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Check the following settings in Outlook:

  1. File > Options > Trust Center > Trust Center Settings > Macro Settings: The first option "Disable all macros without notification" should not be enabled. It's recommended to select "Notifications for digitally signed macros, all other macros disabled".

  2. File > Options > Add-ins: Manage: “COM-Addins”-> Go.

    1. Make sure Outlook Connector for Jira is activated in the "COM Add-ins" dialog.

  3. File > Options > Add-ins: Manage: “Disabled Items” (use the drop down menu) > Go

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Info

If this does not work, run Outlook as an Administrator: Right-click on Outlook symbol → Run as Adminstrator

Info

In case the Add-in is disabled every time when Outlook is started, have a look at Solution 3 and 4.

Solution 2

This solution is works for Office 2013 and later:

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If the Add-in has not been disabled, click “Option” and select “Do not monitor the add-in for the next 30 days.”

Solution 3

You can force Outlook to load the Add-In and to keep it enabled:

  1. Open the registry editor (regedit.exe)

  2. Navigate to

    1. Outlook 2016 and newer: "HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\16.0\Outlook\Resiliency\AddinList"

    2. Outlook 2013: "HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\15.0\Outlook\Resiliency\AddinList"

  3. Add then a new string value (REG_SZ) with the name “o2express.AddinModule” and set the value to 1

Solution 4

  1. Open the registry editor (regedit.exe)

  2. Navigate to HKEY_CURRENT_USER\Software\Microsoft\Office\Outlook\Addins\o2express.AddinModule

  3. Check for the value LoadBehavior, it should have the value 3. If not change it to value 3

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Solution

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5

This is the hard way. We completely remove the addin and reinstall it again. The following steps are at your own risk:

  1. Exit Outook.

  2. Try to uninstall the addin using the installer (setup.exe) or the windows uninstall routine (Add or Remove Programs). When using the installer, make sure it is the installer of exactly the version you would like to uninstall.

  3. Backup your registry before making any changes.

  4. Open the registry editor (regedit.exe) and search for "71EA6BBB-E9AA-434B-BE3D-8D9C9D007626" and "o2jexpress.AddinModule". Remove all keys you find including one of these terms. After that there is nothing left in the registry which is related to the Add-in.

  5. Install the addin again.