Hazel, Automator, or something else?

I’ve recently become a dad which has increased the amount of bills, EOBs, letters, etc. our family receives. Some of these are digital while others come in snail mail and are quickly converted. Once the document is a PDF, I rename it based on the date received, the type of information it is (Bill, Receipt, etc.) then the location or place it’s from. I use TextExapander to help me name the file but it’s manual to move it to the right folder.

Ideally what I’m looking for is an service in Automator that will allow me to select it, put the file in the right folder (specified by the service I selected) then prompt me to finish renaming the file.

The issue I’m running into is getting prompted to what I want to rename the file. I’ve spent the better half of my day looking at Hazel and Automator custom Apple Scripts that I could not get to work on my machine.

Any help on this is greatly appreciate or other suggestions to better optimize my workflow.

Hazel is really the canonical Mac Power Users solution for what you’re trying to do. For instance, Hazel watches an “Action” folder on my hard drive. I have a series of Hazel rules (one per type of bill/statement) that will recognize a PDF that I drop in there, move it to the appropriate nested folder, and rename it based on a date out of the OCRed text in the PDF.

What exactly is it with Hazel that’s not doing what you want?


This is close to what I want to do. However the naming convention is slightly different for each type of file i.e. Date - Bill for Dr Smith [date of appt] vs. Date - Bill for Dr Brown for [date of appt]

With one rule per type of file you can have different naming conventions for each.

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I would use this approach too.

I do the same with Hazel. The date-matching function in Hazel is a great way to automatically name. Sometimes a picture helps. Here is my set up for the optometrist bills.

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Here is what the datematch does in the statement:

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For my rules above, the final “sort into subfolder” uses the datematch field but just selects the year, so all the vision medical bills are sorted into subfolders based on the year of the service.

Hazel is a lifesaver for all this. Takes some time to tweak rules, but after a few months it works very nicely.

You can also take it another level with medical bills that you have to file yourself. (For providers who don’t accept insurance.) I add a step to print out the file and also the insurance claim filing form. I grab them from my printer, date it and send it out to my insurance company. That way I don’t forget to submit claims.

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Our leader David Sparks wrote an iBook called “Paperless” a number of years ago that will walk you step-by-step through this process. The book is a fantastic multi-media iBook that includes text, images, and video walkthroughs of how to do exactly what you are describing.

This approach I created for my Genealogy documents uses Hazel to preview, name and file documents dropped into a folder. It could be easily adapted to suite the processing of your bills etc

Automatic Rename and File

Video Demonstration

Is the printing step automated? What app/tool are you using to do this? I have a ‘hot folder’ on my desktop and want to drop files (99% of the time they are PDF’s) into it that just go to the printer and then are deleted. Auditors love paper.

Yes, the printing step is automated. You can have Hazel print the triggered file with the following embedded Applescript :
tell application “Finder”
print theFile
end tell

If it is a different file that you need to print that is triggered by this one, I also have Hazel “Run Automator workflow” that prints that particular file. Sounds complicated, but it’s not.