Dear Kym Tolson
Good day!
Thank you for posting to the Microsoft Community.
Based on your issue description "My auto replies are on but not sending "I understand that you're having an issue where your auto replies are not working.
To help resolve this, I would like to suggest the following troubleshoot:
- kindly double confirms and try to disable automatic replies and enable it again for your account, to do so kindly follow the steps in the following article: Send automatic replies (out of office) from Outlook - Microsoft Support
- Kindly double check if your mailbox does not have forwarding enabled. if your account is forwarding to another account, kindly try to disable it and check the behavior after.
If the affected user mailbox has SMTP forwarding enabled, OOF replies won't be generated. It can be checked in any of the following locations:

In PowerShell, you may use the following command:
Get-Mailbox -Identity usermailbox| fl DeliverToMailboxAndForward, ForwardingSmtpAddress, ForwardingAddress
For more information. kindly check: **** Understand and troubleshoot Out of Office (OOF) replies - Exchange | Microsoft Learn
Note: If automatic replies are enabled, only one reply is sent to each sender even if a recipient receives multiple messages from a sender. Kindly try to do a test and double confirm if the sender has not received auto replies. only one auto reply per sender.
After trying all those troubleshooting steps, If the issue persists, we recommend that you create a support ticket with Microsoft's frontline support team.
Due to the limited permissions and access resources of our forum moderators, we are unable to collect certain types of registration information in public forums for this reason and for the privacy of our users' data.
it would be useful for the Microsoft backend team (Get support - Microsoft 365 admin | Microsoft Learn) to examine the issue remotely.
Note: If you're an end user, you may need to contact your enterprise organization's Office 365 global administrator to contact a support engineer for further processing.
Important: If any of your organization's Office 365 Business/Enterprise/Education subscriptions are from a federated partner or reseller and the global administrator can't open a service request on your end, you may need to contact the reseller's support provider so that they can help the global administrator open the service request on your end. After that, the Office 365 support team will participate in the service request that was created.
Thank you for your valuable time and cooperation