Outlook horror stories--and remedies

Microsoft Outlook is far from perfect, but the good news is that its most common failings can be corrected. We show you how.

tutorial Microsoft Outlook is the Jekyll and Hyde of the Microsoft Office suite. When Outlook is good, it's very good. But when it's bad, it's a horror show.

To help you chase away those Outlook gremlins, we've identified five common Outlook nightmares--together with expert tips and downloads.

Problem 1: I keep searching and searching…

Searching in Outlook is like a bad dream--the one where you're trying to run and your feet keep moving, but you get nowhere. As one sufferer puts it, "Whenever I try to search for messages in Outlook, the dreaded hourglass pops up, and I stare at it for minutes at a time--that is, if the blasted program doesn't crash altogether. What's the point of having a search feature if it takes so long?"

Although Outlook gets a makeover and new features with every Office update, its sluggish search engine hasn't changed much. Outlook still physically scans each of your messages when you search. This is fine if you have only a few dozen messages in your Inbox. But let's not fool around: if like most people you have more than a thousand messages in your Outlook folders, you have a search nightmare on your hands.

Can this nightmare be banished? Try these ideas:

A. Divide your messages up into subdirectories
Once you've created subdirectories (lots of them) and siphoned all your messages from your Inbox, stop the global searches and restrict your searching to individual subdirectories. By cutting down on the number of messages Outlook needs to search, your search results will speed up dramatically.

B. Install a message indexer
Search engines like Yahoo and Google don't actually scour every page on the Web each time you plug in a search term; if they did, you'd grow cobwebs waiting for your results. Instead, these services continually scan millions of Web pages and create a massive index of their contents. When you perform a Google or Yahoo search, the lightning-fast results come courtesy of the index.

Figure 1: Lookout lets you search Outlook much faster than Outlook's own built-in search.

Email indexers use the same principle to speed up your searches. We're partial to Lookout, a plug-in that installs its own search box into the Outlook user interface. The first time you run Lookout, the program indexes all of your email messages, a process that can take several minutes, depending on how many messages you have. Once the indexing is completed, just type in a search term, and your results will appear almost instantaneously. You can set Lookout (which was recently acquired by Microsoft, of course) to index new messages in the background so that you never have to go through the start-up index process again.

Problem 2: The incredible shrinking inbox

Here's a common lament: "My Inbox is giving me the squeeze! Every few hours or so, I try to send email, only to be stopped in my tracks by a stupid error message: 'Your mailbox is over its size limit'. I have to waste precious minutes pruning my Inbox and subdirectories while my boss does a slow burn in her office. Finally I'll free up enough space to send the email, only to get the same error again a few hours later! I'm at the end of my tether. Can't my email administrators just up my mailbox limit or something?"

Yes, Outlook seems to derive a cruel pleasure in hitting us with the 'Your mailbox is over its size limit' error just when we're sending the most important email of the day. All too often, we have had to scramble to delete messages, sometimes even trashing mission-critical email in the process. And even if you have no email administrator, Outlook can become unstable if your Inbox grows too big.

Can this nightmare be banished? Here are a couple of tips to help cut your mailbox down to size:

A. Archive your messages
Everyone groans whenever we make this suggestion, but taking the time now to set up your archiving settings will save you grief later. Just follow these steps:

  • Right-click your Inbox or a subdirectory, click AutoArchive, and select the 'Archive this folder using these settings' radio button.

  • Decide when messages get archived and where to store the archive on your system. This gets your email off the servers that are under the control of the stingy IT people--who are ultimately responsible for your out-of-space messages to begin with--and onto your local hard disk. When you've finished setting AutoArchive preferences for all of your directories (and don't forget Sent Items), go to the File menu, select Archive, click the 'Archive all folders according to their AutoArchive settings' radio button, and click the OK button.

  • Once Outlook is finished archiving messages, check to see if your mailbox is below your IT department's size limit. Right-click Personal Folders and click the Folder Size button; if the total size of your folders is larger than what your IT administrators allow, adjust your AutoArchive settings until you fall below the limit.

Figure 2: Use AutoArchive to keep your Inbox small and avoid the size limit snag.

B. Strip attachments from your email
Are you prudent about cleaning out your Inbox, yet you constantly run out of mailbox space? You might have a problem with out-of-control attachments. Average Word files might be only 50KB to 100KB, but they add up quickly if your colleagues send them day in and day out. Try Attachment Save, a nifty Outlook add-on that strips away attachments and saves them on your hard drive as they arrive in your Inbox. Attachment Save automatically saves attachments to the directory of your choosing and adds a link to the file in the email. The program can leave the paper-clip icon on a stripped message so that you can keep track of your stripped attachments, and you can set rules for which attachments get stripped and which don't.

Figure 3: The Attachment Save add-in automatically moves attached files to your hard disk.

Problem 3. The two-headed monster

Recently a user complained to us--twice, of course--of his dual-personality problem: 'I'm running Outlook on my office PC and my home computer, and keeping them both in sync is giving me ulcers. I have too many calendar items to update manually, and don't even get me started on syncing my email messages. How can I tame this two-headed beast so that it works for me, not against me? And how do I keep from trashing all my Outlook data in the process?'

Keeping two machines on the same page with Outlook is a tough job. The brute-force solution that many people use is to transfer Outlook's main data file (a Personal Folder file that's typically named Outlook.pst) from one system to another. Sure, copying the file between your two systems should theoretically keep them in perfect sync, but the file itself can get to be huge: even a modestly sized mailbox can have a 150MB or larger PST file. For most people it's too big a file to move back and forth. And if you do, and do it wrong, you'll lose important data.

Can this nightmare be banished? Try these synchronization tips:

Note: We strongly recommend that you use only sync utilities (such as those listed below) that let you review changes before they're made; otherwise, you run the risk of wiping out your precious data in one fell swoop.

A. Exchange users: just go online
If you have a corporate installation of Outlook--that is, you use an Exchange email server--Outlook actually does a very good job of keeping the Inbox in two machines up-to-date. However, this method doesn't work for your archive folders. So...

B. Sync your PST files
Syncing up every Outlook contact, appointment and email between two PCs sounds like a daunting task, but we found a couple of utilities to ease the pain. OutlookSync scans just about every Outlook item, including all of your mail folders, appointments, tasks, notes and contacts, and it creates a relatively small data file (in our tests, the file was about a tenth the size of our Outlook PST file). You then copy the file to a CD or a flash drive and transfer it to another PC that has OutlookSync installed; the program will sync all of your calendar items, to-dos, and address cards. Need your email synced as well? Try Easy2Sync, a program that compares the Outlook PST files for your two PCs, copies over new messages and even syncs up any changes to your mail folders.

C. Sync online
If you need to keep only your appointments, contacts and to-dos synced between two machines, consider using Intellisync for Yahoo to sync up your Outlook info with Yahoo's calendar, contacts, notepad and tasks. Intellisync features a series of conflict resolution options and will check in with you before deleting, adding or otherwise changing your contacts and appointments. Once you've synced your office PC with Yahoo's services, you can sync up the Yahoo info with your home PC. The only challenge is remembering to sync up at the beginning and end of each session with your respective systems, lest you erase any changes by mistake.

Figure 4: A synchronisation tool such as Intellisync can save you from having to copy giant PST files back and forth.

Problem 4: Spam overload

A common complaint: 'What did I do to deserve this? Spammers dump a daily dose of filth in my Inbox, and my colleagues are starting to wonder about me. I've turned on Outlook's spam filter and set it to High, yet the junk just keeps coming. Make it stop!'

As much as Outlook's spam filter has improved in the latest version, plenty of junk mail still slips through the cracks. And if you're using an older version of Outlook, your daily spam delivery can easily outnumber the legitimate messages you get.

Can this nightmare be banished? Here are some tips and utilities:

A. Tweak your spam settings
If you're getting deluged with spam, make sure Outlook's junk filter (in version 2003) is set to High. From the Tools menu, select Options, click the Junk E-mail button, and make sure the High radio button is selected. If you want hard-core spam protection, select Safe Lists Only, which will block all messages except those sent from addresses you put in the Safe Senders list (also known as a whitelist). It's an extreme measure that will probably block many legitimate messages, but you'll never get spam again. Also, be sure you have the latest SP1 update of Outlook 2003; its spam filter is improved over the initial version's.

B. Shore up Outlook's spam filter
If Outlook's junk-mail filter isn't doing the trick, call for reinforcements. Anti-spam add-ons such as Outlook Spam Filter, InBoxer and MailFrontier Desktop use advanced Bayesian filters that analyse your legitimate email and learn the types of messages you send and receive, making the junk mail easier to catch.

Figure 5: Many add-in spam tools give you more flexibility than Outlook 2003's own filter.

C. Try a challenge/response service
Spam usually comes from an automated email server, not a person (and if there are any spammers out there lovingly crafting each junk message by hand, we'd rather not meet them). Challenge/response email services (such as MailBlocks, which is compatible with Outlook) target spam by checking to see if there's a real person behind an incoming message. If anyone who's not in your email address whitelist sends you a message, the service automatically sends a reply that asks the sender to click a link, to enter a series of numbers, or to do some other task that proves there's an actual person sending the message. If the sender passes the test, the message goes in your Inbox. The only problem with challenge/response services is that they might block automated messages that you want, such as newsletters and autoreplies for lost passwords.

D. Use disposable passwords
How many times have you blithely sent your email address over a Web form? Too many to count? Unfortunately, spammers love grabbing email addresses from online forms--and from Web pages, for that matter. Instead of handing over your real email address when you're online, try using disposable addresses. Email services such as Yahoo Mail, Spamex and E-mailias let you create temporary email aliases that you can use in Web forms. If you get a sudden influx of spam from one of the aliases, just turn off the alias and get a new one.

Problem 5: The Outlook hot zone

Computer viruses are like the weather: everybody talks about them. Mostly the complaints run along these lines: 'Outlook is a virus magnet! Seems like I can never watch the news or pick up the paper without a story about yet another killer virus targeting Outlook. The last person at our office to get hit with a virus lost days of work. I'm terrified that my PC will get infected too!'

Be afraid. Be very afraid. Because in this case your fear will serve you well. Outlook is an irresistible target for virus writers. Still, just because hackers have drawn a bead on your system doesn't mean you're destined to get infected.

Can this nightmare be banished? Here are some simple steps you can take:

A. Don't open suspicious attachments… ever
If you're still tempted to open dodgy-looking pictures or click a read-me file from a stranger, we have two words for you: Stop it! Never open an attachment you weren't expecting to get.

Even if the attachment is from someone you know, be careful. Spammers and virus writers can spoof infected machines and make it look like messages from them come from your friends.

B. Check your antivirus settings
This assumes that you have antivirus software. If you don't, stop here and go get some here.

Your antivirus software won't do you much good unless it's set to give you maximum protection. Go to the Preferences or Settings menu of your antivirus software and make sure these options are enabled:

  • Autoprotection: Your security software always should be scanning your files for potential viruses. Make sure this always-on protection is activated, preferably as soon as your system boots up.

  • Automatic updates: Antivirus software is only as good as its virus definition files, which store profiles of the latest threats. Most security programs will download and install the most recent updates automatically; double-check to make sure this option is activated.

  • Scan incoming and outgoing files: Viruses almost always come in the form of email attachments. Make sure your antivirus software is scanning any and all attachments as they arrive and as they depart (in case your system becomes a carrier).

C. Get the latest security updates
Having a hard time keeping track of the latest Microsoft patches? We don't blame you. Quickly scan your system and see if you need any updates by visiting Microsoft's Office Update site. And if you're still using Office 2000, make sure you've installed Service Pack 3, which will help Outlook block EXE attachments and other potentially malicious files (those with Office XP or later already have this protection).

D. Keep viruses to yourself
If, despite your best efforts, a virus slips through Outlook's cracks and your PC is infected, the last thing you want to do is spread the bug to everyone in your address book. We found a couple of utilities that will protect your friends and colleagues if your system falls victim to a virus.

  • ViraLock: This Outlook add-on keeps viruses from emailing themselves to everyone in your contact list by encrypting all of the email addresses in your address book. When you're ready to send a message to a friend, ViraLock seamlessly decrypts the email address.

  • VirusArrest: What if a virus beats the odds, cracks ViraLock's encryption (unlikely, but always possible) and prepares to send itself to everyone in your address book? VirusArrest might be the last line of defence. The program requires you to approve any outgoing email with an attachment. If you're warned that an email message is about to go out and you didn't know about it, you can stop the message (and its payload) in its tracks.