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After adding an attachment in trello how is it possible to have it automatically updated when changes are made to the original word document on your computer?

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The only way to make a document update itself after uploading is to attach a Google Document by selecting "Google Drive" The attachment is basically a link to the Google Document, and all edits made there are online.

Attaching a Word Document (.doc or .docx) means you are uploading a file, and there is no dynamic editing functionality once you upload the file itself.

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