By default, Outlook will automatically disable any plug-in that experiences a delay during startup. Because the SendSafely plug-in checks for updates when Outlook is started, this sometimes results in Outlook disabling the SendSafely Plug-in.
There are two ways to fix this issue:
Option 1 - Choose "Always Enable" from the "Slow and Disabled Plugins" list
In Outlook, check the "File" menu and press the "Slow and Disabled Add-Ins" button. From there, see if SendSafely for Outlook is listed. If so there should be a button that says "Always enable this add-in". More information on how to do this is also available on the Microsoft Office website: https://support.microsoft.com/en-us/office/outlook-add-in-warnings-346f5ae7-b996-46d1-a56d-410b9b082a7c
Option 2 - Add SendSafely to Outlook's "Do not Disable" List
SendSafely has developed a registry file that will add our plug-in to Outlook's "Do not Disable" list of plug-ins. This file will add the appropriate entries to the Windows system so that Outlook will no longer automatically disable the SendSafely plugin.
Download and run this .reg file (choose YES when prompted), and then restart Outlook.
Still no luck?
If the above two options don't solve the problem, there are a few more things you can try to re-enable the SendSafely plug-in.
Check if the plug-in is "Hard Disabled"
Hard disabling can occur if the add-in has caused Outlook to close unexpectedly.
- In Outlook, click the File tab.
- Click the Options button.
- In the categories pane, click Add-ins.
- In the details pane, verify that the add-in appears in the Disabled Application Add-ins list.
- The Name column specifies the name of the assembly, and the Location column specifies the full path of the application manifest.
- In the Manage box, click Disabled Items, and then click Go.
- Select the ‘SendSafely’ add-in and click Enable.
- Click Close.
Check if the plug-in is "Soft Disabled"
Soft disabling can occur when the plug-in produces an error that does not cause Outlook to unexpectedly close. For example, Outlook might soft disable the plug-in if it throws an unhandled exception while starting the add-in.
- In Outlook, click the File tab.
- Click the Options button.
- In the categories pane, click Add-ins.
- In the details pane, verify that the ‘SendSafely’ add-in appears in the Inactive Application Add-ins list.
- In the Manage box, click COM Add-ins, and then click Go.
- In the COM Add-Ins dialog box, select the check box next to the disabled ‘SendSafely’ add-in.
- Click OK.