Hi Leslie Lau,
Thank you for posting your question in the Microsoft Q&A forum.
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Based on the NDR you shared, my understanding of your scenario is that you are using Classic Outlook with an Exchange Online (business) account to send an email that includes an attachment of approximately 33 MB to a recipient who appears to be using Yahoo Mail. The message was not delivered, and you received the NDR shown above.
I conducted a quick review based on this scenario and identified the following insights:
- From the sender side, Exchange Online does enforce message size limits. According to the Microsoft article Exchange Online limits, the default maximum message size for Microsoft mailboxes is 35 MB for sending and 36 MB for receiving. Administrators can configure a custom limit between 1 MB and 150 MB. This confirms that there are defined limits for message sizes within Exchange Online.
- However, in your case, the message was successfully sent from Exchange Online and only then generated an NDR, which indicates that the issue did not occur on the sender side. Further research shows that the error code “550 5.0.350” typically originates from the recipient’s mail server. For Yahoo Mail specifically, the maximum allowed size for an individual email message is 25 MB. This limitation is documented in Yahoo’s official help article: https://help.yahoo.com/kb/SLN5673.html
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As a result, the message was rejected by the Yahoo mail server because the effective message size exceeded the recipient’s allowed limit.
Regarding possible workarounds, if you are acting as an end user, you may consider applying one of the suggestions already provided by the QA assistant above, all of which are valid and commonly recommended approaches. Among these options, the recommended best practice is to upload the file to cloud storage (such as OneDrive) and then share the download link with the recipient instead of attaching the file directly to the email.
Additionally, it is also advisable that the recipient verifies their mailbox storage usage, as a mailbox nearing or exceeding its quota may further contribute to message delivery failures.
I hope the information above is helpful.
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