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Theresa Milewski of All Computers Great and Small with Louis, who chased many clouds in his day.

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iCloud, you're so vain, you probably think this post is about you. Well, it is.

But there are more clouds in my coffee (thank you, Carly Simon) than just Apple's iCloud. When we talk about cloud storage, I feel there are the top four that we must talk about: Apple iCloud, Microsoft OneDrive, Google Drive, and Dropbox. These four are ubiquitous to the point that most people are only tangentially aware that most of their precious memories and files are stored in them.

There are plenty of other cloud services out there, but if you’ve never gone looking for them, that’s exactly my point.

These four are so ubiquitous that most people are only tangentially aware that many of their most precious memories and files live inside them. There are plenty of other cloud services out there, but if you’ve never gone looking for them, that’s exactly my point.

Clouds: Storage, Space, Service… Ugh.

Long before most of us ever heard the phrase cloud storage, the cloud already existed, just not where we could see it. Services like Amazon Web Services were quietly providing the invisible infrastructure that powered websites and apps. But for everyday users, the cloud didn’t really arrive until Dropbox made it feel personal: a simple folder that magically stayed in sync across computers and made sharing files effortless.

That sense of magic became unavoidable with Apple iCloud, which didn’t just store files but began handling photos, backups, and memories automatically, often without much fanfare or explanation. Microsoft OneDrive and Google Drive soon followed, tightly woven into operating systems, email, and everyday work.

The cloud didn’t suddenly appear. It snaked its way into our devices, quietly, conveniently, sometimes annoyingly, and now we can’t get very far without a screen asking whether we’d like to back up our files again. Ugh.

The 5 Cloud W's

Let’s back up and answer a few questions that any good writer reporting on the facts should ask:

Who: We’ve already met the biggest players. Tech giants Apple, Microsoft, and Google dominate the landscape, alongside early trailblazer Dropbox. There are many others, but those tend to be services you’d actively seek out for a specific purpose. Here, we’ll focus on the clouds that have already infiltrated your life, whether you invited them in or not.

What: Cloud storage holds your data (documents, photos, videos, music) on massive computers called servers, maintained by the companies providing the service.

Where: These servers aren’t literally in the clouds, but they might as well be. Your data is stored redundantly, meaning in multiple locations, so it’s usually retrievable even if one data center goes down.

When: Whenever you give a service permission to back up your files, data begins moving into the cloud. With Dropbox, that permission is obvious: you sign up intentionally and choose what to sync. With Apple iCloud, Microsoft OneDrive, and Google Drive, that permission can be much less clear. We’ll come back to that shortly.

Why: We switch devices, upgrade phones, juggle laptops and tablets, and we expect our information to follow us. In that sense, we asked for this. Cloud services constantly sync the data you’ve allowed them to access so it’s available on any device you sign into with that account.

Cloud Storage: Safety Net or Safety Illusion?

Back in college, I once lost what I thought was the best thing I’d ever written. There was no auto-save, no cloud, and one unceremonious computer crash later, the document was gone. I started over, chastened, but wiser.

Today, with the cloud quietly backing things up, it’s easy to believe we’re protected. As long as we can sign back into our account, everything will be there waiting for us, right? Unfortunately (and often surprisingly), that isn’t how cloud storage actually works.

Not every file on every device is backed up automatically. Some settings are turned off intentionally; others are disabled without us realizing it. Photos are a common example. I personally choose not to back up my photos to iCloud. I take too many, and I don’t want to pay for more storage. So, I back them up manually instead. On the other hand, I do back up my text messages to the cloud, because I want them instantly available across my devices, and they’re not easy to save any other way. Documents? Those, too, I back up manually.

Is my system a little idiosyncratic? Probably. But it’s a conscious choice, and that’s the point. I know what’s backed up, what isn’t, and where the responsibility lies if something disappears.

For those who’d rather rely on a more automatic safety net (and most people should), I’ll walk through the most important settings to check on your devices in the next installment of All Computers Great and Small.

Marblehead resident Theresa Milewski runs All Computers Great and Small, providing friendly, local tech support and tutoring for Marblehead and surrounding residents. A teacher of technology for more than 30 years, she works with people of all levels — from complete beginners to advanced users — bringing patient, personalized tech help directly to people’s homes or small businesses.

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