Over at Betalogue, Pierre Igot, who has an eagle-eye for flaws in Apple’s user interface design, unloads on the behaviour of Mail’s Sent mail folder .

He points out:

Sending mail is a pretty essential process. When it comes to e-mail, it does not get much more basic than this. But for some reason, Mail 2.0’s user interface makes the process unnecessarily complicated and non-intuitive. The interface is OK (although still very inelegant) when things work as expected. But as soon as something fails, it’s a disaster.

What really annoys him is the way that the label of the Sent mail folder changes to “Sending…” when outgoing mail is being processed.

It’s ugly, he says, and it’s stupid. If you click on the “Sending…” folder, it displays all your sent messages except the one that is currently being sent. So where is it?

That’s the heart of the interface design failure:

It’s not in the “Sent” box, as we have just seen. It’s no longer in the “Drafts” box either…. So where is it? Well, that’s the kicker: It is nowhere. It is not in any visible part of the user interface in Mail. While the message is in the process of being sent, it effectively disappears from the user interface altogether and stays in some kind of UI limbo, until it’s finally sent—and then it miraculously reappears in the “Sent” box, as expected.

And don’t get him started on what happens next, especially if a message fails to send.

Read the whole post at Betalogue to find out how silly Mail is when that happens. mail.app, apple mail, Sent mail, sending, interface design, dumb dumb dumb, betalogue, bugs

The owner of rtfa.net has posted a list of the things that are annoying, broken or just plain scandalous about Mail.app.

He is an unhappy Apple Mail user: “Well, if Thunderbird integrated with spotlight and OSX address book, it’d be a no-brainer. However, I’m entrenched.”

And life in the trenches with Mail.app is not good.

Three problems score the highest scandal rating — incorrect treatment of IMAP’s “seen flag”, the “lost message” problem and the “invalid pointer” problem.mail.app apple mail, bugs, problems, IMAP, flags, attachments, SSL, encryption, lost messages

A poster on the Apple Discussion Boards is having a very weird experience with attachments in his IMAP account.

Dylan Muir finds that when he views large attachments stored on his IMAP server in Mail.app, they are corrupted. If he views them in a webmail client, they aren’t. If he views them in Thunderbird, they aren’t. It’s only Mail.app.

Unusually, the Apple Mail gods on the Discussion Boards seem to be out of ideas.

I wonder if anyone here has experienced this too (I never have), and knows what’s going on.mai.app, apple mail, attachments, imap, corruption, bug

Some people (notably John Gruber ) find one behaviour in Mail.app “both wrong and endlessly frustrating”.

The problem is this: If you use Shift-Arrow keys to select multiple messages in the Mail’s Message Viewer, hitting Shift-Up to deselect a message highlighted by mistake doesn’t deselect it. It selects the message immediately above the top selected email instead.

Try it. I had never even attempted this before, so it was news to me.

The fault is caused (I learn from John’s post) by the default list controls in Data Browser (Carbon apps like Finder and iTunes) and in NSTableView (Cocoa apps).

Jim Speth has written a plugin for Mail.app that makes the Shift-Arrow key combination behave as many believe it should.

If ⌘-Clicking the offending item selected by mistake doesn’t satisfy, this may be solution for you.

LiveJournal blogger Nevyn has taken the fix a step further by turning the plugin into an Input Manager that will correct the behaviour in all Cocoa apps. One small hitch; it crashes the Adium 1.0 beta.

[Via Daring Fireball ]mail.app, apple mail. Message selection, keyboard shortcuts, bug

Not long ago Daniel Jalkut discovered that Dashboard calls home to Apple to check for widget updates. Today I discovered that Mail.app does the same thing.

Recently at my real work but not at home, Mail has been hanging for 30 seconds to a minute each time I tried to reply to an email. I would hit the Reply button and have time to make a cup of coffee in the kitchenette before the reply window appeared.

Luckily, the network administrator at the College, Tim Bell, has god-like tcpdump powers. He uncovered what was happening.

Each time I reply to a message, Mail attempts to contact an Apple server through port 80. That’s not a problem at home, but it is at work, where port 80 is blocked and a proxy redirects all HTTP traffic through another port. Mail didn’t respect my proxy settings. It carried on regardless with a process that eventually failed after lengthy delay.

Tim opened the port so that we could see what Mail was trying to do.

Mail was sending the following request based on my .Mac username to certinfo.mac.com (17.250.248.148):

GET /lookup?timgaden HTTP/1.1

In response, it was getting:

The third line in base64 decodes to G\x92\x06\x1777V\xd6W2 (where \x?? means the non-ascii character 92 (in hex), etc.) – so Tim tells me – and the fourth line to acceptance (with a trailing space).

Once we understood the problem, we could google for an answer. It turns out that Jonathan Wight experienced the same thing a year ago. He also provides a fix: delete the ~/Library/Preferences/com.apple.security.plist preferences file.

I’m not suggesting that anything nefarious or underhand is happening here, but it still puzzles me on three fronts.

First, what exactly is it checking and what is the undecipherable response? Is it checking my iChat certificate?

Secondly, why should Mail try to do this when I am replying to a message in my work account on my work server?

Thirdly, why is Mail so stupid? What design oversight makes it overlook my system-wide proxy settings and carry on banging away at port 80, giving me endless delays? Normally, Mail.app helps me to get things done, but not here.

UPDATE: MacGeekery has posted an interesting take on this, which is worth a read.

I hope I made it clear in my post above – although perhaps I didn’t – that I do not think Apple is stealing my credit card information or looking for cracked software or turning my computer into a drone for Apple press releases or doing anything else untoward.

I do think it is puzzling that my proxy settings were ignored and that Mail.app was thus unusable for up to a minute everytime I tried to reply to a message. I do think it is puzzling that the fix was so hard to find. I do think it is fair to expect better of Apple than this.

[Thanks for your help this afternoon, Tim. All my tcpdump are belong to you.]mail.app, apple mail, security, certificates, port 80, reply, hanging, spinning beachball of death, bug, proxy

On the Apple Discussion Boards, Steve Jones notes that Mail.app has the annoying habit of adding an extra return to paragraphs quoted in a reply.

It doesn’t happen all the time, and it seems to happen whether the reply is in plain text or rich text format.

I’ve noticed this myself and have shared the concern of another poster in the same thread:

I hope my original messages aren’t being displayed to the recipient like this, ’cause it’d really make me look like an idiot!

This is possibly not the most pressing issue facing a user of Mail.app, but it does nag away in the back of my mind.

Why is it so? Can anything be done to fix it?mail.app, apple mail, bugs, text, replies, extra spaces, looking like an idiot

Hawk Wings reader Leonardo Burci emailed today to tell me something about Address Book and Mail.app that I didn’t know.

He writes:

Create a Group in Address Book. Add people containing valid e-mail addresses plus a person without an e-mail address or with an invalid e-mail address.

Create a new email. Choose your Group as recipient. Send. You get an error saying something like “mail could not be sent using server xyz, etc”. It doesn’t tell you the real reason why the email couldn’t be sent. It should.

Problem: a Group in the Address Book might consist of people and companies with and without e-mail addresses. This group might be used for sending letters, faxes and e-mail. Mail.app should handle such a recipient list intelligently.

Solution: Mail.app should inform the user about missing and invalid e-mail addresses and should give the user a choice whether to send the mail to the recipients with correct e-mail addresses or not. If you do send, it should give the user a list of people and companies that have no or invalid e-mail addresses and that were therefore excluded.

He’s right. This is not the behaviour of an Operating System that “just works”.address book, mail.app, apple mail, groups, error message, invalid email addresses, bugs