I Want a True Alpha Mail for my Macs (♂)

As I've indicated in these posts previously, I was a fully paid up member of 'The Establishment' for many years before going freelance and switching from corporation mandated Wintel boxes to Macs and the Apple infrastructure. I used to receive and process hundreds of emails every day when I was in a senior management position and I have to admit that Microsoft's Outlook was actually pretty good at the job. On the odd occasion that there were problems it was usually a server issue rather than a software problem.

Most importantly, Outlook hasn't really changed much over all the years I've used it. Sure, the appearance of Outlook 2013 is different to its counterpart from 10 years ago, but most of the features and workflows are similar. The guys at Microsoft don't make a habit of tinkering with the programme every release and breaking things that didn't need fixing in the first place.

In fact, when I first switched to the Mac, I eschewed Apple Mail in favour of Entourage, and only ditched it when the volumes of incoming email started to get back up to silly levels and the single database structure became too fragile. I reluctantly moved to Apple Mail and have stuck with it ever since. I have a very complex system of mailboxes and rules which makes sure that all incoming and outgoing mail is stored where I can easily find it. I then use MailTags to highlight specific types of mail like Invoices, Receipts and Licences.

But with every release of OS X I get really mad when I load up Mail for the first time and I find that things no longer work they way they used to, or fail to work at all :-

• Inevitably, Mail add-ons will be broken (my perennial favourite, DockStar, is not even being supported by its original owners because they're fed up of having to keep updating it). I know that Mail APIs are largely unpublished so this is to be expected until Apple decides to make them public
• Sharing Mail across a network of machines of different ages is no longer possible once a Mac loses it's ability to run the latest OS because internal Mail structures are not backwards compatible
• Rules seem to break with every new version of Mail for no apparent reason

Apple Mail 7.0 that arrived with Mavericks has had a lot of press because of its inability to play nicely with Gmail (largely because Google decided to implement a non-standard version of the IMAP protocol). I don't use Gmail directly - but my Virgin UK ISP uses a version of Gmail as its mail manager. Despite having read most of the details of the issues, and now having the latest update installed, I've yet to resolve my specific problem, which is that almost all my mail bypasses the Inbox and goes straight into an Archive mailbox (also bypassing the rules processing). This archive mailbox never existed prior to release 7 so I have no idea who owns it, or how to get rid of it. Or how to stop it taking over my mail!

My only option at present is to regularly process the Archive mailbox using Alt+Cmd+L which forces the rules to run on all messages in the mailbox - that way at least I know there's a copy in the right place. Once I'm happy that things are in their proper mailboxes I then have to delete everything from the Virgin mail servers through webmail. This is not a satisfactory state of play!!

I don't particularly want to ditch Apple Mail. I've got used to it, it mostly does what it's supposed to do, mostly does it pretty well, and third party support is generally very good. But more critically, I can't find a decent alternative - with the possible exception of Outlook, but I'm not buying another full copy of Office for Mac just to get the Outlook programme. (Why oh why, Microsoft, can't you sell it as an add-on or even an in-app purchase?) I have bought of copy of Unibox but haven't got round to setting it up yet, and I know it's a significant departure from the way I'm used to working.

As far as I can remember the best implementation of Apple Mail was probably the one that shipped with Snow Leopard. Every version since has increased the number of niggles.

Please Apple, get Mail sorted once and for all and either publish or stop tinkering with the APIs. Let me get back to focusing on reading and writing mail rather than having to perform all the housekeeping as well!

Sugarsync and Apple Mail

I've just spent a couple of days attempting to set up SugarSync to work with Apple Mail. Sadly all my efforts have been in vain and I've been forced to resort to manual methods to keep my iMac and MBP mail synchronised.

I think that my requirement is fairly common but I'm struggling to find an elegant solution whereby I can keep my mail systems up to date across two different Apple machines; an iMac and a MacBook Pro (strictly speaking it's three machines, but as the Hackintosh is still running under Leopard and the others under Snow Leopard, I'll not include that in this problem discussion). Currently my iMac acts as the primary Mail machine, and all mail is delivered there from my ISP and immediately and automatically deleted from the server. If I'm on the road for more than a day, I'll close Mail down and copy the entire "username"/Library/Mail folder onto the MBP. The laptop then becomes the primary Mail machine until I return home. I then reverse the procedure to revert back to normal. The key to this approach is to make sure that only one machine is the active Mail computer at any one time, and on occasion I forget that I'm not supposed to start Mail up on the "wrong" machine until all necessary transfers have been completed. There are mechanisms to avoid this, like keeping the server copies in place during the trip, but even this requires changes to preferences which are easy to forget.

I recently started using SugarSync to keep my work folders in sync across desktop and mobile devices. I've configured it to work with Things and SketchBox most recently I've solved the problem of managing local drafts in MarsEdit across a network. SugarSync is a relatively inexpensive way to keep files and folders synchronised. I have subscribed to the cheapest plan which gives me 30Gb of storage and allows me to sync across any number of machines. This basic plan costs $49.95 per year. A free plan also exists for users with more modest requirements and gives you 2Gb of storage and sync capability for two computers. A SugarSync app is also available on the iPhone for increased flexibility.

Given the success of using SugarSync with other systems, I decided to see if anyone had set it up to work with Apple Mail. My searches proved fruitless, and I summoned up the courage to act as a pioneer. I backed up my primary Mail system on a USB stick, and did an extra Time Machine backup on both desktop and laptop computers. I then configured SugarSync to manage the "username"/Library/Mail folders on both machines. This folder weighed in at about 600Mb, including all subfolders, and contained about 10,000 items.

For my first attempt I worked on the iMac first and SugarSync duly went off and started uploading all the data from my mail system. This took several hours at an average upload speed of about 0.35Mb/s. I then attempted to sync the laptop and was surprised to see that almost everything from the laptop mail system was also being uploaded and marked as such in the filename. I figured that this must be because the desktop and laptop were completely out of sync and was concerned that the duplication of critical files would cause Mail to have a nervous breakdown. I halted the process, reset both machines, performed a manual copy of the iMac mail folder to the laptop and started again. I left things running over night and in the morning was amazed to find that the same thing had happened. I attempted to start Mail on the iMac but it just spluttered and died requiring a Force Quit, and another reset of both Mail systems, after removing SugarSync from the equation.

I've not got enough technical knowledge about the internals of the Apple Mail system to understand what's going on, and why SugarSync was unable to create a single set of files which Mail could then read. And I'm not sure that I really want to find out. I'm definitely of the opinion that, in certain subject areas, a little knowledge can be a dangerous thing. This is certainly one of those subject areas!

So, SugarSync is not the silver bullet to solve this particular problem and I'm still on the lookout for that elegant solution to synchronise Mail across two Macs. If anyone knows how to do this (without setting up Mail servers) please let me know. I guess the easiest way is to keep all my messages on the ISP servers and once a week ensure that both machines are fully aligned before deleting everything off the server.

But that still requires manual intervention and may still not be foolproof. Or Ally-proof. And it certainly isn't elegant!

Useful Mail Add-Ins and a Small Surprise

I promised to take a closer look at some of the add-ins that make Apple Mail my mail client of choice. But before I do that I wanted to share something I discovered this morning by chance.

Mail Recovery with Time Machine

Like many people who were early adopters of Snow Leopard I had a few teething troubles in the first few weeks with my existing Mail accounts. I've made reference to this in previous posts so won't dwell on it here other than to say that the problem no longer appears to exist. However, there does appear to have been some debris left over from this episode, and I found that I had multiple references to the same account stored in various locations. In an attempt to clear up the unwanted references I had an accident with some of my sent messages (I'm a hoarder and keep copies of everything for years). The message header details appeared in the Sent mailbox but the messages themselves were missing.

By chance I happened to start up Time Machine whilst still in Mail, and discovered that in this instance Time Machine will focus all its attention on your mailboxes. A few clicks later and all my sent mail was restored to its expected state but in a safe mailbox called "Time Machine/Recovered". I referred back to David Pogue's excellent "Mac OS X The Missing Manual (Leopard Edition)" and indeed this feature was available in Leopard and works in a similar way with iPhoto and Address Book.

This is a great feature for recovering from minor glitches with mail without having to resort to a full mail system restore. I wish I'd known about it before!

Letterbox Add-In

Letterbox is one of those "oh-so-simple" things that it really begs the question as to why it wasn't part of the original requirements in the Mail programme. Aaron Harnly's add-in allows a three column view within the main Mail window with the message content in the third column. The current 0.24b5 beta release works with Snow Leopard 10.6.2 and allows a few other goodies like changing alternate line colours in the mail header list, and allowing a two line view also in that window. Letterbox is free, and new updates to support Apple updates are usually very quick off the board.

DockStar

DockStar from ecamm network ($15.00) provides you with a configuration utility for the Mail icon in the dock, allowing the mail count of up to five mailboxes to be displayed on the icon. It does this by adding 'badges' to the icon. Each badge allows different options to be selected, e.g. which mailbox, style and colour of display, and type of count (unread, total, etc.). Badges can also be displayed in the menu bar. Again, a very simple concept but really useful for monitoring incoming mail without constantly having to check the Mail application itself.

MailTags

I've not been using MailTags from indev software ($29.95) for very long so I'm probably not doing justice to its full feature set, but nonetheless I do find it useful. In its simplest form MailTags allows you to tag individual mail messages using categories of your own choice, and to filter messages using those tags. It also allows you to add other metadata to a message such a priority, project, colour, and notes. It also allows you to use your notes to change the visible title of the mail. MailTags are integrated into rules giving you further abilities, and tags are supported by other applications such as Mail Steward, giving you the same filtering abilities in these apps. I find it really useful for marking messages containing invoices and license information using a specific format which allows me much quicker access to the info when I need it, without having to wade through message bodies. Some discipline is required to make full use of such a facility, but it's well worth the effort, especially when it's time to start annual accounts...

I'll cover some of the other add-ins I find useful in a future post, but hopefully there's plenty here to get you salivating. And none of these will make your tongue taste nasty!

A Word or Two about Apple Mail

It's strange to think, but when I started full time work after graduating back in 1984 we didn't have email. In fact my first encounter with email was when I opened a Compuserve account sometime in the late 1980s. It wasn't until the early nineties that I had access to email at work, again through a corporate Compuserve account, but with limited availability. Many of my colleagues had another two or three years to wait before the full roll-out of Novell's Groupwise across the company. By the time I joined a very large Global Outsourcing company in the late nineties, email was more prevalent, and Outlook had become the de facto standard for most businesses. It wasn't long before I was receiving several hundred email messages each day, and by the time I left that corporation I was regularly getting more than a thousand messages a week. I became something of an expert on Outlook simply to be able to manage incoming mail.

When I moved across to the Mac platform I duly purchased Office:Mac 2008 which had just hit the streets. I fully expected Entourage to look and work like Outlook. Boy was I mistaken ! Even getting Entourage to read Outlook data files was a major hassle, although I eventually managed to import my old Outlook messages using third party software. But there was enough of a likeness between the Microsoft's Mac and PC mail offerings to keep me hooked in preference to Mail. I particularly liked Entourage's integration of mail, to-do lists and calendar.

I prevailed with Entourage until earlier this year before deciding to try out Mail in earnest. The Entourage database had started a habit of corrupting itself, and of course Time Machine backups were incorporating the entire database every time it was updated. Archiving in Entourage also left me cursing its designers.

I now use Mail all the time and generally wonder why I ever bothered with Entourage. But it isn't Mail out of the box. I have a set of Add-Ins and tools which give the programme its genuine usefulness. These are Letterbox, DockStar, Growl Mail, Mail Tags and Mail Attachments Iconizer. I also have Mail Act-On installed but I'm still trying to get to grips with that. I use MailSteward for archiving, and this also allows me to get around the problems of incompatibility between the Leopard and Snow Leopard versions of Mail.

Luckily the volume of email that I currently have to deal with is greatly reduced from the madness of a few years ago. But even if it were too suddenly escalate, Apple Mail in the Apple Harvest environment would be more than capable of rising to the situation. It would be even better if:

• Apple would provide a mechanism for properly integrating Mail and iCal without me having to use another third party application like DayLite


• Apple engineers would stop messing about with Mail internals that then break the 3rd party add-ins until the poor developers have a chance to figure out what they've done and are able to catch up (which they generally do very quickly), and leaving the poor user with a broken environment in the meantime

Another time, we'll look at some of the Add-Ins in more detail. Happy emailing...