I often say that the holy grail of going paperless is the ability to scan a document and have your computer automatically rename and move it away. Even better if you can automatically process a bunch of PDFs at once.
On the Mac, the gold standard is a tool called Hazel, which I have written about many times. On Windows, there have been options but they are either not as fully featured or are not well supported.
Thanks to awesome DocumentSnap reader Thomas, I have come across a tool called DropIt, which will do almost everything that Hazel will do, but it is free and open source(!).
Use DropIt To Automatically Rename And Move PDFs
Here is how DropIt and similar tools work at a high level:
- You give it a file or group of files that either already exist or are newly scanned.
- DropIt looks at each file and evaluates it against some rules that you have set up (in our case, the name of the file or the contents of the file).
- DropIt takes some sort of action that you have determined (in our case, usually renaming and moving).
These tools can do all sorts of things with any type of file on your computer, but in our case we are specifically interested in processing PDFs for going paperless.
I want to make special mention of point number 2. There are many, many tools out there that can rename and move files around based on things like date and filename.
However, the ideal is a tool that will look inside the PDF and then rename and move it based on the text content of the PDF. Most tools cannot do this, but DropIt can.
Two Ways To Use DropIt
At a high level, you can use DropIt two ways:
1) A floating icon appears on your desktop (you can move it around or turn it off, of course). Any files you drag onto that icon will be processed.

2) You can set up DropIt to watch a folder and any files you save or scan to that folder will be processed.
I will cover both methods in this article, but once you get up and running it will be more efficient to focus on method #2 so that it does its thing in the background.
Create Associations For PDFs
In DropIt, rules are called Associations. These are where you tell DropIt what to look for and what to do.
To create an Association, right-click on the DropIt icon and choose Associations.

Matching Based On Name
Let’s create an Association based on the name.
In our case, I have a PDF that I have downloaded. I will manually rename it with my naming convention, and then I want DropIt to automatically move it to my Bills folder.
(Of course, you don’t have to manually rename the file first. You can move a bill based on an existing filename that you’ve downloaded from a bank or something too.)
In the 1. Name: field, I will start by giving the Association a name. I will call it National Grid, but it can be anything unique and descriptive.
Next in the 2. Rules: field we get to the heart of the Association. We tell DropIt what we are looking for. You can do some pretty crazy matching, but in this case we keep it simple. I want to match any PDF that ends with NationalGrid.pdf, so I will put *NationalGrid.pdf in the Rules line.
You can hit the blue i icon for more examples, or see this page for instructions on building rules.
In the 3. Action field we tell DropIt what we want to do. In our case, our PDF is already named so we just want to move it. I chose Move from the dropdown, but you will see there are many choices.
Finally in this example 4. Destination Folder: is where I want to move the file to. You can type in a path, hit the Folder icon to choose one, or hit the blue book icon to use some pretty wild variables to customize thing.
Here is my sample rule:

To test it, I dragged my National Grid PDF onto the DropIt icon.

It then popped up this Processing window where I could review what was going to happen. If it all looks good, hit the blue Play button.

Don’t worry, we will disable this window later, but it is there if you want it.
You can see that the file has been moved to my Bills folder as requested.

Matching Based On PDF Content
That’s great that we can move a PDF based on its name, but that’s not what we really want to do. We want to be able to move the PDF based on words that appear in the document.
Let’s say that we have a Sainsbury’s Energy bill that we want to automatically rename and move.
We want to find some words that we could pick out that would always be in this type of document. We want to be sure every month that it is our Sainsbury’s Energy bill. Maybe we’d pick “Sainsbury’s”, “Energy”, “Statement” and the account number. Use your judgement.

We’ll go in and create an Association as before, but this time the 2. Rules line will be different.
I put *.pdf to limit it to just PDF documents, and then I hit the Filter icon.

As you can see, there are many options to additionally filter files, but we are interested in the File Content checkbox at the bottom.
First you want to choose how it matches. I like All words in casual order because it allows us to choose words no matter where they are in the PDF. You can do literal strings, at least one word, and other options.
I put the keywords that we want to look for in the box and then hit OK.

Back in the New Association screen, we are on the 3. Action: section.
We hit a limitation of DropIt: you can only have one action. Unlike Hazel and other tools, you can’t have it (for example) Rename a file and then move it.
Fortunately, we can get around this because the Rename action allows us to specify a path.
In 4. New Name:, you can manually type in the path, or hit the blue book icon and build your file path.
One place to start is the date. You can have it use the Date Created in the filename.

By default the new name will include the variable %FileName%. This is the existing name you had when you scanned or downloaded it. In my case, I don’t want that name so I removed that variable and replaced it with -Sainsbury Energy.
Here’s my resulting Association:

I dragged my Sainsbury PDF to the DropIt icon.

You can see that it has moved the PDF to my Bills folder and renamed it using the rule I set up in my Association.

Set DropIt Options
Once you start using DropIt regularly, there are some options you will probably want to change. You can see the DropIt manual for what all the options do, but here is what I recommend.
Right-click on the DropIt icon and choose Options.

I changed the following options:
- Show target image always on top. I turned this off. Total personal preference there.
- Start the process after loading. I turned this on. I don’t want to have to review the monitor window before starting. I want it to just do its thing.
- Ignore unassociated files/folders. I turned this on. By default, if there is a file that DropIt doesn’t have an Association for, it will prompt you. Personally, I want it to just ignore the file and I will deal with it after.

Read the manual and feel free to set things up how you like.
Set Up Monitored Folders
OK, you’ve seen how to use the DropIt icon, but the most efficient way to go is to scan/download to an “inbox” folder and then have DropIt watch that.
To set that up, right-click on the DropIt icon and choose Options.
Go to the Monitoring tab and check Enable scan of monitored folders. By default it will look at your folders every 60 seconds, but you can change that if desired.
Hit the Add button and add a folder to watch.

Hit OK, and now whenever you save or scan a file to those monitored folders, DropIt will use your Associations to process them. Nice!
What About File Juggler?
Longtime DocumentSnap readers will have a question by this point: “What about File Juggler?”
File Juggler is a similar Windows program that I first wrote about in 2013. I was very excited about it because it was the first real “Hazel for Windows” that I was aware of.
File Juggler a nice program, and has some advantages over DropIt. It is a bit more polished and most importantly it has the ability to pull a date from the PDF content and use that in the filename. I haven’t found a way to do that in DropIt yet.
There are some disadvantages though:
- It is $25 for File Juggler vs. free/open source for DropIt. Now, I don’t mind paying for software as that usually means better support and sustainability, but…
- I have had reports from DocumentSnap readers that support and responsiveness from the File Juggler author is a little shaky. I know that both File Juggler and DropIt are side projects from their respective authors, but with an open source project there is more community support and advice, and that seems to be the case with DropIt.
If you were to ask me which tool you should use, at this point I would probably say DropIt. It’s not the most polished project UI wise, but it has worked well for me and it may be a solution for you if you want to automatically rename and move your paperless documents on Windows.