Yesware 'Processing Message' Pop-up & Potential Email Duplication

After thoroughly reviewing our different backend systems, our Engineering Team found that Yesware's tracking is not triggering the witnessed pop-up message in question. Instead, this particular message is presented when there is a delay longer than 5 seconds between an Outlook user's client and Microsoft's email servers. In other words, this same message could appear for other Outlook Add-ins a user might have in their inbox under the same conditions.

Microsoft themselves has documentation that provides further explanation as to the specific factors that can result in pop-up. They list that the primary contributors are:
- A slow internet connection, specifically when Outlook attempts to send emails
- Firewall rules that impact requests to yesware.com
- No longer being signed into the Yesware Add-in

For more information from Microsoft's team, please see the published article on the topic:
https://learn.microsoft.com/en-us/office/dev/add-ins/outlook/onmessagesend-onappointmentsend-events?tabs=windows

With that being said, we certainly understand how this pop-up and the specific language it uses can be rather confusing, specifically when presenting users with an option to 'Send' or 'Don't Send'. Unfortunately, as to when this message appears is ultimately at the discretion of Outlook itself. For that reason, our team is recommending that should users encounter the pop-up that they allow a few additional seconds for Outlook to handle the request and deliver the email as it normally would. If, after approximately a minute or so, the pop-up does not go away on its own, we encourage users to click on the 'Don't Send' option as the email should be sent with Yesware regardless of the pop-up's appearance.

Once again, we'd like to apologize for any confusion this messaging may come as. We do, however, wish to reassure users that Yesware's email tracking is not impacted by this pop-up and emails will continue to track recipient engagement as they normally have regardless of the pop-up. Any additional questions can certainly be directed towards our Support Team for further guidance.

We are currently experiencing an issue where some Outlook users are reporting a pop-up when sending emails using Yesware. Affected users are seeing the message 'Yesware is taking longer than expected', and are prompted to either 'Send Anyway' or 'Don't Send'. Upon selecting 'Send anyway', these users' emails are being sent an additional time, while selecting 'Don't send' moves emails into the users' Drafts folders.

At this time, for those affected, we recommend selecting 'Don't send' when prompted by this pop-up and deleting the subsequently created draft copy. This will ensure emails are only sent once. Please note, email tracking is not impacted by this behavior and emails sent will collect engagement data as expected.

Our development team is actively looking into this and we will provide an update once we have more information.