Dr. IMAP or: How I Learned to Stop Worrying and Love FastMail


I am a hoarder. If we didn’t keep moving house every few years, I’d be living in a pile of obsolete technology, eating M&Ms from the carcass of a G4 iMac. Fortunately, I married up.

There is one thing that I cannot get rid of though, and that’s email. I have deleted the odd newsletter, spam, and test message, but I retain a large percentage of all email sent to me. This may be due to an unfortunate incident in 1997 where I lost two years of email, or that I’m just a hoarder.

Gmail; Google Apps for two domains, comprising three email accounts; Mail.app with its myriad migrations and imports from deceased mailboxes, Outlook PST files, Thunderbird archives, and even a pine mail file from a 1996 installation of FreeBSD; and several failed attempts at using “smart” tools to “manage” it all. That was, until today, how I rolled.

I had hundreds of thousands of emails, quite possibly half a million. I am the reason Merlin Mann has a facial tic.

The three Google Apps accounts would forward to my Gmail account, which I would see on my phone using IMAP. Then on my desktop, I’d have POP3 downloading all the same messages from Google Apps to OS X Mail. That way I could see the new stuff from my mobile device, and have a copy at home. For those of you who don’t know, Google allows POP3 to archive mail that has been downloaded, retaining a copy just in case. So I effectively had three copies of every email I received.

This was, in my fevered brain, a “perfect” setup, notwithstanding the occasional catastrophic failure, where I might end up with many as TEN copies of every email I received.

This month, after hearing about FastMail (affiliate link) for the umpteenth time, I decided to give it a look. With input from my friend Jason Rehmus, I managed to almost fully replicate my existing four-platform configuration with one single paid FastMail account.

It costs $40 per year if you don’t take the multi-year discount. This is still $10 cheaper than Google Apps per domain (unless you got in early to the free Google Apps for Business programme). I opted for a multi-year plan, because the thought of migrating email all the time makes me ill, and got an additional 25% discount.

Setup and Configuration

After signing up for an account (I picked an address @sent.com), I asked App.net what I should do next, which is when Mr Rehmus offered his sage advice. The magic of FastMail is a combination of Virtual Domains, Aliases and Personalities.

In the Virtual Domains section, I added the two domains that were being managed separately by Google Apps, and then added Virtual Aliases to represent the incoming mail addresses I have in place.

For example, I have a work and a personal domain, and everything eventually points to these two domains. They all now point to a truly universal inbox. Marvellous.

It’s all very well having incoming addresses, but if you want to send mail from a specific address, you need to set up the associated Personality. Admittedly, FastMail blurs the lines between Aliases and Personalities, which was a little confusing at first.

The magic happens where you have all these email addresses, but only one email account. How do I specify the eligible email addresses in OS X Mail? Fortunately it’s a simple matter, one which Jason helped me with: have a comma-delimited list of your eligible outgoing addresses in your account settings.

In your IMAP settings, after you’ve entered you Username, Password, and Full Name, put the comma-delimited list in the Email Address field, and OS X Mail lets you send from any of those addresses without question.

Migrating half a million emails

FastMail has an excellent IMAP migration tool. You just have to plug in your username, password and server settings, and it will move over everything into matching folders (or not) on the FastMail side. Really straight-forward.

My migration had some teething problems, though. Google’s labels, while helpful on Google accounts, turned into a bit of a headache because it resulted in many tens of thousands of duplicate messages PER ACCOUNT. I found out, too late, that you can disable certain IMAP folders from showing up at all, but it provided me an excellent opportunity to test FastMail’s Remove Duplicate Messages feature.

It works like this: pick a folder which you’d like to compare against itself, or the rest of the account. Then simply click the “Remove Duplicates” button. In one particularly memorable instance, over 80,000 duplicate messages were erased from existence.

I ran the deduplication many times over the past few days, for obvious reasons.

Another minor headache was moving mail from OS X Mail that never existed in my Google accounts. I know IMAP can be flaky (I wrote both POP3 and IMAP clients when I worked at the bank), so it’s better to do a few hundred messages at a time. That was probably the most labour-intensive part of this exercise.


And as of this writing, I have 7.5GB of 15GB available. Considering the sheer volume of email I possess, 15GB is enough for anybody. There are 150,000 emails in my Inbox, 14,000 emails in my Sent Items, and now I can worry less about Google “reading my email”, plus management is much easier.

When a new message comes in, I see it in my Unread items. If it requires action, it is flagged with a Red flag. If it requires follow-up, it gets a Green flag. At most I have about 100 emails that are flagged.

Search has rendered email folders moot, in my opinion. For me, Inbox 150,000 is my Inbox Zero. At least I’m not juggling four different accounts now.

Windows Updates gone awry

Tonight, I scheduled Windows Updates on a customer’s server, and decided to sit through the process myself.

After the 1.9GB of downloads to support 31 updates had downloaded and installed, I pressed the “Restart” button on the Windows Update dialogue box, and waited.

And waited.

And waited.

Normally, this server is responsive to Remote Desktop connections after seven minutes. At thirteen, I was concerned. At twenty minutes, I decided to connect to another server on the same network to investigate.

Using Server Manager’s “Connect to Computer” feature, I was able to look at the Services running on the target server. It was up and running, but not responding to Remote Desktop. I restarted the RDC-related services, but still had no joy.

Then I saw that the TrustedInstaller service had failed. It was stuck in “Stopping” mode, which meant I’d have to manually terminate the service to continue the shutdown.

But now I’d have to download PsTools from SysInternals, until I realised that if the server was still running, I could simply connect to the hidden C$ share to grab the files from my user directory.

A few seconds later, I was staring at a command prompt.

First I tried to run it all from one command. I would use psexec to call pskill remotely, to terminate the Windows Installer service.

Eventually I got bored with fighting the commands, and referred to the help on the PsExec page. In order (with appropriate username and password entered), I did the following:

psexec \\remoteserver cmd
pskill TrustedInstaller

As soon as I pressed Enter, the Server Manager window in the background informed me that the server was unresponsive due to a shutdown, and sure enough, the server rebooted and responded to Remote Desktop again shortly thereafter.

Thank you, Mark Russinovich, for PsExec and PsKill.

Move Over, Mrs Markham

I play Philip Markham. I hope you’ll come and see it. The show will be running at the Pumphouse Theatre in Calgary.

Tickets available from Morpheus Theatre direct. Three weeks to go!


3 – 11 October 2014
By Ray Cooney and John Chapman
Directed by Jay Newman

When Philip Markham, loving husband and children’s book publisher, agrees to allow his business partner to borrow his flat to romance his latest girlfriend – well, that’s when everything goes topsy turvy as only a classic bedroom farce can and Morpheus Theatre’s 20th season has officially begun.

All Philip really wants to do is take his wife out for the evening and the conundrums ensue as a parade of lovers begins to arrive to what they believe is an empty apartment, perfectly suited for their planned revelries.

Cancelled plans, couples not expecting anyone else to be home and the unexpected arrival of a popular children’s book author promise to delight, and don’t worry, once you have your ticket booked that seat is yours, no one else will ask to borrow it.


We recently returned from our anniversary trip, which this year was to the Hawaiian islands.

Starting on Oahu, we stayed in Honolulu and saw Pearl Harbour, and paid our respects there.

Then off we went to the Big Island, and stayed in Kona. We took a two-hour helicopter tour over the island, and saw the still very active volcano, plus some magnificent sights including the valleys and waterfalls on the other side. Breathtaking, and it was all on video.

On we went to Maui, which is our favourite of the three islands, but that’s not to say we didn’t enjoy the other two.

This was again through Trafalgar, so a lot of the travellers in our group were older than us. Suits me, because it was a slower pace.

A special shout-out to Reggie Laroche, our tour director. Like Stephanie Glas-Thompson in the UK and Ireland, Reggie took good care of us, was available at all hours, and extremely friendly and helpful. Trafalgar knows how to pick them.







My Holiday To The British Isles

We returned recently from a trip to Britain and Ireland, through Trafalgar Tours.

The coach drove from London through to York, then Glasgow, Edinburgh, across the sea to Belfast and down to Dublin, then back again to Cardiff and finishing up in London again. It was the best time of year to go, and we had good weather throughout.

Highlights included Scotland for M and I, and his mother really liked Ireland, but to single out specific areas is not fair on the rest of them, because it was well worth it.

We’d like to go back to explore sometime in the future.