Apple Peel

Major Improvements Needed for Mac OS X’s Mail Application - Pt. 1

I have already had the opportunity to explain, in a previous column, why and how I decided to move from Eudora for OS X to Mac OS X’s own Mail application as my main email tool. I have now had the opportunity to use Mail on a daily basis with my 18 different email accounts for an extended period of time, and this has given me a chance to write down a number of comments and observations on the 1.2 version of Mail that is included with Jaguar (Mac OS X 10.2) — the version of Mail on which my experience and comments are based.

In this three-part series, I’d like to focus on what I feel are required improvements for Mail. Its version number (1.2) indicates that the application, like many other aspects of Mac OS X, is still in its infancy. But I want to stress that I already consider Mail a perfectly usable tool. It is just that certain things do not work the way they should, as well as they should — or, in some cases, are glaring user interface mistakes that need to be corrected.

Based on my experience with Eudora, Mailsmith, and Mail, I think it is fair to say that there is not one email application that stands out as the best email tool out there, be it for moderate email users or for more demanding users like myself. My ideal email application would probably be a program that combines the best features of all three applications.

At this point in time, however, I feel that Mail is somewhat closer to that ideal than the other two are — and that is why I am using it as my email application of choice. Still, Mail has some rather major annoyances, as well as more minor flaws that get in the way of my computing activities and goals.

General flakiness in low-bandwidth situation

I live in a rural area, which means that my dial-up connection usually peaks at 28.8 kbps. And Mail is clearly not happy about that. If there is any other activity requiring any portion of my modem’s bandwidth (such as a file download in the background or even a web page loading in my web browser), then, if Mail happens to be trying to check my email accounts at the time, I systematically get intrusive, erroneous and annoying alert messages.

(In fact, even Mail itself often causes these alert messages, because its multithreading — and non-adjustable — architecture means that it tries to check several accounts at the same time and, if one of them happens to contain a fairly large message to download, this very downloading process can cause errors in other concurrent email-checking processes!)

If other email applications displayed the same symptoms in the same kind of situation, I would put the blame on my low-bandwidth connection, or on the mail servers that host my email. But this is not the case. For a long time, I used Eudora for OS X as my main mail client, and I almost never encountered such messages. Eudora was almost always able to continue checking the same email accounts, on the same servers, while other processes were using some of my modem’s limited bandwidth. The email checking process was slower, of course, but it still worked.

The only mail server with which I already had similar problems in Eudora was… the <mail.mac.com> server. This particular server (used when checking my <igot@mac.com> account) has always been very finicky, and I would frequently get time-out error messages from the server if I tried to retrieve or send mail while other downloading activites were taking place.

With Mail, however, there are problems with all my email accounts. So the fault rests clearly with the Mail application itself. And it needs to be fixed.

I also share my already very limited amount of bandwidth with my wife. We are both connected via our AirPort cards to a AirPort Base Station, which provides access to the dial-up feed from our Internet Service Provider (through the Base Station’s internal modem). Here again, if my wife happens to be checking a web site on her PowerBook while my Mail application is trying to check my mail on my Power Mac G4, I frequently get errors that interrupt me in my work and are a major annoyance. (My wife still uses Eudora, and this probably won’t change until Mail is improved.)

Poor error handling

This issue of Mail failing when other computing activities are using some of the available bandwidth is made even worse by the way Mail handles such errors. Not only does Mail frequently encounter these errors, but, on top of this, its error handling is extremely intrusive and downright exasperating.

First of all, it displays the error messages in modal dialog boxes. Modal boxes in such cases are simply ridiculous, and not worthy of a Mac OS X application! In a similar situation (with my <igot@mac.com> account), Eudora would simply display a plain-text error message in its “Task Progress” window, but wouldn’t otherwise interrupt my workflow in any way. Using modal boxes for these errors is simply not acceptable.

In addition, if the error happens while Mail is in the background, it causes the Mail icon in the Dock to start “high bouncing”, which effectively forces you to bring Mail right away to the foreground to dismiss the dialog box(es).

This “high bouncing” feature really is a ridiculous piece of user interface. It’s disruptive, it consumes a lot of CPU power (making other activities less smooth and more difficult to control as a user), and it’s downright scary for the uninitiated.

It’s about time Apple gets the message about this and at least provides the option — via a System Preferences pane, for example — to use something far less intrusive instead. I personally would gladly settle for something like a different color shade for the background of the Dock icon in question, for example. Clearly there are many things that Dock icons can do that would be far less intrusive — and in fact much more intuitive — than this high bouncing. This visual effect is a bad idea, and many months of daily use of Mac OS X haven’t changed my mind one bit about this. It’s high time to let it go.

Secondly, the error messages in low-bandwidth situations are almost systematically incorrect. Most of time, the error message says that the server “didn’t recognize the password” for the account. This is obviously not true, since the password hasn’t changed. What’s worse is that this particular error (wrong password) causes Mail to sometimes open another — also modal! — dialog box that asks you to re-enter your password and needs to be dismissed as well! And, if, like me, you have several different email accounts all exhibiting the same behavior, the error alert boxes end up piling up on top of each other in a horrible mess where you can’t even tell what dialog is the front-most anymore and needs to be dismissed first.

This whole situation is simply extremely annoying, and not worthy of a Mac application. It’s actually so bad that, now, whenever I have to download a file that might take any significant amount of time, I actually have to quit Mail first so that it won’t annoy me repeatedly during the process. (I have set my accounts to be checked every 15 minutes, and there is no easy way to take Mail temporarily offline while other processes are taking place.)

But this means that I cannot check my mail during the entire downloading process at all — and if the download takes an hour or more, that’s a long time without checking my mail, which I can’t really afford during regular work hours. I end up having to refrain from downloading anything during work hours, and to schedule my downloads during times when I am away from my computer for other reasons. But, of course, sometimes I have to download big files as part of my work — and in such cases having to quit Mail is a major annoyance and inconvenience.

Activity Viewer

The idiocy doesn’t stop there. Since I have many accounts and Mail acts up so frequently, I like to keep a close eye on things. So I have Mail’s “Activity Viewer” window (available in Mail’s “Window” menu) always open and visible, so that I can see when Mail starts checking my email accounts or whether my out-going messages get properly sent.

Mail's Activity Viewer Window

One interesting aspect of this “Activity Viewer” window is that each process displayed in the window comes with its own “Stop” button. As far as I know, this is the only way to stop a process once it’s started in Mail. The time-honored cmd-period doesn’t work. In a few cases, the “Stop” button is greyed out, indicating that the process cannot be interrupted — but most processes can be interrupted… in theory.

I should actually rather say that using the “Stop” button in the Activity Viewer is the only way to try to stop a Mail process. Indeed, if you try to use this Stop button to prevent an out-going message from being sent out, for example, you’ll soon find out that, unless your message is big enough that it takes Mail a significant amount of time to actually send it (i.e. more than a few seconds), clicking on the “Stop” button will not manage to stop the process before it’s completed — even though it looks as if you should be able to do so. (For the record, Eudora’s Task Progress window has similar functionality, and stopping processes works in most cases, even with very small messages.)

But what is even worse is what happens when you do succeed in stopping a process by clicking on its “Stop” button in the Activity Viewer. For example, you can click on the “Stop” button to stop a mail-checking process, i.e. the process that checks your email account on the mail server and downloads your new messages. However, this stupid (sorry, there’s no better word to describe this) Mail program, each time you’ve succeeded in stopping a process by clicking on Stop, decides to display — guess what? — yet another modal dialog box saying “Unable to receive mail” and asking you to dismiss it by clicking on its “OK” button! How idiotic is this? If I just indicated very clearly to Mail that I wanted to stop the receiving-mail process by clicking on the “Stop” button, then clearly Mail is unable to receive mail for this account! I just asked it to stop doing it! (And sometimes, here again, it even tells you that the password is wrong and opens yet another modal dialog box that needs to be dismissed manually…)

Now multiply this by 18 (my actual number of different email accounts, which I have to check every time because there is no way in Mail to set a different mail-checking time interval for each email account), and you get the picture of what happens when I try to stop Mail from checking my mail because I know it is going to fail due to my limited bandwidth! I might as well buy a joystick and try shooting these 18 dialog boxes like a 1980s teenager hooked on “Space Invaders”.

Finally, although I have not been able to clearly pinpoint the exact cause of this behavior, sometimes when Mail fails to check an email account, instead of only displaying the intrusive error messages (which is already quite annoying in itself), Mail also decides on its own accord to take the corresponding email account offline, so that it will no longer be included in the mail-checking process. This is indicated visually only by Mail greying out the corresponding incoming mail box for the account in the “In” mailbox. (I recommend, therefore, that you keep this “In” mailbox display expanded in the mailbox drawer. Otherwise, you might not even notice that one of your email accounts has been taken offline by Mail.)

It is bad enough that Mail blames the server for its own failure, but automatically taking the email account offline makes things even more annoying. The only way to put the corresponding account back online (short of quitting and relaunching the Mail application itself) is to manually instruct Mail to check the email account in question again by going to the “Get New Mail in Account” submenu in the “Mailbox” menu and selecting the appropriate email account. Given that you never asked Mail to take the account offline in the first place, this is an annoying extra step — and obviously a very unintuitive procedure for people who might not know what exactly is going on with their Mail program.

To put it shortly, the whole error handling process in Mail is just awfully wrong. It’s intrusive, it’s unintuitive, it’s misleading, it’s not adjustable, it’s erroneous — it’s simply wrong. And I would honestly say that this is the major improvement that needs to be a top priority for the next revision of Mac OS X’s Mail.

(I also realize that the fact that I have 18 different email accounts probably makes the problem worse for me — but most of the symptoms I am describing here can happen to anyone, even people with only one email account.)

More error-handling madness

The error-handling madness does not stop here. Server connections being what they are, in the somewhat unreliable real world of online technology, sometimes Mail fails to properly send a message that you’ve just asked it to send.

Here again, Mail’s way of handling the situation is very wrong. It systematically assumes that the error failed because the SMTP server in question refused to send your mail, and offers you to use a different SMTP server instead. This is clearly wrong for several reasons.

First of all, due to security reasons, most SMTP servers today are protected against their use by unauthorized people. If I try to use my ISP’s SMTP server (which is something like: <smtp.sympatico.ca>) to send mail from, say, my <igot@latext.com> account, it will work, because I am connected to my ISP’s network through my dial-up connection and am therefore an authorized user of the SMTP server, even if I am sending mail from a different account. But the same is not true of the SMTP server I normally use for <igot@latext.com>. I can use it for sending mail from my <igot@latext.com> account, but not from my other email accounts. (I know there is a kind of authorization setting that enables you, in theory, to circumvent this problem, but in practice, it just doesn’t work with half of the SMTP servers I am supposed to be authorized to use.)

In other words, most of the time, when Mail offers to send the mail that it has failed to send using a different SMTP server instead, the suggestion is wrong, because it simply is not possible to do what Mail suggests.

In addition, most of the time, when sending mail fails, it is not the SMTP server’s fault, but, once again, Mail’s own fault, because it is unable to properly deal with the limited amount of bandwidth that I have.

Now, Mail does also offer the option to “send later”, which is the one I usually select (and which really should be the default one). But the problem here is that you have very little control over when that particular “later” is going to be — and sometimes Mail will actually fail again and again to send the message in question, as if that particular message you are trying to send had somehow become unsendable.

In such cases, you have no choice but to create a new message, and trash the existing one that is stuck in the “Out” box and that Mail cannot send. Now, I would sometimes encounter similar situations in Eudora — albeit far less often than in Mail — but Eudora’s handling of the situation was usually much better. It would let me try to send the message again right away, for example, by opening it and clicking on its “Send” button again. You cannot do this with a message that is stuck in the “Out” box in Mail. You just have to wait and hope that Mail will be able to send the message out… eventually. When the issue affects important messages that really do need to be sent out right away, Mail’s handling of the situation is obviously inappropriate — and annoying.

Address Book Auto-Completing

One nifty feature of Mail that is sorely missing in programs such as Eudora and Mailsmith (in their current incarnations) is its full support for Jaguar’s new Address Book architecture. It is a relief that the Mac OS now has a built-in database structure for contact information and that applications such as Mail and iChat are able to use it seamlessly for their own purposes. And, on the whole, it works quite well. (I do find the fact that Mail uses its own “mini-Address Book” window rather than the full Address Book application when you select “Show Addresses” in the “Window” menu somewhat confusing, however.)

In Mail, I find that the quickest way to insert an email address in the “To:” or “Cc:” field of an email message is to type the first few letters of the Address Book entry in the field in question. After a short delay during which Mail indicates that it is “searching”, Mail automatically completes the address if there is a single match, or gives you a popup list of all possible matches for what you have typed, which you can then scroll without lifting your hands from the keyboard by using the cursor keys.

You can type the first few letters of a first name, a last name or an email address itself. Mail will automatically include all matches — and having hundreds of entries in the Address Book doesn’t appear to slow down the search significantly.

Once again, however, there are problems in the way Mail handles errors. For example, because I am a fast typist, sometimes I go too fast and move the cursor to another field or to the body of the message (by pressing the tab key) before Mail has had a chance to do the auto-completion. Because of this, I end up sending messages where the “To:” field contains just the few letters that I had typed (like “tom”), instead of a properly formed email address (like Tom’s email address).

Mail will obviously fail to send the message properly — but instead of correctly identifying the error, once again, the program asks me if I want to use a different SMTP server for sending this particular message, as if sending a message to the email addresss “tom” would work any better with another SMTP server!

This is clearly, yet again, a case of Mail being hopelessly dumb about possible errors — and it needs to be improved significantly in that respect.

Recipients

While auto-completion of email addresses is good, it does not make up for the fact that Mail is missing a feature that has been available in Eudora for years, i.e. the ability to identify a few entries in one’s address book as “recipients”. In Eudora, such “recipients” are people to whom you send messages most often, and Eudora conveniently lets you create a “New Message to” any of the people you have flagged as recipients through a submenu in its “Message” menu.

In Mail, instead, you have to create a new blank message and then type the first few letters of the person’s name or address. There is nothing that distinguishes this person from other entries in your address book, nothing that indicates that this person is someone you write to quite often and the most likely intended recipient.

The two approaches are not exclusive. Rather, I would say that my ideal email program would include both: Address Book auto-completion and a “recipients” feature. The key here would be to offer the user several different ways of accomplishing the same thing. Instead, Mail forces you to do things its way.

I would like to be able, for example, to forward a message to one of my “recipients” (the people to whom I write most often) without having to use the keyboard. Instead of providing a simple “flat” Forward button in its toolbar, Mail could provide a “smart” Forward button that behaves like the current one when you simply click on it, and behaves differently if you click and hold the mouse button down, instead showing a popup menu containing a list of your recipients, so that you can tell it to forward the message to Recipient X or Y with a single mouse click (and without using the keyboard).

Stationery

Eudora also includes other features that are sorely missing in Mail, and could help make it the best email client around. One of them is Eudora’s stationery feature. In effect, it lets you create message “templates” with predefined “From:”, “To:”, “Cc:”, “Bcc:”, and “Subject:” fields, as well as a predefined signature and a predefined message body text. In Eudora, you can predefine some or all of these various components of the email message, and then use the “stationery” to create new messages (or replies to existing messages) that already include the contents of these predefined fields.

As I indicated in my first column about Mail, there is a way to mimic Eudora’s stationery feature in Mail, which is to create message drafts with predefined fields, and then do a copy/paste in the “Drafts” mailbox or use the “Open as New Message” command in Mail’s “File” menu. But this is a workaround, not a proper stationery feature. In addition, it is much more limited than Eudora’s stationery feature, in that there is no easy way to use such message drafts for replies. Eudora, on the other hand, lets you “Reply with” a particular stationery to any existing message — and it is smart enough to let you quote the original message in your predefined reply in the body of the message, and to define your reply’s subject line depending on the contents of the stationery: if the subject line in the stationery is empty, then Eudora simply puts “Re:” followed by the original message’s subject line in the reply’s subject line, as expected; if the subject line in the stationery is a specific phrase, then, in the reply created using the “Reply with” command, Eudora inserts the specific phrase, followed by “(was: XXXX)”, where “XXXX” is the subject line of the original message.

This kind of automation is clearly impossible to achieve in Mail. (It might be possible to achieve certain things using AppleScript scripts, but the sample Mail scripts included with Jaguar don’t seem to indicate such capabilities, and then there is also the issue of access to AppleScript scripts from within Mail, and of the performance of such scripts…)

Next Part

The second part in this three-part series focuses on other aspects of Mac OS X’s Mail application that also need improvement, including: keyboard navigation and searches; attachment handling; signature handling; message history; and more.

Click here to read the second part and here to read the third part.

- Pierre Igot

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