Alert sounds.

Sometimes it plays the alert sound for no discernible reason (I think because new mail has arrived in a sub-label/sub-folder, but actually I can’t be sure this), yet at other times, a new mail will arrive in the Inbox (I can see it) and no sound will play. Also it seems to update the Growl notification app at odd points (no discernible reason why it does or doesn’t). Consistent behaviour is critical here. Please guys, play the alert sound when, if and only if, a new email arrives in the Inbox of any account. Worry about configuring this behaviour only (maybe through filters?).

Image attachments.

If someone attaches an image to their message (e.g. a photo), when you select the message you see the image scrolling off the page, i.e. at 100%. However if you resize the window, even by the tiniest margin, the images snaps to the window size.

PDF attachments.

PDF attachments should be viewable in-line.

Gmail ‘important’ feature.

I can mark an email with Gmail’s ‘important’ tag in the message view pane, but not to a message or messages in the message list. Actually it’s because the ‘Assign label’ context menu is available for a message in the message view, but not in the list view. ‘Assign topic’ is on both – and it also has by default, a topic called ‘important’ but it’s not the same things as the ‘important’ tag in Gmail. That’s confusing.

Gmail ‘star’ feature.

‘Starring’ an email in Gmail is called marking the email as ‘To do’ in Postbox. In other mailers this is usually regarded as ‘flagging’ the message. Does not support the new Gmail multi-stars.

Message colours.

I’m really missing the ability to colour message text/background with the filters. It’s the only Mail.app feature I miss currently.

I was, and remain, an email power user (I know that this actually shows my age nowadays). In fact, for many years, I used to use elm, and then mutt in the Unix shell — it was only really once I got the invite to the Gmail beta that made me finally switch from mutt! I was never a pine user although I know a lot of people used to use that, and I never really super-loved any of the Mozilla clients like Thunderbird — its calendar integration is shit. Obviously Outlook, Entourage, and other Microsoft email software is purely for defectively-thinking droolers who hate the internet, send pictures to their friends pasted into Word or Powerpoint attachments, and have an Exchange server stuck up their bum so that doesn’t even enter into the equation. So, I love the keyboard with my mail program, I love seeing a threaded view of email conversations. I mostly love plain text email too (although this is not such a hard-core requirement for me nowadays). And I need it to work with Apple’s iCal and Address Book because I like those programs and I want to get this information onto my iOS devices over the wireless.

However, while Mail.app is probably a reasonable proposition for the average consumer-grade user and does many of these things pretty well, I never really loved it. I suffered with it these past few months. Its search (i.e. spotlight) is OK for email but no patch on Gmail. It doesn’t really play nice with Gmail’s labels and takes a “folder” approach. It has a thread view now but I don’t think it’s spectacular. It sometimes seems to forget that I’ve got a message selected and it should make it as “read”. However, I could live with it, I thought.

But, last night, I found Postbox 3 via a MacUpdate bundle. I decided to give it a burl. It’s actually quite awesome, despite the lead engineer being an ex-Mozilla guy (bearing in my mind my comments about Thunderbird above)! It plays nice with my Mac, and iCal and Address Book. Its integration with Gmail’s labels is also pretty smooth and I haven’t found and issues with it. It even supports Gmail’s keyboard shortcuts which is heaven for me. You can even configure it to connect to Facebook, LinkedIn, and Twitter in such a way that if you don’t have a picture in your address book for an email contact, but have a connection to them in any of those services, it will use the picture from the service. That’s a very nice feature. It has a way to get at all the various configuration parameters and fiddle with them (haven’t really explored that too much other than to look at it).

It’s not without rough edges though. For example, choosing an alert sound for new email; you can choose either to use the “System Alert” sound, or pick and choose any relevant sound file on your hard disk. What you can’t do is select from a drop down list of the available Mac System Sounds. You have to locate the relevant AIFF file in the System Library. And if you do choose “System Alert” you get get a horrible !plink! sound and not the actual System Alert sound from the Sound system prefs. And the ‘whoosh’ sound it uses for sent mail is not configurable other than on or off. It needs to know how to open a message in a new window, not just a new tab. You also cannot select a message’s colour (background or foreground), either manually or through filters (in Mail.app, I used this to highlight in a background colour the messages from people in my Address Book where I was an explicit recipient). It also needs a Unix “biff” style plugin for the menu-bar. It does integrate well with Growl but I don’t really like that for email notification. But that’s all pretty minor stuff. The major stuff, like Gmail integration, it does really well.

But, a really nice feature and a pleasant surprise is that when you reply to a long-running thread, it has a really nice way to summarise the emails from the various participants (see crappy screenshot below).

Overall I rate this program 8/10. Definitely sticking with it. Recommended.

As for non-Google email, my work uses Exchange – and I can’t reach an secure port for that without firing up the work VPN, so usually I use the shockingly clunky webmail alternative anyway – so its not like I am losing out on any functionality. I have a .mac address which truth be told doesn’t get used that much – and Gmail can suck in pop-based email into it’s own accounts anyway. It can be used with an unlimited number of Gmail accounts.

If you are a Gmail user on a Mac, I’d definitely recommend having a look at Mailplane.  It’s a nice way to get the Gmail-native way of handling email (which generally I love)  onto the Mac. I think its needs some improvement, such as integration into Apple’s iCal, and perhaps, if possible, the abstraction of some of the Gmail interface elements (such as gmail’s list of labels) out into native interface widgets.

Thunderbird 2 doesn’t integrate with the Macintosh Address Book, so that rules it out straight away, had to go straight to Thunderbird 3 beta. I got the latest, beta 3, released in July.

After about 5 minutes with Thunderbird 3 beta I was telling it to go fsck itself. Here’s why:

1. Installing Thunderbird 3 – what’s with the “@googlemail.com’ for Gmail? I use ‘@gmail.com’ and always have and always will. That’s the option I want. Oh sweet lord, it will force me to use @googlemail.com – that’s a disaster right there. Can be edited later, however, I discover. But still.
2. Thunderbird 3  “integrates” with the Mac address book, which is to say it will pull addresses from it, but it does this through it’s own horrible, horrible, interface. Bad Mozilla! I want to use – at all times – the Apple ‘Calendar.app’ and ‘Address Book.app’, OK? Their user interfaces. Not yours.
3. I got some mail with pictures in it. I can view the pictures by selecting “view external content” button for this one email. If I select the “always view external content for xxxx” it wants to add the sender to the address book (it’s internal address book). No Mozilla, that’s not what I’m asking for. I just want the graphics for that newsletter I get sent to be shown without me pressing extra buttons every time I get this newsletter. I don’t want their address in my address book!
4. Arrrrgh! My eyes! Jesus it’s ugly. And clunky. It feels like Windows all over again. Good lord. I can’t find any way to change the list display fonts. It’s probably in there somewhere, I will admit, but I can’t find it.
5. Every single folder, I have to individually select “view by thread”, as far as I can tell.
6. Search is an entirely separate window/dialogue. I can’t search more than one account at once. “Search Subfolders” at the top level includes Spam folder. There doesn’t seem to be a way to add a criteria that “Message is not spam”.
7. The terrible search function is the only basis for “Smart Folders” that I can find so far, therefore it won’t work for what I need. In Mail.app, I use three smart folders:
   1. All unread mail in any account or sub-folder thereof
   2. All mail in the Inbox of any of my three “personal” accounts, that is, mail directly addressed to me personally.
   3. All mail in the Inbox of my work mail account.
8. On the plus side, it does have good support for keyboard commands. I’m an old mutt user (before that, elm) so I love keyboard commands in my mail program. Mail.app has rubbish support for this.
9. Also on the plus side, Thunderbird’s threading display is a little clearer. Mail.app just puts all messages in a thread under the one hierarchy, you don’t get any sense of what message is a reply to which.

OK  Apple Mail.app lost some sent mail  once in the middle of a godawful crash (but a crash nonetheless), and I’ve always hated its horrible keyboard support. However maybe I am willing to take those risks and annoyances if this is the alternative experience. I know that Mozilla is open source, and full of all that open sorcery goodness, but I live and die via my email program, right after my IDE, and I want a pretty nice experience with it. Thus, I’m now in a bind – use a program that just proved to me its data integrity is not 100%, or use a program that that just gives me a truly horrible user experience and wants to screw with my choice of Calendar and Address Book?

Mac email program suggestions in the comments if you like (and no, don’t suggest Entourage, it’s completely off the menu).

UPDATE: I should mention that, for me, the deal killers are points 2, 6, and 7.