Keep your paper documents as organised as your iLife


iTunes and its siblings make our digital possessions easy to organise, categorise and search. For years my paper life has lagged significantly behind the organisation that I imposed on my media, with important documents languishing in a drawer just waiting for some impending disaster to wipe them out or even get stolen. This was completely unacceptable for an organisation geek like me, so read on for how I regained control, and kept secure, my paper records on my Mac.

The key, to digital organisation of paper, clearly, is a scanner. I have a really old (by really old, I mean 5 plus years) Epson Perfection 1200 scanner. It’s that disgusting, long-forgotten beige colour, which only stubbornly remains on Windows office PC’s – so it gets well hidden as it is not exactly a joy to behold. Once a week (ish) it comes out to play with a weeks worth of important paper to scan, so I can keep on top of any paper lying around the house and essential admin that has to be done in my life. Image Capture recognises it natively via USB, so no other drivers are necessary.

You should be able to pick up a similar scanner second hand from ebay quite cheaply. For quick reference, here are ebay UK and ebay US searches for that same model. I wouldn’t recommend it for photo scanning, although the quality is definitely respectable, but for documents it’s just fine. Otherwise, scanners start cheaply, and go up to whatever you want to pay – the choice is yours, but make sure that you check it is Mac compatible.

Although having a scanner is not a pre-requisite for this system, it certainly makes the objective much easier. There are a lot of forward thinking companies that issue bills, receipts and invoices in PDF format now, and the following setup will work with them, but securely backing up those paper documents will not be possible without a scanner.

So grab them, your scanner, and we’ll dive right in. First, download kip (currently free) and Knox ($29.95), two separate pieces of software that are well designed and simple to use. I am a fan of good UI and both Knox and kip fit the bill, meaning that I want to get (and stay) organised, which is half the battle.

kip takes care of the scanning and categorisation, whilst Knox keeps your documents secure. Knox is not an essential, as you could use the Apple supplied Disk Utility instead, but it will make your life a bit easier.

kip Icon
Knox Icon


kip is the app that we’ll be spending most of our time in. It’s relatively fresh out of the box, still at the time of writing on a 1.0.1 release, but this also means that it is still freeware too. The developers are planning on charging for it a later date, however it works wonderfully now. It takes care of the scanning and categorisation side of things, allowing you to scan your documents directly to PDF, including adding multiple pages. Scanned documents are automatically added to your kip library, and you can tag, title and date each document as you go. The process and time taken for each individual piece of paper is fairly painless, but if you are working through a backlog then it could take some time and multiple sessions to get completely up to date.

The software has a neat and unique UI, with a few quirks and bugs however. Sessions of scanning are only saved on quitting, which makes a crash half way through an extensive session of scanning extremely annoying. Be sure to keep dropping in and out of the program every so often to make sure the database is saved.

In general though it’s simple and easy to use, with a decent filtering system (selecting multiple tags in the left sidebar drills down through documents to find the one you are after), funky tag rollover effects, like the magnification of the OS X Dock, and a good scanning workflow. For a 1.0.1 release it’s really promising, and depending on the price and new features added, and I’ll probably end up buying it when it becomes shareware.

Adding a PDF document to kip downloaded from the web or received by email is even easier than scanning paper. kip automatically installs an ‘Add to kip’ option in the PDF dialog when printing a document, so it is possible to send documents from pretty much any other program straight into it. It then automatically suggests tags and a title based on the document contents. These often need editing, but it’s normally a good starting point.

kip’s Library window

In the screenshot above you can see the documents in the centre, tags in the left panel, and document info on the right. Mousing over a document gives you a useful magnified preview, showing related tags too.

kip thumbnail mouseover

Mousing over documents in kip gives you a preview of the document with its tags

I then recycled much of the paper that I had scanned. Throwing it out and regaining some space was very satisfying, and well worth the time spent on getting up to speed.

So that’s kip. It stores it’s documents in its own folder inside user/documents as PDFs, so they are completely accessible with other PDF readers. You can open them in Preview or Adobe Reader, and are not tied to Kip in anyway. Kip also offers rudimentary .mac syncing, which does little more than copy these documents to your idisk for retrieval if your lose your data. Scans can take up a fair bit of disk space so beware of using this option as your library grows.

kip – the one caveat

All this scanning of documents means that your entire private info, previously only available to someone who looked in that drawer, is now on your computer. Not only that, it is stored in your documents folder (and iDisk if you wish) both completely unencrypted and fully searchable by Spotlight. I would prefer kip’s developers to err on the side of interoperability with the scanned documents, but it does mean that if you are planning to store any kind of personal or confidential data then you’ll definitely want to encrypt and secure these documents in some way. Until (and if) the developers implement this feature, you are left with a couple of options.

Securing your data using Knox or Disk Utility

Disk Utility, as you may or may not know, lets you create your own disk images that can be password protected and encrypted. The data resides within the image until it is opened and mounted on the desktop, similar to your internal hard disk or a thumb drive. Although these images can be made by Disk Utility, supplied by Apple in your Applications/Utilities folder, using Knox is a much friendlier way of creating, managing and backing up any disk images you decide to create. Knox features automatic backup to iDisk, iPod or external hard drive and can sit in your dock or menu bar for quick access to your ‘Vaults’, otherwise known as Disk Images. It’s very nifty, and well worth the money.

Knox Menu

Knox resides in your menubar for easy access to any of your encrypted vaults

So, first quit kip, and then create a vault using Knox, or to do so using Disk Utility go to the File Menu>New>Blank Disk Image. Next choose disk type: encrypted and your image size, and once you have selected your chosen destination it will ask you for a password. It will then create your new image for you. Open this, type in the password and it will mount on the Desktop / in your Finder sidebar.

Creating a Disk Utility Encrypted Image

Creating an encrypted Disk Image using Disk Utility.

Next, copy all the folder called ‘kip documents’ within user/Documents/kip documents into your newly created disk image (making a backup first would be a good idea). Leave that disk image mounted for now.

Whenever kip launches it looks in the Documents folder for the ‘kip documents’ folder. It is this folder that contains your entire Library and any associated data. As you have moved the kip documents folder away from user/Documents and into your disk image, if you start kip again now you will find that your library will have disappeared into the ether- not good when you have just spent hours scanning and categorising paper.

To fool kip into using the documents on the encrypted, password protected disk image it is necessary to use a symbolic link (aliases won’t work) to the ‘kip documents’ folder in your disk image. I did this using Cocktail, however the great SymbolicLinker contextual menu add-on (freeware) can do this too, and it’s free of charge. It’s a great tool to have, so I recommend downloading it and keeping it on your system for occasions such as these. Once installed, right (or ctrl) click on the ‘kip documents’ folder in your disk image, then select Make Symbolic Link at the bottom of the menu that appears. Finally, drag this new, linked, folder into your documents folder. Make sure it is called ‘kip documents’, fire up kip and you should see all your previously scanned or imported PDFs sitting pretty in your Library.

Encrypting your files means that there are two extra steps that have to be performed at either side of your scanning session – mounting the disk image (via Knox or the Finder) before launching kip, and unmounting it when done. Dead easy. You can then set Knox to backup that image, or use your backup tool of choice. Disk images made by Knox or Disk Utility can be opened on any Mac running OS X, so are ideal for backing up these documents to a server or iDisk for easy access if the worst happens.

Final Word

Now I can sleep safe at night in the knowledge that if anyone does burgle my flat, my most of my documents are out of their reach. If the computer is stolen, unless they can guess the vault/image’s password then they won’t be able to access these important documents, and I can back them up easily to CD or server somewhere. Finally, if I need any of these documents when I’m away from home, I simply have to hook-up my iPod or thumb drive to my laptop, unencrypt the image and all the relevant info is there for me to access.



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there is an old adage that you get what you pay for. i tried kip and it was unwieldy, buggy and very non intuitive. i suggest
trying free demos of yojimbo or circus ponies notebook. i use the latter and havent looked back.


Did you know that iTunes (yes iTunes) can store and catalogue PDFs? This feature was quietly added to support the U2 iPod and associated PDFs. It works. Perhaps you might want to organise your PDFs around playlists? Well, perhaps not.


The only thing that’s missing, from where I’m standing, is indeed having a plug-in to have them searchable by Spotlight or quicksilver. Other than that I don’t think OCR is really necessary (I’d have it only for searches). As this is supposed to be in your computer the same as a filing cabinet or a suitcase would be for your papers, receipts, etc.

If you need to re-edit scanned papers then this is definitively NOT the organizer tool for you. You can use a plain scanner OCR for that.

Having said that, having a way to redirect to an OCR package (if there was a worthwhile one for mac, at least) could be done easily through applescript events internally by the app (click on OCR, have a separate program do the OCR and then link the text to the document).

I also would vote for some kind of hierarchical file listing. Lists and smart lists are a good start, at least.

Couple Kip with an autolaunch desktop scanner (the ones where you feed the paper, and it pulls it, automatically launches the software and scans it in with a popup waiting for more documents or tagging-naming window) and you have the perfect tool for backing up mail receipts and I’m sold.

I also wanted to thank the suggestion of using knox to encrypt the files. Something not all may think of (and that kip could easily integrate, by the way)


@Keith: Acrobat professional already does OCR… If you take the PDF/OCR/spotlight approach the only thing you’ll miss is a good itunes-like filebrowser… maybe pathfinder could do the job…

Keith Mason

Yes we are. I wish kip did embed it’s tags and info into the file itself, not its own database. However, it doesn’t…. but as it is stored in a text file, there must be a geeky way of getting it out, some kind of script.

The thing does it for me with kip is the workflow you use to get the docs in the system in the first place. It’s so simple it makes me want to do it, not leave them hanging around the house, which is half the battle personally.

Plus, all the docs are stored as pdf’s, so you could definitely run them through some OCR software later to get the text embedded into them. This would make them searchable, although without kip’s tags.

The ideal solution would be for to kip to gain OCR integration, and embed its tags into the file’s spotlight headers. kip developers, I hope you are listening, there seems to be demand here!


Aren’t we missing something here? I realize that Kip is a little neato because it is geared towards getting your documents from paper to digital with as little interference as possible –and the .Mac sync is wicked! But the obvious problem is the separate DB metadata which is only useful to and from within Kip.

Why not add searchable/usable metadata that Spotlight can use?

Scan the document to PDF (or an image, I suppose) and then edit it and add your own metadata (OCR would be best but you’ll likely not be able to get something capable for free)? If you had to scan to image, you could insert that into a word processing document and add meta as text and then save to PDF.

Yes, it’d be more work but wouldn’t it also be more useful?


(by the way, I know Visioneer keeps making Paperport software, albeit Windows-only, but their scanners are unexplainably expensive -being that they used to be low-cost solutions for SOHOs- and proprietary)


This reminds me a lot of what Paperport was supposed to do before it went belly-up. The integration and ease of handling of PDF documents in OSX may make it better suited to these days than it was back in the days of Paperport’s proprietary formats.

One question for you guys, though. Paperport used a nifty scanner that was really slim and stood between your monitor and your keyboard. It was an autofeeding rolling scanner, which sensed when you were feeding it a document and would auto-start the software and scan the document without any need to launch the program or press a button. Is there a macosx-compatible scanner out there right now that can do this? Especially useful if it works in color and can work from the keyboard’s USB port (as it’s RIGHT there, although voltage may not be enough).


Okay, i want to take back what i said about Journler. The version 2.0.2b solved many of the issues i had, and now the thing is like an iTunes for my docs. I seriously recommend it to anyone, specially because the keywords you use are read by Spotlight. Plus, you can encript your files if you wish. Cool!

Keith Mason

From the OS X dictionary : whilst conjunction & relative adverb chiefly Brit. while.

I am english. So there!

Keith Mason

@ Prasad – I would not recommend kip for large scale use, as it would become unwieldy quite quickly- it displays documents in thumbnail format only (at the minute), and assigning tags to each one would be a chore to say the least. Take a look at Fazal’s system in the comments above – he has OCR going and everything meaning each document would be completely searchable by content, rather than just tags. Much more useful for large scale use.

@ Eric – I actually don’t use kip for organisation of any other pdf’s than bills and scanned paper. This to me is what it is designed for. I would suggest Devonthink or Yojimbo for any other pdf’s, but even these aren’t perfect. There isn’t, to my knowledge, a versatile pdf browser / filer / cataloguer on the market that will do everything well.


@Prasad: In the last hour I’ve given another look to the new version of DevonThink Pro and I think it could be the one. Some of the bugs it had have been solved and it’s got a very powerful self-generated tag-based search engine.
Maybe you could scan your docs using Kip for faster operations, then get all the documents in its folder, organize them in folders and import them in DTPro… I don’t think DTPro does any kind of scanning, but I can be wrong. So in the end you’ll have a hierarchical docs organization and still a powerful way to browse and search your pdfs.



I am incharge of all documents of a very large Non Profit Organisation. I was seriously thinking of scanning all documents in to PDF and file them in nested folders – tree fashion. Do you suggest I use KIP instead? Please help me


It looks nice but the only way it manages PDFs is by copying them in its folder, inside Documents.
Really useful for paper for its scanning skills but absolutely not for my huge collections of PDF such as newsletters and free e-books downloaded from the web in years… They’re now hierarchically organized in folders and never I would drop this organization for putting them in the kip folder, all together and without any order.
I would really like that kip could keep tracks of the documents without moving them in its folder.
Untill now the only tool that I found for this is DevonThink but, not minding the high price, it creates a multi-gigas database for it’s complex tag system and anyway it looses connections with the original documents (if, for example, I trash some of them I have to manually tell DT to scan again, folder by folder… a huge waste of time)
Isn’t there the right tool to keep PDFs organized in an easy way??
I keep searching…

Keith Mason

@anon – grammar (should be) fixed. I somewhat doubt your claim of phyical pain, and next time don’t be chicken, leave your name!

Kip works well when scanning as it is designed exactly for the job intended – just paper. The files end up being around 1-2MB, and I find the quality acceptable for reprinting. You can’t however change the settings (dpi, colour, etc) used, but they work for me. Maybe this will come in a later release. Adding on multiple pages to a document is fairly painless too. I should be a salesman for this app…


This is a useful pointer, primarily because I haven’t heard of Kip before. Can you comment on how well Kip works as an importer of paper documents with a scanner? How exactly does the scanning process work?

Also, please please please review the difference between “its,” the possessive, and “it’s,” the contraction of “it is.” This caused physical pain at several points while reading your otherwise reasonably literate piece.

Fazal Majid

To do something like this, you need a full-fledged document scanner like a Fujitsu ScanSnap, a flatbed simply won’t cut it. Another option to have searchable PDFs is to use ReadIRIS 11 to perform OCR and save it in the image/text format (you see a bitmap version when you open the PDF, but it has the OCR text in a hidden layer that is indexed by Spotlight). Most of the time, it’s not worth the bother, a hierarchical folder scheme works just fine for the majority of documents (bills, invoices, etc).

FWIW, I documented my paper workflow here:

Keith Mason

@joe- yes, the kip website is rather useless, but as the app is free it’s easy enough to download and try it out. You do get hierarchical organisation, but probably not how you would like. Within the kip documents folder you get ‘my documents’ (amongst text files with database info) then within that a year folder, then a month folder, numerically. PDF’s are saved using the title you give the document in kip as it’s filename. It works for me, but would suck if the app went shareware, (which it will) but really expensive. There is no lock in though, it could be worse IMO.

@Vuong- iPhoto could handle it yes, using another library would be best. kip however just makes life easy by scanning and handling the organisation in one.

@Brandon and Angel – Good luck!


This has inspired me to put my scanner to good use. It will take a while to get through all of the paper I need scanned, but it will free up space!

Brandon Eley

Wow, great app! I can’t believe this one slipped by me… downloaded and installed and I’m playing with it now.

I’ve been looking for a solution to all these piles of paper!

Vuong Pham

hmm.. It would seem iLife (iPhoto) could handle this functionality. With the built in keywords programming and use of a photo library mgr you could be ready to go.

As for Scanning.. well use of a ADF (Auto document feeder) would be sweet. I thought about getting a newer brother scanner with a ADF and network interface.. thus scanning could be a task done solo; without the use of a computer.. just the computer set up to be NAS/ server for the scanned images to be stored.

then iPhoto could import the docs as needed…

I would start doing this but i want a faster USB scanner and /or ADF feature..

Very good home office paper-less office implementation. receipts, bills, important docs other than photos.. nice.


i still don’t buy into the “tags/labels only” organization scheme. If i use this to replace my current paper filing cabinets, it MUST have heirerarchical folder organization. It can be in addition to tags, but I still have to be able to group and nest folders. I would much rather see a tree list on the left side than the “kip cloud”. The kip website is useless – can this do that, like iPhoto can?

Keith Mason

Unfortunately Kips tags are stored within it’s own database, and thus not spotlghtable. As the documents are saved as pdf’s though, if the document title is well named then this is searchable by spotlight, just not the tags. The thing about kip is that it is really geared towards scanned documents, not notes or webpages. It handles other pdf’s well too, but really geared around paper.

For note taking and web page archiving, I’d recommend maybe Yojimbo (fully integrated with .mac and spotlight), maybe Devonnote, and many of the other note taking apps out there. I use Yojimbo and love it, the .mac syncing is well worth the money alone if you use multiple machines, and it handles web archives and other notes well.


I was using Journler (freeware) for a couple of weeks to catalog all of my documents, and the results weren´t very good. It lost many of the webpages saved, along with some pictures and notes kept for a project. So i returned to the good ol´ folder structure and started to look for a new way. Now i see this, and it looks very promising, specially for the iApp look.

But i still have some questions about it. I was about to drop everything in a single folder, motivated by your Metadata Project. So, how kip works with it for you? Does the program deals well with Spotlight, recognizing the metadata already assigned?

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