Calendar link in Playbooks email signature leads to Windows Defender page, but link in Outlook email signature works fine

Overview

You are using Outlook or Office 365 as your email backend connected to Playbooks. You are also using both Playbooks and Outlook to send emails. In both of your email signatures, you have inserted a calendar link for your clients to book a meeting using Playbooks Calendar. However, the link in your Playbooks signature does not work, though the link in your Outlook email signature works fine. When your clients click on the calendar link in your Playbooks signature, they see a Windows Defender page instead of seeing your calendar link.

Solution

This issue occurs because of Microsoft Safelinks, which is an antivirus or security software feature of Office 365 that hijacks links in your emails and replaces them with a redirect, for safety purposes. Links that are deemed safe will redirect successfully, while suspicious links will not redirect.

Most likely, your email signature in Outlook contains a working link because the link redirection detects that Playbooks is a safe destination, so you then copied that working link into your Playbooks email signature. However, this can inadvertently create a double redirect for your clients who are also using antivirus or security software that implements a similar link redirection safety scheme. Having multiple nested redirects is generally considered suspicious behavior, so this will cause the link to no longer load successfully.

To avoid this issue, make sure to copy and use your direct Playbooks calendar link in your Playbooks email signature instead of a link copied from Outlook. A convenient calendar link can be found on the signature editor page. See Adding Calendar Links to Emails for more information.

<supportagent>

As a support agent, you may impersonate the customer and edit their email signature for them if necessary.

</supportagent>

Testing

After that you have updated your Playbooks email signature to include a direct link to schedule a meeting with Playbooks Calendar, you can now send a test email to an address that you can access in order to test that the link is working.