Get Rid of 10 Microsoft Outlook Aggravations

Microsoft Outlook is a nearly ubiquitous presence in PC computing -- and, seemingly, a universally reviled one. Outlook has countless features, ranging from e-mail gathering to calendaring, contact tracking, to-do list creation and more -- yet its tendency toward bloat, sluggishness and unreliability can make it maddening to use.

The Internet is rife with people complaining about Outlook, and I admit that I've been mighty annoyed with the program myself over the years. But I'm ready to move beyond that -- I've found solutions for the problems that most bedevil Outlook users. So whether you hate Outlook, love it or fall somewhere in between, read on to find fixes to some of the most common problems that drive Outlook users (including me) off the deep end.

Note that I focus here on the most recent version of Outlook, Outlook 2007. Many of these fixes will work with earlier versions of Outlook, but not all of them, so be aware of that. Also, I focus here on using Outlook for POP3 mail; I don't cover Outlook used in an Exchange environment. There are simply too many variations with Exchange that are specific to enterprises for us to cover well. However, you should find that many of the fixes we offer below work in Exchange environments as well.

Ready for the roster? Here it is, in rough order from most to least annoying:

Annoyance No. 1

Outlook is too darn slow. How can I speed it up? Outlook sometimes seems to have three speeds: slow, slower and slowest. It takes too long to load, and it's sluggish when it sends or receives mail -- in short, it takes too long to do anything at all. There must be some way to goose this thing.

How to fix it: There's no single action you can take to speed up Outlook, but a combination of fixes should make Outlook zippier. We can't promise it will ever be a speed demon, but follow our advice and most likely you won't feel stuck in the slow lane.

First, slim down your Outlook .pst file, as we recommend in Annoyance No. 2. That by itself will do a world of good.

Then make sure that Outlook has the latest patches, via Windows Updates. There's one patch in particular that is important if you have sizable .pst files: Update for Outlook 2007 (KB933493). The patch is designed to speed up Outlook when using large .pst files, and many people have found it has made a significant difference in Outlook speed. In fact, they report that installing that patch alone solved their speed problems.

Next, kill any Outlook add-ins you don't need, as outlined in Annoyance No. 5.

Quite a few people have reported that iTunes installs an Outlook add-in -- though for what purpose is unclear -- and that deleting it speeds up Outlook.

And some people have reported that Windows XP Fax Services causes their version of Outlook 2007 to behave sluggishly for whatever reason. If you don't fax in XP, you may be able to speed up Outlook by removing that feature. (To remove it, choose Control Panel --> Add or Remove Software --> Add/Remove Windows Components.)

Along the same lines, a number of users say the Business Contact Manager seriously slows down Outlook 2007, so if you have that installed, try uninstalling it using the same procedure.

Finally, check your RSS feeds. Outlook's RSS Feeds editor is a great feature, but using it can significantly slow things down. It comes preconfigured to receive a number of feeds that you may or may not want to receive. And over time, you may have subscribed to feeds you no longer read.

Select Tools --> Account Settings and click the RSS Feeds tab. You'll come to a screen like the one shown above. Scroll through your list of feeds. For the ones you no longer want, highlight them and select Remove. When you're done, click OK.

Annoyance No. 2

Outlook's attachments make it massively bloated. If you regularly send and receive attachments, your Outlook .pst file can quickly become massively bloated. It's pretty easy for your .pst file to quickly get to 250MB or more, and I've known people whose files range up to 1GB and beyond. Among other problems, this slows down the speed at which Outlook loads and can lead to instability.

How to fix it: It's time to put Outlook on a diet. First, find out where the fat is. Outlook 2007 has a very useful folder called "Larger Than 100 KB." Find it underneath Search Folders in your list of Outlook folders. As the name implies, it lists all e-mail messages that are larger than 100KB. By default, they should be listed with the largest files first, but if not, click the Size heading in the folder until you get them listed that way.

Now that you can see the largest e-mails, start trimming. If you're like me, you'll be surprised how many of the e-mails with attachments you no longer need; delete those. If you need the attachment, but don't need the accompanying e-mail, save the attachment to disk, then delete the e-mail.

If the opposite is true -- you want to save the e-mail but not its attachment -- you can save space by either saving the attachment outside of Outlook or deleting it altogether. First, save the attachment to disk. Then open the e-mail, right-click the attachment and choose Remove. The attachment will be deleted from Outlook, but the e-mail itself will remain.

The attachment problem in Outlook is so notorious that a third party has stepped in with a solution that helps you cut down the size of your .pst files by removing attachments. The free Kopf Outlook Attachment Remover saves attachments from Outlook, stores them on your local disk and replaces the attachments with a link to the stored file. You'll be able to open the attachment as you would normally, except that Outlook will grab the file from disk, rather than from inside its .pst file.

You can have the program automatically go through entire directories, removing attachments and replacing them with links, or you can instead do it e-mail by e-mail. Note that in Outlook, it will look as if the file is still there -- you'll see the file icon as you normally do for an attachment. But the file is actually on disk, not in Outlook.

Outlook 2007 includes another tool for shrinking the size of your .pst file by targeting your fattest folders. Select Tools --> Mailbox Cleanup and click the View Mailbox Size button. You'll see a screen like the one shown below.

There will be a list of folders, along with the total size of each folder. That will tell you where you'll be able to get the most reduction by cleaning out e-mails -- and their bloat-inducing attachments. After you find the largest folders, go back to the Outlook main screen and tackle those first, searching for unnecessary e-mails and attachments and deleting them.

After you've used all of these techniques for deleting attachments and e-mails, it's time to compact your .pst file. Normally, when you delete files and attachments, there are essentially blank spaces left in your .pst file that take up bytes.

Compacting the file eliminates those blank spaces and shrinks the total size of the file. To do so, select File --> Data File Management and double-click the Personal Folders entry. Then click Compact Now.

Annoyance No. 3

Why can't I find where my $#%^(@"* Outlook data is stored? All of your mail, contacts, attachments, calendar information and so on -- pretty much the whole Outlook data shebang -- is stored in a single .pst file. You often need to know where that file is located if you want to, for example, back it up or move it between machines. But Microsoft has a penchant for changing the .pst location from version to version of Outlook, and you might have a hard time finding it.

In addition to the .pst data file, Outlook uses a variety of other files that do things such as store your personal preferences. You often want to know their locations as well.

How to fix it: Outlook 2007 generally stores its .pst files in different locations depending on whether you're using XP or Vista. In Vista, you'll find it in C: \Users\YourName\AppData\Local\Microsoft\Outlook, where YourName is your Windows user name. In XP, it's usually in C: \Users\YourName\Local Settings\Application Data\Microsoft\Outlook.

Of course, there's also a chance that Outlook has stored them in a different location, but at least it's easy to find their location: In Outlook, choose File --> Data File Management. You'll see a screen like the one below. Look for the Personal Folders listing for your Outlook .pst file. Next to it, you'll see its location listed.

As for all the other Outlook files, in Vista, you'll find them in C:\Users\YourName\AppData\Roaming\Microsoft\Outlook, and in XP they're in C:\Users\YourName\Application Data\Microsoft\Outlook.

Annoyance No. 4

Outlook doesn't offer much help with e-mail overload. Outlook's limited searching, filtering and sorting functions can take you only so far if you're looking to better organize your e-mail and improve your productivity. It won't let you view entire message threads, for example, and its search features could use some help.

How to fix it: A lot of Outlook add-ins make big claims about helping with e-mail overload, and I've found one that actually delivers -- and in a big way. The free Xobni (that's inbox spelled backwards) makes it extremely easy to find e-mail, information and contacts. It may be the best Outlook add-in I've ever used.

Xobni appears as a sidebar on Outlook's right-hand side. When you read an e-mail message, the sidebar displays information about the person with whom you're communicating, including a list of all "conversations" you've had with him, a list of all files you've exchanged, the person's phone number and your "social network," which is essentially a list of shared contacts with whom the two of you have exchanged e-mails or been cc'd on.

That means for every e-mail you get, you can see a quick history of all of your previous e-mail exchanges with the sender, a tremendous timesaver when you want to review your communications with someone. Xobni also lets you review all of the e-mails in the sidebar itself by clicking on any of them, and it shows the e-mails as threaded conversations so you can trace their history.

There are also convenient icons in the sidebar screen for sending an e-mail to the person and scheduling a meeting via Outlook's calendar.

And at the top of the screen is great information for data addicts, although it's unclear how useful it actually is. You'll be shown the total number of e-mails you've exchanged with the person, the rank of the person among those you've exchanged e-mails with, and a graph displaying the hours of the day and how many e-mails you typically receive from that person during each of the hours.

In fact, statistics lovers can quickly get lost in this program; there's a Xobni Analytics feature that provides a mind-boggling amount of information about your e-mail use, such as the average amount of time it takes you to respond to people by day, month and week. And that's just the beginning. You can, for example, even see the median time it takes you to respond to individuals, to individuals in a domain ... well, you get the picture.

Don't get this program for the analytics, though. Get it to cut through your Outlook e-mail and information overload.

Annoyance No. 5

Outlook crashes constantly. Sometimes it seems as if Outlook crashes more than it actually runs. Didn't anyone tell Microsoft that the point of an e-mail program is to get e-mail -- not to turn belly-up every other time you open it?

How to fix it: We can't offer fixes for every Outlook crash, but we can address what is most likely the primary cause of problems -- add-ins. Some Outlook add-ins will crash the program on their own, and others will crash Outlook when they're installed in concert with other add-ins. So your best bet for stopping crashes is to first figure out which Outlook add-in or add-ins might be causing the crashes and then delete them.

One good way to find out if add-ins are the culprit of crashes is to first run Outlook in safe mode and see if it crashes. Safe mode disables all add-ins, so if you run it in safe mode and it still crashes, add-ins aren't the cause of your problems. Conversely, if you run it in safe mode and it does crash, then an add-in is likely the cause and you're then free to go through the steps I outline below for finding the culprit.

Run Outlook in safe mode by going to a command prompt, navigating to the directory that contains Outlook.exe (most likely C:\Program Files\Microsoft Office\Office12\) and typing this command:

Outlook.exe /safe

That runs Outlook without any add-ins. If it doesn't crash, then add-ins are your problem.

Here's how to find exactly which program is the problem. Start by discovering which add-ins you have installed. Select Tools --> Trust Center and click the Add-ins button. You'll see a screen like the one pictured below.

You'll see add-ins organized into three categories: those that are currently active, those that are installed but aren't currently active, and those that are installed but have been disabled by Outlook because they cause the system to crash. (Yes, Outlook does try to fix itself when possible -- it just doesn't always succeed.) To see a description of each add-in, highlight it, and you'll see the description at the bottom of the screen.

Now it's time to find out which add-in or add-ins are causing the crashes. There's no logical way to do this; you'll have to use the process of elimination. At the bottom of the screen, make sure that the COM Add-ins drop-down is selected, then click Go. You'll see a screen like the one pictured below.

Those add-ins that are active have check marks next to them; those without check marks are inactive. Uncheck the box of the add-in that you think might be causing the problem, click OK, and then close and restart Outlook. Outlook will now run, but the add-in will be inactive. If Outlook works properly, you've discovered the cause of your problem.

You can keep running Outlook with the add-in inactive or instead remove it from your system. Some add-ins can be removed using Windows' normal Uninstall routine. Others, though, won't be visible there. To remove those, get back to the screen you used for disabling add-ins. Highlight the add-in you want to remove and click Remove. Be careful before you do this, because you won't get a dialog box asking if you really want to remove it, as you do when you use Windows Uninstall. Click it, and it goes away immediately.

If it's an add-in that you would prefer to keep using, check with the publisher to see if there's a workaround or fix before deleting it.

Annoyance No. 6

My .pst file is corrupt. If you've used Outlook long enough, at some point, your .pst file may get corrupted and no longer load. What can you do?

How to fix it: First off, prevention is better than recovery. When .pst files get up to 2GB, they can easily become corrupt, so make sure that your .pst file does not get to be 2GB or larger in size. (See Annoyance No. 3 for details on how to find the location of your .pst file. Then simply open Windows Explorer, navigate to the correct location and click on the file icon to check its size.)

In addition, it's always a good idea to back up .pst files so you can revert to them if any gets corrupt. Now that you know where Outlook 2007 files reside, take advantage of that knowledge by making sure to back up those files regularly.

Now on to fixing the corrupt file. There's a free Microsoft utility called the Inbox Repair Tool that's designed to fix corrupt .pst files.

The file name is Scanpst.exe, and its location seems to vary from machine to machine, but a good place to look is in C:\Program Files\Microsoft Office\Office12. Before running the program, back up your damaged .pst file. Then run the program (as you can see at right), choose your .pst file location and tell the program to do its work.

The program should fix the corrupt file. If not, try using it three or four times; sometimes it takes several passes in order to fix the file.

If that doesn't work, you do have one other option. Though we haven't had a chance to test them, there are a variety of programs that claim they do a better job than the Inbox Repair Tool of fixing corrupt files. A Google search will turn up several if you want to go down that path.

Annoyance No. 7

How can I kill duplicate Outlook entries? In Outlook, duplicate e-mails, contacts, tasks, notes and other information have an annoying habit of appearing out of the blue. Sometimes this happens when you import data from an earlier version of Outlook. And other times ... well, I simply don't know why it happens, but it does. You say you'd like to be able to kill duplicates without devoting your life to tracking down every single one and deleting by hand?

How to fix it: Once again, a third party has stepped up to the plate with a solution. Download the free Outlook Duplicate Items Remover, close Outlook, and install the software.

Once you do that, you'll find a new Outlook menu option, ODIR. Click the menu option, select Remove Duplicate Items and, from the screen that appears, select a folder from which you want duplicate items removed. Click Remove Duplicate Items, and it searches for duplicates in the folder. At that point, it copies the duplicated items to a folder, so you have a backup, and removes the duplicates from Outlook.

Annoyance No. 8

Why can't I synchronize Outlook on multiple PCs? If you've got multiple computers from which you want to access e-mail -- a desktop and a laptop, let's say -- this one may well top your all-time annoyance list. You have Outlook on both machines, but there doesn't seem to be a way to keep your mail in sync -- the mail on your laptop doesn't match that on your desktop. What you'd like seems simple: No matter which machine you use, you'd like it to have all of your e-mail and be up to date.

How to fix it: As I've explained, Outlook keeps its data in one big .pst file. So if you want your mail to be up to date on whatever machine you're currently using, you'll have to manually copy that file between machines.

For example, let's say you're using your desktop PC, and you're about to head out on the road with your laptop. You must copy the desktop's .pst file to your laptop before you go. Then you can use Outlook on your laptop as you would normally. When you return, copy the .pst file back from your laptop to your desktop, and your desktop will be up to date. (See Annoyance No. 3 for ways to find the location of your .pst file.)

Although this back-and-forth copying will solve your problem, it's a major-league pain in the hindquarters. And it's prone to error as well -- you may accidentally overwrite a newer .pst file with an older one.

If you're willing to spend a little money, there's a more bulletproof solution: Get a program that will automatically synchronize your Outlook data between PCs. I found two good pieces of software that do the trick.

SynchPST for Outlook and PSTSync both do similar tasks and come with extras, like the ability to copy and synchronize only individual folders instead of entire .pst files. They're both shareware, so you can try them before you buy them. SynchPST costs $39.95 for the Basic version and $69.95 for the Professional version, which has extras such as the ability to schedule automated syncs. PSTSync costs $59.99.

If you use a laptop and a desktop, and have set up your desktop for remote access, then there's an even simpler solution. When you're on the road and need to check your e-mail, make a remote connection to your desktop and run Outlook remotely. That way, you won't need to do any synchronization at all.

Annoyance No. 9

People complain my e-mails have weird characters and spaces in them. Outlook 2007 uses Microsoft Word as its mail editor. Even if you don't have Word installed on your system, Outlook uses a Word .dll, and so Word is what you get when you compose mail. Because of that, when you type an apostrophe, quotation mark or some other special characters, they may show up in other people's e-mail as blank spaces or oddball characters.

How to fix it: The problems are caused by Word's use of so-called smart quotes, which from some points of view aren't so smart. They're not plain-text characters, and so other e-mail readers may interpret them oddly, particularly if the e-mail reader uses plain text instead of HTML.

To fix the problem most easily, in Outlook select Tools --> Options --> Mail Format, and from the drop-down box in the Message format area, choose Plain text and click OK. From now on, Outlook won't use smart quotes. However, it also won't use HTML, either, so you won't be able to use fonts, colors and so on.

If you'd prefer to use HTML text for most messages but use plain text only for some, when you create an e-mail message, select Options from the ribbon at the top of Outlook, and click Plain Text. That way, only that message will be created using plain text; all others will still use HTML.

There is a way to use HTML for your messages and turn off smart quotes at the same time. Select Tools --> Options, click the Mail Format tab, and click the Editor Options button. Click Proofing, select AutoCorrect Options, and then click the AutoFormat as You Type tab. Uncheck the boxes next to "Straight quotes" with "smart quotes," "Ordinals (1st) with superscript," and "Hypens with dash." Click OK, and keep clicking OK until the dialog boxes go away. You'll be able to compose HTML mail from now on, but without the oddball characters.

Annoyance No. 10

Why won't Outlook work seamlessly with Gmail? Gmail can be used as a POP3 client, just like any other ISP. But users have complained that they can't get Outlook to work properly with Gmail because of the complexity of configuration. Is there any way it can be done more simply?

How to fix it: Yes, it's confusing to configure Outlook to work properly with Gmail. But I'm here to report that it can, in fact, be done -- and to show you how to do it.

First, you'll need to tell Gmail you want to use it as a POP account. In Gmail, click Settings, and then click Forwarding and POP/IMAP. Select "Enable POP for all mail" if you want to download all mail to Outlook -- including existing mail -- in your Gmail account. If you only want to download mail that you receive in the future, select "Enable POP for mail that arrives from now on."

Next, select how you want Gmail to handle incoming messages -- whether to keep copies of messages in your inbox after they've been downloaded to Outlook, delete the messages or archive them. After you've done that, click Save Changes.

With that done, you're ready to tell Outlook how to work with Gmail. Here's how to do it:

1. In Outlook, select Tools --> Account Settings and click New.

2. From the screen that appears, select "Microsoft Exchange, POP3, IMAP, or HTTP" and click Next.

3. On the screen that appears, type in your name, Gmail e-mail address and your password in the appropriate boxes. Check "Manually configure server settings or additional server types" at the bottom of the screen and click Next.

4. From the screen that appears, select Internet E-Mail and click Next.

5. A screen like the one above appears. For Account Type, select POP3. For Incoming mail server, enter pop.gmail.com. For Outgoing mail server (SMTP), enter smtp.gmail.com. In the Logon Information area, enter your username and password. Check the box next to Remember password.

6. Click More Settings and select the Outgoing Server tab. Check the box next to "My outgoing server (SMTP) requires authentication." Then select "Use same settings as my incoming mail server."

7. Click the Advanced tab. Check the box next to "This server requires an encrypted connection (SSL)" under Incoming Server (POP3).

In the box next to Outgoing server (SMTP), enter 587. Select TLS from the drop-down menu next to "Use the following type of encrypted connection:".

Make sure that 995 is in the box next to Incoming Server (POP3). The screen should look like the one below.

8. Click OK. From the screen you're returned to, click Test Account Settings.

You should see a screen like the one below, showing you that you've set it up successfully. Click Close. From the screen that appears, click Finish. You're now ready to use Outlook with Gmail.

It's ironic -- or perhaps prophetic -- that we end with Gmail, since surveys indicate that more and more people are switching to Web-based mail.

In the meantime, Microsoft Office continues to dominate in corporate environments, which means workers must find ways to make peace with Outlook. I hope I've managed to set you on the path to Outlook enlightenment.

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