Executive summary: After trying Apple Mail again, seriously and exclusively, for more than a month, I’m giving up and going back to Gmail. It’s just plain better—at least for me.

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Well, I gave Apple Mail a good solid month, on my iMac and on my iPad 2. I read and reread Joe Kissell’s outstanding Tidbits article on achieving email bliss with Apple Mail accessing Google’s IMAP servers and I followed his instructions for configuring both Gmail and Apple Mail to the letter. It did help. During this same month or more, I’ve also been trying my best to return whole-heartedly to the Apple fold, by using Safari instead of Chrome, Pages instead of Google Docs, Apple’s Address Book and Contacts apps on my iMac and iPad 2 respectively (why do they have different names?), and by trying to persuade myself that Apple Knows Best.

But I said it first many years ago and I’ll say it again: Gmail isn’t simply the best web-based email service, it’s the best email client anywhere, pure and simple. Of course, different people have different needs and there’s no question that Gmail isn’t the right solution for everybody. I don’t care if you prefer Outlook, or Mail, or Eudora. More power to you. But me, I’m going back to Gmail. Yet again.

In the last week or two of my attempted reconciliation with Apple, I began to realize I wasn’t happy and I started making notes. Here’s what I have come up with. The notes are in no particular order.

Apple Mail’s Cons (compared to Gmail)

• Mail has no undo-send feature. This is one of the best things about Gmail!
• No missing attachment check.
• It is actually harder to add an attachment in Mail, at least if you aren’t going to drag and drop.
• Mail marks messages read instantly. Gmail offers you the option of requiring that the message be selected for 3 seconds before being marked read. I find the Gmail option useful. If I simply click by accident on a message it isn’t marked as read immediately.
• Note that the previous option found in Gmail and missing in Mail (3 seconds before a message is considered read) only matters if you use Gmail’s two-pane view, which is similar to Mail’s. If you use Gmail’s one-pane view, this option isn’t necessary, because you can view messages in a list without seeing the message content at all until you want to. In Mail, you can set the preferences to Classic View, which shows a list of messages with or without a preview; but this isn’t a serious option in my opinion, because, well, Classic View is downright ugly, and one of the most compelling things about Mail is that the latest version of the UI is quite attractive.
• I can’t insert a picture by reference (URL) in a message composed in Apple Mail.
• I have come to like very much Google’s prioritized inboxes, which put important messages first. Mail can’t do this.
• It’s harder in Mail to select a whole bunch of messages, for deletion, archiving, labeling/filing, etc. In the Mac OS, you have to command-click to select multiple messages. (And before you command-click, you have to figure out for yourself that this is the thing to do; it isn’t obvious.) Anyway, selecting multiple messages is easier in Gmail. On the iPad, you have to click Edit before you can select multiple messages.
• While I’m talking about deleting: on the iPad, it’s a pain to delete a single message in Mail because, inexplicably, there is no delete button. You have to click the Move button, and then click the Trash folder.
• Harder to work from the keyboard in Mail. Gmail provides keyboard shortcuts for practically everything — moving from this mailbox to that, moving from one message to another, selecting messages, deleting selected messages, etc. You can do a lot in Mail with keyboard shortcuts, but not as much as in Gmail. I might add that there’s a particularly odd and dangerous problem with keyboard shortcuts in Mail. The delete key has its normal function while you’re editing a message, but if “focus” is in the message listing rather than inside the message editing window, then the delete key will delete an entire message. In Gmail, the del key is only for deleting characters in the editing window. There’s a different shortcut for deleting a message.
• Apple’s IMAP implementation uses folders and this seems to be responsible for certain confusions. Sent messages for example do not automatically appear in conversations in Inbox. Labels are better than folders, by a lot.
• In Mail, if I start a reply but don’t complete it and save it as a draft, it doesn’t appear as part of the thread or conversation in the inbox. So when I return to Mail later, there is no visual cue to let me know that I had already started a reply. In Gmail, a reply saved as a draft appears in the inbox as part of the conversation.
• In Mail, when I reply to a message that I sent, Mail assumes I want to send a message to myself. Gmail is smarter: it knows that I probably want to send another message to the person I wrote to last time and it addresses message accordingly. (Yesterday this caused me a serious problem with a client. I sent them an important message, except that it didn’t go to them at all, it went to me. And I didn’t realize the mistake until late in the day.)
• In Mail, I keep sending messages from the wrong account. Working with a single inbox — which I thought was the big advantage of using Mail — robs me of context, leaves me unaware of which account I am “in” because I am not in any account. NOTE: This matters to me only because I have four main accounts that I use actively. If you use only a single email account, this wouldn’t matter to you.
• Searching in Mail is not as good as searching in Gmail.

Apple Mail’s Pros (compared to Gmail)

• On my iPad, Gmail Mobile doesn’t allow me to format messages at all — no bold, etc. Mail on the iPad does now let me apply simple formats although the process is somewhat awkward. This is almost a wash. On my computer, on the other hand, Gmail (whether using the desktop UI or the Mobile UI) supports a very full range of formatting options.
• I can’t get my iCloud/me.com mail in Gmail. I don’t think I can get my me.com mail in Safari for iPad. So if this account mattered to me I would have to use Mail at least for it. Fortunately I don’t care about my @me.com address. All I get there are ads from Apple.
• Mail for iPad works better in portrait orientation than Gmail. In Mail, the message list disappears, so the messages are easier to read.
• Spotlight (and the search feature on the iPad, whatever it’s called) can search your Mail messages. I find this a non-issue because if I want to search email messages, I go to my mail client. What if I don’t know where it will be? Theoretically possible, but as a practical matter, I don’t think it has ever happened to me.

I have omitted some advantages that don’t seem to me to be real advantages at all. For example, you’d think that Mail would integrate better with other apps on the Mac OS or iOS, and in a few cases that might be true, but I haven’t personally figured out what those cases might be. I could also have mentioned that Apple Mail is attractive, but so is Gmail, especially the new Mobile app (used also by Gmail Offline in Chrome on my iMac). Apple Mail can provide notifications via Growl; but when I use Gmail in Chrome, I also get notifications. Mail integrates well with iCal (and the differently named Calendar app on the iPad) but Gmail works beautifully with Google’s Calendar service, which I like even better than iCal. What’s with that faux leather look, anyway?

Email bliss isn’t free

I want to add a note about Joe Kissell’s remarkable article, which I mentioned at the top of this article and to which I have referred before. Like me, Kissell isn’t selling anything. He doesn’t recommend his approach. But if you choose to use Mail to access a Gmail account via IMAP, Kissell tells you how to do it right and he explains the why, as well, if you’re interested. He knows what he’s talking about better than anybody else I’ve found on the Web. However, following his instructions is a pretty big hassle. It may be beyond the ability (and/or patience) of many non-technical users. And there’s a big downside if you’re not really sure you’re going to stick with Apple Mail and that is that the changes Kissell describes really mess up your Gmail account, if you decide to return to Gmail in a web browser. Not Kissell’s fault. He warns you. I’m just sayin’….