Hello Jason Arlo,
Good day! Thank you for publishing in Microsoft Community. We are happy to assist you!
Based on the information provided, the error code 19738 and the associated Non-Delivery Report (NDR) message, "Your message wasn't delivered to anyone because it's too large." Based on the information you provided; I have a general understanding of the issue.
The error code 19738 indicates that the email you attempted to send exceeded the size limit for delivery. This could be due to large attachments or an extensive amount of content within the email itself. I recommend reducing the size of the attachments or splitting the content into multiple emails to ensure successful delivery.
As per Microsoft documentation, you can increase the message size limit on the Exchange server to allow for larger email messages to be sent from Outlook for Mac clients and other EWS clients. For more information, see the following TechNet articles as appropriate for your version of Exchange Server. Exchange Server 2016 and 2013: Configure client-specific message size limits Exchange Server 2010: Set message size limits for Exchange Web Services
For more details, kindly refer this: Error when you use Outlook for Mac to send a large email through Exchange Server - Exchange | Microsoft Learn
If there is any update or I misunderstand you, please feel free to let me know. I will continue to assist you. Your understanding and co-operation are highly appreciated.
Thanks for your precious time. Have a nice day!
Sincerely,
Nafis Iqbal Shuvo