These articles (my annoyances on this page and my response to the ComputerWorld annoyances article) were first published in Exchange Messaging Outlook, January 15, 2009. It's interesting to see how much has changed over the years and how much hasn't changed.

My Outlook Annoyances

My annoyances are really feature requests and are based on both my experience and the complaints I heard from users, in no particular order of importance:

1. The monthly calendar doesn't offer the option to put "this week" at the top.

We get a lot of questions about this, especially at the end of months that fill 6 calendar weeks. Some users want "this week" to always be the first row, others want it to always be the second row. Microsoft gets enough requests for this that if they could make it work, it would be added. Instead, they fixed the monthly views in Outlook 2007 so the full month fills the screen. Now, instead of displaying five weeks for every month, Outlook displays the full month using 4, 5, or 6 weeks as needed. There are some issues with screen drawing as you move through months, these are fixed in a future update.

2. You can't make subtasks, link tasks or otherwise prioritize tasks.

If I had a dime for every person who asked if tasks could be nested, linked or prioritized, I would retire and move to somewhere warm and sunny, where it never snows. There isn’t a good workaround for this problem; most people who need this number the tasks.

3. Syncing or sharing mail and calendar between users or computers

This is everyone's top annoyance. Outlook 2007 is better with the calendar publishing feature but its not perfect and anyone who needs to share their calendar with others or access it from two computers needs to use a utility if they don't use Exchange server.

For workarounds and utilities, see Sharing Microsoft Outlook Calendar and Contacts and Synchronizing Outlook on Two Machines.

4. Printing calendars

Most printing issues are bugs, not annoyances and in many cases, it worked "as expected" in older versions. Printing options seem to get worse with each version of Outlook. The environmentalist in me says "Stop printing and save a few trees." but I know there are a number of people who need printed calendars, either out of habit or because they don't have a handheld device to sync to.

Microsoft released the Calendar Printing Assistant to address users complaints. You can find links to this and other utilities at Calendar Printing Tools for Outlook. The Word templates are worth a try.

5. Recurring appointments that don't follow a pattern

It's easy to tell who used to use GroupWise when recurrence questions come up. Groupwise allows users to select random dates and create a recurring appointment. Outlook makes you use a specific pattern: every xx days, weeks, months, years. You can move appointments around to create exceptions, but they aren't as easy to set as GroupWise's random dates and if you change the appointment series later you'll lose the exception.

There is an add-in, WS.Repeat Appointment, you can use.

6. Wildcard and regular expressions in Rules Wizard

This is a popular request. Wildcards would be useful in both Rules Wizard and Search/Advanced Find but I'm not convinced enough users know what regular expressions are or how to write them (or would want to learn) to make it worth Microsoft's time. Fortunately Outlook is extensible and there are several add-ins that do make it easier to find and manage messages.

See Search Tools for Personal Use for search tools.

7. All day events don't show in the To-Do bar list.

This one is pretty much self-explanatory: only timed events show on the To-Do bar. While I don't expect this will change in Outlook 2007, there is a good chance this popular request will make it into Outlook 14.

Top 10 Annoyances?

A recent "Top 10 Outlook Annoyances" article in ComputerWorld listed the author's top 10 annoyances and in my opinion, some of the solutions weren't the best way to address the problem. Several of the problems are caused by add-ins, not Outlook.

1. Outlook is too darn slow

Yes, Outlook is too slow for some users. There are a number of causes and unfortunately, removing attachments to make a 250 meg PST smaller isn't going to do much to make it faster.

Outlook may be slow when it loads because its checking the consistency of a PST or OST. This happens because Outlook doesn't close properly, and yes, a smaller PST will help because its faster to check. But you'll do better in the long run to figure out why it's not closing properly and fixing the cause - usually an add-in or application (such as sync tools for handheld devices) accessing Outlook data.

Users who upgraded to Outlook 2007 and kept their profile and PST may experience slowness. We recommend a new profile but it may help to delete 4 files: Outcmd.dat, Extend.dat, Frmcache.dat, and Views.dat. Outlook 2007 will recreate these files as needed. For more information see Outlook 2007 is very slow

RSS feeds (and Internet calendars) appear to slow Outlook down because they begin updating. This is especially true if you subscribe to a lot of RSS feeds or a few very busy feeds. Outlook is fine for limited RSS feeds, but a dedicated RSS reader is often better for large numbers of feeds.

Antivirus integration can causes issues, from slowness to missing message to crashes so we don't recommend scanning email for viruses. Other add-ins can also cause problems. Check your list (and disable them) in Outlook 2007's Tools, Trust Center, Add-ins dialog.

2. Attachments make Outlook massively bloated

Massively bloated? Hardly. Outlook can easily handle a 1 GB PST, provided the file doesn't need repaired every time you restart Outlook. What will help Outlook feel faster is keeping fewer messages in the Inbox. Move messages to "completed" folders as you’re finished with them. Or use the Rules Wizard to sort messages into folders and use the Unread mail folder to read them, just don’t go nuts creating an elaborate folder system. Keep it simple and use a limited number of folders.

I don’t use a lot of rules to move messages to folders, I prefer using Auto-Mate to move messages to a "Completed" folder after I've read them. I usually have between 500 and 1000 messages in my Inbox and Outlook is very snappy.

If you really want to remove attachments from messages, there are a number of utilities available or you can roll your own solution using VBA.

A list of utilities that do this (and more) are available at https://www.slipstick.com/addins/attachments.asp
Many of these utilities offer additional features that make them cost effective for anyone who needs to save attachments often.

Sample VBA code and instructions are at https://www.outlook-tips.net/code/saveatt2.htm

3. Outlook's data file is $#%^ hard to find

While it would be easier to backup the PST if it were in My Documents, its not hard to find. You can go straight to Data File management (on Outlook's File menu) and click on Open folder to open the default folder location. Unless you moved the PSTs, they will all be in this folder.

If you use Outlook 2000 or 2002, you won't have Data File Management, but you can use a userprofile command line in Windows 2000 or XP and Outlook 2000 or 2002, to open the folder:
%USERPROFILE%\Local Settings\Application Data\Microsoft\Outlook
Paste it in the Start menu, Run command or the address bar of Windows Explorer. It works with Vista and Outlook 2003/2007 too, if you need to access the PST location when Outlook is closed.

If you just want to browse your hard drive looking for the folder, you'll need to show hidden files and folders in Windows.

Why isn't the PST in My Documents? Because both PST and OST (offline files) are stored in the same location. Corporate users with roaming profiles sync their My Documents folder with the network server and because of file size issues, most sites don't want OSTs synced with the server.

For more information, see:
Outlook & Exchange/Windows Messaging Backup and Dual-Boot
Where Are My Files?

4. Searching, filtering and sorting are sub-par

While Find in older versions of Outlook wasn't fast and often found the oldest messages before newer ones, Outlook 2007's Instant search is very good. The problem for many users is that they file everything into hundreds of folders then can't find anything. Stop treating Outlook like a file cabinet, with many subfolders Instead, use more of Outlook's features, like views and search folders to find things.

If you need more powerful searching, there are several search tools available, from Google Desktop Search to add-ins made specifically for Outlook.

My preference is to keep all mail in my Inbox until I mark it complete. Since Outlook only runs rules as the messages arrives, I use Auto-Mate to move the completed messages later.

See Search Tools for Personal Use for other search tools.

5. Outlook crashes constantly

If Outlook is crashing constantly, something is wrong with your system. Always, always send the crash reports to Microsoft when asked. This will help them to identify and fix problems, including problems with third party add-ins. Outlook will disable add-ins it identifies as a cause of crashes but it can't always identify the problem add-in. You should restart Outlook using the /safe switch. This loads Outlook without add-ins so you can verify the problem is with the add-ins. Disable or uninstall add-ins you don’t need. Run Detect and Repair (Outlook 2003) or Office Diagnostics (Outlook 2007).

6. Its .pst files get corrupted

Each time Outlook crashes it runs scanpst automatically the next time you start Outlook to check the consistency of the file. This doesn't mean the PST is corrupt, it just means Outlook is checking it and fixing any problems it might find so it doesn't become corrupt and result in data loss.

One cause of this dialog is closing Outlook while something is still accessing Outlook data. This is often software that syncs Outlook with handheld devices, but shutting down Windows without closing Outlook may also cause it, as will scanning the PST with an antivirus scanner.

The solution? Close all utilities that are using Outlook data and stop syncing before you close Outlook.

A few years ago a popular Office author frequently recommended making a new PST every 6 months and importing the contents of the old PST, to prevent corruption. This was bad advice then and now. It also causes you to lose hidden items, like custom forms. Again, if the PST is corrupt, making a new one is not the answer - you need to identify the cause. Most often, its because Outlook isn't closing properly. You can check this by looking for outlook.exe in the Processes tab of Task Manager. The most common cause is a poorly written add-in.

See OUTLOOK.EXE continues running after you exit Outlook for more information.

7. Duplicate entries appear out of the blue

Rarely does anything happen "out of the blue". It's either a problem syncing with a device or a problem talking to the mail server. Quite a few people end up with duplicates when they decide to import mail from their archives, rather than just opening the archive in Outlook.

My record for duplicate email was 99 messages each of some 2000 messages. Back in the days of dialup, I had Outlook 2000 set to check for new mail every 3 minutes and left the office. The cause was two-fold: the connection often dropped before Outlook sent the QUIT command and I received a large number of messages, which took longer than 3 minutes to download. Outlook kept trying to restart the download before it marked messages as previously downloaded. Duplicate contacts were frequent in these days too, thanks to my PDA and NetFolders.

If duplicates are a problem for you, there are a number of utilities available that cam identify and remove duplicates, many work on all folders but a few are folder-specific. See Duplicate Remover Tools for Microsoft Outlook for a list.

8. Syncing Outlook on multiple PCs is tough

The ability to sync your data with two computers or share it with others is a major annoyance for many Outlook users. Exchange server users have it easy - Exchange server makes it easy to share Outlook data with other users at your organization and view your email and calendar on other computers. As long as you have a web browser, you can use OWA to view your mailbox.

POP3 users can leave mail on the server and download it on each computer or move the PST between computers but each method leaves a lot to be desired. The best solution for email, if your provider offers it, is an IMAP account. With IMAP, messages stay on the server and copies are stored Outlook. It won’t help you with calendar or contact sharing though.

If Exchange server is not in your cards (hosted Exchange accounts are about $10 a month) look for utilities that can make sharing easier at Sharing Microsoft Outlook Calendar and Contacts and Synchronizing Outlook on Two Machines

9. Recipients see e-mails with weird characters

There are occasional problems with font encodings. It doesn't annoy me, because I know email and understand it’s an imperfect method of communication. You can spend hours designing a perfectly formatted message in Outlook, but it may look totally different on my Blackberry, in OWA, Gmail or Yahoo mail clients. Plain text isn't immune to problems - you may use fixed width fonts and I use proportional.

10. Outlook won't play nice with Gmail

It works fine for me using IMAP, but there differences in how gmail works compared to how traditional mail clients work. In many ways, gmail gets it right but the "right way" not the way most users are used to. One of the biggest complaints is that it doesn't deliver mail you send to yourself.

If you're having problems with gmail, begin by checking your POP or IMAP account settings on the gmail site.