If computer files were physical objects, we probably wouldn't let so much clutter build up in our system folders. At first glance, a file is no more than a single line item in Explorer, making it all too easy to ignore. But files are much bigger and more deep-rooted than that, of course; and whether they happen to be installers and content that we've deliberately downloaded or temporary files created by the various programs we use, they add up.

Manually sorting or deleting hundreds of files is a tedious task, but leaving them where they lie can be even worse: They may contain fragments of personal information or drafts of sensitive business documents. And they may prevent you from using drive space for more important things. To get a quick idea of how bad the problem is on your system, you can try SpaceSniffer or TreeSize Free, two free applications that visually map out hard drive use, and reveal what's occupying all that space.

Then there’s the matter of deleting files: When you delete a file, you usually want it gone for good. But the Recycle Bin leaves the file on your drive, where anyone motivated enough to try can easily retrieve it. Fortunately, I've found several free and low-cost tools that can automate file management and securely delete your unwanted files, so you won't ever again have to worry about your downloads and temp files.

DropIt lets you tell files where to go

DropIt is a free, open-source utility that processes collections of files according to rules you define. For example, you might set it loose on your Downloads folder, telling it to sort all of the .jpg and .png files into an images subfolder, but only if they're larger than 30KB (so you don't have to save small images). It could then gather all of the .zip files and put them in another folder, and delete all of the .tmp files. Whatever result you're looking for, you configure a bunch of rules to accomplish it, and DropIt does the rest.

DropIt's interface for configuring rules is simple to use, though a bit basic.

You can use DropIt by dragging and dropping files onto its desktop overlay (hence the name), or you can have DropIt sit in the background and constantly monitor one or more folders for changes. Once you've established a solid set of rules, the latter option offers a distraction-free way to get rid of file clutter—but only after you tweak the way DropIt works. By default, DropIt shows a progress bar whenever it's processing files, and it also prompts you when it stumbles upon a file it doesn't know what to do with.

These behaviors make sense when you've manually triggered DropIt, but they can be maddening when you've set it up to run in the background: Imagine seeing a progress bar streak across your desktop every 60 seconds, 15 minutes, or however long your system's automatic scanning interval is). Wisely, DropIt's Options dialog box lets you disable the progress bar and/or the file prompt.

For DropIt to be useful, you must carefully configure it to suit your particular needs. After all, only you know how you like your files to be organized. But with time, it can become an extremely helpful file management assistant, sorting and removing needless files in ways that make sense to you.

RoboBasket makes file management much easier

If you like the idea of DropIt but want a more robust, commercial tool, take a look at RoboBasket. At its core, this $20 utility works very similarly to DropIt: You configure file-handling rules, and set the app loose to bring order to your messy folders.

RoboBasket's filter configuration interface lets you use drag-and-drop and natural language to set filters.



The biggest difference between the two apps (other than price) is that RoboBasket has a much nicer interface for configuring filters, thereby permitting fine-grained control. A vertical bar on the right side of the window reflects file conditions and actions. If you want your file to apply to all .zip files, just drag the 'Extension' condition onto the filter, and set it to ZIP. If you want it to apply only to old .zip files, drag the 'Date Created' condition onto the filter and set it accordingly. In this way you can create very precise conditions that apply to specific files, but the filters themselves will remain easy to read and manage. The same goes for operations: You can move files and rename them, for example.

Before touching any files, RoboBasket can show you which files match which filters, so you'll know in advance what it will do with them.

The only point of confusion I had with RoboBasket involved recursive operations: You can instruct RoboBasket to apply a set of filters to a folder and to all of its subfolders. I had it move all of the .zip files in my Downloads folder into a 'Zip' subfolder (so, Downloads\Zip). I then ran it again on the Downloads folder, but recursion caused it to create Downloads\Zip\Zip, and put all the .zip files there. Every time the operation ran, it buried my .zip files another level deeper in the file hierarchy. This is because recursion isn't handled on a per-filter basis (as would have been sensible), but on a per-folder basis.

The workaround is to create two sorting profiles for the same folder, and set only one of them as recursive. So you put all of your recursive rules in one profile, and all of the others (say, file moving operations) in another. The result isn't elegant, but it's functional.

SortMyBox organizes shared Dropbox folders

Not all messy folders are alike: The stuff in your Temp folder differs considerably from the stuff in your Downloads folder. But one system is uniquely disorganized—at least on my system—because it's not all my clutter: Dropbox. Once you start sharing Dropbox folders with other people, the folders quickly become unmanageably messy: You, Jane, and John share a folder, and files quickly start popping up. No one wants to delete anything, in case another user may still need one of the seemingly superfluous files. SortMyBox is a free online tool that might be able to help, though it requires some discipline to use.

With its simple rules and clear log, SortMyBox can help you see exactly which files went where.

To use SortMyBox, you have to go to its website and permit full, unconditional access to all of your Dropbox files. If that idea makes you uncomfortable, you aren't alone: I feel the same way. One reassuring fact is that SortMyBox is open source, so anyone who can understand the code can audit it. Once you let SortMyBox into your Dropbox, it will set up a SortMyBox folder at the root of Dropbox. You can then configure rules that will apply to any file that pops into that folder, much as you can with RoboBasket or DropIt on your local machine. Once someone places a file into that folder, the app will sort it accordingly. SortMyBox will take files only from that folder, but it can plant them anywhere else in your Dropbox.

To use SortMyBox effectively in a team setting, everyone involved must place new files into SortMyBox; and doing so requires disciplined users and (as with all such systems) accurate filters. But if you satisfy these two simple requirements, SortMyBox might be able to help you organize your messy Dropbox.

Command-line utility SDelete securely removes files

Sometimes, you don't want to sort your files carefully; you just want to delete them, and be sure that they really are gone for good. At such times, the simplest, most bare-bones option is SDelete, a free command-line utility from Microsoft's Windows Sysinternals.

SDelete's noninterface is as old-school as you can find, but it gets the job done well.

You can use this 81KB download to delete specific files, or you can have it wipe all free space on your hard drive to securely remove all traces of old files. After running it with the -c ('Clean free space') command-line option, your drive should be virtually impervious to attempts to recover deleted files (as long as they're not sitting in the Recycle Bin awaiting easy retrieval, of course). When properly set up, SDelete works well as a scheduled task, periodically cleaning your drive; but because the utility is so minimal, you'll have to set up the task manually, using the Task Scheduler built into Windows.

Eraser scrubs data until it's gone

If SDelete is a tiny scalpel, Eraser is an enormous all-in-one toolbox devoted to the same task. It's free, it comes with a beautiful interface, and it can do just about anything related to wiping files securely.

Eraser can securely delete files at your command, or according to a schedule.

Eraser includes its own interface into the Task Scheduler, so you can set automated disk sweep schedules from within the application. Aside from wiping free space, Eraser can securely delete the contents of any folder on a set schedule. That sounds like a scary proposition (remember, there's no way to recover files securely deleted), but brave souls may appreciate having the option. Also, if you'd like to purge your recycle bin regularly and securely, Eraser can help you there.

Last but not least, Eraser integrates with the file context menu built into Windows: You can right-click any file or folder and get an Eraser submenu. From there, you can securely wipe the file or folder, either at once or the next time your computer reboots. All in all, if you're serious about wiping files regularly, Eraser is a very solid tool to use.

CCleaner offers two kinds of overwriting

Finally, no discussion of keeping your computer clean and tidy is complete without mention of famous freebie CCleaner. It completes a spectrum of cleaning options: SDelete is a minimalistic unitasker; Eraser is a bigger toolbox, but it still focused on file deletion; and CCleaner is a do-it-all tool that tries to rid your computer of many different types of bloat.

CCleaner lets you configure how thoroughly you want it to remove files.

CCleaner scans your computer, looking for temporary files, browser cookies, and other information that can be removed without danger. Then, when you're ready to remove it, you can opt for secure file deletion. Unlike Eraser, CCleaner doesn't let you pick a secure deletion algorithm to use, but it does let you choose one of four levels of overwriting.

Most people would probably go with the Simple Overwrite option, which does just one pass; but if your information is very sensitive, you can go all the way to Very Complex Overwrite, overwriting your data with 35 passes. Making so many passes can be time-consuming, but that's a common trade-off with encryption and security: You can arrange processes to be fast and comfortable, or secure and comparatively slow (or even cumbersome).

Like SDelete and Eraser, CCleaner includes a feature for wiping free disk space clean. It can't sort files, as DropIt and RoboBasket can, but in combination with one of those tools, it can do a great job of keeping your files orderly while securely disposing of things you don't need.