Links
Amazon

A few recommended books, movies, games, and albums. If you want to look for more recommendations, feel free to look at the larger selection over at Amazon or my Amazon Store with more recommendations.

  • Cryptonomicon
    Cryptonomicon
    by Neal Stephenson
  • DreamCypher
    DreamCypher
    Dancing Ferret
  • Tron: Legacy (Amazon MP3 Exclusive Version) [+Digital Booklet]
    Tron: Legacy (Amazon MP3 Exclusive Version) [+Digital Booklet]
    Walt Disney Records
  • The Moon Is a Harsh Mistress
    The Moon Is a Harsh Mistress
    by Robert A. Heinlein
« CONFIGURING MAIL.APP FOR A BETTER GMAIL EXPERIENCE, PT. 2 - Junk Mail | Main | Exercise and Life »
Monday
Nov072011

Configuring Mail.app For a Better Gmail Experience, Pt. 1

  1. Configuring Mail.app For a Better Gmail Experience, Pt. 1
  2. Configuring Mail.app For a Better Gmail Experience, Pt. 2 Junk Mail
  3. Configuring Mail.app For a Better Gmail Experience, Pt. 3 Advanced Junk Mail
  4. Configuring Mail.app For a Better Gmail Experience, Pt. 4 Smart Folders

 If you’re running Snow Leopard or Lion, adding a gmail based email account to your mail application may seem trivially easy. Go to the accounts tab of the preferences and add a new account, and let Mail.app configure itself.

The problem of course lies in the fact that while Gmail may pretend it’s an IMAP service, it isn’t, quite. One of the largest differences is that Gmail uses “labels” instead of folders. The advantage to this is that if a message belongs in several categories, you can actually effectively file it under multiple labels without having to make copies. While Google makes an effort to bridge this very different view of how mail should be organized, it means that Gmail can behave very differently than typically expected. As a result they have a knowledge base article on recommended IMAP settings, and an article mapping out how certain actions in a mail program translate to Google.

IMAP, for those who are wondering, is one of the two most common systems for retrieving mail. POP3, the older standard, downloads the mail to your machine just like recovering it from the cubby in a mail room, and now your computer has the only copy.  IMAP allows easy web access because the master copy always stays online. Whenever you log in via the web or a mail program and read new mails, delete mail, or move mail, those changes are also made to the original copy so that the next time you check your mail, no matter what you check it on, you see the same view. 

I’ll address one other issue right up front: Why bother using a separate mail program?

I don’t mind Google’s web interface. On those occasions where my laptop is unavailable or inconvenient (I’m working at another computer that I need to access email from) I’ll gladly use the web interface. That said, I also have several email accounts (work, Gmail, and an older personal account that I’ve had for years that isn’t Google-based), so being able to get to all of my mail from one place is a necessity. Factor in some nifty keyboard shortcuts courtesy of Mail Act-On and better integration and handling of attachments with the rest of my computer, and it’s a done deal.

The problem of course lies in the conflict between how every other IMAP mail service talks to Mail.app (or Outlook, etc.), and how Google does. I don’t want to treat one account differently from the others. 

So here’s a guide to tweaking both Google, and Mail.app, to work the way you want it to . Some of these hints have parallels in Outlook or Thunderbird, especially the ones dealing with online Google settings.

Stop Checking Your Mail

First things first, turn off all automated, scheduled email checks if you can. Google (and Mobileme/iCloud, and many other IMAP mail services) use a feature of IMAP that allows them to  get email as soon as it lands in your inbox without having to ask the server if anything new is in. Not only do you not need it in most cases, but if you are using the web service, or a phone to check your email as well, this can result in enough simultaneous connections (the desktop mail programs can make a lot of connections) to trigger Google into blocking access to your account as a potential spammer, and you won’t be able to download new mail.

In Mail.app this is found under the general tab of the mail preferences. The applies to Thunderbird and Outlook as well, though Outlook does give you the ability to isolate some accounts to check for new mail, but not others. 

If you must update your inbox on a schedule, set it to hourly, or even less often.

 

Recommended Settings

Let’s walk through the recommended settings for Google, and see why each of them exists. Before we do that, let’s look at how Mail.app sets up a Gmail account by default:

 

  • Do NOT save sent messages on the server. If your client is sending mail through Gmail's SMTP2 server, your sent messages will be automatically copied to the [Gmail]/Sent Mail folder.

This one is plain enough, but not mentioned here is that since Google automatically copies all outgoing mail to “sent”, if you copy all sent messages to the online sent folder as well, you get duplicates of everything ever sent. You also waste time uploading a second copy of your message just to park a copy in “Sent Items”.

If you look at the earlier screen shot, you’ll see that Apple doesn’t set it the way Google recommends. I strongly recommend unchecking it.

The only downside is that your default “sent” folder in Mail.app may not reflect any messages sent via the web, or from your phone or another computer. That said, if you look at the list of IMAP folders (usually to the left), under the folder “[Gmail]” you will find a folder called “Sent Mail” that contains every email sent, no matter where it was sent from.

Since I have multiple accounts, I still want one place I can go to and check for sent messages that may not have been sent via Mail.app. That’s where smart folders come in and I’ll cover those later.

  • DO save draft messages on the server. If you want your drafts in your mail client to sync correctly with Gmail's web interface, set your client to save drafts to the [Gmail]/Drafts folder.

This is generally good advice, and Apple sets this by default. Unfortunately, there’s a known “bug” in how Mail.app deals with Google and drafts that results in two wonky side effects. First, when you finally finish a draft and send it off, it doesn’t always clear the draft out of the drafts folder. Second, there is an auto-save behavior of the drafts that can result in dozens of draft copies being saved as you keep the draft open and keep working on it. I generally recommend to follow Google’s guidance here, but people who don’t care about accessing the same drafts folder no matter where they are may consider unchecking this.

  • Do NOT save deleted messages on the server. Messages that are deleted from an IMAP folder (except for those in [Gmail]/Spam or [Gmail]/Trash) only have that label removed and still exist in All Mail. Hence, your client doesn't need to store an extra copy of a deleted message.
  • Do NOT save deleted messages to your [Gmail]/Trash folder because this will delete a message in all folders.

You’ll notice that Apple doesn’t follow this by default, and personally, I prefer the way Apple sets it by default.

Google wants you to actually drag a message to the trash to delete it. “Deleting” the message by using the delete button or key merely hides it and is treated like archiving a message that hasn’t had a label/folder applied to it - and it is still available in “All Mail”. Given that email programs don’t differentiate between “Archive” and “Delete” like the web interface does, this is a reasonable compromise, and if I was using only Google accounts, I would probably do it their way. 

The problem is that it makes Google based accounts behave differently from the non-Google ones I use. As a result, I DO save mail on the server, and DO move deleted messages to the trash folder. I want the messages I delete to actually be deleted. I don’t even use “All Mail” - even in the web interface, since I figure if I want to keep the message, I’ll file it under a label/folder, even one as generic as “other.”

  • Do NOT save deleted messages to your [Gmail]/All Mail folder as some clients will try to empty this folder and ultimately fail. This can lead to delayed mail access or excessive battery consumption on a mobile device

Solid advice. Though the only harm in doing so is duplicate messages, why waste space?

  • Do NOT enable your client's junk mail filters. Gmail's spam filters also work in your IMAP client, and we recommend turning off any additional anti-spam or junk mail filters within your client. Your client's filter will attempt to download and classify all of your existing messages, which may slow down your client until the process is complete.

In short - turn off junk mail filtering entirely if you can, and just look in Google’s “Spam” folder for anything that may have been misfiled. If you can’t turn off all junk filtering (say, you use it for an iCloud or other account), there are some advanced settings I’ll show you in a bit that allow you to selectively filter some accounts but not others. You can also use smart folders so that you can still look at all of your junk mail folders in one place.

As a result, my “Mailbox Behaviors” under Preferences > Accounts tends to look like this:

 

Before we settle in to email friends and family, we need to do one more thing - designate our drafts and trash folders. Otherwise, Mail will end up creating its own folders, and you’ll end up with the confusion of duplicate folders to sort through whenever you look at your mail elsewhere.

In the folder list to the left, expand out the folder named “[Gmail]” and select the folder named “Drafts”. Then go to the Mailbox menu , then select “Use This Mailbox For”, and choose “Drafts”. Then select [Gmail]/Trash on the left, and go to Mailbox > Use This Mailbox For > Trash.

The next articles will cover setting up smart folders, advanced Junk Mail settings, and how to manage junk filtering in Gmail.

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