If you send email to a distribution group that is running off an Office365 Hosted Exchange account that is running in Hybrid mode with your on-premise Exchange server, the email may never be received. The email happily shows in SENT folder, has no errors or email bounces, and if you trace the email it shows as DELIVERED:
Fortunately there are two ready solutions for this problem:
Set-DynamicDistributionGroup -Identity sales@contoso.com -IncludedRecipients "MailboxUsers,MailContacts" -RecipientFilter {((RecipientType -eq 'UserMailbox' -or 'MailUser' -or 'MailContact'))}
If you want the full Microsoft explanation of the problem see THIS KB article.
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