Replace existing file and upload as a new version in a checkout enabled document library

Hello @Rijo Rajan, 

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You’re running into “by design” behavior in SharePoint when Require check out is enabled. When the library requires check out, others can’t overwrite a file until someone checks it out. Only after you check out → upload same name → check in does SharePoint store a new version. Microsoft also cautions that requiring check out is not ideal for co‑authoring and can slow collaboration—something to consider if your scenario doesn’t strictly need enforced locks.  

For more information, please refer to: 

• Check out or check in files in a document library - Microsoft Support 
• Set up a library to require check out of files - Microsoft Support 
• Top questions about check out, check in, and versions - Microsoft Support 

You can Use Power Automate to Automate File Replacement: 

Before create your flow, Ensure target library is configured: 

• In the target document library (the one with your “real” files), confirm:  
  • Versioning is ON (Major versions at minimum). 
  • Require Check Out is Yes (since you chose Option 2 earlier). 
  • (Optional)Content approval if you need review before final visibility. 

How to use Power Automate to Automate File Replacement:  

Step 1: Trigger the Flow 

• Access to Power Automate (flow.microsoft.com) > Sign in to your account
• Click Create > Automated cloud flow
• Use: 
  • Trigger: “When a file is created or modified” in SharePoint. 
  • Inside your trigger, choose your Site Address and Library Name 

Step 2: Get File (Properties only) 

• Action: “Get file (properties only)” > SharePoint 
• Use the file name from the trigger to search in the target document library. 

Step 3: Apply to Each File 

If multiple files are uploaded: 

• Add “Apply to each” loop to process each file individually. 

• Under Select an output from previous steps, type: "/" > Insert dynamic content > choose body/value from the Get files step 

Step 4: Check Out Existing File 

Inside the loop: 

• Add “Check out file” > SharePoint  Use the Identifier from the file properties. (Refer to step 1) 
• Under Id, type: "/" > Insert dynamic content > Choose ID under Get files step 

Step 6: Update Existing File 

• Add: “Update file” > SharePoint 
• Use the Identifier of the existing file 
• Use the new file content from Step 5 

Step 7: Check In File 

Add: 

• “Check in file” > SharePoint 
• Use the same Identifier 
• Add a comment like “Updated via automated flow” 
• Check in type: similar to your Versioning Settings. 

• Click Save 

After Saving, you can try to upload the file again. You'll see 2 options below: 

You can use this image as a reference to your flow: 

Please feel free to reply if you need any further assistance. Thank you for your patience and understanding!

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