencies)

Recommended for a first-time installation.

Option 2: Workstation Package (Without Dependencies)

 Recommended for upgrading an existing version.

Option 3: Enterprise Package (32 & 64 Bit)

Automatic deployment using Microsoft Active Directory. For a detailed guide check this link.