Hi, @Kareem Culbertson
I agree with Aleksandr.
When performing a message trace, if the status shows as "GettingStatus" instead of "Delivered" and the message is not delivered, it may be due to the terminal event not found.
You can get to know Scenario: Message Trace shows GettingStatus | Transport TSGs (eng.ms)
You will need to confirm the following information:
1.Is the sender or recipient from the same domain?
2.Are all messages with GettingStatus status? Does the issue only appear in a specific message?
3.Whether NDR (Non-Delivered Report) was received?
4.Do you find any other characteristics of the affected messages?
Here are some suggestions you can try:
1.According to the message trace instructions, Office 365 received the message, but it was delayed in delivering to the recipient. Office 365 System is working hard to deliver it. You can check the status of your message later.
2.Exchange Online delivers messages to the user's mailbox after passing through multiple Exchange servers. Message Trace is displayed when the message cannot be retrieved at the time of search (delayed). More information can be found About '?{$_.status -like "GettingStatus"}' of Get-MessageTrace - Microsoft Q&A
3.Verify that the email has not been misclassified as spam. Check if the emails are in quarantine, which can happen if you suspect that they are spam or contain malicious content.
If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".