By Stephen Hackett

January 31, 2018 1:40 PM PT

The Hackett File: Living with Multiple Macs

For a long time, I used a notebook as my only computer. Through a string of MacBook Airs and MacBook Pros, I would carry my entire digital life around in my backpack, then dock it at my desk to an external display, keyboard, mouse, hard drives and more.

That changed when I bought my 5K iMac about a year and a half ago, when I built out my studio and office space. I wanted an iMac to have more screen real estate and power for editing, but the biggest upside was that work suddenly had a place. Sitting down at this door I chopped into a desk, in front of a 27-inch Retina display tells my brain It’s time to work.

For the times I need to record podcasts on the road or elect to work from the couch or my favorite coffee shop, I have an Early 2015 13-inch MacBook Pro. It’s a middle of the road model, but it more than meets my portable needs. It even has a keyboard that works and ports and stuff.

(AHEM.)

Using more than one Mac is a lot easier than it used to be. Even in the iDisk days, file syncing between computers was hit or miss, and often very slow. Files were often duplicated and mis-synced.

Then the miracle of Dropbox happened, blessing us all with reliable file syncing that worked cross-platform. I remember first setting it up in college on my 15-inch PowerBook and being blown away at how quickly files showed up on the Blue and White PowerMac G3 I kept running under the desk in my dorm room.

Dropbox is still critically important to how I work. Outside of my iTunes and Photos.app libraries, almost everything in my home directory is in Dropbox.

I’m in a whole bunch of shared folders for the various podcasts and projects I am a part of, and with the iOS app, it means I have access to much of what’s on my computer anywhere my iPhone can connect to the Internet.

Apple’s services have come a long way from the iDisk days of .Mac and MobileMe. iCloud can sync your Desktop and Documents, but I’ve avoided those features after hearing horror stories from some users.

Much of what iCloud excels at is behind the scenes, shuttling data back and forth between Apple’s various apps like Calendar, Notes, Reminders, Safari, Keychain Items and more.

This ever-present, all-knowing nature of iCloud means it’s powerful, but we often don’t notice its features until they break down. I don’t ever think about my Contacts database until I need a phone number I entered on my Mac that hasn’t found its way to my iPhone yet.

Thankfully, those hiccups have become less and less frequent over time as Apple has continued to improve iCloud and its various tentacles into the company’s operating systems.

Between Dropbox for my files and iCloud for just about everything else, I can move between my iMac Pro and MacBook Pro with relative ease, knowing my important data is present on both machines. Thanks to Dropbox selective sync and Photos’ ability to just download thumbnails, I can fine-tune what I need on my notebook, keeping in mind its smaller SSD.

I think Apple could take iCloud farther, equipping it to keep Macs running in sync in even more ways. The possibilities that come to mind are nearly endless.

tvOS 11 can keep home screens in sync across multiple Apple TVs, so why can’t I enable that for something like my Mac’s Dock or login items? Mail syncs smart mailboxes across Macs via iCloud, so why do I have to set up Finder favorites separately on each computer I use?

I can imagine a world where Handoff is broader than whatever app happens to be in the foreground. What if, when I logged into my MacBook Pro, iCloud had all the open apps, browser tabs and Finder windows from my iMac Pro ready for me? True session syncing could make picking up my notebook and walking out the door far more appealing than it is now.

These are things Dropbox will never be able to do, as iCloud is baked-in at the operating system level. However, Apple’s service lacks all but the most basic controls and settings. For the most part, a user can only turn something off then back on again to troubleshoot it.

Dropbox, on the other hand, offers numerous settings and a far more robust file recovery system on their website. If iCloud eats a bunch of your calendar data, you’re more or less stuck unless you can dumpster dive with Time Machine.

Apple has been unwilling to put a lot of user options into its iCloud preferences, and I understand why. How can it just work if a user has a bunch of toggles they can flip around? Apple wants iCloud to be seamless and invisible, quietly delivering data to your apps and devices in the background.

I firmly believe is that if Apple continues to expand what iCloud can do, especially on the Mac, it will need to cede some ground on this point. Right now, the “Optimize Mac Storage” option under iCloud Drive is about as complex as it gets:

For iCloud to grow in scope, it will need to grow in complexity. That’s not a bad thing, and I hope it doesn’t hold Apple back when thinking about how our devices can be made smarter and better by Internet services.

[Stephen Hackett is the author of 512 Pixels and co-founder of Relay FM.]