How to transfer files from Windows to the iPad

Lincoln Spector

The iPad (and other iOS devices) might be the coolest computing device, but it lacks a clear and simple way to share files with Windows PCs.

Sure, iPads contain storage and connect to PCs via USB, but they don’t behave like flash drives or Android phones. Here are three tricks for moving files on and off an iPad.

Apple’s world of invisible file management

If you’re used to the way personal computers (even Macs) work, an iPad can throw you for a loop. There must be files and folders in there somewhere, but the pad’s operating system (iOS) does a good job of hiding them. Where’s the one-stop, Explorer-like app for moving, copying, and deleting iPad-based files? And just where is the simple — or even eccentric-but-insanely-great — tool for moving files between PC and iPad?

Sadly, basic file management is the most glaring casualty of the iPad’s new computing paradigm. Fortunately for PC users, there are easy ways to resurrect it.

These file-management issues exist with any iOS device, including iPhones and the iPod touch. But there are two reasons to focus on the iPad: First, because I own one; and second, because iPad owners are more likely to use the device as a computing platform — a system suitable for light-duty content creation, not just content viewing. Which means you need an easy way to move files to and from the device.

On a PC, files are associated (via the file extension) with the application that created them. iOS takes it a step further and ties every file (or at least every one you can see) directly to a specific app — and only that app. The file remains in that app’s storage area. When two iOS apps show the same file, such as a PDF, each app has its own, separate copy.

To my mind, that’s ridiculous. For PC users, it’s trivial to organize files by project rather than application. For instance, all the files connected with this article — the manuscript, my notes, screen captures, and so on — reside in the same folder on my Windows PC. I can’t do that on my iPad.

Apple’s insistence on storing the file with the app also makes transferring files more complex than it should be. No matter which of the following three file-transfer options you use, you’ll still have to match a file on your PC with a specific app on your iPad.

The simplest solution: Send it through the mail

You can always e-mail a file to yourself. I’m sure you already know how to do that on your PC. You might even know how to view the file in the iPad’s native mail app — Mail.

The trick, however, is to copy the file out of Mail and put it somewhere else on the iPad. The following instructions are for Mail, although other e-mail apps might work in a similar way. (I can say with certainty that it doesn’t work with the Gmail app.)

  • In Mail, open the e-mail message from yourself and tap the attached file, typically at the bottom of the message. In most cases, Mail opens the file in a viewer. In the top-right corner of the screen, you’ll see a small icon of an arrow pointing out of a rectangle. Tap that icon.
  • If the icon (with its title bar) disappears before you can tap it, tap the screen and the icon will reappear.
  • When you tap that icon, a menu comes up, offering programs that iOS thinks appropriate for that file. You may get more than one. You may also get a default app plus an Open in … option that will list other apps.
  • Pick an app, and the file loads into it. Remember that the app is saving a new copy of the file within its own library, where you can open it again or delete it. Depending on the app, you may also be able to copy the file to another app or e-mail it.

Not all file formats behave that way. When I tapped a .zip file, nothing displayed. But a popup gave me two choices for opening it. One of them, GoodReader (site), actually worked.

Oddly, some attached files sent from Microsoft Outlook might be unreadable. (They showed up as winmail.dat files.) But if sent to Gmail and then forwarded to Mail, they came through fine.

Use Dropbox for heavy-duty file transfers

If you’re doing a lot of file transfers to and from the iPad, e-mail gets old fast. Not so with a Cloud-based service that automatically syncs files on multiple devices. After setting up Dropbox (an easy process), the files you keep in the Dropbox folder always remain synched — as long as your devices are connected to the Internet. There’s really nothing to think about.

A number of similar Cloud-storage services are available. Most, like Dropbox (site), offer both free and paid accounts. But Dropbox is extremely popular and easy to use — and there’s a good chance that you’ve already installed it on your PC. Currently, a free Dropbox account gives you 2GB of storage, which should be plenty as long as you’re not moving large music or video libraries.

(Apple’s iCloud is already built into the current version of iOS and is better than Dropbox for moving large music or video libraries. But iCloud seems opaque and confusing for basic file synching, making Dropbox the better choice.)

Unlike the Windows version, the Dropbox iPad app doesn’t automatically sync all files in the background (so as not to overtax the iPad’s limited storage). Launch Dropbox on the iPad, and it syncs only the directory structure, showing what files are available in what folders. You tap a folder to open it and then tap a file to download it.

Downloaded Dropbox files are treated in much the same way that Mail handles attachments. Dropbox displays the contents of the file if it can, and it has the same standard iOS icon for copying a file to another iOS app.

Use iTunes for quick, local file transfers

When your PC and iPad are sitting near each other, it seems ridiculous to upload a file to the Internet from a PC, then download it from the Cloud to an iPad. That’s especially true when uploading large files (which can take a long time to travel to and from the Cloud) or if you’re concerned about file security.

If you own an iPad, you already know that iTunes is the official bridge between your computer and iPad. Not only can this free Windows app send music and videos to your iPad, it can also export other file types — provided, of course, that there’s an installed iOS app that will accept them.

Here’s how to do it:

  • Connect the iPad to your PC. This action brings up iTunes.
  • In iTunes’ left pane, select your iPad in the DEVICES section. Then click Apps below the Apple logo near the top of the window, as you see in Figure 1.
  • Scroll down until you find the File Sharing section.
  • Here you’ll see a list of all the apps that can accept files. Select the appropriate one.
  • In the box to the right, you’ll see the files currently stored by that app on the iPad. Open Windows Explorer to the folder containing the file you want to move, and drag the file to that iTunes box.
  • Press the Sync button in the bottom left of the screen.
PC-to-iPad file transfers via iTunes

Figure 1. iTunes allows you to move files between iPads (or other Apple devices) and PCs.

There are other PC/iPad file-transfer solutions. But these three cover the most common applications — or at least those Apple feels you’ll ever need.



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All Windows Secrets articles posted on 2012-06-06:

Lincoln Spector

About Lincoln Spector

Lincoln Spector writes about computers, home theater, and film and maintains two blogs: Answer Line at PCWorld.com and Bayflicks.net. His articles have appeared in CNET, InfoWorld, The New York Times, The Washington Post, and other publications.