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My problem is that I want to backup my Chrome bookmarks, but the file doesn't seem to have a file extension so DropIt can't associate it with a task. Can it be done?

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Yes, it can be done.
Since you only want to backup Chrome bookmarks, you can use absolute path as a rule.
Create a new rule, enter a name, then enter the absolute path of the bookmark file as rule, then define an action, done.

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