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When the Send To command is used to copy a file from one library to another, if the destination library already has a file with the same name, will that file be overwritten?

I suspect this is related to whether the "Overwrite Existing Files" checkbox, but would you at least get prompted if you weren't sure how this was set?

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Yes it will overwrite the file without prompting. I just tested it to make sure my memory was correct. If you enable versioning on the library, you can then revert back to the previous version. The "Overwrite Existing Files" check box is for uploading documents only as far as I know.

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