dosubot[bot]
commented
2 weeks ago The issue you're experiencing with booking and rescheduled email alerts going straight to the "Deleted Items" folder in Outlook could be related to specific email headers or configurations used in the cal.com codebase.
One known configuration that might affect email delivery is the bypass_list_management filter enabled in the email headers for smtp.sendgrid.net. This setting can influence how emails are processed and delivered by email clients, including Outlook, potentially causing them to be categorized differently [1].
Additionally, the email templates for booking confirmations, updates, and cancellations include various dynamic and conditional content elements, such as formatted text and conditional sections, which might be treated differently by email clients like Outlook [2].
To address this issue, you might consider:
- Reviewing and possibly modifying the email headers to ensure they align with best practices for email delivery.
- Checking if any specific content or formatting in the email templates could be triggering Outlook's filtering system.
If the problem persists, further investigation into Outlook's filtering rules and settings might be necessary to identify any additional factors contributing to this behavior.
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kmaity-9563
keithwillcode
jkdowdle
Issue Summary
Once a booking has been made the Host’s email message alerting that an booking has been made lands in Outlooks “Deleted Items” folder as well as any email messages about updates to the booking go straight there as well.
To be more clear about which email alerts these are they have a subject line like “Meeting between Host and Participant” and “Your meeting between Host and Participant has been rescheduled to…”
This seems to be specific to the host and not the participant, who does get all email notifications.
The calendar stays in sync across meetings being created or updated but we miss those emails.
Steps to Reproduce
Using round robin event types
Expected behavior: Both emails go to the inbox (not deleted items)
We've checked org wide spam and other settings and don't see any reason why this would happen nor are there any Outlook Rules to automatically send any emails to trash.
One interesting note, if the booking is canceled then the email notification seems to land in the inbox just fine.
Actual Results
Expected Results
Technical details
Evidence
IT Admin was able to see some information about these emails and could verify that they went right to deleted items