Troubleshooting the Microsoft Outlook Button

Button is Disabled by Outlook

This section describes the issue where the button appeared after you installed it, but is now disappearing. If the button has never appeared for you, refer to the  Button Does Not Appear or is Dimmed  section later in this article. 

This issue is caused by the way Microsoft Outlook handles COM/.NET plugins. When Outlook starts up, any plugins that run over a threshold for loading time are timed out. There are no problems with the button itself – Outlook prevents it from loading.

Use of these methods, described below, to address the issue:

• Add the Outlook Button to the List of Managed Add-ins in the registry (preferred)
• Switch to the Exchange Button (only available if you are running Exchange 2016 or Microsoft 365)

Add the Outlook Button to the List of Managed Add-ins (preferred solution)

You can use group policy to configure Microsoft default timeouts to support plugins that take longer to load. Group policy overrides user settings and users cannot change settings for plugins configured in the group policy List of Managed Add-ins.

To make these configurations, you need a tool that can manage registries on all the client machines at your organization. You can use a third-party tool or Group Policy Objects (GPOs) in Microsoft Active Directory. GPOs are managed using the Group Policy Management Console.

Refer to the Microsoft article Support for keeping add-ins enabled for instructions and details of the required registry settings.

For additional information refer to this third-party article about preventing Outlook from disabling add-ins. 

Switch to the Exchange Button

If you are using Exchange 2016 (or newer) or Microsoft 365, consider moving to the Exchange Button. The Exchange Button is recommended for all those just starting out with Security Awareness Training.

The Exchange button has the following advantages over the Outlook button:

• Eliminates deployment timeouts
• Available on MAC OSX
• Available in-browser for Outlook Web Access (OWA)

The Exchange and Outlook buttons have slightly different functionality – most notably, the Exchange button lacks the Report Spam option. Compare the functionality for each of the buttons before making a final decision on this option.

To install the Exchange button, refer to Installation Instructions - Microsoft Exchange Button.

Button Does Not Work As Expected

If your Microsoft Outlook button is not working as expected, try the following steps in order. You might come to a solution before you reach the end of the list of steps.

1. Confirm that .NET Framework 4.6.1 is installed.
2. If .NET Framework 4.6.1 is installed and the Phishing button appears under Add/Remove Programs: Confirm that you have chosen the correct version of the button. This is the most common cause of button issues.
   • Install the version that corresponds to your version of Office/Outlook. If you have the 32-bit version of Office/Outlook, install the 32-bit version of the button plugin. Your version of Windows is not relevant.
3. If .NET 4.6.1 is installed and you chose the appropriate 32- vs 64-bit button version, but you are having problems retrieving the JSON configuration file or the custom button image, check the phishline.log file (%LOCALAPPDATA%\Phishline) for any messages related to an error.
4. Check the same directory (%LOCALAPPDATA%\Phishline) to confirm that the JSON configuration file and custom button image are present. If they are not present:
   1. Check the phishline.log, if present, for any error messages related to downloading config.json or button.png. Usually, this would be a timeout or a 404-type error.
   2. Check to make sure the directory permissions allow the logged-in user to write files to that directory.

Button Does Not Appear or is Dimmed

This section describes if the button has never appeared. If it appeared after you installed it, but is now disappearing, refer to the Button is Disabled by Outlook section at the top of this article. 

Review your phishline.log file, usually located in C:\Users\ExampleUserName\AppData\Local\Phishline\phishline.log

Example Error 1:

2020-12-19 09:23:01.5630 ERROR Failed to download config

System.Net.WebException: The request was aborted: Could not create SSL/TLS secure channel.

   at PhishlineService.Configuration.ConfigService.UpdateConfig(String configUrl, Boolean fileExists)

   at PhishlineService.Configuration.ConfigService..ctor(Boolean loadRemoteConfig)

What it means: This message implies that the version of the button on that computer is an older, deprecated version of the Security Awareness Training Outlook Button.  Versions less than 1.5.*.* use an old version of TLS that is no longer supported. The version of .NET used by that button does not support modern TLS versions.

How to fix: Uninstall the old version of the button, then install and configure the newest version of the button, following the instructions in Customization Options - Microsoft Outlook Button.

Example Error 2:

2020-12-13 10:26:45.9222 ERROR Error configuring button

System.InvalidCastException: Unable to cast COM object of type 'System.__ComObject' to interface type 'Microsoft.Office.Core.IRibbonUI'. This operation failed because the QueryInterface call on the COM component for the interface with IID '{000C03A7-0000-0000-C000-000000000046}' failed due to the following error: Library not registered. (Exception from HRESULT: 0x8002801D (TYPE_E_LIBNOTREGISTERED)).

   at System.StubHelpers.StubHelpers.GetCOMIPFromRCW(Object objSrc, IntPtr pCPCMD, IntPtr& ppTarget, Boolean& pfNeedsRelease)

   at Microsoft.Office.Core.IRibbonUI.InvalidateControl(String ControlID)

   at Microsoft.Office.Tools.Ribbon.RibbonComponentImpl.PerformLayout()

   at Microsoft.Office.Tools.Ribbon.RibbonPropertyStorage.SetDynamicValue[T](T& field, T value)

   at Microsoft.Office.Tools.Ribbon.RibbonControlImpl.set_Visible(Boolean value)

   at PhishlineAddIn.PhishLineRibbon.SetButtonView(String whatToShow)

   at PhishlineAddIn.PhishLineRibbon.OnDoWork(Object sender, DoWorkEventArgs e)

What it means: This error is related to an incomplete Office upgrade and/or having multiple versions of Office installed. This issue often occurs when an old version of Office has been upgraded to a newer version, but some registry keys were not adjusted in the upgrade.

How to fix: The fix can vary from computer to computer. We cannot provide a specific recommendation because this error is caused by the Office installation, and not the Security Awareness Training Outlook Button. The fix is usually one of the following:

• Examine the error. Using regedit, look up the keys mentioned and fix them.
• Run a repair on Office from the Windows program Install/Uninstall page.
• Uninstall and reinstall Office.

See the following link for suggestions on dealing with this and similar errors: https://stackoverflow.com/questions/12957595/error-accessing-com-components/12962795#12962795

Button Appears in OWA, But Not in Outlook

If your Microsoft Outlook button appears in OWA, the web-based version of Outlook, but does not appear in the Outlook application, follow these steps:

1. In the Outlook application, open Privacy Settings. (Navigate to File > Options > Trust Center > Trust Center Settings > Privacy Options > Privacy Settings.)
2. In the Privacy Settings window, select the Turn on optional connected experiences check box. Then click OK. 
3. Restart Outlook. 
   When Outlook opens again, the button should be visible. 

Email Not Delivered

When using this button, check that the email you want to report includes at least a subject or content in the body – preferably both. Emails with blank subjects and bodies cannot be reported.