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

Option 1: Full Package (All Dependencies)

Recommended for a first-time installation.
Compatible with Outlook 2007, Outlook 2010, Outlook 2013 & Outlook 2016 & Outlook 2019
Size: 237 MB
Download Full Package - 5.1.1 (Latest)
To install it, go to installation section

Option 2: Workstation Package (Without Dependencies)

Recommended for upgrading an existing version.
Compatible with Outlook 2007, Outlook 2010, Outlook 2013 & Outlook 2016 & Outlook 2019
Size: 30 MB
Pre-requisites needed on client's machine:
- .Net Framework 4.5
- VB Power Packs
- Only for Outlook 2007: Office 2007 Primary Interop Assemblies
- Only for Outlook 2010 & above: Office Run-time 2010
Download Upgrade Package- 5.1.1 (Latest)
To install it, go to installation section

Option 3: Enterprise Package (32 & 64 Bit)

Automatic deployment using Microsoft Active Directory. For a detailed guide check this link.
Compatible with Outlook 2007, Outlook 2010, Outlook 2013 & Outlook 2016 & Outlook 2019
Size: 476 MB
Download Enterprise Package - 5.1.1 (Latest)
To install it, go to installation section