Outlook, How I Loathe Thee

Posted: September 16th, 2009 | Author: | Filed under: Software | Tags: , , , , , , , , , , , , , , , , , , , , , , , , | 5 Comments »

I fucking hate Microsoft Outlook. I cannot think up another English language sentiment that more accurately sums up my feelings regarding Microsoft’s Outlook application. As much as I hate on the Almighty Goog, I long for the days when I could use the simple, clean interface of the superbly well-designed Gmail web application. Then I went and got myself a Blackberry. All hate aside, I love my phone – it is the best phone that I’ve ever carried, and I wouldn’t consider downgrading if you paid me to do so. However, without an Exchange server, the Blackberry is inexplicably linked to Microsoft Outlook. It is the only well-supported application that the device can sync calendars and contacts with. This, in turn, forces me to use the bloated, cluttered, buggy, and altogether frustrating behemoth that is Outlook.

My current problems began with The Linux Experiment, a blog that I helped start whose purpose is to record the experiences of seven computer users with varying amounts of Linux experience who have committed to running various distributions of Linux on their primary platforms throughout the next four months. Previously, I had maintained two devices that checked my google mail account – my Blackberry, which pulled new email down from the server via the IMAP protocol, and Outlook on my Vista PC, which did the same via the POP3 protocol, and immediately deleted the messages once they came down. It was a fine balance that owed its existence to more than a few quirks in the Gmail, Blackberry, and Outlook systems, but in the end ensured that I got my email on both devices, but that it wasn’t stored on the Gmail servers, which the tinfoil-hat wearing paranoid inside of me greatly appreciated. Unfortunately, I then decided to add a third client to the mix, the Evolution client for Debian Linux, which frankly, is an extremely impressive Outlook clone that seems (initially anyway) to do some things better than Outlook itself.

In order to add a third client to the email mix, I had to remove the fine balance between IMAP and POP3 that had originally existed, and set all three devices up as IMAP clients. Further, Outlook was set to delete all messages on the server that were over 30 days old. This provided some modicum of security, while allowing all three devices to share my email. Along the way, I found out that Evolution actually has the best IMAP support of the bunch, and (unsurprisingly. If there’s on thing I’ve learned recently is that Linux does everything, and usually does it right the first time), Outlook the absolute worst that I have ever seen. For easy reference, my various complaints have been summarized into the ordered list presented below:

  1. IMAP folders appear outside of the “Personal Folders” area, forcing me to maintain multiple email inboxes, instead of allowing me to funnel all of my email into a single inbox. (This may be an issue common to other clients as well – I honestly don’t know).
  2. Outlook tends to keep IMAP connections open for too long, resulting in Gmail forcibly closing the connection, and Outlook bitching that said connection was closed by the server. There is no option (that I can find, but hey, have you looked at the option dialogs in Outlook lately?) to adjust this timeout length.
  3. The program does not accurately reflect message status. For example, if I receive an email on my blackberry while away from home and read it, the message status is set to read on the server, and Outlook should reflect this change. It doesn’t. Evolution does, as does the Blackberry. What the hell?
  4. When an email message is deleted on the Gmail server by another client, Outlook does not delete the message locally – it simply shows the message with strikethrough formatting on the subject line. In the same vein, when you delete a message in Outlook, there is no way (that I can find) to delete that message from the IMAP server so that it is reflected on other devices.
  5. The Linux Experiment uses a self-signed certificate to verify it’s identity to connecting mail clients. Granted, this isn’t how certificates are meant to be used, but it’s better than nothing, and we don’t have the money to pay for a CA. Outlook (as one would hope) complains that the certificate is self signed, but lacks an option to ignore this fact. In theory, this is a “feature” that notifies a user that their transaction is potentially insecure, but in practice, it’s a pain in the ass. I know that the email server has a self-signed certificate. I helped set it up. Now shut up and do your job.

Those are the big complaints about IMAP support in Outlook. I have other complaints about the application, but they’re the same as many people’s and I don’t want sore fingers, so just Bing the issue if you’re looking for a half hour rant. The point to take home is that this lackluster support is inexcusable. According to Wikipedia, the IMAP protocol has been in it’s current revision since 1996, and Gmail is hardly a fly-by-night mail server.

In any case, at the same time that I got everything set up and working between all three devices, Outlook became crash-happy, and started going down three times a day. Sometimes it would crash when I wasn’t using it at all, sometimes while I was changing account settings, occasionally when I tried to open an email, and even once while I was trying to retrieve email from the Gmail servers. The idea that Outlook (previously rock-solid stable, among it’s few good attributes) could start regularly crashing for no apparent reason whatsoever seemed far fetched. So what had changed? Well, I’d added an IMAP account and disabled a POP3 account. These changes modified the Outlook PST files (the unreadable binary blob in which the program stores everything including it’s kitchen sink), which could have potentially been corrupted in the process.

So I backed everything up, deleted my PST files, uninstalled and reinstalled Outlook. I did not realize that the program had littered my drive with settings files in both C:\Users\Username\AppData\Roaming\Microsoft\Outlook and C:\Users\Username\AppData\Local\Microsoft\Outlook, as well as (likely) numerous registry keys, and when I launched my fresh install, it attempted to read from these files, and to recreate it’s missing PST files. Balls. So I closed the application, re-deleted the newly recreated PST files, and also nuked the settings files in the two locations. Upon launching Outlook, it again somehow managed to restore all of my settings, including my RSS feeds and both of my IMAP accounts.

Fine. You restored my settings. Not the via the method that I had hoped, but the effect that I was after has been achieved. The old and possibly corrupted PST files have been recreated, my email accounts are once again being monitored by my Vista PC, and the program hasn’t crashed yet. Then I tried to sync my Blackberry with Outlook using the RIM Desktop Manager software (an application almost as poorly written as Outlook itself), and the whole house of cards came crashing down. Somehow, whatever I’d just done absolutely ruined the underlying Intellisync process, and resulted in an error that merely said “Function OpenFolder failed” with no further explanation. A quick web search resulted in nothing of value, and the sync process refused to restore my calendar and contacts from the device. The synchronization log files state only that Internal Error #4238 occurred, and that the translation of contacts failed. I Bing’d up a post on the Blackberry Forums that instructed me to delete my Intellisync folder to restore my synchronization abilities.

After following the instructions and recreating my sync profile within Desktop Manager, everything worked as expected, and my contacts and calendar were restored to Outlook. Needless to say, this entire enterprise was far more painful than I felt it should be, and only time will tell if I’ve actually fixed the crash problem, or if it will resurface in a couple of days. Regardless, I will be exploring alternatives with renewed interest. There are plenty of other email/calendar managers out there including Mozilla’s Thunderbird, which I use for my small business and absolutely love. Unfortunately, Blackberry sync is high on my list of requirements from an email client, and so far, Outlook is the only client that can do that reliably without writing a bunch of intermediary code. As a part of the Linux Experiment, I will be looking into the Barry project, which is promising, but seems to be Linux-only.

Stupid Outlook.


5 Comments on “Outlook, How I Loathe Thee”

  1. 1 Tyler said at 6:50 pm on September 29th, 2009:

    You should just dump Outlook ASAP. Seriously how many issues have you had with it in the last month alone?

    [WORDPRESS HASHCASH] The poster sent us ’0 which is not a hashcash value.

  2. 2 Jon said at 5:49 am on September 30th, 2009:

    You’re not kidding. The problem is that I like to be able to sync my contacts and calendar with my phone. I’m putting a lot of work into figuring out the Barry project over at http://www.thelinuxexperiment.com, hoping that it will allow me to use Thunderbird on Linux instead.

  3. 3 jack said at 10:23 am on November 20th, 2009:

    outlook is the biggest productivity drag on my day, every fucking day. the searching is ridiculous — typically i start an email search in outlook, and it takes so EFFING LONG that i can actually log onto web gmail, search, and get an answer, before outlook has finished it’s useless search. wtf???? and, outlook crashes on launch about 30% of the time because it is so eager to launch business contact manager. i am also stuck b/c i need to sink something with the iphone.

  4. 4 Jon said at 2:02 pm on November 20th, 2009:

    Jack, I suspect that your problems are fairly common. Unfortunately, a lot of hardware and software relies on Outlook being installed on your system to take full advantage of all of its features.

  5. 5 Finally Synching my Blackberry on Linux | The Linux Experiment said at 10:09 pm on January 2nd, 2010:

    [...] I disliked Evolution, seeing it as a Microsoft Outlook clone, which is a platform that I have had considerable problems with in the [...]


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