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For example, everytime I click on the same attachment in Gmail it downloads a new copy and renames it to something like file(x).bar where x is the current number of copies.
Is there any way to get it realise it is the exact same file as the one it is trying to avoid overwriting?

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The only thing i found is: go to settings, then advanced and check the box to specify the location of the file save all the time. Then, on each save, select original file name and click yes to overwrite.

Not automatic at all, but keeps from saving *(12).doc files.

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