A group of Microsoft Products and technologies used for sharing and managing content, knowledge, and applications.
Hello @Silas Wharton
From what you have shared, the SharePoint check-in/check-out feature works as expected the first time. However, when you perform the same action again, even with the same file, the file is no longer saved to the expected location.
Given this behavior, I would recommend reaching out to the Microsoft Support team for further investigation. They are in the best position to work with you directly and have access to the necessary resources and diagnostic tools. If required, they can also arrange a screen-sharing session to reproduce the behavior, collect additional information and diagnostic logs, review your SharePoint configuration, and escalate the case for further investigation.
Since this is a user-to-user community forum, I can provide guidance and troubleshooting suggestions based on my experience as a Microsoft user and the information you have shared.
If you are not a Microsoft 365 administrator, please contact your IT administrator and ask them to create a support request on your behalf. They can refer to the following Microsoft documentation: Get support - Microsoft 365 admin | Microsoft Learn
When opening the support request, please make sure to disable the Support Assistant (AI) in the Help panel first. After that, enter a brief description of the issue. Once the AI assistant is turned off, the Contact Support option should become available, allowing you to submit a support ticket directly to Microsoft's support team.
When submitting the support request, I would recommend including as much information as possible about the behavior, particularly:
- Whether the issue occurs across all SharePoint sites or only a specific site.
- Whether it affects all file types, such as Word and Excel files, or only a particular file type.
- Any recordings or screenshots showing the behavior.
Providing these details in the initial support request should help the support engineer better understand the scenario and determine the appropriate troubleshooting steps.
I hope your issue will be resolved soon. If you need any further support from me, please feel free to share it any time.