Attachments does not go out with the mail when scheduled to send later.

Hi He, 

I’m sorry you’re going through this, especially since this involved an important job search email. Thank you very much for the detailed explanation of what happened. 

As a forum moderator, I genuinely wish I could directly access your account or review the backend systems to diagnose and resolve this issue for you. However, our role here is limited to providing general guidance by offering clear next steps, sharing applicable resources, and directing you to the appropriate support channels so you can work with the right team to investigate further. 

Based on what you described, it sounds like the attachment was not successfully saved to the scheduled draft before Outlook sent the message. When an email is scheduled, Outlook keeps it as a draft until the scheduled send time. If the attachment does not appear on the scheduled message after scheduling, it usually means the file was not fully uploaded, synced, or retained with that draft. 

This can happen for a few reasons, such as an incomplete upload, a browser/cache issue, an unstable connection, account attachment limits, or a temporary issue with scheduled send and attachments. 

To help prevent this from happening again, please try the following: 

1. Try scheduling a test email with a smaller file or a different file type, such as a DOCX, image, or another PDF, to help determine whether the issue is specific to that 12 MB resume PDF or happens with all attachments. 
2. Wait until the attachment fully uploads before scheduling the email. 
3. After scheduling, open the scheduled email from the Drafts folder and confirm the attachment is still visible. 
4. If the attachment is missing, cancel the scheduled send and attach the file again. 
5. For important or larger files, consider uploading the resume to OneDrive and sharing it as a link instead of attaching the PDF directly. 
6. You may also try using the Outlook desktop app, if your license includes it, or try another browser or a private/incognito browser window. 

If the issue still continues even after following the steps above, it may be related to your school tenant configuration, attachment policies, or mail flow/security settings. Since this is a school account managed by your organization, I recommend contacting your school IT administrator so they can review the account settings, attachment size limits, and any policies that may affect scheduled emails or attachments. 

Additionally, if needed, your IT team can also raise a support ticket with Microsoft Support through the Microsoft 365 Admin Center for deeper investigation. They have access to backend configurations and can perform a more in-depth investigation. At the very least, they can provide the most effective workaround to ensure your experience remains smooth and secure.      

In case you do not know who is your IT admin, kindly refer to this article: How do I find my Microsoft 365 admin? - Microsoft Support  

I sincerely hope everything goes smoothly with your job search and future email exchanges. Should you have any further questions or need additional assistance, please feel free to share them in the comment below. I'm very happy to help.  

Thank you again for your patience and understanding. 

Have a wonderful day ahead.

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