DropIt: Automatically Rename and Move PDFs On Windows

DropIt: Automatically Rename and Move PDFs On Windows

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:

  1. You give it a file or group of files that either already exist or are newly scanned.
  2. 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).
  3. 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.

DropIt Floating Arrow
DropIt Floating Arrow

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.

DropIt Associations
DropIt 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:

Dropit Name Association
Dropit Name Association

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

DropIt Drag Icon
DropIt Drag 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.

Dropit Moved
Dropit Moved

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.

PDF Sample
PDF Sample

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.

DropIt Filter
DropIt Filter

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.

DropIt File Content
DropIt File Content

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.

DropIt Create Date
DropIt Create Date

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:

DropIt Rename Rule
DropIt Rename Rule

I dragged my Sainsbury PDF to the DropIt icon.

DropIt Drag
DropIt Drag

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.

DropIt Rename and Move
DropIt Rename and Move

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.

DropIt options
DropIt 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.
DropIt Options
DropIt Options

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.

DropIt Monitored Folder
DropIt Monitored Folder

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.

About the Author

Brooks Duncan helps individuals and small businesses go paperless. He's been an accountant, a software developer, a manager in a very large corporation, and has run DocumentSnap since 2008. You can find Brooks on Twitter at @documentsnap or @brooksduncan. Thanks for stopping by.

Leave a Reply 17 comments

Liselotte - September 26, 2018 Reply

I am about to scan a lot of old drawings and I am looking for a tool that can ‘snap’ the drawing number from the pdf and save the file with the name.

I first thought DropIt could do it, but after reading your above (great, down to earth) article I am not so sure any more.

Any thoughts on how to solve this issue … via DropIt or other tools.

Thanks 🙂

divinity666 - November 18, 2017 Reply

Hello everyone,

I am one of the developers of DropIt and also added the “FirstFileContentDate” feature. I am wondering, why you are asking that questions here and not writing them to the developers 🙂

Basically the feature looks in the file content (for PDFs it needs to be OCR’ed as stated above). Then it filters for a specific date pattern. As there exist billions of different date formats, you are able to define the date format in regular expressions since DropIt 8.4 in the settings.ini (yes I know… not very user friendly, but flexible as hell!).

Anyway I am very happy to see, that you are promoting and using DropIt for your purposes. And to be honest: I also started using DropIt because of the paperless office thing 🙂

If you have additional questions or requests, please leave us a message in the sourceforge bugs or feature requests. This is the only way for us to have it manageable.

Best regards

    Maya - February 17, 2018 Reply

    I left some queries but have yet to receive an answer.
    I don’t know how to get it to read different date formats from content.


Hafid - September 21, 2017 Reply


First I would like to thank you to present us this nice tools. I had some questions if someone can help me with it:
– Is it possible to move a pdf in the folder that correspond with the association name in dropit?
– As I have almost 150 rules, is there a way the import them by excel or other programme?

Thanks in advance for your answer.

Crystal - July 1, 2017 Reply

I’ve finally, after much thought, decided I should go paperless and, Brooks, I’m so happy to say that but for you, I am not sure I would have taken the leap or been as excited about it as what you have got me!

I’m working with a lot of historical data and I desperately want automate file sorting using the actual document date. I purchased a ScanSnap ix500 which is AMAZING – it’s now set up as per your unofficial guide. I have also enjoyed the PDOG document and included interviews. I’ve played around with DropIt but although it has the option for FileContent – first date, I can’t seem to get this working. Given this is a not negotiable feature for me, is there some way to get this working, or should I switch to File Juggler?

And, no, switching to a MAC is not a desired option although Hazel sounds fantastic!! 😀

Thank you for your help and for building this community!

Kunal Parikh - May 8, 2017 Reply

In the latest release of Dropit (V8.3) they have introduced the following custom Abbreviations under Text Content:

%FirstFileContentDate% = first date from file content in unchanged format [“29.04.17”]
%FirstFileContentDateNormalized% = first date from file content normalized [“20170429”]
%FileContentMatch1% = 1st match from file content filter [“Bill”]
%FileContentMatch2% = 2nd match from file content filter [“Bill”]
%FileContentMatch3% = 3rd match from file content filter [“Bill”]
%FileContentMatch4% = 4th match from file content filter [“Bill”]
%FileContentMatch5% = 5th match from file content filter [“Bill”]
%FileContentMatch6% = 6th match from file content filter [“Bill”]
%FileContentMatch7% = 7th match from file content filter [“Bill”]
%FileContentMatch8% = 8th match from file content filter [“Bill”]
%FileContentMatch9% = 9th match from file content filter [“Bill”]

Unfortunately, in the absence of documentation on how to filter the abbreviations, I was only able to get it partially working.

Is there anyone who can provide input on how to use these?

PS: I was able to use the %FirstFileContentDate% and extract the Month and year from the PDF file for one of my invoices to the name, however it only comes up in “Nov 15” format.

Bob Blizzard - March 18, 2017 Reply

I currently using Evernote to save all my paper importing directly from scansnap. Are you suggesting using a program like Dropit to save all my pdf’s on an external drive also? Can Dropit and Evernote work together?

Simon Allison - February 5, 2017 Reply

If your NAS is setup as a mapped drive , it works perfectly. Thanks for the article brooks ! I too have been looking at both file juggler and drop it , and yes open source wins ! Also I use to have one called beleverde but it stopped working the way it did. I didn’t know dropit can do content filtering so a valuable asset to the program , thanks again.

Katie - January 30, 2017 Reply


I loved your article!
Did you find a way to add the content date to the file name?
This program sounds perfect with that critical exception.


Alex Luu - June 30, 2016 Reply

Hi guys,

Question regarding the content recognition filter, do the scanned pdfs have to be scanned and OCR in order for the content recognition function to work in DropIt? I am not able to get DropIt to successfully associate pdf files through the content recognition filter. Any thoughts or help would be greatly appreciated and duly noted!

    Brooks Duncan - July 2, 2016 Reply

    The PDFs definitely need to be OCRed/searchable. Otherwise, DropIt doesn’t have anything to work off of when it tries to recognize the text.

Rae - March 16, 2016 Reply

Thanks for yet another wonderful article, Brooks! I really appreciate you looking after us Windows and Android users (or to say it more concisely, us non-Apple users). I have also looked for over a year and a half for a Windows Hazel alternative. Free open-source software is a huge bonus! I really appreciate you going through how to use the program and showing the pros and cons. Great job!

    Brooks Duncan - March 16, 2016 Reply

    Glad you liked it. It’d be easier for everyone involved if Noodlesoft would make a Hazel for Windows, but until that day (which will probably never come), the search continues.

Ebert Mahon - January 21, 2016 Reply

Thanks for the suggestion. I just downloaded DropIt and it works fine for me. This is a great utility app which makes filing so much easier.

Richard - January 16, 2016 Reply

thx for this article. I am looking for a hazel alternative for windows since a while. The last 1,5 years I was using filejuggler, too.
But there are some issues with regard to the UI:
In filejuggler you can not search / filter the rules. And you can not group them. You can not sort them. I have hundreds of rules, so it is much afford to organize and administrate them at the moment. If I m searching a specific rule, I m looking at the moment in the XML-File with STRG-F 😉
Unfortunately, there are no updates in the last 18 month with regard to all the Top-Features, the community suggested (my opinion).

So I will definitely give dropit a chance now. As it is opensource, there might be a chance, that soon someone will create the “grep the date”-feature… That is very important for me, too – as every filename starts with the corresponding document-date.

If I’ll find a way how to solve the “date-issue” in dropit, I will of course report it here.

Thanks again for the dropit-hint!


Anil - January 8, 2016 Reply

Hey Brooks,

This is an excellent article. I do have FileJuggler and had reported a problem of it “unchecking ” the rules when the network connectivity is lost, say, when the laptop goes to sleep and then wakes up because my folder to be monitored are on a network drive (Synology NAS). The author acknowledged that as an issue several months ago, but no solution.

With DropIt, I need to check if it can handle network mapped drive and not able to read a date from within a file is an issue for me at the moment. Maybe, I need to scan my docs the same day I get it, like, receipts and stuff 😉

Thanks again

    Brooks Duncan - January 8, 2016 Reply

    Let us know how it deals with the NAS. I don’t have one (sadly) so I wasn’t able to check that out.

    The date thing is unfortunate. I almost think there must be a way to do it, but I haven’t a) figured it out and b) dug into it too much. Will update if I find anything.

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