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Searched for something better than Gmail. Didn't find it.

WP, 2015–04-12

When I first used Gmail more than a decade ago, I was surprised at how good it was — surprised and impressed. It was a lot less capable than it is today, but even so, I thought Gmail was, at least in some important respects, better than the best desktop clients. As soon as Google Apps for Your Domain became available two years later (late 2006), I moved my work accounts to Google and they stayed there for the next eight years.

Then in early 2015, I talked myself into abandoning Gmail — and most of Google's other services, as well. I thought I had something better to go to.

I was wrong.

[Just to be clear: I’m talking here mainly about paid Google for Your Domain accounts; but for the purposes of this essay, the slight UI differences between a paid Google account for a custom domain and a free Google account with an email address are largely irrelevant.]

Why? Why?

Why did I quit Google? Good question. After all, I was rather happy with my Google accounts for years.

I don't recall ever experiencing email outages like those that Joe Kissell reported in a 2013 Macworld article titled "Why (and how) I'm saying goodbye to Gmail". And I was using the Gmail web app to access Google's servers, so it certainly never bugged me the way it bugs Joe that Google uses what he calls "highly nonstandard" IMAP. On the other hand, I do agree with Joe about another thing: like him, I was never very worried about Google's snooping.

No, as far as I can reconstruct them, my reasons for switching were more personal.

Although I wasn't worried that Google was spying on me, I was experiencing low-level anxiety. Staring into the dark at night, waiting for the melatonin to kick in, I worried that too many of my eggs were in Google's basket. In addition to multiple email accounts from Google (some paid, some free), I was using Google Docs, Google Maps, Blogger, Picasa and Google+, Google Voice, the Chrome browser (about 50% of the time) and Google as my primary search engine.

Another and perhaps even stronger motive for my switch may have been vulgar technical Wanderlust. I was tired of looking at Gmail, in particular. Initially I was just curious about the alternatives, but pretty quickly curiosity turned into an itch to move, which turned into an urge, and then a compulsion.

Anyway, before I fully realized what I was doing, I signed up for multiple email hosting accounts with my domain registration service, Hover; downloaded the data from both of my Google Apps for My Domain accounts; deleted the data on those accounts; and closed them.

It seemed like a good idea at the time.

Hosting Schmosting

The problem of email has two parts: the front-end (what app or client you use to read email and composed and send new messages) and the back-end (on the servers used by your email hosting service). If you're using an ordinary free account that you access in your web browser at, you don't need to think about this distinction — until you switch to access your email using a different app like Mailbox or Apple Mail. Canceling Google completely meant I had to find not just a new app, but a new hosting service, too.

I might have moved my email service to Apple, but it wasn’t and isn't an option. Apple’s iCloud email hosting won’t let me use my own domain.

There are plenty of other options, but I went with Hover. I like Hover's domain registration service a lot and I know their customer service is great. And they have a very reasonably priced “big mailbox” account that offers an unbeatable 1 Terabyte of storage.

There were two small downsides to using Hover. The first is that Hover doesn't currently support two-step authentication. I gave my accounts really strong passwords and decided I could live with that. The other problem was that Hover doesn't currently support email aliases within an account. With a Google for my domain account, I can have (for example) a email address in addition to my primary address, and I don't need to pay for a separate account. So I had to sign up for four accounts at Hover to replace two accounts with Google.

But in other respects, the server-side of the issue was by and large a wash. Hover was very good, but then I never had a problem with Google's servers, either.

The real problem was with the front-end.

Apple Mail

For weeks after giving Gmail the boot, I tried in good faith to like and then simply to live with Apple Mail. I couldn’t make it happen.

From the start, I had trouble configuring my accounts, and since I was now using a "standard" IMAP account hosted by Hover, I couldn't blame Gmail's supposedly "non-standard" IMAP for my problems. From what I see in Apple’s support forums, I’m apparently not the only person who’s had trouble configuring Mail. It seemed easy at first, then I noticed stuff wasn't working right. Until I figured out how to override Mail’s defaults, it kept changing my settings, apparently in a misguided effort to be helpful.

And I had odd performance issues. For example, outgoing messages often went out, yet stayed in my Drafts folder inexplicably. On my Macbook Air, Mail crashed on me again and again.

There were basic design issues. I don’t want to look at the subfolders for all my accounts all the time. When I'm in one of my work accounts, I'd prefer to focus on that account and forget about the others temporarily.

Inserting images inline is another key feature for me, and it is more awkward in Mail than it should be. Google's user-interface distinguishes between adding attachments and inserting images inline. Apparently Mail's doesn't and I found this somewhat confusing. In Mail there's a single "Attach Files" command in the File menu (= the paper-clip button). Whether the file gets attached or inserted where the insertion point was when you invoked this command, is decided by Mail, apparently based on what type of file it is (zip files get attached, pictures get inserted). This is simply not very well thought out. I’m still not sure if there’s a difference in mail between inline images and attachments.

Finally, Mail simply doesn’t have a number of features I really want in my email program, like undo-send, or a missing-attachment warning, or some form of temporary "snoozing" of messages. You can get some of these functions by paying for third-party plug-ins, but I regard send-delay in particular as an essential feature and it bothered me to pay for things that, in Gmail, I'd gotten for free.

Unwillingly, I resorted to plug-ins. Began using workarounds. Making compromises. Not the experience I’d been hoping for. And I'll even confess (so you'll know just how superficial I am), the more I used it, the less I liked the way Apple Mail looks on my computer. I liked exactly one thing very much: the ability to specify my favorite font and font-size for plain-text messages. In other respects, Mail on my computer lacks the fresh and clean look I'd prefer.

Nowhere else to turn

During much of the time I was struggling with Mail, I was hedging my bets and trying other clients as well. In my opinion, Airmail 2 is easily the best of the alternatives to Mail. Indeed, if Airmail is not better than Apple Mail already, it’s darned close. I had fewer configuration and performance problems with Airmail than with Mail. Airmail 2 supports send-delay and allows me to see one account's folders at a time. But I wasn't perfectly happy with Airmail 2, either, and in the end, none of the alternatives grabbed me.

So I spent an enormous amount of time and energy (and some money) trying to make this transition work. But after a couple of weeks, I could deny it no longer: I’d made a mistake in abandoning Google. A big, fat, unforced error.

So I did the only thing I could think of. I decided to go back.

Listing of "All Mail" in one of my free accounts, one that I use mainly for bills and promotions. Not beautiful, true, but it's very functional and very usable. 

A few reasons I prefer the Gmail app

If I were writing a review of Gmail, I'd be talking at least a little about important features like canned responses, integration with calendar and contacts, vacation responder, themes, multiple inboxes, filters, offline access, encryption, etc. But I'm not writing a review and these features were never issues in my little drama, so I'm skipping over them. I do however want to mention some of the things that were issues for me, things I missed badly about Gmail during the weeks that I stopped using it and was using Apple Mail instead.

FINDING MESSAGES. I remember reading an article many years ago by famous computer scientist David Gelernter in which he offhandedly asked his reader, "You're not still spending time organizing your files into folders, are you?" On my computer, the answer was, of course, yes, and alas, still is. But I was already using Google Mail every day, so I understood what he meant: All you need to be able to do is find stuff when you want it. In Gmail, finding messages is easy, flexible, fast, and effective. After all, this is Google we're talking about, and what they don't know about finding isn't worth knowing.

ORGANIZING MAIL. One word: Labels. They're simply a better idea than folders. The advantage of labels is that you can assign a single message to one label, no label, or as many as you like. By contrast, filing a message in Mail in two different folders requires duplicating the message—and duplicate copies of messages are almost always a bad idea. There simply isn't anything you can do with mailboxes that you can't do with labels at least as easily. You can even nest labels within labels.

But you probably won't. The point of elaborate folder hierarchies is to put things in their place so you can find them later. In a way, with folders, you find stuff before you actually want it, and the folder helps you remember where it was. Given how good searching is in Gmail, you don't need to find stuff until you want it, and thus, the need for labels is minimized. So instead of using labels as pseudo-folders, I tend to use labels mainly for special cases. For example, in my photography practice, when I receive a print order, I label it "needs processing." When the prints ship, I change the label to "shipped." Anyway, I make minimal use of labels, and, other than trying to keep my inbox empty, I spend almost no time managing or organizing anything. I take the same approach to my physical office, but unfortunately it doesn't work so well there.

SECURITY. First, Google supports two-step authentication, so someone (including me) trying to access my email from another computer or device is challenged not just for my password but, periodically, for a one-time code sent to me as a text message. Neither Apple Mail nor Hover's email service provided this protection. Additionally, Google makes it easy to see when my account has been accessed recently, from what IP address, and on what type of device (mobile, etc.).

The very first Gmail account I ever had was hacked and stolen five years ago, while I was away on vacation. At that time Google's account recovery options were pretty bad, I was never able to talk to a human being, and I lost the account. That was when I learned the importance of good passwords and two-factor authentication. With the long, strong passwords I have on my Google accounts, plus two-step authentication, I’m not too worried about losing an email account again.

A thread or 'conversation' in Gmail with multiple messages, in its default presentation, with older messages collapsed. If I wanted to expand, say, the second message in the thread, I could, simply by clicking it.

READING MESSAGES. Couple of important things here.

First, Google's way of displaying multiple messages in a "conversation" (thread) strikes me as about as good a response to this challenge as you can find. Apple Mail shows the full content of every message, with a lot of repetition (the subject line is repeated in each message, even though the subject usually doesn't change from one message to the next) and wasted space (each message's signature area and quoted text is also displayed in full). By default, Gmail collapses messages and shows you only the most recent one; so if the conversation has six messages in it, you see the sender and the first line of the first five messages, and the full text only of the last message. But it also allows you to expand an individual message anywhere in the conversation if you need to, without expanding the ones around it; and it doesn't repeat the subject or show the signature or quoted text in each message. Cleaner, more efficient.

Second, in Gmail, there are two ways to view messages on their own, that is, where you aren't looking at the list and an individual conversation in the same window. In Mail, an individual message opens in a window that you can't move and can't resize. In Gmail, if you have your inbox configured the right way, you can view conversations in a list, then double-click a conversation to have it reveal its messages in place of the list; in other words, it doesn't create a new window, just shows the conversation in the space where the list had been. Alternatively, you can open the conversation in its own window—a window that you can resize and move.

COMPOSING MESSAGES. Gmail gives you multiple ways to write a message: inside a thread (with other messages visible), in a small window useful for quick messages, or in a large window. I prefer the large window and use it most of the time. I can easily quote selected text in a reply; or I can reply and quote the entire previous message. My biggest complaint about Gmail is that it doesn't let me set my preferred font and/or font-size for composing plain text messages.

SENDING MESSAGES. Google provides three tools for sending that I find it difficult to live without.

The first is undo-send. After you hit send, there’s a short delay before messages actually leave your outbox. During that short delay (say, 30 seconds), if you realize you wrote that nasty paragraph about your boss after hitting reply to a message from your boss—you can hit cancel and save your job. I’ve never had exactly that situation, but I use undo-send several times a month.

Another key feature in Gmail, for me, is the missing-attachment warning. It doesn’t work perfectly, because sometimes I don’t use the keywords the feature is on the lookout for. Nevertheless it has cut by at least 50% the messages I get from clients saying “Did you mean to attach something to that last message?”

Finally, there’s Boomerang. Technically this is a third-party utility (from Baydin) but it’s built into Gmail now, and I love it. It allows me to schedule when messages go out; to move messages out of my inbox, then have them pop back in automatically in, say, 7 days; and a few other things. It's similar to the "snooze" option in Mailbox and Google's own brand-new app, Inbox.

You can get undo-send and missing-attachment warnings in Apple Mail by using plug-ins from a third party, which is fine. But those plug-ins aren’t free, and they require downloading, configuring, etc. The same functionality is built into Gmail at no extra cost. And Boomerang’s not available for Mail and I was too annoyed at this point to go looking for an alternative.

KEYBOARD NAVIGATION. Gmail has an extensive set of simple, mostly one-key shortcuts that don't require me to use the Cmd-key. In Gmail, I can do almost everything from the keyboard, including assigning labels and even moving messages around.

MOBILE SUPPORT. Gmail for iOS is an excellent app. (Mail for iOS is, too: in fact, Mail for iOS is, in many respects, better than Mail for OS X.) Even in the browser on my iPhone or iPad, Gmail works well. And now Google's developing something new called Inbox that looks interesting.

Let me conclude by mentioning a big advantage that Gmail shares with other web-based services like Yahoo Mail or even Hover's web client: no setup or configuration headaches. All you do is log in. You don't need to worry about server addresses or what port to use for POP or IMAP or SMTP. No need to care if your server supports the IDLE command or ask, if it does, should you use it. No need to worry about whether your messages are going to be downloaded twice. Things just work. All the time.

Composing a message in Mailbox. This makes me happy. Mailbox for Mac OS is still in early beta and lacks many features I find it hard to live without. Even so, it's so beautiful, I find myself opening it for a bit almost every day.

Alternative Gmail clients

Some people actually use Mail as the front-end for Google email accounts. I am not crazy about that idea personally, not just because I don't like Mail for reasons mentioned above, but because Google’s IMAP servers and Apple Mail have had a lot of problems working together in the past and I don't think those problems have entirely been resolved. (Check out this article by Joe Kissell.) For me, anyway, Airmail 2 worked with Google's servers better than Apple Mail did, but Airmail, like Mail, is trying to work with everything, and logic suggests and experience confirms that the best client for Google's email service is going to be something designed specifically for that service. And obviously, that primarily means Google's own web app, a.k.a. Gmail in your browser. It ain't sexy. But it’s absolutely trouble-free and the user-interface is amazingly functional.

Now, aside from a beautiful face, the only thing Gmail in your browser lacks is the ability to be the default email client for your OS. This may or may not matter to you; to be honest, it seldom matters to me. If I click an email ("mailto") link in Chrome and I'm already logged into my main Google account, Chrome seems in most cases to start a new email in Gmail, which is nice. And I don't actually click very many email links in other apps like Preview or Adobe Lightroom or FileMaker Pro. But if you do, and if you don’t have anything else defined as the default email app in your system settings, Mac OS X will automatically launch Mail: Yikes! (Why can’t Apple allow you to enter or some other URL as your default email client?) Anyway, remedying this one weakness is the raison d’être of Mailplane. Mailplane adds a number of bells and whistles you won’t get in your browser, like integration with various other apps (Evernote) and services (AppleScript or the “Send by Email” option in Mac OS X print dialogs), but basically, Mailplane is a custom browser for Gmail that can be designated as your default email client. I use Mailplane most of the time and I like it a lot. It doesn't look very different from Gmail in a browser, but Mailplane helps me keep my email and my browsing separate, which I find helpful. I could live without it, but I think it's worth paying for.

And now I’m keeping an eye on two other new apps: Mailbox for Mac OS X and Google's own new app, the clumsily-named "Inbox for Gmail".

Mailbox got its brilliant start two years ago as an app for the iPhone. It is now being brought to the desktop. It is, without a doubt, the most visually appealing email client in history. It's so beautiful, it has made me realize how ugly most of the email I get is. Unfortunately, even with the February 2015 release of beta 0.4, the desktop app is still a good ways from competing with the native Gmail client (in a browser or in Mailplane). Mailbox, originally the brain-child of UI wizards at Orchestra, is owned now by Dropbox, so it's got a lot of expertise and clout backing it up.

As for Google's Inbox for Gmail, it also has a clean, fresh look. And it may be more innovative than Mailbox. It challenges users to think about email in a rather new way and, while I've been playing with it for weeks, I'm not yet sure if I am going to accept the challenge or not. But it's different and I give Google credit for continuing to rethink things from the ground up.

Google Inbox for Gmail is not exactly reinventing email but is rethinking it—and will force you to rethink it too. This is an example of the "Low Priority" bundle in, um, Inbox's Inbox. Google thought that I'd consider these messages "low priority." Corporate modesty? I doubt it.

Joe Kissell's very different conclusion

One of my very favorite tech writers, a guy from whom I've learned a lot, is Joe Kissell. In late 2013—more than a year ahead of me—he did something like what I did earlier this year and abandoned Gmail in favor of Apple Mail and "standard" IMAP service. Unlike me, Joe seems to have stuck with his decision, perhaps because he already had a lot of effort invested in Apple Mail. Anyway, note how Joe talked about this in an article at Tidbits just a few months ago ("Apple Mail: The Yosemite Progress Report"):
[A]s I’ve often lamented, Mail’s default configuration is awful. In order to make Mail usable, I had to display and rearrange the mailbox list, create smart mailboxes, customize toolbars and message headers, fiddle with numerous preferences, and set up a bunch of sorting rules both on my mail server and within Mail. I also had to add several third-party plug-ins, of which the most important to me are Mail Act-On, SpamSieve, and GPGMail. But the end result is a client that behaves almost exactly the way I want it to. I’ve tried lots of other Mac email clients, and despite their many virtues, none of them give me all the capabilities that my customized copy of Mail does.
This is what he had to do to make Mail "usable." Remember, this was intended as a defense of his decision to stick with Mail! Then he sums up:
In short, if you think about email approximately the way I do... you use a conventional IMAP provider, and you’re willing to spend a bit of time fiddling with settings and plug-ins, Mail in 10.10.1 is just fine. The further you find yourself from that position, the greater the chance Mail will annoy you.
I suppose this means I don't think about email the way Joe does. To each his own.

Wrap Up

I do not think I have any moral obligation to "be faithful" to Google, Apple, or any other business out there. I dislike the concept of brand loyalty. I don't dislike the practice. No doubt, a lot of people feel their lives run smoother when they stick with a brand or product or service that is working for them, instead of constantly reviewing their options. That makes sense, in terms of efficiency, and I respect it. I wish I had such discipline and self-control. But I suffer from technological ADD and I'm never happy with anything for very long.

Still, even by my own standards, it was dumb for me to cancel my Google for my domain accounts (one of which was a legacy free account—sigh). It was a costly mistake, both in terms of time and money. The only thing I can say, weakly, in my defense is that the mistake wasn't that I thought that the grass was greener on the other side of the fence and was willing to hop the fence. The mistake was: the grass was not in fact greener.

Anyway, aside from the waste of time and the loss of (as near as I can tell) a thousand or two very old emails, no real harm was done. I'll probably stick with Google for a while now. At least until next year.

And of course I hasten to add that these are my opinions, based on my experience, and are not offered as a criticism of you and your preferences. Happy with that AOL Mail account you've had for years? Stay happy and stick with it. Grateful to your boss for giving you the opportunity to work in Outlook all day, every day? I envy you. Excited about the ability to draw circles on a pdf right there in the latest release of Apple Mail, without having to move the pdf over to Preview first? Charmed by Airmail's ability to punch way above its weight level? That's terrific. Heck, an old friend recently wrote me enthusiastically recommending Unibox! It does not offend me that your email needs and/or preferences differ from mine and I'm not trying to convert anybody. Google doesn't need my help.

And if you want to “news you can use”, here it is, in two parts. First, before you make a big change in your technological life, give it more careful thought than I did. But second — and this is the more important part — don’t put up with crap software from Google, or Apple, or anybody else.


  1. Unfortunately, ever since I upgraded from Windows 8.1 to Windows 10, gmail no longer works with Outlook 2013 for me. I've tried everything on Gmail's troubleshooting page, and every Microsoft suggestion, but absolutely nothing works for me. So, I have no choice but to make this change in my technological life. I've had my personal and professional emails with gmail for so long, I had no idea what else to use, so thank you for the article.

  2. @sschriver: Well, as I said in the essay, the front-end (the app) and the back-end (the servers) are two entirely different things. Apps designed specifically and exclusively to work with Google's servers, work wonderfully: I'm thinking of course of the Gmail web app, but also Inbox and Mailbox. But Outlook, like Apple Mail, was designed with very very different ideas about how the servers would work, and that no doubt explains why Outlook and Apple Mail have had problems dealing with Google's servers. For what it's worth, Google's servers continue to work brilliantly for hundreds of millions of users. Anyway, since going back to Google's own app, I've had zero problems with email. It helps that I increasingly use Google apps for nearly everything else, too: calendar, phone, productivity, etc. Good luck to you.


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