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Hi @Derrick Simpson
Thank you for posting your question in the Microsoft Q&A forum.
To help narrow down the issue, please provide more details:
-Are you signing in with a personal Microsoft account (for example, @outlook.com or @hotmail.com) or with a work/school account?
-What type of account is configured in Outlook (POP, IMAP, or Exchange)?
-Which version of Outlook are you using (Classic Outlook or New Outlook)?
-Do the contact group members appear correctly in Outlook on the web?
Also, please confirm whether you followed these exact steps when creating the contact group:
Open Outlook > Go to People (Contacts) > Click New Contact Group > Select Add Members > From Outlook Contacts > Choose the contacts and click OK > Then click Save & Close.
Please know that while our initial response might not resolve the issue right away, your input is incredibly valuable. With a bit more detail, we’ll work together to find the best solution for you.
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