Everything there is to know about texting from the desktop (and why it’s so much easier on iOS than Android)

pc_messaging_640It’s happened to all of us. While sitting in front of our ultra-powerful, multi-thousand-dollar laptops, we’ve reached for our phones to send or read a text.

Think about that for a second: instead of applying the veritable supercomputers in front of us to the task of transmitting a few bits-worth of emoji — machines, incidentally, with obscene connectivity, full keyboards, mice/trackpads, and excellent spell checking — we’ve opted instead to pick up a phone, biometrically unlock it, open a messaging app, and risk autocorrect humiliation while laboriously tapping out a dispatch with less efficiency than a nineteenth-century telegraph operator. Then: lock phone, set down, complete approximately twenty additional seconds of work, and repeat.

For some of us desktop texters, such onerous workflows are a thing of the past — anecdotes to be passed down to our children and grandchildren in futile attempts to make them appreciate the extravagance of modern life. But for others, the loathsome cycle is seemingly unbreakable.

If you bask in the privilege of texting from both your desktop and your phone interchangeably, chances are you are an iOS and Mac user who has discovered the brilliance of Apple’s Continuity. Or you’ve allowed yourself to be subjugated by a more closed and proprietary messaging platform like Facebook Messenger. A few of you might even be Android users who cling to the false hope of Google Voice, or who have sworn lifelong allegiance to Nexus devices for the privilege of testing Project Fi.

What follows are all the ways I know of to text from both your desktop and your phone, along with the pros and cons of each approach. If you are already intimately familiar with the problem and you’re just here for a solution, skip ahead to the “Apple Messages” section and go from there. But if terms like “text” and “iMessage” sound to you like distinctions without differences, you might want to start with the glossary below.

What We Mean When We Talk About Texts

textingOne of the reasons cross-device texting is so complex is the fact that there are so many different types of messages. Even the terms “message” and “text” are, at best, context-specific, and at worst, vague and ambiguous. While I don’t claim that the descriptions below are necessarily definitive, they are sufficient for the purposes of this article.

  • Instant Message: What we all used to send back in the day using AIM, ICQ, and MSN Messenger (or, if you were a power user, Adium or Trillian). Though once considered the cornerstone of the virtual social scene, the term “instant message” is no longer widely in use (though the concept certainly lives on). Messages sent through WhatsApp, Facebook Messenger, Apple Messages, WeChat, Snapchat, Viber, Line, Skype, Hangouts, etc. are all, at their core, instant messages; we just don’t call them that anymore.
  • Message: If you’re using AIM, you’re sending an instant message. If you’re using WhatsApp, you’re just sending a message (or a text; more on that below). It’s mostly a generational thing as opposed to a fundamental technological distinction. The default assumption is that if it isn’t an email, it’s instant, so why bother with all the extra syllables?
  • iMessage: Apple’s messaging platform. The apps you use on your phone and laptop are both called Messages, but the things you send to other Apple users, as well as the messaging platform itself, are collectively called iMessage. (I know: it’s about as intuitive as using an app called iTunes to manage your smartphone.)
  • SMS: An acronym for Short Message Service. Generally speaking, SMS is a communications protocol that allows mobile devices to exchange short sequences of text over carrier networks (typically 160 characters, though modern clients can break longer messages up into multiple SMS messages where they are seamlessly reassembled on the other end). Though ancient on the evolutionary scale of technology, SMS is still relevant because it enables almost any mobile device to communicate with almost any other mobile device, regardless of OS or carrier. You might even say that SMS is a modern-day Rosetta Stone.
  • MMS: An acronym for Multimedia Messaging Service. MMS is an extension of SMS that supports the transmission of images, audio, and video over cellular networks. Like SMS, MMS works across mobile operating systems and carriers.
  • Text: Generic term for just about any kind of informal, predominantly mobile message. Texts were once text based (hence the name), but they are increasingly getting much richer through the inclusion of emojis, animated GIFs, audio and video, effects, etc. The term “text” used to imply SMS, but once platforms like iMessage began blurring the line between bundles of media sent over data networks, and SMS-based text messages sent via cellular protocols, the world decided it could no longer be bothered with implementation details, and everything that wasn’t an email or something sufficiently novel (like a Snap) became, simply, a text.

Apple Messages

apple_messages_120.pngApple’s messaging solution is, in my opinion, the easiest and most powerful messaging platform currently available. All you have to do is associate your phone number and email address(es) with your Apple ID (which generally happens automatically), and thanks to a set of features Apple collectively brands Continuity, you can send both iMessages (Apple’s proprietary protocol and message format) and SMS/MMS messages from all your Apple devices including your Mac, iPhone, iPad, and even your Apple Watch.

Pros

  • Carrier independent. Unlike Project Fi (see below), Apple Messages is carrier-agnostic. As long as your SIM card will work in your iPhone, Messages and Continuity will also work. Want to switch carriers? Just port your number, drop your new SIM card into your iPhone, and you’re back up and messaging. You can even associate multiple phone numbers with a single Apple ID (provided those numbers have been provisioned to iPhones) and share messages across multiple phones.
  • Excellent cross-device support. All your Apple devices get modern, feature-rich, native messaging clients that you can be certain will continue to be well supported long into the future. (While Apple users may take robust messaging clients for granted, those of us in Google’s ecosystem are secretly envious.)
  • Calls from your desktop. There are two ways Mac and iOS users can make and receive calls from their desktop machines. If both your Mac and your iPhone are on the same Wi-Fi network, you can use Continuity to make and receive calls from your Mac through your iPhone. If your carrier supports Wi-Fi calling, you can also make and receive calls from a variety of Apple devices without your iPhone even being turned on.

Cons

  • Platform-specific: Windows and Android users are basically pariahs in the world of Apple messaging (though it is important to note that Apple’s Messages app will happily send SMS/MMS messages to Android users).
  • Remnants of a walled garden. Some iPhone users who switched to Android were allegedly punished for their infidelity by erratic messaging behavior that clearly favored the iOS ecosystem (leading to a lawsuit that was ultimately dismissed). If you plan on leaving Cupertino’s warm embrace, be sure to deregister from iMessage either through your iPhone, or through Apple’s web-based tool.

Google Voice (with Hangouts)

google_voice_128Google Voice was Google’s first attempt at approximating the role of a carrier through a VoIP-based telephony service. Though an ambitious and admirable initiative, by any and all modern standards, Voice is antiquated technology, so I won’t even bother listing its pros and cons. It’s enough to say that the Google Voice service has always been incredibly convoluted, unreliable (I suspect the number of MMS messages, group chats, and texts I never received from application providers over the years easily reaches into the hundreds), and mysterious (Google has been about as transparent with their plans for Voice over the years as North Korea has been about their human rights record). If you’re currently a Google Voice user, my advice to you is to port your number out to a real carrier as soon as you can. Or give Project Fi a try.

Project Fi (with Hangouts)

project_fi_160Project Fi (my current solution) is Google’s MVNO, or Mobile Virtual Network Operator. It seamlessly combines T-Mobile, Sprint, and encrypted Wi-Fi for voice and data while also allowing you to send and receive messages through Hangouts. And I’m happy to report that it works extremely well.

Pros

  • Relatively platform inclusive. Since Hangouts is a web application, I can message from my phone (both my Nexus and my iPhone), my Mac, my Windows gaming computer, and anything else that runs a modern web browser.
  • “Native” SMS support. The issue of some application provider texts failing to reach my Google Voice number thankfully went away with Project Fi. Although texts directly from Google only appear on my phone, all others texts are seamless forwarded to Hangouts.
  • Voice calls through Hangouts. An added benefit with Project Fi is that you can make voice calls that originate from your phone number right through Hangouts in the browser. If your experience is anything like mine, expect about one in ten Hangouts calls to end in “Hello? Can you hear me? Shit!” But if you spend as little time on traditional phone calls as I do, it won’t matter much. Plus, there’s a good chance you didn’t want to talk to whoever called you anyway, so think of the occasional dropped call as a feature.

Cons

  • Carrier-specific. Unlike Apple’s messaging solution, if you want to be able to text from your desktop using Hangouts (meaning both Hangout messages, and SMS/MMS texts), you have to use Project Fi which means you’re stuck with T-Mobile/Sprint, and with Nexus phones. Want to try out the LG G5? Nope. Seduced by the latest powerhouse from OnePlus? Sorry. Interested in giving an iPhone a try for a while? Don’t even think about it. (Note that even though you can configure Hangouts as your default SMS application on any Android phone, unless you’re using Project Fi, those text messages won’t appear in the browser version of Hangouts.)
  • Hangouts. Google seems to be about as flummoxed by messaging apps as they are by social networking. While Hangouts gets a lot of things right, it can be confusing at times, and it’s somewhat underpowered. I’ve been using Hangouts for messaging and SMS texting for as long as it’s been possible, and in my opinion, it’s only gotten more convoluted over the years.

Proprietary Messaging Platforms

facebook_messenger_150What counts as proprietary in the messaging world — or in the larger world of data formats and protocols, for that matter — can be somewhat subjective. To be clear, I’m talking about messaging platforms that make no attempt to play nicely with any other messaging platform. Using SMS, I can send a message to any phone, regardless of carrier or operating system. But with proprietary messaging platforms like Facebook Messenger or WhatsApp, all your contacts have to be using the same service. (Don’t be fooled by the fact that you can configure Facebook Messenger to be your default SMS client on Android; all you’re really doing is consolidating two apps into one, and your SMS messages will not appear in the web-based versions of Messenger.)

It’s only fair to point out that iMessage and Hangouts are proprietary in that they use their own formats and underlying protocols for messages inside their respective ecosystems, and they aren’t directly compatible with other messaging services. However, both use what I would call a “progressive enhancement” approach which ultimately make them fairly compatible with other ecosystems. For instance, if you’re sending an iMessage to another iMessage user, you can take full advantage of Apple’s enhanced messaging features (audio, video, effects and animations, etc.). But you can also send your nerdy, Android-obsessed friends messages via SMS/MMS, and those messages can be received and responded to inside any SMS-compatible app on the other end. It’s a fine distinction, but one that I think is extremely important in today’s multi-ecosystem world.

Probably the most practical way to distinguish overly proprietary messaging platforms from those that are more inclusive is this: overly proprietary messaging platforms mean you have to use multiple messaging platforms and apps in order to get messages to everyone you know. Conversely, because they can fall back on SMS/MMS, services like iMessages and Hangouts (with Project Fi) can, if you want, be the only platforms and applications you need.

For the purposes of the lists below, I’ll focus on WhatsApp and Facebook Messenger — currently the two most popular mobile messaging platforms.

Pros

  • Completely free. With the exception of costs associated with wireless data, you don’t have to pay anyone anything to send or receive messages via WhatsApp or Facebook Messenger.
  • Cross-platform. Facebook Messenger and WhatsApp have all kinds of clients that run in all kinds of contexts. Some are native, others are web-based; either way, you’re covered whether you’re on macOS, Windows, iOS, or Android.

Cons

  • Gardens with very high walls. Proprietary messaging platforms generally will not interoperate with one another.
  • You are the product. When you use Facebook (and, increasingly, WhatsApp), you are agreeing to be monetized in ways that you don’t have to worry about when you use a service like Apple’s messaging platform. The reality is that there’s no such thing as a free message. You can either pay in fiat currency by buying an iPhone, paying for Project Fi, etc., or you can pay with your personal information which will ultimately be used to target you with ads.

Third-party Message Syncing Services

mightytext_150Third-party message syncing services are an interesting solution to the desktop messaging conundrum. Rather than being standalone messaging service in and of themselves, they typically work by listening for incoming messages on your phone, then forwarding them to servers which, in turn, forward them to a web or desktop client. (Sending messages works in reverse). Good examples of third-party message syncing services include MightyText and MySMS.

Pros

  • Texting from the desktop. Android users can feel as smug as their iPhone-wielding colleagues and friends by sending and receiving text messages right from their desktops.
  • Semi-cross-platform. These services only work with Android phones (iPhones don’t allow third-parties the required API access), but your desktop setup can typically be Mac or Windows.

Cons

  • Security. Keep in mind that you’re allowing a third-party to access all your messages. In fairness, the same is true with most other cross-device messaging solutions, but it’s one thing to trust Apple or Google with your texts, and quite another to trust a company you’ve never heard of. That’s not to say third-party message syncing services are inherently insecure, or that they don’t follow security best practices. But if you decide to try one, you’d better be 100% positive it’s trustworthy. (Note that apps like AirDroid can work without sending your data to third-party servers, though in “Remote Connection” mode, your data will leave your local network, and hence, your control.)
  • Device dependency. Since messages are always routed through your phone, your phone always has to be on, and you have to have a good signal. One of the best reasons to text from the desktop is that you can continue the conversation even when your battery is dead, or when you’re 40,000 feet in the air using in-flight Wi-Fi.
  • Yet another moving part. There are already a lot of parties involved in mobile messaging on Android including Google, the manufacturer of your phone, and your carrier. Adding an additional third party into the mix (and at least two additional applications) just to handle cross-device messaging introduces even more complexity and uncertainty. These services tend to have issues with various combinations of phone manufacturers and default messaging apps, and any one of them could disappear at any given moment.
  • Cost. In addition to what you’re already paying for voice, data, and SMS, you’ll also have to pay a few bucks a month for the privilege of synching your messages across your phone and desktop.

EOM (End of Message)

As is often the case with technology, when it comes to messaging, choice is inversely proportional to convenience. Being an Android user means getting to choose between several diverse and alluring devices with features like configurable modules and wrap-around screens, but at the expense of timely software updates and full-stack features like robust cross-device messaging. On the other hand, if you’re an iPhone user, you sacrifice a diverse landscape of phones, but you’re guaranteed the most up-to-date software, and (arguably) the most coherent cross-device computing ecosystem ever created. (And let’s be honest: iPhones have always been one of the highest quality consumer electronics ever built.)

Many of us Android users subsist on feelings of superiority and, secretly, the hope that life will get easier. Maybe Google will finally take Google Voice seriously. Maybe this update to Hangouts will clarify what the hell Hangouts is actually for. Maybe Allo and Duo (neither of which appear to have desktop counterparts as of yet) will finally provide Google devotees with more modern messaging solutions.

Maybe. But probably not. My best guess is that things will get significantly more confusing for Android users before they get appreciably better. And even if Google does recognize that they have a serious problem with messaging across their ecosystem, it could easily take them years to get all the necessary moving parts synchronized.

While I’m primarily an Android user myself (Nexi are my devices of choice), I also always keep the most up-to-date iPhone around just to remind myself of how easy life could be if I weren’t so stubborn. When it comes to cross-device collaboration — and in particular, robust messaging solutions — unless you really enjoy bending technology to your will, I highly recommend Apple’s ecosystem.

But if you just refuse to give up on Android, and if you want the best overall Android experience possible (including robust cross-device messaging), give Project Fi a try paired with the latest Nexus (Pixel?) flagship. Otherwise, be sure to keep your phone close by because secure and dependable messaging across all your devices will probably remain well out of reach.

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