It’s time to revisit Apple buying Dropbox

Dropbox once told Apple’s Steve Jobs that it wasn’t for sale, but now might be a good time to change its tune.

The bottom’s dropped out of Dropbox’s market. In 2011, it was invaluable. But now, in 2015, it’s clunky — an unnecessary step that feels a bit too far removed from the dozen or so apps we use regularly. Dropbox is decently integrated, but it doesn’t feel like enough now, when we can easily send files through interoffice chat and collaboration platforms like HipChat and Slack that do much more than file-sharing. While many individuals did (and still do) use Dropbox for sharing photos and big, totally legal files, Dropbox is largely for business, used by colleagues to exchange big folders and files. In fact, Dropbox says that 60 percent of its basic and pro users use Dropbox primarily for business.

It’s vital to businesses, this service of making file-sharing easy. Unfortunately for Dropbox, file-sharing is just a portion of the connected service suite that digital work today requires. To put it simply, Dropbox is underpowered for 2015. And given it’s incredibly (read: actually insane) high valuation, that’s a big ol’ $10 billion problem.

A better solution than iCloud

While we’re on the subject of services that just don’t quite pull their weight in 2015, let’s chat about iCloud.

My mom calls me all the time to ask if a photo she mistakenly deleted is in iCloud. I tell her what I’ve told everyone else who has ever asked me anything about iCloud: “I have no earthly idea.”

I don’t know what’s in my iCloud. 22.1GB worth of miscellaneous things, apparently, but I don’t actually know what makes up all of those mysterious gigabytes (edit: I checked — it’s a lot of photos, Contacts, and maybe half of my total Reminders), and I definitely don’t know how I would go about retrieving any of that purportedly precious data in the event of a catastrophic iDevice meltdown. I’m confident that I could figure it out, but I haven’t attempted it.

I don’t use iCloud at all. And that’s because iCloud is garbage. It’s only recently graduated from “glorified landing page” to “somewhat usable interface”, but it remains a part of my Apple life that I feel no real need to interact with at all, unless something goes absolutely and horrifically wrong and I’m forced into the iCloud interface as a data Hail Mary.

To be fair, I’m glad that iCloud exists. I’m glad that Apple’s making an effort to save the data that I’m too stubborn or lazy to back up. I’m glad that it’s trying to save me from myself. Or maybe it’s just trying to save a Genius or two from having to explain to a customer that all of his photos are gone because he carelessly dropped his iPhone 6 Plus into a chocolate fondue fountain. Maybe it’s both.

Either way, the fact remains that iCloud is trash, even when it’s helpful, and that’s largely because it is so underachieving. iCloud could be better, but first it has to be useable, and maybe that’s where Dropbox comes in. Because iCloud, too, is underpowered.

When Dropbox founder Drew Houston met with Steve Jobs in 2009 to talk about Dropbox, Houston famously shut down Jobs’ approach to buy the file-sharing service. According to a report from Forbes in 2011, Jobs let Houston know that he was making something of a mistake banking on Dropbox’s service to sustain a company, telling him that Dropbox was “a feature, not a product.”

Now, it sort of feels like Jobs was right. Dropbox doesn’t feel like it’s future trajectory is up. In fact, it kind of feels like the rain has started and the Dropbox is getting soggy. Dropbox isn’t going to get much further without becoming easier, more meaningful and high-powered. Dropbox isn’t going anywhere but down as a standalone app, but if it can find a way to make itself a part of our lives the way it began to before iCloud, Google Docs, Box and the rest, it might stand a chance. And, well, if there’s one company that’s become the leading expert on making itself an essential part of daily life, it’s Apple.

Theoretically, if Dropbox were to see the soft, brushed aluminum, backlit writing on the wall and decided that it wanted to take Apple’s offer six years later, would Apple even want to buy?

Well, yeah. It should, anyway.

Tiptoeing into enterprise with iPad Pro

Apple wants a bigger piece of the enterprise pie. iPad Pro proves that. Dropbox has a very solid base of enterprise users (for now), and perhaps a more robust file sharing, synching and management platform for the super-sized tablet would tip the business scales in favor of Apple’s answer to the Surface Pro.

Furthermore, as previously discussed, Apple’s iCloud leaves a lot to be desired–bringing in the world’s most valuable cloud service is far from the worst idea Apple’s ever had (a right that I have assume is reserved for the rollerball on the Mighty Mouse). Beyond that, Apple could really benefit from something of an ecosystem overhaul. Between iPads, Apple Watches, iPhones, Apple TVs and iMac/MacBook/MacBook Pros, many people now find themselves with more than one iDevice. The better those devices communicate and sync data, files, photos, contacts, etc., the more things “just work”, as Apple likes to say.

Perhaps best of all, never again would a Genius have to try to explain what the hell iCloud actually does.

The web version of Apple’s iWork suite exits iCloud beta

Apple moved its web-based versions of its iWork office suite, including Pages, Numbers, and Keynote out of iCloud’s beta site and onto on Thursday. The web versions are free, and they come with 1GB of iCloud storage. You don’t need an Apple device to use the web-based iWork suite: Recently, Apple started supporting Firefox, Chrome and Internet Explorer, meaning Chromebook, Windows and Linux users can use the software in their browsers. Previously, they had to go to to access the web apps. If you don’t already have one, you’ll need to create an Apple ID. Apple’s FAQ has more information.

Apple makes iWork for iCloud beta free on Windows, Linux, Chrome OS

Add another option to the freely available online productivity software suites: Anyone can sign up for and use Apple’s iWork for iCloud, even if they don’t have a Mac or iOS device. The open access is actually in beta, so to use it, you’ll have to head over to, according to BetaNews, which reported the news.

icloud web

Previously, if you visited the beta site for iCloud, you had to do so from [company]Apple[/company] hardware to create a new Apple ID. The key change here is that now you don’t need a Mac, iPhone or iPad to create that ID, which is your golden ticket to the iWork suite of Pages, Numbers and Keynote. Browsing to the iCloud beta site from a [company]Microsoft[/company] Windows PC, Linux box, or [company]Google[/company] Chromebook, for example, now lets you create your Apple ID, which can be any valid email address. Signing up for the Apple ID from non-Apple hardware will also net you 1GB of free iCloud storage for documents and data.

Why would Apple bother opening up the Apple ID creation process, offering a small bit of cloud storage and free access to its productivity suite? While the company is a leader in the smartphone and tablet markets, there’s nothing but up side for it to open up cloud services and software to a larger audience.

Those who have never used OS X, iOS or any Apple hardware could test the waters to see what Apple has to offer. If they like the iWork suite, that could lead to browsing for a device that can use the software, which could turn into a hardware sale. And with the Apple ID creation, Apple adds yet another contact to its growing database of users, where it can gently remind them how well its hardware works with its software, encouraging a trip to the Apple Store nearby or online.

iMessage just got secure: Apple expands iCloud two-factor authentication

Since the embarrassing revelation that iCloud’s two-factor authentication didn’t actually cover many of Apple’s online services, partially responsible for a rash of leaked celebrity photos last year, Apple has been gradually adding the security setting to many of its other services. On Thursday, users with iCloud’s two-factor authentication enabled will need to complete extra steps when logging into iMessage and FaceTime, the Guardian reported. The feature is rolling out now, but may not be available for your specific devices yet.

For users who have two-factor turned on, when you log into iMessage on a new iPhone or Mac, your Apple ID password won’t be enough to gain access. According to MacRumors, FaceTime and iMessage are using app-specific passwords, in which you generate a unique code on Apple’s website, instead of having a four-digit PIN texted to your device.

Now, a miscreant with your Apple ID password — possibly gained through phishing, other social engineering, or even a lucky guess — won’t be able to set up iMessage or FaceTime and pretend to be you without your phone. Because of the way iMessage uses encryption, simply logging into a new device doesn’t recover old iMessages, even before Apple turned on the new two-factor authentication.

If you don’t have two-factor turned on for your iCloud account, you should do it. Here’s Apple’s guide. After all, even if you’re not a celebrity, you don’t want to get hacked and have your life turned upside down.

This post was updated on 2/13 to clarify that iMessage and FaceTime are using app-specific passwords, and not two-factor authentication with a PIN code. 


Apple previews its cloud-oriented iPhoto replacement for OS X

Apple announced a new cloud-oriented app called Photos last June at its developer’s conference, which we later learned would replace iPhoto and Aperture. The new Photos app for iOS came as part of iOS 8 last year, and on Thursday, Apple previewed its OS X counterpart in a new pre-release preview version of Mac OS X Yosemite.

Developers can download the beta version of OS X that includes Photos now. For non-developers, Apple had promised that the new Photos app would be available in “early 2015” — which we now know includes April, according to Apple. Previously, users could check out the web version of Photos at

The key to the new Photos app is that is relies on Apple’s iCloud storage to sync photos from a user’s iPhone to her computer and vice versa. Cloud storage isn’t required for Photos to work, and all photos can be stored locally. But iCloud integration is likely to be most users’ favorite part of the new Photos app and the area where Apple has made the biggest strides. According to the Wall Street Journal, the new Photos app includes “some behind-the-scenes intelligence to prevent large collections from eating up” limited built-in storage space — like the relatively tiny 128GB hard drives that come with most entry-level MacBook models.

In many ways, the new Photos app is the completed version of the photo-syncing vision that Steve Jobs presented in 2011 and was internally called “Hyperion” at Apple. If it works as promised, it’s likely to convince a lot of people they need to pay for extra iCloud storage. (Only 5GB is free.) The increased number of synced photos Apple will be handling may be why it’s investing $2 billion in a new data “command center” in Arizona.

The Photos interface appears to be simplified and streamlined from iPhoto and the professionally-oriented Aperture. While it might be a godsend for many amateur photographers snapping shots with their iPhones, pros will probably move to Adobe Lightroom. (Adobe even recently released an export plugin for Aperture users.) But for consumers, has Apple finally cracked the problem of photo backups and syncing on smartphones? We’ll find out when Photos is officially released to the public later this year.

The iCloud Photos web app quietly disappeared

The iCloud Photos web app, which allowed users to access photos uploaded from iPads and iPhones in a web browser, has been taken down. Users navigating to the beta app’s permalink now receive an message that Apple “can’t load Photos.” The web app launched for iOS 8.1 users in October. Remember that Apple has promised to launch a new photo app for OS X in “early 2015” to replace the native Mac versions of both iPhoto and Aperture — so the iCloud Photos web app could be coming back in a new form when that app launches.

Update 2:20 ET: As pointed out by commenter patrick2, the iCloud Photos web app is back up. I was able to load it a few minutes ago.

The software that helped hack the iCloud nudes got a scary update

The software tool that was used to exfiltrate many of the photos that comprised the infamous iCloud celebrity nude dump of 2014 has received a big update. Elcomsoft Phone Breaker now supports the two-factor authentication process that Apple added as a result of the iCloud hacks.