Mac OS X’s Mail: Time to end the password dialog madness

Posted by Pierre Igot in: Mail
December 7th, 2009 • 6:16 pm

Today, I got an e-mail from my dad in France about Mac OS X’s Mail. While he was a math teacher by training, my dad was there at the beginning of the personal computing revolution in the late 70s and early 80s and ended up teaching various computer science courses at the community college level in France. (That’s also how I caught the computing bug as a teenager.)

For a long period in the 80s and 90s, for his personal computing needs at home, he was a Windows guy, and that was the source of many passionate, yet light-hearted Mac vs. PC arguments between him and me (and my brother, another long-time Mac user).

Then, when Apple came up with Mac OS X and its Unix underpinnings, my dad made the switch and, as far as I know, he hasn’t regretted it one bit. He takes care of his own tech support needs. But from time to time, since I am the “Mac expert” in the family, I get an e-mail from him about something that puzzles him.

And so today I got this e-mail about Mail. The gist of it was that he wondered why, even though all his settings were correct, sometimes Mail didn’t check for new mail for certain accounts (he has several) when it was supposed to do so, i.e. during the automatic mail checking procedure that takes place at regular intervals. And he wondered whether that was linked to the fact that, “quite frequently” (his words), Mail would ask him for the password for this or that account… a dialog box that he usually got out of by clicking on the “Cancel” button.

I thought our e-mail exchange would be a good opportunity to revisit the long-standing and pretty serious problem with Mac OS X’s Mail and less-than-ideal network conditions.

Now, you need to know that, unlike me, my dad lives in an urban environment and is subscribed to a fast DSL Internet service with plenty of bandwidth. But of course, he uses a MacBook Pro laptop with its wireless connection to his router. That means that, even with more than enough bandwidth for his needs, he can still encounter occasional problems with his network connection, either because of a temporary failure in his wireless connection due to interference, physical obstacles or software or hardware flakiness beyond his control, or because of occasional problems with the provider itself.

This, in my experience providing tech support services over the years to a variety of clients with a variety of means to connect to the Internet, is pretty much the norm, and not the exception. (The exception is my own situation, i.e. a lousy satellite-based Internet connection that, in addition to all of the factors mentioned above, can also be affected by weather conditions and bandwidth throttling during peak hours.)

The single most scandalous thing about Mac OS X’s Mail is that its behaviour when checking for new mail appears to have been “designed” (if you can call it that) based on the assumption that network failures never occur. I don’t know what kind of weird bubble Apple’s Mail engineers live and work in, but one thing is for sure: it is completely disconnected from reality. I don’t know a single person who has never experienced network outages. Even with the best equipment, the most up-to-date software, and the most ideal technical environment, there will be occasional failures. It’s just a fact of life.

That means that the job of an Apple engineer working on Mail includes ensuring that the application’s behaviour when such a failure occurs will be reasonably user-friendly.

But that obviously is not part of the job description. Because Mail’s behaviour in such conditions is appallingly bad, and it has been that way for years now. How any self-respecting software engineer working on Mail at Apple can sleep at night knowing that thousands, if not tens or hundreds of thousands, of Mac users are currently experiencing the idiotic behaviour that I am about to describe once again is beyond me. These people should be ashamed of themselves.

If Mail tries to check for new Mail while a network/connection failure of some kind is occurring, here’s what happens.

If you are lucky, Mail takes your e-mail account off-line without telling you.

If you are not so lucky, Mail’s Dock icon starts bouncing endlessly, because the application is displaying a modal dialog box asking you to… re-enter your e-mail account’s password.

If you are wise enough to know better, you do like my dad and you click on the “Cancel” button in that modal dialog box. It gets rid of the dialog box, but it also takes the account off-line.

If you don’t know better, you actually follow Mail’s request and re-enter your password. But of course, like most people, you have set Mail to remember your password for you, so you are not sure you actually remember it correctly. “Is it the name of my dog or the name of my grandmother or something else entirely—maybe something weird that Pierre Igot asked me to use the last time he visited me because he was concerned about the safety of my e-mail account and didn’t want me to just use as a password the name of my dog or my grandmother, which dozens of people who know me directly or indirectly know very well themselves?”

“Oh well, let’s try the dog’s name.”

And then all hell breaks loose. Unless you are really lucky and you remembered the correct password, and then, if the network failure has not miraculously stopped during the interval (and even then, I am not sure that’s enough for Mail to recover at this point), the same thing will happen again and you’ll get the dialog box again. And this time you’ll hit “Cancel” and Mail will stop trying to check for new mail and take the account off-line.

If you’re not really lucky, you’ve typed the wrong password, and now you’re really screwed. Because even if you hit “Cancel” after getting the same dialog box five times and entering five different variations on that password and giving up—and then wait for the network failure to stop and try to check for new mail manually, the mail checking will fail, of course, because the password that Mail now remembers and uses is wrong, and you’ll be caught in an endless loop of the dialog asking for your password and Mail taking your account off-line.

Time to call Pierre, and hope that he can remember your password. If you’re lucky, this has happened before, and he’s stored your password in his encrypted password database. Otherwise, you’ll have to call your ISP’s tech support line and wait for half an hour until you can speak to a live individual and then identify yourself with personal questions and confidential information and so on and then the ISP might give you your actual password or reset it for you. (By that time, one hopes that the network failure will be resolved and you’ll be able to verify that it is the right password indeed.)

And all this, because Apple’s engineers apparently have not noticed this idiotic behaviour and how aggravating it is for so many people using Mac OS X’s Mail in the real world, where network failures do occur.

Now, let’s analyse this behaviour for a second here. First of all, why does Mail ask for your password when your password is perfectly correct, simply because there is a network failure? Is it really impossible for Mail to tell the difference between a failed connection and a wrong password? Is it really reasonable to assume that, if the connection to the server fails, the most likely explanation is that the user went behind Mail’s back and changed his e-mail account’s password using his ISP’s web interface or by calling the ISP on the phone?

It is not. It is not just unreasonable. It’s completely stupid. How often does the average user change his e-mail account’s password or have it changed by someone else?

And then, there is that thing with taking accounts off-line. Who on earth got that idea that e-mail accounts should ever be taken off-line when the user does not explicitly ask Mail to take them off-line? Why on earth does cancelling this idiotic modal dialog box asking for a password that Mail already knows and is perfectly correct cause Mail to take the account off-line even without the user’s permission?

It’s bad enough that this dialog box appears in the first place. But on top of it, whichever way you choose to respond to the dialog box, you will probably screw things up. The least disastrous option is indeed to hit the “Cancel” button, as my dad correctly figured out by himself, possibly in part because he has 40 years of computing with various user-hostile systems behind him. But even that least disastrous option is still a major pain in the neck, because it means that you have to know and remember that you have to take your account back on-line manually, either by forcing Mail to manually check for new mail or by clicking on the warning icon that appears next to the account’s Inbox in the mailbox drawer.

Of course, you cannot take your account back on-line until the network failure is gone, so there’s no point in trying to do it right after you’ve clicked on that “Cancel” button. No, you have to actually wait until the network failure is resolved, and then remember to take the account back on-line manually.

And then, if you were lucky or wise enough not to screw up your account’s password, things will work properly again.

But even a seasoned computer user like my dad couldn’t bring himself to think that Apple’s engineers would be so clueless that they didn’t even design Mail to recover automatically once the network failure is resolved. So, while he correctly figured out that he had to click on that “Cancel” button and that this particular weirdness probably had something to do with the fact that Mail didn’t seem to reliably check for new mail in all his accounts automatically all the time, he didn’t go as far as to think that he actually had to manually bring these accounts back on-line after the end of the network failure, even though he had never taken them off-line himself in the first place.

And if my dad with his 40 years of experience couldn’t quite figure it out, you just know that there must be hundreds of thousands of Mac OS X users enduring that very same problem and not knowing how to deal with it “properly,” i.e. by doing manually what Mail is utterly unable to do by itself automatically.

Who knows how these users finally get out of the situation that Mail has put them in. Maybe quitting and relaunching Mail actually forces Mail to take the accounts back on-line. I don’t know. There are so many different situations in Mail that it is impossible to even tell when an account is actually in an off-line status that requires the user to manually take the account back on-line or just in a greyed-out status that will somehow resolve itself without user intervention.

I have seen greyed out Inboxes with the warning icon (exclamation mark inside triangle). I have seen greyed out Inboxes with the danger icon (lightning bolt). I have seen Inboxes not greyed, but still with the warning icon, itself greyed out or not. I have seen it all. I have never understood what the difference is, and how to tell whether Mail will actually try to check for new mail in the affected account automatically or not.

The whole thing is just so stupid, and so incredibly frustrating. And it’s not just me and my lousy Internet connection. I have talked about this problem before, and I have received feedback indicating that it happens to all kinds of people, in all kinds of situations, with all kinds of Internet connections.

There clearly is something very wrong here. It’s been like this for years, and it does not look like Apple is interested in doing anything about it. What do we need to do? Do we need to start a petition? A boycott? Do we need to sabotage the Internet connections at 1 Infinite Loop so that Apple’s own engineers get a taste of the action? What exactly will it take?

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