You can create new versions of files that already exist in Alfresco Outlook Client. There are two ways to trigger versioning for one or more files: implicit and explicit versioning.
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Implicit versioning
Drag and drop one or more files into a site or folder in the Alfresco sidebar, and it will determine if files of the same name already exist.
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Explicit versioning
Drag a file into the Alfresco sidebar and explicitly drop it on an existing file.
In both cases, the Alfresco Outlook Client lets you decide if you'd like to create a new version, rename it on upload, or ignore it.
Note
Versioning only applies to files, so emails can't be versioned. If you add an email with a subject that already exists, in a specific location, you'll be asked to rename it.