21st Century Email Remains a Mess

May 7th, 2009

One of the earliest features folks embraced when they discovered the Internet was obviously email. As with the rest of the online world, it wasn’t originally designed to accommodate the needs of hundreds of millions of users, and so there were problems. Number one with a bullet is spam, and I won’t even attempt to deal with that mess. Clearly the engineers who continue to work on the technology need to devise something that makes your email more secure and gives you more freedom from endless annoyances, and that also includes malware, although it’s mostly an issue on the Windows side of the planet. At least for now that is.

However, the most troubling issue remains unsolved, and that’s how to make email accounts easier to set up on your Mac or PC. You have two major systems, known as POP and IMAP.

POP, short for Post Office Protocol, the one used by most ISPs and such free services as Yahoo! and Gmail, downloads your email direct to your computer. From there, you’re on your own. If you lose it, and have no backup, that’s too bad. There are options to leave mail on the server with some systems, but if a message is flagged as read, good luck getting it again, unless you check your messages via a Web-based client or another computer.

Of course, if you only manage your email in your browser, the back-end scheme is not important. You probably only care whether it works or not.

POP’s other limitation comes into play when you have more than one device to check your messages. Here if you leave the messages on the server, each computer gets them, but messages flagged as read on one computer aren’t treated that way on another. Sent messages will be found on one computer and not the other. Synchronizing all of this stuff can be a chore and then some, even with a good backup system.

The other popular email system, the one I favor, is IMAP, short for Internet Message Access Protocol. Basically, under IMAP, your messages are all stored on the email server. If you read a message on your MacBook Pro at home, it is flagged as read also on your Windows PC at the office. The response you sent on one computer is found in the Sent mailbox on another.

In theory, IMAP ought to be a simple affair, but it’s not, because different email server software will manage the whole shebang differently. That makes it cumbersome for your email software to figure it all out.

Compounding this mess is the way it’s handled at Gmail’s recently-established IMAP system, where, unlike the common way IMAP is handled, messages aren’t stored in separate folders. Instead they are flagged with Labels. What this means is that a single message can end up in multiple categories. Depending on your sense of organization, that can be a good thing or a nightmare.

Rather than explain Gmail’s IMAP implementation, let me refer you to a lengthy and clear-headed article from my friend Joe Kissell for all the particulars. Let me just say in passing that I am rather old fashioned in my way of handling email. I separate the messages from each domain, so I can better focus on the matters at hand, and I also use extra folders for organization. That may be retro to the developers of Gmail, but it’s the way I prefer to work, and that’s how the standard IMAP system was designed to function.

However, setting up an IMAP account on your Mac may not always be as simple process. First, you need to check to make sure that the mail server you’re using supports IMAP. From there, both Apple Mail and Microsoft Entourage will handle the basics of the account setup process, but it’s not seamless.

A troubling and sometimes downright frustrating feature in Mail, for example, is the way it maps your local email folders to the ones on the server. Different systems may call your Sent box, for example, Sent Items. Junk mail folders may be labeled, instead, as Spam or Bulk. Rather than sort this all out, and frankly I can’t see where it presents a serious programming issue, Apple expects you to do it all by yourself.

So when you set up an IMAP account, and it’s configured properly, there will be a separate listing for that account in Mail’s Mailboxes pane. When you expand the listing, you’ll see folders representing the additional mailboxes. To properly integrate them in Mail, you have to select each mailbox, in turn, choose Use This Mailbox For, in the Mailbox menu, and designate what purpose it serves. The choices are, in order, Drafts, Sent, Trash and Junk.

Now you shouldn’t have a problem picking the right one, except that some email systems don’t create all the extra folders until you attempt to use the account. So I suggest you keep several headache pills around in case you find yourself prepared to open the nearest window and scream appropriate epithets at the top of your lungs.

Now, that’s not why they created “primal scream therapy,” but it’s also true that Apple needs to use more intelligence to help people sort out these email organizational issues. It would also be nice if they made an effort to make sense of the way Gmail has established its IMAP system.

Maybe I’m expecting too much, but my favorite surprise feature wish list for Snow Leopard includes some desperately needed changes for Mail. But I don’t expect any of it to happen.

| Print This Article Print This Article

2 Responses to “21st Century Email Remains a Mess”

  1. Kaleberg says:

    One reason I haven’t used IMAP is that I don’t trust it and I am not sure it can do the job.

    What happens when my IMAP provider goes under or their service levels degrade? Do I lose my email? Does IMAP keep a local copy? My own computers have proven much more reliable than those of my ISPs over the past ten or fifteen years. If nothing else, I haven’t gone broke or been bought out or changed my domain name.

    IMAP may be an answer for someone just getting an email account, but what about us long time users? I have email saved from back in the mid-90s. Can I move my filed mailboxes to the IMAP server? Should I? If I don’t, does that mean I will wind up with a Frankenstein mail system with each category of filed mail broken into a series of IMAP folders and filed mail folders.

    Does IMAP work with Spotlight? That is, can I go into Mail and simply search? Will this work even when the Internet is down or I am between IMAP providers?

    Does IMAP let you delete a message just on one machine, but not another? I may want to delete a message on my mobile device, but have it available for me when I get home. Similarly, I may want to delete a message, but my significant other may want to keep it around. Do we have this level of control using IMAP? (We do with POP.)

    I think one reason people are reluctant to switch to IMAP is sheer ignorance. I know relatively little about it, and what I have heard is not encouraging I hear a lot more horror stories about changing IMAP accounts as opposed to horror stories about changing POP accounts.

    Since I share some mailboxes with other family members, I am the first to admit that POP is not the perfect solution. Now and then the message counters get mixed up and one of us misses a few messages. Would IMAP be a step forward or a step backward?

  2. @ Kaleberg: You make a good point. But the normal setup for Mail and Entourage caches your messages locally, so if your server goes offline, you’re not stuck.

    Your search capability works fine.

    So, considering the oddities of setup, IMAP is definitely the way to go.


Leave Your Comment