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FileZilla 3.53.1 seems to skip files when the file exists on the target and is newer. Is this possible and how can I prevent this from happening?

Status:         Starting upload of master.cfg
Status:         Skipping upload of master.cfg
Status:         File transfer skipped

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I do not think it's the default behaviour. You have probably changed the defaults in settings.

Go to Edit > Settings > Transfers > File exists action.

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