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Wed, 17 Sep 2008
More on Mail and Gmail

In Mail and Gmail, I discussed the settings I used in Mail. Some are different than what Google recommends in Recommended IMAP client settings. I want to explain why.

First. Drafts. I did not select store messages on server as Google recommends. I have now changed that. Google recommends: “Store draft messages on the server > checked.” I don’t usually leave draft messages around. I usually write and send. But, I think storing on the server is a good thing. If I am writing email and need to come back to the draft to finish later, I can do it from my Mail client or—if away from my computer—from the web interface.

Sent. Google recommends “Store sent messages on the server > do NOT check.” I’m sticking with “DO Check.” Google’s reason is that all email sent through their server will automatically be put in the Sent box. I believe this, but I am not sure of the harm in putting mail into Sent in the Mail application. Google suggests it will cause duplication of messages. I’ve not seen this. In Mail, I often Move a message from Sent into a project folder. For example, today I received an email message regarding an interview for a graduate school program. I replied to it. I was at my day job, so using the Gmail web interface. I labelled both the received message and the reply “Grad School. The messages were still in my Gmail Inbox, but labeled. So, I clicked, “Archive.” The result when I got home and used Mail? The messages were in my “Grad School” folder. Brilliant. 🙂

Trash. Google says “Move deleted messages to the Trash mailbox > do NOT check” and “Store deleted messages on the server > do NOT check.” Google’s reasoning is that it makes no sense to delete. Google says, “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.”

But, (I assume) since that was written, Gmail has created a “Delete” button, which puts deleted messages in the Trash. There are some messages I do not wish to save. There are some messages no one wants to save. No matter how cheap disk space is. My set-up allows me to delete things I really want to delete, putting them in the Gmail Trash. . Further, they say “Do NOT save deleted messages to your [Gmail]/Trash folder because this will delete a message in all folders.” Correct. When I delete I mean delete!

Junk mail and spam. Google says, “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.” The way I have things set up in Mail allows me to tag spam that Gmail’s spam checker misses and have Mail move it into the Spam folder.

No regrets about the move to Gmail nor about using Mail with Gmail.

Now I remember why someone suggested not saving drafts on the server. Every time the draft automatically saves, you end up with another copy of the draft. You can see this in the screen shot I captured looking at my Trash. On the other hand it is just in Trash, and so will be deleted eventually.

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Tue, 09 Sep 2008
Mail and Gmail

In commenting on David Strom’s column Ten years of email, I said,

I’ve long ago switched from POP to IMAP, but cannot imagine having to rely on Internet access to read or manipulate e-mail. I’d love for you to talk about the changes that doing that requires. I just cannot imagine.
He replied (see it in my entry Strom’s Ten years of email) and it got me thinking.

Of course, I have used Google’s mail (gmail). But, I never linked it to my email, except to forward email to my gmail account to my account. E-mailing back and forth with David convinced me to try it, but I wanted to do more. Dave is almost always connected. So, he just uses Google’s webmail interface. It suits his needs and he likes the interface. I like using Apple’s mail application (cleverly called “Mail”). So, I decided to use it to read Google Mail and go one step further: to have my email hosted on Google.

My email was hosted by a “true friend”. Google, with Google Aps, gives clear directions for setting up a Gmail account for a domain. In fact, you can start immediately using it, even before MX records are changed through temporary gmail email addresses. The MX record change took about 10 minutes, because Google automates it’s side and my domain records are run, as I mentioned, by a true friend. That is to say, email to “” started showing up on username’s email box on Google. Coolness! It was working. (Now, almost nothing in DNS-land is immediate; information needs to propagate. So, I did check my old server location some that transition day.)

Set up on the Google side was easy and I set it up to be an IMAP server. (The major benefit is that it is stored on my client and on the server and I can access it from anywhere on the Internet.)

The next step was to set up my Mail application. Before I did anything else I backed up my email.

Google recommends setting for Mail and the Internet has many comments about the “best” settings. These are mine and my reasons.

  • I set the incoming and outgoing servers to be as Google instructs.
  • I set the IMAP Mail Prefix to be “[Gmail]” (This is under Advanced for the Account in Mail.)
  • The Trash mailbox showed up under my account in Mail. I selected it, went to Mailbox, and Use this mailbox for… Trash. I made similar settings for the Google Spam mailbox (use for Junk) and Sent.
  • I don’t store drafts on the server.
  • I store Sent messages on the server.
  • I have Junk processing enabled. I do this so that the Junk mailbox shows up. Mostly, Google does a great job of Spam catching. When it doesn’t Mail might. When it doesn’t, I can click on the Junk button and off it goes.
  • I set “Move deleted messaged to the Trash mailbox” and Store on the server. (I know Google has this store everything forever, but there are some things that I want to delete: notices from the library when my requested books are waiting, Facebook notifications, “Send this to all everyone you know” email, etc.) See the Mailbox Behaviors.

I started moving IMAP mailboxes from my old account to my new (Google-based) account. I found that I needed to move one mailbox at a time. I have a lot of mailboxes and folders of mailboxes (see MailFolders, and I found that while the Labels were being created on Google (more on that in a minute), not all mail transferred. This should never happen, but it did. I am not sure if it is a client or server problem.

A word about Google mail and storage. Google mail stores all the mail in one big mailbox called All Mail. It uses labels to organize email messages. So, when one “archives” a message, Gmail removes the “Inbox” label; it stays in All Mail. If I have a message in mailbox “Accounting,” it is labeled “Accounting.” (See Labels.)

There was one thing that really bothered me. My PowerBook now has 2 copies of every email message. Gmail doesn’t; Mail does. Here’s why. When I move a message from my Inbox to, let’s say, “accounting,” the files associated with that email message get moved in my directory hierarchy; the file(s) get moved. Gmail sees this as one file with 1 or 2 labels. When the client syncs with the Gmail IMAP server, I will end up with 1 copy in the place I moved it and an additional copy in “All Mail.” Because the client sees the message in 1 mailbox and it sees another message in All Mail. It has no way to link them. Hence, 2 messages on my PowerBook.

This really bugged me. Until today. What changed? Nothing. I just said, “Oh, what the heck.” Disk space is cheap, and my email takes up less than 1G of disk space. I still delete some mail rather than keeping everything. I have started Archiving mail, which in my Mail application means moving it to “All Mail.” Eventually, my local storage may become a problem. But, not today.

I mentioned Dave Strom’s help. Check out a video he made How to become master of your domain for less than $20 a year in which he touches on some of the things to do. Consider buying his other video tutorials. (This one is free.)

A friend wrote:
Google feels free to read and copy the mail of anybody using their service. I try to be careful not to say anything of much importance by email if I think there is any chance that email will be delivered to a Google server.

So, let the buyer beware. I’ve read their privacy statements (for example, their Gmail Privacy Notice) and I am not concerned.

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Sun, 24 Aug 2008
Strom’s Ten years of email

In a recent posting, David Strom, who might be trying to rejuvenate sales for his very excellent, but old, book he co-authored with Marshall Rose, Internet Messaging: From the Desktop to the Enterprise , discusses Ten years of email. I recommend reading it for the history, for a sense of how far we’ve come, and to be disappointed that we’ve not progressed further. Then check out my Secure E-mail Collection

I commented the following to David’s post:

I’ve long ago switched from POP to IMAP, but cannot imagine having to rely on Internet access to read or manipulate e-mail. I’d love for you to talk about the changes that doing that requires. I just cannot imagine.

David replied:
About two years ago, I lost some saved emails using T-bird, and I decided to look carefully at what I was doing and what I could to ensure that didn’t happen again. I saw that 99% of the time when I am composing messages, I am sitting online, usually in my office, or someplace else where I have a Net connection. I had heard about Gmail and took a look and was immediately hooked. There were four things that motivated to switch over (and these might not be as important to you as they were for me):

First, I don’t have to worry about saving and storage of messages Google does it for me. And as their mailbox keeps getting bigger faster than I need, it is limitless as far as I am concerned. Now others may have run up against this limit, and now Yahoo email is truly infinite, but I hate their UI. I think I have about 2 of GB of mail, and as I mentioned in my post Gmail is above 7 GB and adding more every day. At the time, they didn’t have IMAP, but now that they do it makes for some choices here.

Second, they did a great job with labels, making it very flexible to store messages in multiple buckets. The latest versions of Outlook also do this, and I haven’t checked the Mac, Vista, and T-bird versions lately but at the time I switched they didn’t do as good a job. If you do use IMAP and have lots of labelled messages, you will find this vexing however.

Third, I use multiple machines, both PC and Mac, and having all my email and contacts in the Gmail cloud is a real plus for me. I don’t miss having local email on my desktop at all.

Finally, they did a great job with groups of contacts, and making it easy to organize my contacts is really at the heart of what I do with my email. I can have one contact as a member of multiple groups, to make it easier to find and communicate with people. Again, the newer versions of many email programs all support this, but at the time I was switching this wasn’t the case. I usually have two windows open in my browser at all times the Mail and Contacts windows.

There are some issues with Gmail, however, not enough to make me switch at this point. First, the numerous outages over the past few weeks that is troubling. Second, the latest UI doesn’t work with the large volume of contacts and the many groups of them that I have I still have to run the older UI, luckily they have a switch to “older version” that I use. And exporting your contacts doesn’t export the groupings, so once again I am captive to Gmail until I can figure this out.

Since I switched Gmail supports now both POP and IMAP access to their mail store, and there are programs like’s MailShadow for Google Apps that can synchronize an Outlook/Exchange account with a Gmail one. That makes the line between online/cloud email and local email more blurred. It all comes down to what UI you like, and where you want to keep your contacts, and how much offline composition and contact lookup you do: in my case, very little, and these days just about everywhere I go I can find a connection.

The other thing going for Google is that Google Apps is free to host your email for your domain, so you have the best of both worlds — you have the large online storage, the Gmail UI, and your own domain dot com — plus I think up to 100 mailboxes — all for free. It used to take a few days to get this going, but last week it took about an hour to setup, switch my MX records, and I was good to go. I don’t see why anyone would want to host their emails anywhere else.

Of course, this gives me a single point of failure with Google now, so I might keep that Yahoo email box around a bit longer :-).

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Tue, 22 Jul 2008
E-Mail Cleanup

While this series of articles is Mac-specific and Mail-specific, most of the tips offered can be used with other e-mail clients on other platforms. It is all about productivity. I know people who have no such scheme and are burdened by the guilt (or just stress) of hundreds (or more) unread or “undealtwith” e-mails in their inbox.

As the waiter in the 1971 television advertisement for Alka-Seltzer urges his customer, “Try it, you’ll like it.” Unlike the customer, trying these suggestions should lessen the need for an antacid.


Here are other excellent resources for getting a handle on e-mail. And, as you probably know, handling ths problem is very important. (See the comment in Hi-tech is turning us all into time-wasters, that says, “Even the beeps notifying the arrival of email are said to be causing a 0.5 per cent drop in gross domestic product in the United States, costing the economy $70bn a year.”)

So, the additional resource:

Bother are from Merlin Man.

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Tue, 08 Jul 2008
E-mail “Stationery”: Just Say “No”

Short version: using e-mail ‘stetionery’ is evil. Don’t do it.

In my posting Leopard: The Good Stuff I say

One feature Mail could have done without: stationery. Stationery is terrificfor hand-written mail. All it does is add an image attachment that may or may not be seen as a “background” to the e-mail. (Many times it will not show upit depends on the e-mail client. The user will then click on the attachment to see it and it will make them wonder why you send them a fabric swatch.)

I have repeatedly suggested against it every time someone has mentioned it in the Apple discussion forums. I’ve written, “As I’ve stated before on these forums, just because it looks good in your e-mail client does not mean that it will display correctly in someone else’s. Sometimes the ‘stationery’ will be transmitted as an attachment. The recipient will get your e-mail and an attachment. They will have to click on the attachment to see it. And they will see the ‘stationery’ only. It would be like sending a postal letter with the words written on a plain white sheet of paper, and sending along with it a nice piece of colored stationery.”

A friend sent me e-mail the other day. He “signed his name” at the bottom with a GIF image of his handwritten name, “Joe.” It, was, of course, an attachment. It showed up fine in e-mail, but when I forwarded the message, I forwarded his plain text e-mail plus the attachment with his name.

Someone else consistently sends me e-mail with a fancy signature image, containing her company logo. Every time I reply—and include the e-mail—the fancy signature is sent along. She replies, and now there are two copies if it, and so on.

You, the sender, have no control over what the recipients’ e-mail client can and cannot view. Sticking to plain text e-mail means that you can communicate with the greatest number of people. If you must have fancy fonts, and colorful backgrounds, send it in a PDF.

Plain text is best.

Use Rich Text if you must.

But, don’t use stationery (unless it is in hard-copy, postal mail).

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