From time to time, I find myself needing to send some files from my Mac to my iPhone, or from my phone to my computer. This is especially true with things like screenshots for reviews. In the past I have used Photo Streams or email to get the images from my phone to my Mac, but both of those are a little more annoying than they need to be.

Using a Photo Stream requires me to open iPhoto on my Mac, which means it will probably take forever just to grab a few images. For email I have to select all the images from my Camera Roll and either mail them five-at-a-time from the photos app, or copy them, switch to Mail, paste them into a message (which somehow bypasses the absurd five-image limit on in-line sharing in the Photos app) and then address the message to myself and wait for it to send, then wait for it to arrive on my computer.

There are also a ton of apps that allow you to connect to your phone through a web browser to transfer files, but those require the app to be running on your phone, and for the app to be in a specific mode to receive the files. It’s not seamless and it’s not as effective as it could be.

This is not a good workflow. That’s where DeskConnect comes in. DeskConnect is an pair of apps for iOS and Mac that avoids all of the unpleasantness of connecting the two devices and allows you to seamlessly send files from one to the other.

Let’s talk iPhone

First lets talk about getting files onto your phone from your Mac. DeskConnect for Mac sits in your menu bar and waits for you to drop files onto it. Once you’ve dropped a file, it is immediately transferred to your iPhone or iPad. You don’t have to start the app on your iOS device at all. I force-quit the app from the multitasking tray and still received an immediate push notification when sending a file to my phone.

Tapping the notification brings you into the DeskConnect app for iOS where you can view the file (if it’s one of a few standard types, such as an image or iWork file). You can also pop files out into a different app to continue working with them. Some examples include Pages or a photo editor.

Unfortunately, the app seems to have a hard time with some other file types. I zipped up a few images and sent them to my phone. Normally most apps can unzip these archives without any issue, but not only does DeskConnect not open them, it doesn’t let me send them out to other apps that I know can open them (even though Mail allows me to send the same zip file to other apps). I suspect this is a bug rather than a deliberate design choice, but it’s still a big problem to have to work around.

Back to the Mac

Going the other direction—from iOS to Mac—can be a little more frustrating for several reasons.

The first is developer support. While third-party apps do not need to directly integrate with DeskConnect, they do need to use the “Open In…” sheet that you may have seen in Mail and a few other apps. DeskConnect will appear as an option on that sheet and allow you to quickly send your files to other devices. This is supported in a variety of apps, including iWork, but some app developers choose to design their own file sharing sheets instead, in which case they would need to specifically include DeskConnect support.

The DeskConnect app on iOS supports sending photos, websites from Safari (or Chrome), and plain text from your device’s clipboard. Sending any other kind of file will require proper sharing support in whatever app you use to handle those files (for example, to share a Pages document, you have to use Pages for iOS to send the file to DeskConnect).

Another reason going to this direction is a bit more difficult is lack of batch photo uploads. You can’t select multiple photos to share to your Mac at a time. When sending the screenshots for this very review to my Mac, I had to locate each one separately and wait for it to send before I could send the next one. It quickly got old and definitely made me wish I had decided to use email instead.

However, the Mac app is still fairly solid. Like the iOS app, it can receive push notifications for new files even if it isn’t running at the time. Clicking the notification opens the file in Quick Look and allows you to save it to your hard drive (via the sharing button on the Quick Look window, which is unfortunately not very obvious).

One very cool feature of the Mac app is that it can detect which app you’re working in and figure out if there are any relevant files that can be shared. For example, which working in Pages for Mac, clicking on the DeskConnect icon in the menu bar will reveal an option to send your current document to one of your other devices. Highlighting a file in Finder and clicking the menu bar icon offers a similar option, as do websites in Safari, and so on. The developers have said that DeskConnect also allows you to right-click a phone number in the Contacts app and click a button to initiate a phone call on your iPhone  remotely, but I have not been able to get that function to work.

Lateral pass

Transferring files from Mac to iOS and back again isn’t the only way to use DeskConnect. As the name implies, the primary use is sharing files back and forth with your “desk,” but the app actually allows you to send files to any device on your account, including from one Mac to another, or between iOS devices.

The iOS app doesn’t provide a way to target a specific device, meaning all of your devices will probably get a push notification when you send a file from that app, but it’ll still get where it needs to go.

The Mac app, on the other hand, does provide a way to specify which device you want to send the file to. Holding the file over the menu bar icon for a second shows a list of devices connected to your DeskShare account. Dropping the file onto one of those devices will send it there.

Both apps keep a list of recent files for up to 30 days, at which point they’ll be purged from your history. If you want to keep anything you send, you’ll need to save it elsewhere before that happens.

Final word

In the continuing search for a way to efficiently get files from one device to the other, the abliity to share files without having to first open a specific app on the target device is incredibly convenient, and I actually wonder why Apple’s AirPlay implementation doesn’t work more like this.

DeskConnect could be the ideal solution to this issue, but struggles with a few key points, such as batch file sharing from mobile devices and reliability problems. In its current for, the app works very well for occasional use.

Single images, web links, and everyday usage work almost flawlessly. For power users looking to transfer giant files or archives quickly, you’ll probably want to consider a few of the existing options already on the market until DeskConect gets a few more of the bugs ironed out.

DeskConnect is available now on the Mac App Store for and the iOS App Store. Both apps and the account required to use them are free.