Based on the information provided in the context, there could be several reasons why an email sent to 90 recipients via Contact Groups was flagged as spam. One possible reason is that the email was sent from a mail-enabled security group, which can be treated as an external address by Microsoft 365 groups and blocked by default. Another reason could be that the email content triggered a spam filter, which can happen if the email contains certain words or phrases that are commonly associated with spam. It is also possible that the email was flagged because of the volume of recipients, as many email providers implement filtering and blocking mechanisms to defend against spam and keep users' inboxes clean.
To troubleshoot this issue, you can try the following steps:
- Check if the email was sent from a mail-enabled security group and if the Microsoft 365 group's settings allow email messages from external addresses. If not, change the settings to allow external senders to email the group.
- Check if the email content triggered a spam filter. You can run a message trace to view specific details about the message and see if it was marked as spam due to the content of the message.
- Check if the email was flagged because of the volume of recipients. Some email providers implement filtering and blocking mechanisms to defend against spam and keep users' inboxes clean, so sending a large volume of email could trigger these mechanisms.
It is also worth noting that just because one colleague's emails were not flagged as spam does not necessarily mean that the same will be true for everyone. Individual email clients apply their own filtering algorithms that can filter based on each user's personal history of interactions, which can mean that an identical message that gets delivered to one recipient could get blocked by another recipient's email client.
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