Does uploading to server/deployment overwrite files?

If I manually select a file, does it overwrite the file in the server? I know if I download it asks if I am sure I want to do it but I am unsure if it thats true when sending uploading files.

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Yes, it does. If you want to get protected from accidentally overwriting recently changed files, you can enable Settings/Preferences | Build, Execution, Deployment | Deployment | Options | Warn when uploading over newer file.

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