Dear Drew_939399,
Good day! Thank you for posting to Microsoft Community. We are happy to help you.
As per your description, it seems that you have tried to upload file to cloud, however, it disappears both from cloud and local disk.
If the understanding above is right, generally, OneDrive have cloud backup in backend service for the files that have been uploaded to the cloud.
For your reference: How to recover missing, deleted or corrupted items in SharePoint and OneDrive for work or school - Microsoft Support
Given this, we'd recommend you navigate to OneDrive and search for the file to check if it appears in the result.
Please also check if any log available for this file in Restore your OneDrive - Microsoft Support as shown below.
If the file cannot be restored via the Recycle Bin or Files Restore, as mentioned in the official article, an administrator can contact Microsoft Support to request a restore any time inside the 14-day window. Restorations from backups can be completed only for site collections or sub-sites, not for specific files, lists, or libraries. Given this, we'd sincerely recommend you contact your Microsoft 365 administrator, follow the steps in this article to create a support ticket to contact Online Support. The support team over there has higher permission than us, they can remotely help check the situation on your side, involve more resources to help you check if this can be restored from backend. This would be a more efficient way in handling this case for you.
For reference: How do I find my Microsoft 365 admin?
At meantime, as you have mentioned that you are using a Mac, if you have created a backup of your Mac using Time Machine, you can enter Time Machine to restore specific files from that backup. For detail steps, see Use Time Machine to restore deleted files or older files. You may also contact Apple support for further help.
Third-party link disclaimer: Microsoft provides no assurances and/or warranties, implied or otherwise, and is not responsible for the information you receive from the third-party linked sites, or any support related to technology.
Hope the above can help! If our understanding of the scenario is not consistent with yours, please feel free to point it out.
Thanks for your cooperation and understanding! We hope that you are keeping safe and well!
Sincerely,
Rhoda | Microsoft Community Moderator
