After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Google’s Gmail. In this first of a multi-part series, he explains why he chose Gmail and what some of the pros and cons are. Future installments will explore the ins and outs of Google’s free mail service.Show full article

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For the record, it has now been some time since I used Eudora 6.2.4 as my everyday email program, and I have instead switched to Google’s Gmail. I realize that may come as a surprise, considering that I wrote the “Eudora Visual QuickStart Guide” back in 1997 and was long a vocal supporter of the program. But Eudora had started crashing more frequently and corrupting mailboxes in the process. I could fix the damaged mailboxes (see “How to Fix Corrupt Eudora Mailboxes,” 4 April 2008), but doing so had become an annoying interruption when I just wanted to move forward with the day’s work.

I held onto Eudora as long as I could because I liked the way the program worked. I liked the fact that it was tweaky and customizable, that it reported clearly what it was doing, and that it was entirely straightforward. I’ve used and written about most other Mac email programs over the years, and if I was forced to generalize, I’d say that they all feel to me as though they’re starting from the same conceptual base as Eudora, but with a different set of priorities. Since I had become utterly familiar with Eudora’s mindset, all these other programs simply felt like awkward take-offs.

That’s why, when it came time to choose a new email program a while back, I picked Google’s Gmail. Alone among my choices at the time, Gmail’s engineers decided to rethink the entire concept of email, throwing out many basic assumptions and designing from scratch. I felt that if I were going to make a major leap (and since email is my primary communication medium, it truly is a huge leap for me), I wanted to develop a new and better way of working, not merely adjust my old habits to a new program that lacked the parts of Eudora I liked.

The classic email program, Eudora included, takes its architectural cues from the stereotypical 1950s office environment, where incoming mail arrives in a single location, is routed according to various rules, and ends up in a single destination where, after being read and potentially replied to, it will be filed away in a hierarchical filing system or deleted. This approach is functional, but many of the advances in email programs over the last few years have been aimed at making it easier to deal with a large influx of mail, easier to file messages, and easier to find them after they’ve been filed. In other words, these changes are simply trying to build robots into the 1950s office environment so everything moves faster. Meanwhile, the world has moved on from those days of secretaries taking dictation from snazzily suited executives.

Gmail’s engineers instead focused their efforts on search, a far more modern concept. After all, Google’s skyrocketing fortunes gave some indication that search was a winning idea. With search at its core and Google’s unimaginably massive server farms backing it up, Gmail could do some seemingly simple things that standalone email programs have been either unable or unwilling to do, most notably trading the old “folder” concept for a modern “label” approach and generating every collection of messages via a search.

As an aside, I’m quite depressed that only Google has been able to do this successfully. I see no reason that a modern Mac couldn’t offer the same level of functionality, and the fact that Gmail can be made to work offline via Google Gears shows that it should be possible. That said, I don’t use Gears; it was flaky last I tested it, and if I don’t have Internet access, there’s not much I can do anyway, since most of my work requires more than just the capability to read and write email.

The other reason I chose Gmail was that, although I wanted to use its Web-based interface, since that’s where all the innovation is, I also appreciate the fact that it provides access to my email via IMAP, for a local backup and in case I want to switch to some other email program in the future. (For some people, the capability to access Gmail from any computer with a Web browser is a big deal. Since I seldom use any computers but my own, this isn’t a significant advantage for me.)

Giving even more weight to my decision was the fact that, although I have my own mail server, I’d rather forward mail to Gmail and let Google’s engineers deal with keeping things running. Acting as my own email admin hasn’t been fun for years, between dealing with spam and the stress of being responsible for the email accounts of a number of local users.

So here’s my new philosophy of email, which has proven significantly less stressful than the last few years of using Eudora:

• I forced myself to let go of the need to file obsessively, via either filters or manual operations. I’m a professional, not the clerical help. I don’t even approve of the concept of clerical help — technology should eliminate the need for obsessive filing, and I’m letting Gmail do that for me now. This reduced a lot of stress, and after two years of usage, I haven’t yet missed my old filing system. Similarly, I’ve given up on managing an address book, which is possible because Gmail’s auto-fill of previously used addresses, both in the address fields and the search field, is wonderfully instant and accurate.

• Email is a constant stream, and while I want to be able to ignore it for a weekend, while I’m working, I want the option of seeing and responding to messages quickly and concisely. By eliminating the concept of checking mail, Gmail allowed me to escape the check/send cycle. Mail is either present in Gmail or it’s not; there’s no intermediate server where it could be. (In fact, because I still use Postini for server-side spam filtering for some tidbits.com addresses, this isn’t quite true.)

• While I don’t want to file messages, email should naturally collect into appropriate groups. Gmail does this brilliantly, automatically collecting messages with the same Subject lines into conversations, and making it trivial — far more so than in traditional programs — to collect messages associated with specific individuals or groups via a search.

Gmail Limitations -- Though I’m currently a big fan of Gmail, I think it’s important to acknowledge Gmail’s limitations up front. None of these are more than a minor irritation for me, but not everyone will agree.

First, some common concerns: privacy, security, and advertising. Although Google has a privacy policy that claims it won’t share information in unreasonable ways, the fact remains that Google stores all your email (as does any IMAP email provider). Since I’ve long subscribed to my mother’s advice not to say anything in email that I wouldn’t want on the front page of the New York Times, I’m not particularly concerned about Google having theoretical access to my email. Nor am I worried about Google somehow selling access to my mail; if such a thing ever happened and became known (and it would, given the scrutiny Google is under), it would cause irreparable damage to Google.

Also, with all your email online, all that protects it is your password (so pick a good one!). If that’s not sufficient for you, Gmail recently added two-step verification that requires a level of security beyond your password when your account is accessed from a new device. Lifehacker has a good explanation and tutorial, but beware that two-step verification can be a pain to use if you use other desktop or Web applications that access Gmail or other Google services and aren’t yet updated for two-step verification.

And the ads? Gmail analyzes every email message and displays contextual ads at the right edge of the message, ranging from the ridiculous to the occasionally creepy. Honestly, I seldom even noticed them, and now that I’ve installed the Rapportive plug-in, they don’t appear at all (see “Rapportive Plug-in Replaces Gmail Ads with Sender Info,” 27 March 2010). Similarly, Gmail’s distracting Web Clips, which display news items in a little box at the top of the Inbox, can contain ads; I just turn them off in the Web Clips screen of Gmail’s Settings (to access them, click the gear icon at the top of Gmail’s Web interface page and click Mail Settings in the menu that appears).

While Gmail’s Web interface is extremely good overall, there are certain areas where it falls down. Most notably, Gmail is occasionally slow to send a message or load a new one, showing a small progress message while I sit and stew. Most of the time it’s not an issue, which makes it all the more annoying on those occasions when it takes five to ten seconds to send a message or open a new one. Those are the only times I wish for a desktop application.

That’s not quite true. Gmail’s Web interface is designed for a single window, which is generally fine, since most email either doesn’t require reference to other messages or requires only checking back in the same conversation. But on those occasions when I need to refer back to a message in a separate conversation, it’s clumsy to pop an in-progress message into its own window so I can get back to the main Gmail window, perform a quick search, and refer to the older message while writing the new one. Gmail does offer both on-screen controls and keyboard shortcuts for generating separate windows, but it’s clearly of secondary importance and harder than it would be in a desktop application.

And of course, while you can download a local copy of your email via Apple Mail or any other IMAP client, you do have to do that if you want a backup of your mail. There’s no reason to believe Google would lose your mail permanently, but it’s always best to have a backup you control as well.

Most of the rest of Gmail’s problems are part and parcel with its innovations. For instance, as fabulous as conversations are the vast majority of the time, they sometimes get in the way. As an example, when we send out email about a new Take Control book, Tonya receives a number of email messages that all need individual attention. But because people often reply to incoming mail as a way of generating a new message, she’s often faced with a multi-message conversation where each message is actually an independent unit that’s harder to work with in the conversation than it would be on its own. (You can turn off conversation view entirely in Gmail’s Settings screen, but that’s overkill.)

Similarly, threads in mailing lists sort into conversations too, which is almost always a help. But if there’s private mail with participants of the thread, it can occasionally be confusing to have the private messages mixed in with the public ones. It would be nice if Gmail enabled us to explode any given conversation into its component messages.

There are a few areas where Gmail doesn’t compete with traditional email programs. For instance, when building spam-catching filters, it’s nice to have access to grep capabilities so you can match patterns of text. Gmail can’t do that, and in fact, all searches are word-based, so you can’t even do partial-word searches. Also frustrating is that you can’t search on arbitrary header lines, which can be useful for eliminating foreign language spam, for instance. Gmail does support searching on From, To, Cc, Bcc, Subject, and Delivered-To, along with dates and attachments, and realistically, I haven’t felt hampered by Gmail’s search limitations.

If you receive a ton of email, with lots of large attachments, it’s possible that the 7.5 GB of free space you get with a Gmail account might not be enough. However, at $5 per year for 20 GB (up to 16 TB), it’s hard to be too concerned about this.

Lastly, it’s not particularly easy to import old local email messages into Gmail. There is a Google Email Uploader for Mac, but it works only with Gmail within Google Apps, not with standalone Gmail accounts. The alternative is to connect your old email client to Gmail via IMAP (or import your old mail into Apple Mail or Thunderbird, which talk fairly well to Gmail via IMAP) and then copy messages manually, mailbox by mailbox. When I tried this with Eudora, I lost original dates on the imported messages, rendering it useless, and I’ve heard that it’s difficult to import significant quantities of mail at once, with the actions timing out and messages failing to transfer.

After considering the situation, I decided there was no significant win in importing my old Eudora mail. Eudora still launches and runs fine on my Mac Pro under Mac OS X 10.6.6 Snow Leopard, so when I need to find a really old message, it’s all still there. If Rosetta really does disappear in Mac OS X Lion, I may have to import all those messages into another program. Starting from scratch required some visits to my Eudora archive for the first month or two, and it took Gmail a short while to learn the email addresses of my most frequent correspondents. But the switch was otherwise entirely painless.

If nothing else, Gmail is free, offers excellent spam filtering, can accept mail forwarded from another account, and provides access to all your mail via POP and IMAP, so it’s easy to test.

In the next article in this series, I’ll explain in some detail how Gmail’s search-centric approach to email enables an entirely different technique of reading email (see “Zen and the Art of Gmail, Part 2: Labels & Filters”). Then, in “Zen and the Art of Gmail, Part 3: Gmail Labs,” I’ll delve into the many ways to extend and improve Gmail via Gmail Labs, and in “Zen and the Art of Gmail, Part 4: Mailplane,” I’ll look at the Mac program that makes using Gmail far more palatable than just having it in a Web browser tab.

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Gmail. In this second of a multi-part series, he explains how the fact that everything in Gmail is a search enables a Zen approach to email.Show full article

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After initially making the decision to try Gmail (see “Zen and the Art of Gmail, Part 1: Why I Switched”), I put a lot of thought into what I wanted to get out of email. This required some soul searching, since I’m generally an organized person who likes hierarchical filing systems. Spotlight has never helped me in the Finder, since I know where all my files are stored, and in Eudora, I had hundreds of carefully organized mailboxes that made searching merely a matter of looking in the right place.

But on the downside, my saved search strategy in Eudora was failing me (see “A New Way to Use Eudora,” 20 December 2004). The problem was that I had to do too much, in filing messages that couldn’t be filtered and marking messages that required later action in some way. The marked messages were the crux of the matter — labeling them Act On in Eudora was the kiss of death — I was almost guaranteed never to see them again. For a while I merely marked such messages as unread, so they’d nag me every day, but I quickly became capable of ignoring those as well, though their mere presence in my Unread Mail saved search made dealing with new messages all the more awkward.

After much consideration, I decided go for a Zen approach, and to see email as a river, where my goal was to do as little as possible to any given message as it flowed by. The first step in my journey was to set up labels and filters that would help manage much of my mail automatically.

Labels Are Searches -- Labels are one of the most powerful and subtle aspects of Gmail. Most people think of Gmail’s labels as being like folders in a traditional email program, but that’s missing two key points:

• A message in Gmail can have multiple labels assigned to it, whereas a message in a traditional email program can exist only in a single folder. A corollary to this fact is that every message in a traditional email program must live in a single folder; that is, everything must be filed. That’s not true in Gmail, where a message can have no label attached to it (it then shows up only in the All Mail collection).

• A label in Gmail is nothing more than a minuscule bit of metadata that can be used in a search. In essence, then, labels are saved searches, and are thus merely shortcuts. If you can identify all the messages from a mailing list with a filter (again, just a search), you can apply a label to those messages, even retroactively. But you may not need to, because you can always find exactly the same set of messages again later with a manual search.

If you think deeply about these two points, you realize that most filing that’s necessary in traditional email programs is a waste of time in Gmail. In those programs, you must file messages, because they have to live somewhere, and because searching isn’t fast enough or good enough to assemble a collection of related messages quickly. Neither of those problems exists in Gmail.

In contrast, you need to create a label for only three reasons in Gmail:

• You want to collect together messages that share little in common. For instance, I have an Order Receipts label that I apply manually to receipts from various Web merchants so I can verify credit card charges and check back on vendors I’ve used in the past. A filter assigns that label automatically to a few vendors that I patronize regularly, such as the iTunes Store and Amazon, but most receipts can be identified only by sight and labeled once they’ve arrived.

• You want to collect together messages that can easily be identified by a search for quick access as a group, and optionally as a way of removing them from your Inbox. Mailing lists are the canonical example here — you likely want to read the messages from a list all together, but that’s not necessarily true of all lists. In a traditional email program, you’d have to go to some lengths to display filtered mailing list messages along with other unread mail; in Gmail, you have to choose to separate mailing list messages via the Skip Inbox filter action.

• You want certain messages to be marked in the Inbox so you can tell at glance, for instance, that it’s a message to a mailing list rather than something sent only to you.

It may not seem as though this lets you create many fewer labels than you had mailboxes, but in my experience, it really does. In particular, I seldom create project-based labels, because I’m confident that I can find any message I need via a search for a sender or list address.

For instance, I could create a label to track messages related to my iPhoto Visual QuickStart Guide book for Peachpit, but that would basically entail collecting messages from my colleagues at Peachpit with peachpit.com or pearson.com email addresses, along with messages from the indexer, whose name I know. So there’s no significant win from labeling these messages; I don’t need to deal with them as a group, and if I did, a search would give me exactly the same results.

That’s not to say that other people don’t have the need to maintain project-based groupings of messages, and Gmail can handle that, just not any better than any other email program. You’d need to collect messages via filter (messages from a client’s domain, for instance) and via manual labeling (messages from a colleague about that particular project).

Labels have one small advantage over searches: message count. For unknown reasons, Gmail only estimates the number of results from a search, but displays the exact number of messages that have a certain label.

Sometimes, I’ll pass up a label in favor of a Quick Link, which is a Gmail Labs widget that puts a list of links in the left sidebar. I’ll talk more about Gmail Labs later in this series, but I like Quick Links a lot because it gives me fast access to a group of messages without making a label. Just like labels, Quick Links are saved searches, and can encapsulate anything you can search for, but they don’t apply any metadata to found messages. For instance, one Quick Link I use finds messages in TidBITS Talk or to our internal press release list that have also been marked as spam so I can identify any false positives.

Filters Are Searches -- Gmail has no lock on the concept that filters are searches — that’s how all email programs work. But it’s such an important point that I want to emphasize it.

Filters let you search for messages that match certain criteria: from a certain address, with a certain word or phrase in the Subject line, and so on. Once a message is caught by a filter, the filter can perform certain actions on it, the most important of which is to apply a label.

To be specific, filters can look for text in the From, To, and Subject lines, and anywhere else in the message, though Gmail unfortunately lacks the capability to search any arbitrary header line, like Content-Type or X-Sender. When looking for text in the body of the message, you can match messages that both contain certain words and don’t contain others, but there’s no grep searching or partial-word searches. You can also filter messages based on their attachments.

Once you’ve defined your criteria, the actions you can perform on a message are:

• Skip the Inbox (Archive it): All this does is remove the Inbox label. I use it heavily with non-essential mailing lists to keep them out of my Inbox.

• Mark as read: Since the unread status of a message is important to me, the only time I use this action is to mark messages from me to a mailing list as read. (Most of the time I don’t even see such messages, since Gmail usually doesn’t display messages you’ve sent to a list, knowing that the incoming message from you to the list would just duplicate the outgoing message already stored in the conversation. This is generally welcome, but can be annoying when testing or troubleshooting.)

• Star it: The star is equivalent to Apple Mail’s flag, and is a simple on/off way of marking a message. I use it manually to mark messages that need further action, so I don’t use it in any filters.

• Apply the label: Applying labels is the most common thing filters do; I have only one or two that don’t apply a label.

• Forward it to: Be very careful of filter actions that can send mail for you; if you need such a feature it’s here, but it’s awfully easy to have it go awry.

• Delete it: I would use this filter action only to clean up a large archive of mail; if I was receiving messages that I wanted to delete every time, I’d try to figure out some other way of stopping them.

• Never send it to Spam: Some mailing list messages can look an awful lot like spam; check this option to ensure that Gmail doesn’t accidentally mark a good list message as spam. I have to mark a few list messages as spam manually each month because of using this option, but that’s better than suffering false positives.

• Send canned response: This action, provided by Gmail Labs, is again the sort of thing I would be hesitant to use without very careful testing, since it’s easy to spew canned responses to the wrong people.

• Always mark it as important: This action tells Gmail’s new Priority Inbox feature that the message is important. I haven’t used it, since I want to tell Gmail manually when things are important, and Priority Inbox learns well from past actions.

• Never mark it as important: Also related to Priority Inbox, this one is more important from a filter standpoint, since you can use it to make sure that other filtered messages (such as automated messages and mailing list messages) never appear in your Priority Inbox.

Gmail’s filter capabilities are limited in comparison with traditional email programs, not surprisingly, since there’s less manipulation that can be done with messages on the Web — you can’t execute an AppleScript, for instance. (For that, you’d need to let a Macintosh email program access your Gmail messages via IMAP, which is totally possible.)

Where Gmail’s filter interface shines, though, is in showing you the results of a filter you’re creating on your current archive of email (with the Test Search button), and giving you the option of applying it to existing messages as well as future ones (with the “Also apply filter to X conversations below” checkbox in the final filter creation screen). That’s huge, because it means you can use filters for one-off actions like finding and deleting all the messages associated with a mailing list you’ve decided you don’t like.

Forget Inbox Zero -- Now that you understand how labels and filters work, let’s return to how I suggest you use them. The main use is to manage the flow of incoming messages, reducing the number that hit your Inbox to just those that you need to see as they arrive.

My goal with my Inbox is to read everything that comes into it, replying to those messages that require replies and labeling manually those very few messages that only I can identify. Thanks to the hundreds of email messages I receive each day, I need to filter non-essential mailing lists and various automated messages (Twitter follower notifications, Netflix shipping alerts, and so on, all of which receive an Automated Messages label) out of my Inbox. These filters apply the appropriate label and include the option to Skip the Inbox.

But I do want messages from key mailing lists, like the TidBITS staff list and the Take Control authors list, to appear in my Inbox, since they’re equally as important as messages sent only to me, and often more so. The filters that set labels for these mailing lists simply don’t use Skip the Inbox, so every message from the lists gets both the list label and the Inbox label.

Finally, of course, there are the messages sent directly to me from random people all over the globe. There’s no effective way to filter these messages in any way, and although I could label them after the fact, my Zen approach to email discourages that. The simple fact is that in over a year of use, I have yet to need such an arbitrary collection; a search has always produced the message I need.

The astute reader will note that most of my mail will continue to live in my Inbox, or, rather, will continue to keep the Inbox label. In other words, forget Inbox Zero. I have over 40,000 messages with the Inbox label, and you know what? It makes absolutely no difference in my usage, because Inbox is just another label, and there’s no reason to perform an additional action for every message to remove it. This bothers many people who want to simulate the email programs of yesteryear, so Google added an Archive button that, when clicked, removes the Inbox label. That’s all it does, and thus qualifies as entirely unnecessary work, since there’s no liability to leaving the Inbox label in place.

Not only do I file hardly any messages manually, I almost never delete messages. Gmail automatically deletes messages marked as spam after 30 days, but the only other messages I delete are test messages (TidBITS issues, Take Control orders, notifications from the TidBITS Commenting System) that I don’t need and that could confuse future searches.

You might think this is folly, since it would seem easy to lose unread messages among everything else in the Inbox — especially since Gmail cannot sort messages in any way other than by date. But in fact, there are two reasons this works: the search “is:unread is:inbox” and Google’s new Priority Inbox feature.

The “is:unread is:inbox” search shows all the messages with the Inbox label that are unread, ensuring that I can at any moment focus on just those messages. And remember the Quick Link widget I mentioned earlier? I’ve encapsulated that search into an Unread Inbox Quick Link that has become my default view on my Inbox.

I relied heavily on that search until Gmail gained Priority Inbox; now I use the search only to find messages that both Priority Inbox and I have failed to see when they were new.

Priority Inbox to the Rescue -- Priority Inbox is a relatively new feature for Gmail, and another example of how Gmail is rethinking email. You’re probably familiar with how spam filters can analyze messages and decide if they look like spam, based on other messages that you’ve marked as spam? Well, Priority Inbox works the same way, but instead of identifying spam, it identifies messages that are important to you.

How? Gmail just starts guessing as to what’s important and what’s not, and you correct it as it goes. Within a remarkably short time, you’ll find that the messages you most care about appear in your Priority Inbox, and the rest show up in an Everything Else list at the bottom of the Gmail window. If you ever want to see why Gmail thought something was important, just hover over the little yellow icon that indicates the message is important, or, if you’re in the message, click the Show Details link.

Priority Inbox is fairly malleable, in fact, providing up to four sections, the first three of which are configurable. For each of these, you can set Gmail to show messages in the Inbox that are Important and Unread, Important, Unread, or Starred, or you can have Gmail display the contents of a label in the section. For all four sections, you can choose how many messages should display.

I’ve configured Priority Inbox’s sections as follows. The first one shows Important and Unread messages, the second shows Starred messages (things I need to come back to), the third shows my Press Releases label (messages I want to scan, but don’t want cluttering my Inbox), and the fourth is Everything Else. I actually spend a fair amount of time in Everything Else, since new messages that aren’t deemed important appear there, as do important messages once I’ve read them.

What I’d really like to see from Priority Inbox is the capability to have Gmail automatically label messages based on previously labeled messages. That way I could train it to collect messages about certain topics or projects and have those added to automatically over time.

Shortly after I wrote that last paragraph, Google introduced a new Gmail Labs feature called Smart Labels that promises roughly what I want. Unfortunately, Smart Labels can assign only three hard-coded labels to messages: Bulk, Forums, and Notifications. Since my filters are far more specific, they’re more useful to me. If you were entirely new to Gmail, I could see trying Smart Labels for a while to see if it proved to be sufficient.

My Email Flowchart -- To summarize then, here’s how my email works. Messages come into Gmail. Filters assign labels to incoming messages from mailing lists, along with a few other predictable types of messages. Important mailing list messages retain the Inbox label so I see them sooner; secondary mailing lists lose the Inbox label. That all happens without me even noticing (unlike in traditional mail programs, which are always checking for mail and showing filtering status and whatnot).

To start reading mail, I just look at the top of my Gmail window, where the Priority Inbox’s Important and Unread section lists the most recent messages. I then click the first unread message and read it. From that point, there are only seven actions I might take on that message (listed in order of how often I perform them):

• Do nothing, merely absorbing the information in the message and its attachments. One nice touch in Gmail — many common attachment types can be viewed online without being downloaded and opened in another program. I can’t tell you how many random attachments I have cluttering my hard disk from my Eudora days.

• Reply to the message. Because Gmail always lumps messages with the same Subject line together, replies are stored with the messages they’re in reply to, making it easy to follow discussions as they evolve; I depend heavily on this feature.

• Mark the message as unread. Sometimes I want to pretend that I haven’t read a message. Perhaps I’m glancing at something just before leaving for an appointment, or it’s too near the end of the day to think of an appropriate response. Or, because I sometimes read email on my iPhone (where the mobile Gmail client is quite good, but can’t make up for the iPhone’s clumsy text entry capabilities), I often mark messages that need a real response as unread.

• Star the message, whether or not I’ve replied already. This is my marker that indicates “I should really do something based on the content of this message, so I’m going to mark it in such a way that I could theoretically find it in the future.” In reality, the star is my new kiss of death, and although I sometimes explicitly look at and deal with starred messages, it often turns out that I’ve already dealt with the issue or it has become irrelevant in the interim. So it goes.

• Apply a label manually, if it’s an order receipt or another type of message that can’t be identified by a filter for labeling. Again, I do this only occasionally, since it’s usually make-work.

• Click the Report Spam button, if the message slipped past both Postini’s server-side filtering and Gmail’s own very good spam filtering. Postini is now owned by Google, though I can’t tell how that affects spam filtering.

• Delete the message. I do this only occasionally, and only for test messages. I never use the Archive option in Gmail that removes a message from the Inbox, since there’s no benefit when clearing messages out of the Inbox ceases to be an amusing game.

Because the Report Spam and Delete buttons remove the Inbox label and apply the Spam and Trash labels, respectively, thus-labeled messages disappear entirely (since they no longer match the search), switching me to the list of unread messages again. Marking a message as unread also has the effect of switching back to the message list, which makes sense.

With all other actions — replying, starring, applying a label, and doing nothing — I follow that by pressing the keyboard shortcut — the k key — to move on to the next message, where I once again go through the simple steps. For most messages, I have only to decide if I wish to pretend I haven’t read the message yet, or if I need to reply. And in only a few situations, I also have to think about if I should mark the message for later dealing in some way, and if it needs additional labeling.

Every so often, I use my Unread Inbox Quick Link to display all the unread messages in my Inbox, regardless of their importance. That’s useful because every now and then an unimportant unread message can fall off the bottom of the chronologically sorted Everything Else list, and without this explicit check, I’d likely never see it.

That’s it for reading and replying. Composing messages is easy too, but the overall task is so simple that Gmail doesn’t have much room to improve on what traditional email programs do. It does an awfully good auto-complete as you type a few characters in someone’s name, and presents the list of possible matches sorted by how often you write to them. And of course, there are some useful enhancements available from Gmail Labs that help prevent addressing mistakes. That’s where we’ll turn in the next article (see “Zen and the Art of Gmail, Part 3: Gmail Labs”), after which we’ll look at Mailplane, the Mac application that breaks Gmail out of the browser (see “Zen and the Art of Gmail, Part 4: Mailplane”).

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Gmail. In this third of a multi-part series, he looks at how Google engineers have extended Gmail in a wide variety of optional — but sometimes very helpful — ways.Show full article

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In this series so far, I’ve explained features of Gmail that are standard (see “Zen and the Art of Gmail, Part 1: Why I Switched”) and “Zen and the Art of Gmail, Part 2: Labels & Filters”). But as much as I’ve liked using Gmail, the fact that it has met my needs in large part has been due to the optional enhancements provided by Google engineers via Gmail Labs. I presume these are the sort of features that Gmail’s product managers consider unnecessary for most users, but they’re made available to anyone who wants them, and some are essential to my workflow.

To access Gmail Labs, click the gear icon at the top of Gmail’s Web interface page and click Labs in the menu that appears. (For Google Apps accounts, there’s a Settings link at the top instead of the gear icon.) Then scroll down through the long list of items, clicking the Enable radio button for any that look interesting. I recommend being somewhat conservative in how many you enable at a time, since a flaky Gmail Labs feature can in theory cause Gmail to fail to load. I won’t attempt a laundry list, but here are the ones that I find make an actual difference to my Gmail use, in rough order of importance.

Quote Selected Text -- I consider this Gmail Labs feature essential for cutting some replies down to size. Much of the time there’s no need to quote an entire original message in a reply, and with this feature enabled, you can select just the text you want quoted before replying. This feature is commonplace in traditional email programs, and I would miss it horribly if it weren’t available in Gmail.

Undo Send -- One of the things I liked about Eudora was that I could queue messages for later delivery, which would happen either on my next mail check, or when I manually released them. It was entirely common for me to remember something I wanted to add to a queued message, so I appreciated that approach, even though it created a little more work.

Gmail, like many other email programs, lacks the concept of queuing outgoing messages, instead offering only a Drafts mailbox for in-progress messages that you haven’t yet sent. That’s not good enough; I need to be able to add to a message that I previously thought was done, and the Undo Send feature of Gmail Labs gives me that.

Once enabled, it displays an Undo link on the screen next to where Gmail reports “Email Sent.” Click it within 30 seconds (configurable in the main Settings screen), and Gmail moves the message (which hasn’t really been sent yet) back into Drafts and lets you edit it again. I use it regularly.

Quick Links -- I really like the Quick Links widget, which enables me to create a single-click link to any bookmarkable URL in Gmail, most notably unread messages in my Inbox. So, anything you can encapsulate in a search, such as the following, can be turned into a link for instant access.

• is:unread in:inbox — This displays all unread messages in the Inbox.

• in:spam (label:tidbits-talk OR label:press-release) — This one looks for messages sent to TidBITS Talk or our press release reflector that have been marked as spam — every now and then Gmail produces a false positive. I scan this occasionally and mark good messages as not spam.

• from:(tonya@tidbits.com OR tc-comments@tidbits.com) -{label:tc-order label:automated-message} — This one shows all messages from Tonya, eliminating some automated messages that also send mail from tc-comments@tidbits.com.

One tip: Complex searches in Gmail are easier to build if you first click Show Search Options (in tiny text to the right of the search field). Then build your search, make sure it finds the right messages, and copy the search phrase from the “Search Results for:” line to the left of Gmail’s main interface buttons. Then paste that into the normal search field and make your Quick Link. If you make a Quick Link with Search Options showing, it will show every time you use the Quick Link, which is a waste of screen real estate.

Alas, Quick Links can’t have keyboard shortcuts, which would be helpful.

Navbar Drag and Drop -- Gmail puts quite a number of items in the left-side navigation bar, but they aren’t always in the order you want. With this Gmail Labs feature, you can rearrange them, at least somewhat. I like to put Quick Links near the top, but it often moves down on its own for unknown reasons.

Multiple Inboxes -- Like Priority Inbox, the Multiple Inboxes widget in Gmail Labs tweaks Gmail’s default list of messages, offering you up to five additional boxes that you can use to display the results of any search. (Remember, everything is about search.) Of course, the most likely searches are for labels, but you can display anything you can find. You can set how many messages appear in the boxes, though they all use the same number.

The various boxes can be displayed below, above, or to the right side of the main Inbox. I could see above being useful for particularly important messages, and I prefer below, but because the right-side display shrinks the Subject area of the message list, it would be helpful only with a very wide window.

You configure the searches for Multiple Inboxes in its own settings screen, accessible from a link added to the others at the top of the main Settings screen.

Unfortunately, Priority Inbox overrides Multiple Inboxes, so to see the Multiple Inboxes display, you must click the Inbox link in Gmail’s left-hand nav bar instead of the Priority Inbox link. Since Priority Inbox came out, I don’t use Multiple Inboxes nearly as much.

Previews in Email -- A number of Gmail Labs features enhance Gmail by embedding content right in the message, based purely on links included in the message. So, if a friend sends you a link to a set of Flickr photos, the Gmail Labs feature lets you view see previews of the photos right in Gmail, without having to bounce out to Flickr.

Currently, you can get previews for Flickr, Picasa, Google Docs, Google Maps, Yelp listings, and even Google Voice messages (so you can play your Google Voice voicemail right from the email notification). YouTube previews used to be available via a Google Labs feature, but are now built into Gmail by default.

Smart Addressing -- A pair of Gmail Labs features make Gmail the best email program I’ve seen for helping the user avoid addressing mistakes. Once you add one or more recipients to a message, “Don’t forget Bob” enables Gmail to suggest other people, based on groups you have sent email to in the past. And “Got the wrong Bob?” alerts you when you address a message too quickly and accidentally send to Bob (your boss) rather than Bob (your friend). It kicks in only once you’ve added more than two recipients (since it needs the context of groups you’ve sent email to in the past to guess that you might have the wrong Bob). For more information, see “Gmail Further Foolproofs Group Emailing ” (15 October 2009).

Google Calendar Gadget -- Since I have full access to my calendar in BusyCal on my Mac at all times, and reminders from it and on my iPhone, Google Calendar isn’t that important to me. But since we use Google Calendar as the intermediary for sharing certain calendars via BusyCal, I’ve added the Google Calendar widget to Gmail as well, so I see a little box showing the next couple of events in Gmail’s left-side navigation bar.

Advanced IMAP Controls -- Although I read my mail in Gmail’s Web interface, I also back it up by retrieving it in Apple Mail via IMAP. That way, should something awful happen to Google or my mail in particular, I have a local copy that’s backed up along with all the rest of my data. This Gmail Labs feature makes working with IMAP a bit easier. My understanding is that Gmail’s IMAP is, shall we say, kind of weird, since it has to map labels to IMAP folders (meaning that a message can appear in multiple IMAP mailboxes). For more information, see Joe Kissell’s essential article on the topic, “Achieving Email Bliss with IMAP, Gmail, and Apple Mail” (2 May 2009).

Canned Responses -- This feature attempts to mimic Eudora’s stationery feature, at least as far as the boilerplate text goes (Eudora’s stationery could include message header information as well). Although I like the idea of having canned responses, in the real world, I don’t use it much, and I use it only manually since I don’t trust software to send mail for me automatically. But that’s just me. Of course, you could also use something like TextExpander or Keyboard Maestro for this functionality, though such utilities don’t appear within Gmail’s interface.

Add Any Gadget by URL -- I don’t use this Gmail Labs feature, but I like the idea of it, and I tried using it briefly to put a Twitter gadget in Gmail’s left-side navigation bar. There are oodles of Google gadgets, which are roughly similar to Dashboard widgets. The only problem is that a lot of them are bad, and not all display well in the limited width of Gmail’s navigation bar.

While Gmail Labs widgets can go a long way toward improving the overall Gmail experience, there’s one more thing you can — and should — do to make Gmail into a first-class citizen on your Mac. For that, you’ll need to use the Mailplane application to free Gmail from the confines of your Web browser, and I’ll look at Mailplane in the next installment in this series (see “Zen and the Art of Gmail, Part 4: Mailplane”).

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After spending more than 16 years using Eudora for email, Adam has switched, perhaps unexpectedly, to Gmail. Although he likes Gmail’s Web interface, since that’s where most of the innovation lies, he uses Mailplane to enhance the experience on the Mac.Show full article

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So far in this series, I’ve said a great deal about Gmail’s innovations, which are available only through its Web interface. (If you haven’t seen the earlier articles, check out “Zen and the Art of Gmail, Part 1: Why I Switched,” “Zen and the Art of Gmail, Part 2: Labels & Filters,” and “Zen and the Art of Gmail, Part 3: Gmail Labs.”

But there’s a problem with a Web-based interface, which is that it requires a Web browser. Don’t get me wrong, I have nothing against Web browsers for browsing the Web, but for the most part, Web browsers do a mediocre job of hosting Web applications like Gmail. That’s because we often think of and use Web applications in much the same way we think of and use desktop applications, and mixing them in with static Web pages that we open and close with abandon can be a recipe for frustration.

Just think about accessing your email program. You might do so via an icon in the Dock, or via LaunchBar, or some other common mechanism. But if your email program is just a bookmark to a Web page, any of those methods will create a new Gmail tab in your browser, and you’ll get another new Gmail tab every time you click it (this isn’t universally true; Safari 5 sometimes reuses a tab, and Firefox 4 now features app tabs; see “Firefox 4 Improves, But Not Radically,” 2 April 2011). So unless you switch to Gmail by switching to your Web browser and then finding the open Gmail tab, you’ll be constantly opening and closing Gmail tabs, which is an annoying waste of time.

One solution is a site-specific browser like Fluid (which uses WebKit, the technology Safari is based on) or WebRunner (which replaces Prism and essentially encapsulates Firefox). These can effectively turn any Web site into a standalone application that appears in your Dock and doesn’t mingle with other Web pages. But my experience with both is that while they work for some sites, there are plenty of sites where they either don’t work or are clumsy to use for a variety of reasons, including authentication issues, tab-handling, lack of support for plug-ins or extensions, and so on.

Prepare for Takeoff -- Luckily, there’s a much better solution: Mailplane, a highly site-specific browser that’s just for Gmail. Mailplane is based on WebKit, like Safari, but developer Ruben Bakker of Uncomplex has done a truly amazing job of turning what is essentially a Web browser into a real Macintosh application.

Uncomplex has a page comparing Mailplane to using Gmail in a browser, and I won’t list out the many ways in which Mailplane outdoes the browser experience. But I do want to touch on those that I’ve found to be a big win in my everyday use.

Most important is of course the separation of Gmail from the rest of my browsers and tabs. That lets me map the F3 key on my keyboard to Mailplane, something I’ve done for my email program for more years than I can remember. And as a real desktop application, Mailplane can set itself as the default mail application on the Mac, accepting clicks on mailto links and other actions that would normally be sent to Mail or Eudora or whatever.

I also like being able to drag files onto the Mailplane window or its icon in the Dock to attach them to a message (Google has now made it possible to attach files via drag-and-drop into the Gmail window in Web browsers, but that wasn’t true when I started using Mailplane).

Mailplane simplifies certain things that are tough in browsers, such as maintaining multiple accounts. Until August 2010, in a browser, if you wanted to switch among multiple Gmail accounts, you had to log out of the current one and log into the second one, reversing the process to go back. Although Google now allows multiple account sign-in, the process is still clumsier than with Mailplane, which enables quick switching among accounts with a simple double-click in the Accounts drawer.

Because I test a lot of software and report on behavior to developers and designers, I adore Mailplane’s built-in screenshot capability. While writing a message, I can click the Screenshot button in Mailplane’s toolbar and take a screenshot of a selection, a window, or an entire screen. Once I’ve made the appropriate selection, Mailplane takes the screenshot and attaches it to the message with no more interaction (and I don’t have to throw out any temporary screenshot files later).

Although Mailplane provides Mac-like keyboard shortcuts for a slew of Gmail actions, I’ve intentionally avoided them in favor of Gmail’s own internal shortcuts (press ? to see a cheat sheet of all of them, and check out Lifehacker’s “Become a Gmail Master Redux” article for suggestions on using them). That’s because, as much as I like Mailplane, I’m a keyboard-focused user, and I don’t want to become dependent on Mailplane’s version of Gmail’s keyboard shortcuts for those times when I do use Gmail in a Web browser. But I could see some people really appreciating the familiar keyboard shortcuts.

Mailplane also integrates with Growl, notifying me of new messages as they come in. But it’s not just any message that comes in; Mailplane triggers Growl notifications only for messages that hit my Priority Inbox, so the tons of automated messages and mailing list discussions that flow into my mailbox don’t bother me.

Finally, and this is an improvement over only the generic site-specific browsers, Mailplane supports a few Gmail plug-ins: Rapportive, TrueNew, and 0Boxer. Rapportive is wonderful, since it replaces Gmail’s ads with information about your email correspondents (see “Rapportive Plug-in Replaces Gmail Ads with Sender Info,” 27 March 2010). TrueNew is relatively trivial, but shows the unread count for your Inbox and, separately, the number of new messages since your last interaction with your Inbox (I’m not sure this is working since Gmail’s last minor revision). And 0Boxer is essentially a game where you score points by reading and replying to email; you can compare yourself to friends or to the world at large. It was amusing briefly, but after a while, it wasn’t worth the interface space at the top of the window.

While it’s great that Mailplane supports these plug-ins, plug-in support is actually something that points toward using Gmail in a normal browser, and mostly in Firefox or Chrome. That’s because there are a bunch more Gmail-based Web apps and plug-ins that work only in browsers. Of course, many of them attempt to provide features that Mailplane already does better, but there are some I’d love to use.

For instance, there’s Boomerang, which lets you schedule when messages should be sent and can automatically remind you if you haven’t heard back from someone in a couple of days. (Note that Mailplane has now added support for Boomerang; see “Mailplane 2.3.1 Adds Support for Boomerang for Gmail,” 11 April 2011.) And ActiveInbox gives Gmail a Getting Things Done-style makeover. Then there’s socialGmail, a Chrome-only plug-in that displays avatar photos next to senders in Gmail message lists. And although CloudMagic currently requires that you allow IMAP access to your All Mail label (which causes normal IMAP clients to download a lot of unnecessary duplicates), it’s an interesting Gmail plug-in that provides instant searching no matter where you are in the Gmail interface. I could go on, but I think you get the point — there are ways of extending Gmail that just aren’t available until and unless Uncomplex can build them into Mailplane.

In the end, despite my occasional yearning for one of these Web apps or plug-ins, Mailplane provides so many features that I rely on every day that I never end up using Gmail in a normal Web browser for more than testing. It’s well worth the $24.95 purchase if you use Gmail on a Mac.

What about Sparrow? -- There’s been some excited chatter about a new Gmail-focused application called Sparrow. I’ve looked at Sparrow, and while I’m tremendously happy to see Mac developers building a pretty interface on top of Gmail, Sparrow simply doesn’t act enough like Gmail to make it worthwhile for me. That may change as the program evolves, but for now I have these problems with Sparrow.

• While Sparrow does support Gmail conversation view, it reverses the order of the messages, showing the most recent at the top, which is just plain wrong. For instance, if you come into a mailing list thread after messages have arrived, you have to read it from the bottom up.

• Although Sparrow can hide quoted text, it doesn’t do nearly as good a job as Gmail at minimizing reply attributions and signatures, resulting in a messy reading view.

• In Sparrow, you can see your labels only by clicking a pop-up in the lower-left corner; I’d like to be able to pin specific labels to the left sidebar, which has a lot of unused space.

• Speaking of unused space, Sparrow takes the idea of providing white space to an extreme, which forces a lot of unnecessary scrolling in both the message list and the conversation view.

• Sparrow supports some of Gmail’s keyboard shortcuts, but not all of them, which can be a little confusing if you’re trying to switch back and forth.

• Following in the steps of the Twitter app, Sparrow eschews standard interface elements, and a lot of controls, even including such standards like scroll bars, appear only when your cursor is in the right place. I’m all for user interface experimentation, but not when it hurts usability and discoverability, as do a number of Sparrow’s design decisions.

• Sparrow seems notably slower than Gmail at loading messages, so I see its spinning progress wheel fairly frequently. Ideally, a desktop email client would be faster than a Web-based app.

In short, I think Sparrow is simply not sufficiently baked yet for anything but minimal email use. Nonetheless, I have high hopes for it, since it’s the only desktop application I’ve seen yet that acknowledges and attempts to replicate Gmail’s innovations.

Gmail on iOS -- One thing I haven’t mentioned much is using Gmail on the iOS devices, in part because although I do occasionally read email on my iPhone, I don’t do it much. The main thing to consider is that when you’re using an iOS device, you can access Gmail either using the Mail app using Gmail’s IMAP interface, or using Gmail’s mobile Web interface using Safari. There are also a number of apps, such as Mailroom, iGmail, and MultiG, that encapsulate Gmail’s mobile Web interface in a standalone app, much like Mailplane does on the Mac. There’s nothing wrong with them, but the few features they add — like multiple account support — aren’t generally those that I need on my iPhone or iPad.

Although I’ve set up Apple’s Mail app to access my Gmail, since it’s a standard IMAP client with none of Gmail’s innovations (like conversation view, great searching, and so on), for those times when I do want to access Gmail on my iPhone or iPad, I always go to the mobile Web interface.

Google has done a bang-up job for both the iPad and iPhone/iPod touch, creating custom interfaces that react well to the available screen size while providing most of the standard features you’re used to having in Gmail. In particular, I appreciate the conversation view, since it turns reading threads into a simple scroll action, and the capability to search across all my email, since I often look for directions or an address from my email when I realize I don’t quite know where I’m going while driving. The iPhone/iPod touch version of the interface uses multiple screens, one for listing messages and another for displaying them, so there’s a bit more back and forth than with the iPad interface, which can display the message list at the same time as a message.

Honestly, though, the main thing I do with Gmail’s mobile clients is read messages, marking them either as unread or starred for dealing with later once I’m back on the Mac with a real keyboard. I haven’t tried doing all my email on the iPad with an external keyboard; it should be pretty reasonable, but I haven’t yet had the need.

Getting into the Gmail Mindset -- I won’t pretend that switching to Gmail is a trivial step to take, but if you don’t get bogged down in the morass of moving all your existing email and contacts into Gmail and replicating every system you had in your previous email client, you can turn Gmail into a lean, mean, email machine with a little help from Mailplane. I’m not just saying that, I’m living it, and I get one heck of a lot of email. So while I won’t pretend that Gmail is the right email solution for everyone, I have no trouble recommending that anyone who is not happy with their current setup give it a try.

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