Email is one of the most important communications tools for businesses. When it stops working, people start to get nervous.

While there are many things that a user can do to mess up their email, many of these problems can be resolved with a restart of the software or the computer.

However when the old standby of restarting doesn’t work, it is time for the email administrator to start looking into the issue a bit more deeply.

Here are some of the more common errors found in Outlook 2007 along with some of the ways you can make things right again:

1. Error message that reads: “Cannot open your default e-mail folders. The information store could not be opened.”

This issue can be fixed by first locating Outlook.exe that can be found here: C:\Program Files\Microsoft Office\Office12.

Next, right click Outlook.exe and then click on Properties.

On the Compatibility tab, clear the check box that reads ‘Run this program in compatibility mode’. Then click Ok and restart Outlook.

2. Error message that reads: “Your Microsoft Exchange Server is unavailable.”

This error is a bit trickier to resolve only because there can be many different causes.

No data connection – test your SMTP connection using telnet. If you are unsure how to do this, Microsoft has provided a guide on their TechNet site that walks you through this process: http://technet.microsoft.com/en-us/library/bb123686.aspx.

Office Outlook files are locked – there are times when .ost and .pst files are accidentally, or purposefully, set to read only. Check the permissions of these two files by navigating to:

C:\Users\<username>\AppData\Local\Microsoft\Outlook\ for .pst files and C:\Program Files\Microsoft Office\Office12\ for .ost files. Make sure that neither is set to read only.

Third party applications are interfering with Outlook – many programs, including anti-malware solutions, can interfere with Outlook connecting to the Exchange Server. To check to see if this is the cause, start Outlook in safe mode.

Outlook files are corrupted – this can happen after an upgrade is applied to Outlook. If any of the .dat files listed below are present they should be deleted or renamed.

• Extend.dat – Located in C:\Documents and Settings\<username>\Local Settings\Application Data\Microsoft\Outlook\
• Frmcache.dat – Located in C:\Documents and Settings\<username>\Application Data\Microsoft\Forms\
• Views.dat – Located in C:\Documents and Settings\<username>\Application Data\Microsoft\Outlook\
• Outcmd.dat – Located in C:\Documents and Settings\<username>\Application Data\Microsoft\Outlook\

All the files, with the exception of Outcmd.dat will be re-created. The Outcmd.dat file saves customized toolbar settings so if it is removed these settings will have to be re-applied.

3. Office Outlook will not open personal folders or personal folders do not show up in Outlook.

Personal folders are often the root of many problems related to Outlook. Microsoft has published the Inbox Repair tool, Scanpst.exe, that can be used to scan .pst and .ost files for errors in the file structure. If this is not intact, it will reset the file structure and rebuild the headers.

This tool will only work on the files that reside on your computer’s hard drive, not the files on the Microsoft Exchange Server.

This will also help to resolve the error message: “Cannot open your default e-mail folder. The file c:\users\owner\documents\software info\outlook.pst is not a personal folders file”.

4. Error messages that read either: “The action cannot be completed. The connection to the Microsoft Exchange Server is unavailable. Your network adapter does not have a default gateway” or “Your Microsoft Exchange Server is unavailable”.

This error occurs when Outlook is unsure of the default gateway address. The former is the error message that shows when the Outlook profile is configured automatically and the latter appears when the profile is manually configured. Both have the same fix.

To repair this you will need to edit the registry so clicking on Start and then Run is necessary. Then, enter regedit in the Open box and click OK.

Next, navigate to the registry key: HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\RPC. On the Edit menu, point to New, and then click DWORD Value.  Type DefConnectOpts, and then press ENTER. Now, right-click DefConnectOpts, and then click Modify. In the Value data box, type 0, and then click OK.

5. None of the authentication methods supported by this client are supported by your server.

This happens to people when they use their computer in multiple locations. For example, a laptop is taken home and connected to the home network or perhaps a computer is taken on the road. Basically, it comes from authentication rules for the SMTP server.

When this error occurs go to the Account Settings tab and click on Change then More Settings. Now select the Outgoing Server tab.

The option that reads: “My outgoing server requires authentication” and the one that reads: “Log on to incoming mail server before sending mail” should both be looked at. If there is a check in the option box remove it.

5 Common Outlook Errors and How to Fix Them

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Over the years, Microsoft has taken its lumps when it comes to security however as a company, they have taken some pretty impressive strides to make sure that their products are more secure.

However, their security efforts have not been limited to just their products. They have launched several educational campaigns aimed at helping users better secure their computers and networks.

These efforts can be seen by Microsoft’s latest report, Microsoft Security Intelligence Report, and its corresponding website.

This project was set up to provide businesses and consumers with hard data concerning security risks and best practices from Microsoft themselves on how to mitigate the various risks.

Being the producer of the most popular email client software packages – Outlook, Hotmail, Outlook Express and Windows Live Mail – they have a definite interest when it comes to helping users guard against email threats.

Spam, according to Microsoft:

• Wastes resources
• Distracts recipients
• Puts assets at risk for greater security problems
• Provides an avenue for social and criminal hacking attempts
• Provides an avenue for phishing scams against users

While stopping these issues definitely is a concern for Microsoft internally, educating their customers on how to eliminate the problems associated with spam will certainly help them sell more products to people looking for the most secure product on the market.

A Look Inside Microsoft

According to their website, Microsoft filters between five to ten million email messages every day that contain malware and/or spam. On a daily basis, they see threats that include spyware, worms, attacks from botnets and polymorphic viruses attacking their email messaging systems. Each day more than 100 different types of executable files are removed from incoming messages sent to Microsoft employees.

So we can safely say that as an organization, there is little that they haven’t seen when it comes to protecting email systems.

To best fight the many different threats facing email, all inbound email to Microsoft much pass a three-tiered process to include anti-malware scanning, file removal and spam filtering.

The importance of this approach is simple. Stop threats before they reach the user.

Incorporating an anti-malware scan into messaging systems helps protect the integrity of your systems because threats can be stopped before a user has the opportunity to allow infected files to compromise a computer or network.

Likewise, a file removal process prevents malicious executables sent via email attachment from ever having the chance to launch. Followed with adequate spam filtering, this process reduces the need for organizations to rely solely on a desktop based security solution or a network firewall. Both of which do not provide comprehensive protection on their own.

These strategies seem like common sense steps that we would hardly need to rely on Microsoft to provide. However many organizations neglect to incorporate these simple strategies into their planning.

Other Ideas from Redmond

Keeping systems protected cannot be done by simply scanning incoming messages for threats. Other steps need to be taken. The best practices that Microsoft recommends to organizations are as follows:

• Provide email submission services on port 587.
• Require SMTP authentication for email submissions.
• Abstain from interfering with connectivity to port 587.
• Configure email client software to use port 587 and authentication for email submission.
• Block access to port 25 from all hosts on your network other than those you explicitly authorize to perform SMTP relay functions.
• Monitor outbound email traffic patterns and look for deviations from normal behavior, such as abnormally large bursts of email traffic.
• Disable computers or individual email accounts that have been compromised and are being used to send out spam.
• When possible, process abuse complaints from third parties for email that originated from your mail servers. These complaints often point the way to a compromised computer.

As email administrators, we tend to look to hardware and software solutions to keep things running smoothly and securely. However, protecting systems and users from threats is ultimately our responsibility. Knowing the best way to do so is part of the job description.

Turning to experts for advice when it comes to security does not mean we are unable to do things on our own, it means we are wise enough to use what works and smart enough to know where to look.

Email Security Best Practices from Microsoft

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There was a time when using PST files were thought to be the solution to file storage problems. Getting emails out of the user’s mailbox and onto a shared repository not only freed up email inboxes from increasing file sizes, but also gave admins a central location in which all emails could be backed up and archived.

Add to these benefits the fact that PST files could be separated so emails related to a project, client, subject, etc could be stored and archived separately, and many would think that this solution was all that an IT department would need to manage their archiving and storage needs.

Of course PST files aren’t a panacea; they have many problems associated with them.

Working offline

More and more frequently, workers find themselves working remotely. When this happens, they don’t always have access to network resources so they find themselves working offline. This makes accessing PST files stored on a network device difficult, if not impossible, to use.

Workers who need to refer back to emails in their personal folders are pretty much out of luck.

Another, more common situation, arises when PST files are stored on a desktop computer at the home office and a remote worker is using a different computer; let’s say a laptop at home.

This user could not access his or her PST files if they cannot access that desktop computer where the file is housed. Now you may wonder why anyone would keep their PST files on the local computer as opposed to a shared network resource, but the scenario is actually quite common.

In fact, it was considered a best practice since Exchange 4.0.

According to the Technet blog:

“A .pst file is a file-access-driven method of message storage. File-access-driven means that the computer uses special file access commands that the operating system provides to read and write data to the file.

This is not efficient on WAN or LAN links because WAN/LAN links use network-access-driven methods, commands the operating system provides to send data to or receive from another networked computer. If there is a remote .pst (over a network link), Microsoft Outlook tries to use the file commands to read from the file or write to the file, but the operating system then has to send those commands over the network because the file is not on the local computer. This creates a great deal of overhead and increases the time it takes to read and write to the file. Additionally, the use of a .pst file over a network connection may result in a corrupted .pst file if the connection degrades or fails.”

Bad files

Anyone who has worked with PST files knows that they have a tendency to become corrupted or damaged. There is an entire industry dedicated to developing tools to help email administrators fix damaged PST files, and Microsoft themselves have published a number of tools to help fix specific problems.

These problems can occur due to hardware failures, such as:

• A failure in the storage device
• A power failure
• Failure in a networking device
• Failure in the network infrastructure

Of course, the software itself also has been known to create problems:

• Incorrect file system recovery where PST data is incomplete or incorrect
• Malware infections that damage PST files
• Outlook being terminated abnormally
• Deficiencies in Outlook itself

Regardless of what caused the problem, if you encounter damaged PST files it costs money to repair them. It can cost even more if you are required to provide information from them but can’t because they are corrupted.

The intent behind personal storage tables makes perfect sense. However, in practice email administrators need to find a better solution if they want to stop wasting time with the hassles presented to them by Outlook’s PST problems.

Solutions that are made to be stored on network file stores and less likely to be corrupted by common tasks, not only make life easier for the IT department, but legal departments as well, since accurate, reliable information can be provided when it is requested, not when a company eventually finds a specialist to piece everything together.

Two Big Problems With PST Files

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Continuing my predecessor’s efforts, in this post we are going to take a deeper look at resource mailboxes in Exchange 2010. These special purpose mailboxes are used for scheduling conference rooms, audio-visual equipment, bridge lines, loaner laptops, and any other resource that may be in broad demand and for which Outlook is a good choice to use for reserving the resource.

Meeting or conference rooms are a natural fit, since in the process of scheduling a meeting, most of the time you will need a place to hold the meeting. Extending this paradigm to other shared resources is a natural fit. When you want to use Exchange and Outlook to manage a shared resource, you create either a room mailbox, or an equipment mailbox using the EMC or EMS. This will create a disabled user account in Active Directory to represent the item. Then mailbox is used to hold calendar entries, and you populate the user object with attributes appropriate to the resource. For rooms, this can include the seating capacity, location, and whether or not there is a projector or display system. For other resources this may include details such as where to pick up the resource.

When creating a resource, one of the key decisions has to do with how requests from a user will be approved. In larger organizations, frequently a request will be routed to a facility manager or a receptionist who will approve or deny the request, while other organizations opt for an automatic approval on a first-come-first-served basis. You can also create more granular rules, including users whose requests will be automatically approved versus those who must be approved by someone else, what to do with conflicting requests, etc.

To create a room, use the EMC to create a new mailbox, and select the option to make it a room mailbox on the first screen. It helps to have a naming convention in place for rooms, especially if you have more than one location. The wizard will walk you through setting up a room, including the capacity and how requests should be processed. You can modify the properties of a room at any time to change the capacity or acceptance policy, and to add custom attributes to note whether the room has additional features like a conference phone, projector, etc. You can use the EMS command New-Mailbox to do the same thing, adding the -Room attribute to the end of the command to identify the mailbox as a room. Whether you tick the box in the GUI or use the -Room attribute, the mailbox is created with a disabled account in AD, and given additional attributes for RecipientTypeDetails, ResourceType, ResourceCapacity, and ResourceCustom. You can modify these in the EMS, or in newly exposed tabs in the EMC.

Best practices include the following administrivia:

• Create an OU in Active Directory to store resource accounts.
• Establish a naming convention that allows users to readily identify rooms by site and location.
• If you decide to have a user approve requests, make sure they have a backup who can approve things in their absence.
• Resource mailboxes will be smaller than normal users, and require less resources from Exchange, but are just as important as users’ mailboxes. Make sure to use DAGs to provide redundancy for these mailboxes the same as any other user.

Here are some examples tweaked from the Exchange Team’s blog on how to create resource mailboxes at the shell.

Create a Room mailbox:

New-Mailbox -database “FirstStorageGroup\RoomMailboxDatabase” -Name ConferenceRoom1 -OrganizationalUnit “Conference Rooms” -DisplayName “ConfRoom1″ -UserPrincipalName ConfRoom1@example.com -Room

Create an Equipment mailbox:

New-Mailbox -database “FirstStorageGroup\EquipmentDatabase” -Name LoanerLaptop1 -OrganizationalUnit Equipment -DisplayName “Loaner1″ – UserPrincipalName loaner1@example.com -Equipment

Create Custom Properties for Resource Mailbox

Set-ResourceConfig -ResourcePropertySchema (“Room/TV”, “Room/SpeakerPhone”, “Equipment/Auto”)

Configure Resource Mailbox Properties

Set-Mailbox -Identity “ConferenceRoom1″ -ResourceCustom (“TV”,”SpeakerPhone”) -ResourceCapacity 12

With a better understanding of resource mailboxes, you should be able to provide your users with a great experience for reserving resources. And since that experience is the same for remote users even if they use OWA, you’ll find your meetings take place without a hitch…at least as far as where they happen. Donuts are another story.

Inside Exchange 2010: Resource Mailboxes

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If you receive tons of emails daily then it is imperative to know how to manage your inbox.  Emails, if not removed regularly, can clog your inbox making it look messy and disorganized.  An overloaded inbox would definitely not help you do your job better or quicker.  In fact, it may even be a cause for delays since there would be so much information that you have to deal with. An inbox that is brimming with messages can also cause your system to crash, which can delete all information from Outlook.

Another reason why you should clean your inbox regularly is that an inbox that is clogged with information would make it easy for you to lose track of important emails that require immediate action.  This is because mails would be piled up on top of each other, making it hard for you to locate critical and crucial messages.

What’s the Inbox For?

The inbox was designed to be a temporary holding area for your mails and should remain that way.  The wrong attitude towards the inbox is to treat it as an address book, calendar, filing system, and bookmark list.  Inboxes should be cleaned at least once a day.  This would require some discipline on your part but it would definitely be of big help to you over time.

Cleaning your inbox

Cleaning your inbox means emptying it of emails.  When you find emails that are important you need to save them somewhere else.  You should make folders for different purposes.  Pictures should have their own dedicated holding area as well.  The goal is not to leave any file or email in your inbox.   You may want to do “general cleaning” before you step out of your office or prior to bedtime.  This way, you would be able to start the next business day with a clean inbox.

A good practice that can be implemented in your company is to have all personnel name their emails appropriately.  This would make scanning faster and so you would be able to distinguish right away if a particular email would need your immediate attention or not.  Titles should be specific and should accurately represent the content.  When you respond to an email that does not have a good title format, change the subject first before sending.

Do not forward urban legends, chain letters or jokes.  Have your friends and colleagues do this as well. These types of files are really unnecessary and you would be better off without them.

Dealing with Spam

You should abide by a zero tolerance policy when it comes to spam mails.  If you ever do get spam mails, delete them immediately, or better yet report them to your anti-spam vendor right away to improve their detection rates.  Do not even try to open spam mails for kicks as these might harm or endanger your computer.   Many spam mails contain viruses or malware infections that can steal sensitive information from your PC or wreck havoc in your system.  Spam can easily be detected.  Some may come from legitimate sources but their absurd or lame title messages are dead giveaways.   Spam creators also love using links that have no logical title.  A better option would be to set your Outlook to block Spam mail from entering your inbox.  Outlook can be configured to distinguish and block low value emails such as Spam.

Newsletters

When you get newsletters read the title first.   The more interesting ones can be opened and scanned.  Afterwards, delete it.  Always remove newsletters from your inbox whether they are worthy of your attention or not.  You will find that most newsletters are just marketing ploys designed to lead you into buying products or services.  Many will have exaggerated content.  For unwanted newsletters, block them using anti-spam software.   If you keep getting newsletters from a reliable source, just unsubscribe.  However, there are some unscrupulous companies out there that will make it hard for you to unsubscribe from their newsletters.  If they ask you to write them an email, do so.  These little inconveniences will be worth your time in the end.

Best Practices for organizing your Inbox

1. There are some internal tools in your computer that may send out automatic emails once in a while.  In these instances, just quickly scan the mails then delete them afterwards.  Most of the time, these mails would contain information that are already present in the internal tool.
2. Another way that you can organize or manage automatic emails is to use Outlook filters.  These tools can direct unnecessary files (e.g. quarantine reports from anti-spam software programs, newsletters, updates from internal wikis and internal issue tracking systems, and mailing lists) to specific folders.  You may check these folders daily and see what files need to be saved or deleted.
3. For general FYI mails that do not require a direct reply from you, read through them then delete.  If it is about a scheduled meeting, mark it in your calendar using a calendar software program or wait for an invite from the host.  If an email is about a significant milestone, you may want to move it to a special project folder.
4. For To Do mails, use the 2 minute rule.  If you can finish the job in two minutes, get on it right away then delete the email.  If the job would require more time, move the mail to your To Do folder, then remove it permanently from your inbox.
5. Another way to manage your inbox is to organize emails by date and sender.  Select the ones that are relevant and important to you, for example emails from people who you communicate with on a regular basis.  Go over the titles then select which ones need to go and which ones need to be moved to a dedicated folder.
6. An indirect way to de-clog your inbox is to reduce the amount of emails you send out.  An email to most people will require a response so keep outbound emails to a bare minimum.  Instead, use the phone or just go directly to the person you would like to communicate with.

6 Tips for Effective Inbox Management

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In his blog, UDP Notification Support Re-added to Exchange 2010, Kevin Allison announced that Microsoft is now going to include User Datagram Protocol (UDP) notification functionality support with Microsoft Exchange Server 2010.

When Exchange Server 2010 was originally released, back in 2009, it did not include support for UDP for new mail notifications. Exchange Server 2010 UDP notification support should be available in Exchange 2010 SP1 Update Rollup 3 (SP1 RU3), scheduled for March 2011. The RU3 schedule has been adjusted in order for the engineering team to complete the requisite work to include UDP support within the rollup.

Previously, whenever Outlook 2003 displayed new messages, or needed to display changes to folders, it was expecting to use UDP for those notifications. Because of the UDP change those updates would take much longer than expected. The send/receive process was also affected and would take more time than it did before with prior releases of Exchange Server. Specifically, folders would take a long time to update when an Exchange Server 2010 user used an Outlook 2003 client in online mode.

This problem affected Outlook 2003 because it used UDP as its primary method for receiving notifications from an Exchange server. Outlook 2007 was mostly unaffected by this problem because, by default, it used an asynchronous notification method that did not rely on UDP notifications.

Adding UDP back into Exchange Server has been welcomed by many in the administrator and user community. Without the UDP functionality being added some customers were facing having to upgrade all their client versions. This would have meant much time used for what is now an unnecessary project. More time can now be spent on improvements and enhancements rather than on corrections and fixes that would have been spent on client upgrades. In addition, many administrators and IT departments were delaying the rollout of Exchange Server 2010 to avoid having to deal with the performance issues and the expected blowback from their user community.

The Update Rollup 3 for Exchange Server 2010 SP1 (KB2492690) also contains a number of other fixes that were reported by customers reported. It also includes fixes for internally found issues since the release of Rollup 2. Highlighted fixes include the following:

• ‘Database Copies’ list is being populated incorrectly (case sensitive) in EMC with DAG in place after upgrade to E14 SP1
• Users without mailbox can’t delete items in shared mailbox via OWA premium
• Folders take a long time to update when an Exchange Server 2010 user uses Outlook 2003 in online mode

Update Rollup 3 for Microsoft Exchange Server 2010, Release to Manufacturing (RTM), has been made available.

The recommended order of updates for your Exchange servers is:

1. Internet-facing Client Access servers
2. Other Client Access servers
3. Hub Transport servers
4. Mailbox servers
5. Edge Transport and Unified Messaging servers

Once the update rollup 3 has been applied to the Exchange 2010 SP1 client access servers, administrators should also configure the servers to support UDP based push notifications. UDP based push notifications is the most ideal method for Outlook 2003 clients to receive notifications from an Exchange server. The benefit is that users will see a performance increase when using online mode for their email communications. UDP push notifications can be enabled by creating a new DWORD registry key named “EnablePushNotifications”.

After an administrator installs the update, they should create the following registry subkey to enable the UDP notifications support feature:
Subkey location: HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\MSExchangeRPC\ParametersSystem
Subkey name: EnablePushNotifications
Type: REG_DWORD
Value: 1           <———-this will enable push notifications.

After enabling push notifications the Exchange 2010 Client Access Server (CAS) should be restarted.

When UDP push notifications have been enabled, the Outlook 2003 clients will connect to the Exchange 2010 CAS servers using TCP. Once logged on, the port number and IP address that the Outlook clients expect to receive push notifications on are communicated to the CAS server. By default, the RPC Client Access service on an Exchange 2010 Client Access server uses the TCP End Point Mapper port (TCP/135). For outgoing connections, every time an Outlook client connects to Exchange server, an RPC port number in the dynamic RPC port range from 6005 to 59530 will be used.

Additionally, enabling push notifications on the CAS servers will result in something similar to frame number 440 being displayed by the Microsoft Network Monitor (NetMon) whenever a UDP based push notification is sent from the CAS server to an Outlook 2003 client.

Exchange Server 2010 and UDP Support

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We’ve all heard it about a hundred times already: “Don’t open attachments from unknown senders.” And yet there will always be someone who has either forgotten the last time their system locked up and stopped functioning or they believed their system was protected from viruses. But although administrators are constantly on guard they cannot prevent attachments from being opened.

Attachments which contain viruses are most commonly sent out denoted as executables and sometimes scripts. The reason is because unsuspecting users will expectedly double click on the attachments to perform some function which they thought would help them. Sometime the attachments are sent as documents intended to inform users about some new subject.

But there are many other filename extensions that can contain viruses. Here is a list of filename extensions that can contain viruses and are typically blocked by Outlook:

Extension     File type description
.ade     Access Project Extension (Microsoft)
.adp     Access Project (Microsoft)
.app     Executable Application
.asp     Active Server Page
.bas     BASIC Source Code
.bat     Batch Processing
.cer     Internet Security Certificate File
.chm     Compiled HTML Help
.cmd     DOS CP/M Command File, Command File for Windows NT
.cnt     Help file index
.com     Command
.cpl     Windows Control Panel Extension (Microsoft)
.crt     Certificate File
.csh     csh Script
.der     DER Encoded X509 Certificate File
.exe     Executable File
.fxp     FoxPro Compiled Source (Microsoft)
.gadget     Windows Vista gadget
.grp     Windows program group file
.hlp     Windows Help File
.hpj     Project file used to create Windows Help File
.hta     Hypertext Application
.inf     Information or Setup File
.ins     IIS Internet Communications Settings (Microsoft)
.isp     IIS Internet Service Provider Settings (Microsoft)
.jar     JAVA archive file
.its     Internet Document Set, Internet Translation
.js     JavaScript Source Code
.jse     JScript Encoded Script File
.ksh     UNIX Shell Script
.lnk     Windows Shortcut File
.mad     Access Module Shortcut (Microsoft)
.maf     Access (Microsoft)
.mag     Access Diagram Shortcut (Microsoft)
.mam     Access Macro Shortcut (Microsoft)
.maq     Access Query Shortcut (Microsoft)
.mar     Access Report Shortcut (Microsoft)
.mas     Access Stored Procedures (Microsoft)
.mat     Access Table Shortcut (Microsoft)
.mau     Media Attachment Unit
.mav     Access View Shortcut (Microsoft)
.maw     Access Data Access Page (Microsoft)
.mcf     Manifest configuration file
.mda     Access Add-in (Microsoft), MDA Access 2 Workgroup (Microsoft)
.mdb     Access Application (Microsoft), MDB Access Database (Microsoft)
.mde     Access MDE Database File (Microsoft)
.mdt     Access Add-in Data (Microsoft)
.mdw     Access Workgroup Information (Microsoft)
.mdz     Access Wizard Template (Microsoft)
.msc     Microsoft Management Console Snap-in Control File (Microsoft)
.msh     Microsoft Shell
.msh1     Microsoft Shell
.msh2     Microsoft Shell
.mshxml     Microsoft Shell
.msh1xml     Microsoft Shell
.msh2xml     Microsoft Shell
.msi     Windows Installer File (Microsoft)
.msp     Windows Installer Update
.mst     Windows SDK Setup Transform Script
.ops     Office Profile Settings File
.osd     Application virtualized with Microsoft SoftGrid Sequencer
.pcd     Visual Test (Microsoft)
.pif     Windows Program Information File (Microsoft)
.pl     Perl script file
.plg     Developer Studio Build Log
.prf     Windows System File
.prg     Program File
.pst     MS Exchange Address Book File, Outlook Personal Folder File (Microsoft)
.reg     Registration Information/Key for W95/98, Registry Data File
.scf     Windows Explorer Command
.scr     Windows Screen Saver
.sct     Windows Script Component, Foxpro Screen (Microsoft)
.shb     Windows Shortcut into a Document
.shs     Shell Scrap Object File
.ps1     Windows PowerShell
.ps1xml     Windows PowerShell
.ps2     Windows PowerShell
.ps2xml     Windows PowerShell
.psc1     Windows PowerShell
.psc2     Windows PowerShell
.tmp     Temporary File/Folder
.url     Internet Location
.vb     VBScript File or Any VisualBasic Source
.vbe     VBScript Encoded Script File
.vbp     Visual Basic project file
.vbs     VBScript Script File, Visual Basic for Applications Script
.vsmacros     Visual Studio .NET Binary-based Macro Project (Microsoft)
.vsw     Visio Workspace File (Microsoft)
.ws     Windows Script File
.wsc     Windows Script Component
.wsf     Windows Script File
.wsh     Windows Script Host Settings File
.xbap     XAML browser application
.xnk     Exchange Public Folder Shortcut

Upon receiving emails with the above named attachments Outlook will display a message at the top of the email message or at the top of the Reading Pane. The message will say the following:

“Outlook blocked access to the following potentially unsafe attachments”

The reason for this is a security feature included in Outlook designed to block attachments that may contain viruses or malicious code. Users cannot save, delete, open, print, or otherwise work with the attachments. Although the attachments are blocked they can still be opened using a combination of operations.

Here are some techniques for gaining access to blocked attachments:

1. The sender of the email can save the attachment to another site such as an FTP site that will be accessible by the intended recipient.
2. The sender of the email can compress the attachment or “zip” it up. Using this technique, the file can then be resent to the recipient with a filename extension that won’t be blocked.
3. The sender can always try to rename the file using a different filename extension that will not be caught by the security screening feature.
4. An administrator can modify the security settings on the Exchange server for the user’s mailbox to allow specific attachments to pass through unblocked.

List of Filename Extensions Blocked by Outlook

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In Outlook, email is contained in a folder for incoming mail that is known as your Inbox. Sent email messages are contained in another email folder for your Sent Items. Outlook also has folders for Deleted Items, Drafts, Junk E-mail, Outbox and Search Folders.

Search Folders do not store email messages – they are virtual folders that use the concept of “views”. It is these views that present the email messages which match search criteria that have been defined by the user. The benefit of Search Folders is that once the search query has been executed the results will remain in the appropriate Outlook folder. Those folder results can then be used over and over again without having to run the same query.

Such Search Folders include: “Unread mail”, “Mail flagged for follow up”, “Mail either unread or flagged for follow up”, “Important mail”, “Mail from and to specific people”, etc.

Search Folders are either active or inactive. Inactive Search Folders are displayed with italic text and transparent icons. Active Search Folders are displayed with typical font and solid icons.

The three folders “For Follow Up”, “Large Mail” – email items larger than 100KB – and “Unread Mail” are default folders which can be modified or deleted. It is important to note that deleting a Search Folder does not delete the actual email messages. Remember that Search Folders are simply views for those email messages. But if your end users delete one or more of those email messages from within a Search Folder then the actual email messages will be deleted from their original Outlook folder.

Oftentimes administrators will receive calls from end users asking why they can still see what they thought were previously deleted email messages. Educating users about how Search folders work and how simply deleting the search folder does not result in deletion of the original emails can be time consuming. It is especially time consuming when you have hundreds or thousands of users. So it is a good idea for email administrators to include a section about Search Folders on the Frequently Asked Questions page of the company’s internal email support web site.

Sometimes if your end user is trying to use the Find feature in Outlook they will receive an error message such as: “Outlook cannot perform your search. Outlook cannot display this view. The folder already exists.”

What has happened is that a previously defined Advanced Find has been saved and is now corrupted. To resolve this problem an administrator should run the following command from within a command prompt window: “outlook.exe /cleanfinders”. Just click the Start button, then Run, and type the command in the Open text field. This command will remove all saved searches from the mailbox.

There are other issues that users can have with their search folders. Here are some rules and methods for troubleshooting typical problems encountered when using search folders:

• When reading email messages, sometimes the Unread email view will not show the email messages as being removed. A solution is to click away from the Unread email folder, or to hit the F5 key, and then click the Search Folder. These actions should then update the Unread mail folder.
• All search folders can be manually deleted from the information store by executing the following command: “outlook.exe /cleanfinders”. An administrator should exit out of Outlook and then execute the command string by clicking Start, then clicking Run and then typing the command string in the Open text box. Then restart Outlook. The deleted Search Folders will appear as inactive folders.
• If an end user wishes to continue to use the recently deleted Search Folders – now inactive – then they can just click on the Search Folder that they want to use.
• If they do not want to continue using one of the deleted Search Folders then they can just right-click on the Search Folder and click on the Delete action.
• An inactive Search Folder can be reactivated by clicking on the Search Folder. Outlook will re-index the Search Folder query results based on the original criteria.
• As mentioned earlier you can manually delete the three default search folders: Unread Mail, For Follow Up and Large Mail. But you cannot force the recreation of those folders. You must manually recreate them.
• Search Folders in Outlook 2003, 2007 and 2010 cannot be copied.
• Sometimes a Search Folder is deleted by an end user and then later they try to restore it. Unfortunately, Search Folders are not recoverable and cannot be restored with the Recover Deleted Items feature. An administrator will need to manually recreate the accidentally deleted Search Folder.

Troubleshooting Search Folder Issues

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The process of making a connection between Outlook and Exchange can sometimes be problematic. Sometimes the network is not up or the connection information for either the client or the server may have changed or become corrupted.

When unable to make a connection between the client and the server a variety of error messages can be displayed: some alone and others in combination with each other. One such error message that a user or administrator may see displayed is the following:

“Exchange is currently in recovery mode. You can either connect to your Exchange server using the network, work offline, or cancel this logon.”

There are a couple different reasons for this message as well as multiple solutions. Most of the time the error message is displayed because of a difference in the cached copies of the mailboxes stored on the local client and of the cached copies stored on the Exchange server. This problem can be resolved by disabling the cached Exchange mode on Outlook, restarting Outlook and then resetting the cached Exchange mode on Outlook back to enabled status.

The “Exchange is currently in recovery mode” can also indicate that there are configuration issues with the Domain Name System (DNS) settings. This could also be the result of a connection problem either on the client or on the server. And it could also mean that the DNS server itself is down and thus not providing name resolution services.

If you want to verify that DNS is working then you can try the “ping” command of a well known server such as yahoo.com. For example, you can open up an MS Dos prompt window and enter the command as such:

C:\Documents and Settings\Administrator>ping yahoo.com

Pinging yahoo.com [209.131.36.159] with 32 bytes of data:

Reply from 209.131.36.159: bytes=32 time=23ms TTL=53
Reply from 209.131.36.159: bytes=32 time=25ms TTL=53
Reply from 209.131.36.159: bytes=32 time=22ms TTL=53
Reply from 209.131.36.159: bytes=32 time=26ms TTL=53

Ping statistics for 209.131.36.159:
Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),
Approximate round trip times in milli-seconds:
Minimum = 22ms, Maximum = 26ms, Average = 24ms

This will help an administrator to know that the problem is not a DNS issue.

Another reason why you may receive this message is if the client mailbox was moved to a different Exchange Server. This can also occur if Cached Exchange mode is enabled. The result is that the signatures do not match between the one on Exchange Server and the signature of the offline folder file (dot ost). The dot OST file is an encrypted file that is linked to a user’s mailbox.

The intent of Cached Exchange Mode on Outlook was to improve the connection speed between Outlook and Exchange server. While Cached Exchange mode is enabled Outlook will keep a local copy of the Exchange server mailbox data. Then, when Outlook goes to access mailbox data normally stored on the Exchange server it will instead go to its own cached copy. Not only does this improve user response time but it also avoids unnecessary network traffic. Of course, synchronization will have to occur periodically to keep the two copies as consistent as possible.

In Outlook 2007 an administrator can enable Cached Exchange mode with the following procedure:

1. From the Tools menu select Account Setting.
2. Select the email tab.
3. Select Microsoft Exchange Server.
4. Click on the Change button.
5. From the Server Settings check the checkbox for the Use Cached Exchange Mode.
6. Click Next.
7. Click Finish.

You should receive an advisory notification asking you to restart Outlook. Once restarted, Outlook will be running in Cached Exchange mode and the contents of your mailbox will be copied and stored locally. Depending on the size of your mailbox and the speed of your connection this reproduction may take some time. You will need to advise your end users not to expect to be able to immediately access their email messages.

One last thing to note is that if your clients are running earlier versions Outlook, such as Outlook 2003, there is a functionality called “Recovery Storage Groups” which will allow an administrator to remotely mount a copy of the user’s mailbox database so that your end users can quickly gain minimal access to their mailbox while an administrator restores full access by recovering the data from the “Recovery Storage Group”.

How to solve the Exchange in Recovery Mode Error

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One very useful feature of Exchange server is that of the Autodiscover service. Microsoft Exchange Server 2010 provides a feature known as the Autodiscover service which is used to configure the user profiles of Outlook 2007 or Outlook 2010 clients. Additionally it is also supported on phones running Windows Mobile 6.1 or later versions.

The Autodiscover service also allows clients to get access to the various features of Exchange server while connected. Using the user’s email address and password profile the Autodiscover service provides profile settings for Outlook 2007 and Outlook 2010. It can also leverage the domain accounts of clients that are joined to domains.

Some of the benefits of using the Autodiscover service include the time savings and often cumbersome process that email Administrators had to go through when configuring user profiles manually for Exchange 2003 SP2 (or earlier) and Outloook 2003 (or earlier). Further adding to the sometimes moribund tasks that administrators have to periodically perform was also the fact that if changes or updates were made to any of the users’ profiles then the process would have to be repeated manually to reconfigure those profiles. Without these manual changes administrators would run the risk of Outlook clients no longer working in their normal manner.

Another benefit of the Autodiscover service is to reduce the downtime associated with a disaster recovery scenario. Downtime can be reduced to minutes when the time required for reconfiguring user profiles after a disaster could take much longer when done manually as opposed to letting the Autodiscover service handle it.

Some of the profile settings that are presented to the clients by the Autodiscover service include:

• Users’ display names
• Connection settings for internal and external connectivity
• Locations of Mailbox servers for each user
• URLs of Outlook features that give access to free/busy information, Unified Messaging, and the offline address book
• Outlook Anywhere server settings

One of the problems with Autodiscover service that some email administrators have complained about is that they are unable to stop the Autodiscover redirect warning messages in Outlook 2007. The Autodiscover redirect warning messages are displayed for HTTP and DNS Service Location (SRV) records redirections. The Autodiscover redirect warning message will be displayed as:

“Allow this website to configure user1@cust1.com server settings?
https://mail.hosting.com/autodiscover/autodiscover.xml
Your account was redirected to this website for settings.
You should only allow settings from sources you know and trust.”

This new feature which allows Outlook 2007 to use the DNS Service Location (SRV) records to locate the Exchange Autodiscover service was discussed in article 940881 that can be found in the Microsoft Knowledge Base.

However, this problem was fixed in the Outlook 2007 post-Service Pack 1 (SP1) hotfix package (dated September 24, 2008). The hotfix is described in the Microsoft Knowledge Base article 957909.Once the hotfix has been downloaded and installed it still needs to be enabled which requires some changes made to the registry. Those changes include modifications to the following registry subkeys:

HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\AutoDiscover

Or

HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\12.0\Outlook\AutoDiscover

As always only administrators should be making changes to the registries and they should always make backup copies prior to making changes in the event that changes are inadvertently made while typing new settings.

Another problem that an administrator may encounter is during the process of configuring Outlook 2007 Autodiscover service to be able to use a remote domain. When configuring the service they may receive a “certificate mismatch error”. Other administrators have already noted this error and a hotfix is available to correct this problem. Administrators can download and install the hotfix package 939184. Once applied, the AutoDiscover service will then use DNS Service Location (SRV) records to locate the appropriate AutoDiscover URL. This will result in Outlook 2007 being enabled to use DNS Service Location (SRV) records to locate the Exchange AutoDiscover service

Another issue related to using the Autodiscover service with Outlook 2007 and Exchange server 2007 can be indicated if the following error message is received:

autodiscover.yourdomainname.com

“Information you exchange with this site cannot be viewed or changed by others.”

This error message often indicates that there is a problem with the security certificate associated with that web site. This can be explained when the client and the Exchange server are on different subnets and the router that is used to connect from the subnet listens to TCP Port 443 (HTTPS). The result is that the Autodiscover mode of Outlook 2007 and Exchange 2007 may fail. If there is a problem with DNS name resolution or the socket cannot support a Secure Socket Layer (SSL) connection then the above mentioned error message may be produced.

Outlook would attempt to use a secure channel (socket) to communicate between the client and the server which could lead to a certificate mismatch condition.

A workaround that can be used on Cisco routers is to disable them from listening to TCP Port 443. A network administrator can use the following command to disable listening on this port:

“no ip http secure-server”

Another diagnostic step an administrator can take is to use the “NSLOOKUP” command to verify that the correct DNS settings have been configured for the particular DNS Service Location (SRV) record:

autodiscover.yourdomainname.com

In summary, there are many benefits to using the Autodiscover service the most important of which is the ease and automation of configuring user email profile settings.

Outlook and Autodiscover Errors

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Email administration can involve a variety of tasks. Some of these tasks are complex while others are fairly mundane. Oftentimes administrators have to support memory problems; sometimes it is configuration issues and settings, while other times it is underperforming or, at worst, non-performing clients and servers.

One of the easier issues an administrator has to support is the problem is space allocations in regards to disk or file space. On a system of limited disk space this can be a minor challenge. Conserving space on a hard disk will require the administrator to delete unwanted or unnecessary for business items from the various dot pst (.pst) and dot ost (.ost) files.

But if all your data resides on an Exchange server then this process in not needed. Most often, though, the relevant user data can be found in personal folder files such as the dot pst files. These files can be found by searching for files with the dot pst (.pst) extension. Outlook data items such as email messages, tasks, contacts, etc. reside within the dot pst files.

Once the non-critical information has been deleted then the administrator can begin the process of compacting the files which will reduce the size of those files and thus free up critical space on the system.

If an administrator has deleted and then compacted a lot of space but still finds that the space freed up is not enough to meet his needs then the administrator can do one of two things:

1. Backup or archive mid-tier (or medium level) critical information to free up additional space.
2. Delete items from the Deleted Items Folder.

Creating backups and archiving data should be a part of any administrator’s normal day to day activities as it is important to keep critical data in permanent storage mediums should the need to restore data for any reason come up. I’ve discussed on other occasions the reasons why a regular maintenance schedule should include backups but as a brief review they can include: risks of loss of data due to corruption, hardware failures, power failures or spikes, viruses, intentional or unintentional data being overwritten, etc.

The second thing an administrator can do to free up additional space is as simple as deleting items from the Deleted Items Folder. This can either be an overlooked task or just be a lack of knowledge to delete those items. In their haste administrators will sometimes mistakenly delete items but will forget or get distracted and not remember to take the next step and empty out the Deleted Items Folder.

After those files have been deleted from the Deleted Items Folder then those files can be compacted. Now the process of compacting the files does not remove all the free space associated with those files. About sixteen kilobytes (16KB) or four percent (4%) of the original file size will be left uncompacted.

There are a couple of file size requirements before a dot pst or dot ost file can be compacted.

1. The file must be sixteen kilobytes (16KB) or greater.
2. The file must have at least sixteen kilobytes (16KB) of free space since the last time that it was compacted.

Compacting Outlook files can be run manually or run in the background.

Running the compact process in the background has the advantage of allowing the administrator to perform other administrative tasks while the compacting process is occurring. The administrator might want to monitor the file sizes or their directories as they are being compacted. There are few requirements for the compacting process. At the very least is that Outlook must be running. And in the interests of performance the administrator ought to run the background compacting process during low CPU demand periods.

It’s very easy to manually run the compacting process. Administrators can manually compact files with the following steps:

1. From the File menu, select Data File Management.
2. Select the user’s Personal Folder and then click on Settings.
3. From the General tab, click “Compact Now”.
4. Click OK or hit enter.
5. Click  on “Close”.

How often an administrator should compact files is a matter of personal experience and should be included and be consistent with the maintenance policies in place for the corporation. This will make it easier for new or backup administrators to maintain the corporate email environment. One compact scheduling suggestion is to compact Outlook files once or twice a year. But if you find that Outlook is increasingly running slow or that your system is running out of space then you might want to consider compacting your Outlook files sooner than is scheduled.

Delete Item Space in Outlook

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One of the fastest end user communications you can have will be from everybody’s least desired scenarios: slow startup performance with Outlook.

We’ve all become so accustomed to almost instantaneous response times that a five or ten percent drop in startup times can cause a major increase in complaints from end users. From small office operations to larger enterprise corporations those five to ten percent drops in startup times can sometimes be translated into lost revenue especially when the slow startup time bleeds into continuous slower performance and reduced availability and access to data.

There can be many causes for slow startup performance:

1. Folder updates are interrupted.
2. Interference or incompatibility with anti-virus or anti-spam software.
3. Problems with recent add-ins.
4. Inbox messages may be corrupted.
5. Critical file corruption.
6. TCP/IP communication problems.
7. Server/Client hardware configurations
8. User Interface customizations

If you suspect file or folder corruptions then one way to check for this is to check the size of some of your critical system files. Some very easy fixes include renaming or deleting these files and then letting Outlook recreate them as necessary. In Outlook 2007 such files that can be deleted or renamed include: outcmd.dat, extend.dat, views.dat and frmcache.dat.

You can find these files at the following locations in Windows XP and Vista respectively:

Outcmd.dat:
C:\Documents and Settings\(username)\Local Settings\Application Data\Microsoft\Outlook
C:\Users\(username)\AppData\Roaming\Microsoft\Outlook

Extend.dat:
C:\Documents and Settings\(username)\Application Data\Microsoft\Outlook
C:\Users\(username)\AppData\Local\Microsoft\Outlook

Frmcache.dat:
C:\Documents and Settings\(username)\Application Data\Microsoft\Outlook
C:\Users\(username)\AppData\Local\Microsoft\FORMS

Views.dat:
C:\Documents and Settings\(username)\Application Data\Microsoft\Outlook
C:\Users\(username)\AppData\Local\Microsoft\Outlook

If you have recently upgraded your anti-virus, anti-spam software or recently added in new applications then an administrator can try disabling the new software upgrades temporarily and then reinstall them if necessary. And to reduce the number of variables the administrator can also try closing any archives.

Follow the steps below if you suspect problems are being caused by Outlook add-ins.

1. Click Tools, then Options and then Other
2. Select Advanced Options
3. Click COM Add-Ins
4. Click Add-In Manager
5. Deselect all add-in (check boxes)

These diagnostic steps should not be combined as troubleshooting the cause or causes of a problem should be done on a step by step process so as to eliminate potential issues one by one. If you disable or close one application in one step and then the problem goes away with that one step then you’ll have most often identified the one issue which caused the original problem. Sometimes the problem is the result of a combination is two or more issues and will be harder to identify.

Another potential trouble spot when starting Outlook can occur between the communications of the client and the server. This can happen if the Transmission Control Protocol/Internet Protocol (TCP/IP) host name cannot be resolved.

TCP/IP issues can be diagnosed by starting with the user profile properties on the Exchange server. An administrator can measure the name resolution time by logging onto the Exchange server and then, using the correct server name and mailbox for an end user, click on the “Check Name” button. This will give an administrator an indication of any problems with name resolution. If the time it takes to resolve the name is more than thirty to forty seconds then further diagnostics in this area should be conducted.

One very useful utility that any Outlook administrator should be familiar with is “rpcping”. The RPC Ping Utility (“rpcping”) can be used to troubleshoot connectivity issues between Microsoft Office Outlook 2007 or Outlook 2003 and Exchange server. An administrator can use the RPC Ping Utility to confirm the Remote Program Call (RPC) connectivity between Microsoft Exchange Server systems and any Microsoft Exchange Client supported system. The rpcping utility can also be used to verify that RPC service requests are being recognized by the Exchange Server as they come in from the clients.

An administrator can implicitly run the “rpcping” test by typing in the IP address instead of the server name and then clicking on “Check Name” for the client profile properties section on the Microsoft Exchange server system. This method will test for IP address resolution instead of name resolution. If this test fails then the administrator should review the IP address for the Exchange Server. If the IP address is correct then there is a problem with the RPC communications to the server. More information on how to correct the RPC issues can be found on the Microsoft Support web site.

Outlook Startup and Slow Performance

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Having multiple mailboxes can be a benefit for users who want to direct email to specific mailboxes based on subject material, audiences or other personal reasons. But it can also increase the workload of not only the corporate servers but of the administrators as well.

Exchange server allows users to access those multiple accounts while using only one profile and not having to re-log in under a different username. To support this functionality it is necessary for an administrator to configure Outlook such that it will enable a user to access those multiple email boxes from one profile.

An administrator should start Outlook using the profile that is configured for the Exchange server mailbox of the account (#1) that is going to be used to add a “delegate” account. Validation may be required. If so then log in to the network as the user of the account (#1). Then, follow the steps outlined below for Outlook 2002 and 2003:

1. From the Tools menu, click Options to add a delegate.
2. Select the Delegates tab and click Add.
3. Type or select a username for the delegate account (#2).
4. Click Add, and then click OK or hit enter
5. Locate the Delegate Permissions dialog boxes. Then select Editor (read, create, and modify items) in each of them.
6. Click OK or hit enter two times.
7. Click on Folder List on the View menu to make it visible.
8. Right-click the Mailbox – user name (to begin adding a new user).
9. Then click Properties for Mailbox – user name on the shortcut menu.
10. On the Permissions tab, click Add.
11. Type or select the username of account (#2) you wish to add and then click Add.
12. Click OK or hit enter.
13. From the Name box, click the newly added user for the account (#2).
14. From the Roles box, click Owner, and then click OK or hit enter.
15. Repeat steps 8 through 14 for the rest of the other folders in the mailbox.
16. On the File menu, click Exit and Log Off.

You are now ready to restart Windows and log in as the newly created username for account (#2). Once Windows has restarted you should then start Outlook with the corresponding profile for the newly created username.

Then follow these steps to add the new user for account (#2) to Exchange Server:

1. From the Tools menu, click E-mail Accounts.
2. Then click View (or change existing e-mail accounts).
3. Select the Microsoft Exchange Server and then click Change.
4. Select the More Settings button and click on the Advanced tab.
5. Click or select Add.
6. Type the username of the original account (#1) and then click OK three times.

You should be able to see the mailbox for the original account (#1) in your Folder List. The beauty of this is that your user is now able to send messages and meeting requests from the user account (#2) as if they were originating from the user of account (#1). All user (#1) needs to do is to enter the name of the user for account (#1) in the From Field. The messages sent will contain the names of the users for both accounts: one (#1) and two (#2).

Although this is a useful feature to have – multiple mailboxes – it can also be somewhat difficult to disentangle when problems occur with having multiple mailboxes.

Some users have reported that after installing a service pack update they will sometimes receive warning messages when they try to read their emails of some of these multiple accounts. The message will say something like:

“This item cannot e displayed in the Reading Pane. Open the item to read its contents.”

Double clicking the message will produce an error box which displays another message:
“Cannot open this item. Unknown Error.”

And attempts to re-add the mailbox can lead other error messages:
“The name cannot be resolved.  The connection to Microsoft Exchange is unavailable. 
Outlook must be online or connected to complete this action. “

This error message may occur even if the user is still able to send and receive emails from their primary account with the Exchange server. This type of problem can occur as a result of incorrect routing groups leftover or not fully cleaned out as a result of a recent Outlook migration. This can happen if Outlook is storing the names of the mailboxes internally with an “AD” syntax used to describe the location of the mailbox. The confusion occurs because Exchange 2007 is using a different location than the stored location in Outlook.

End users will see the effects of out of sync mailbox locations with delegates, email replies and the use of frequently-mailed-contact lists.

The cause of this out of sync mailbox location is that after a migration from Exchange 2003, each user migrated would have an attribute called “LegacyExchangeDN” that pointed to the old AD location. But a user created in Exchange 2007 did not have the same attribute. This out of sync issue can be corrected by adding a new X.500 address to each mailbox with the value of the previous “LegacyExchangeDN” attribute. Cached entries in Outlook would now be able to locate the users’ mailboxes and prevent those error messages from being generated.

In a future post I’ll discuss other issues with having multiple mailboxes and how to fix them.

Working With Multiple Mailboxes

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If you have set up Outlook to use Internet Message Access Protocol (IMAP) and also read receipts then you may have some users who will report errors or problems related to junk email.

A read receipt is a tracking mechanism that allows the sender to request a receipt indicating that the recipient has received and read their email message. The recipient has the option to acknowledge receipt and/or that the email message has also been read.

Whether or not the sender receives that receipt is not only dependent on the recipient’s acknowledgement but more so on the email server, specifically the email server’s support of read receipts. Additionally, although the email server might support sending out read receipts it may not support delivery receipts which is usually a setting configured to prevent spammers from determining mailbox addresses.

Read receipts make sense for internal communications and critical email messages. They help to establish a paper trail useful in legal matters. However some users may consider this an intrusion or a disruption in their normal business flow and may thus disable this option.

Some users have reported that when Outlook synchronizes with the email server and purges the junk email folder that read receipts will be returned. This can happen when messages that have receipt requests are being moved to the junk email folder and you then empty the junk email folder from another client. This can happen even though the settings in Tools, Options, Email Options and Tracking Options indicate otherwise.

Read receipts are enabled via the email tracking options within Outlook. Some of the information returned can include the time and date that the email message was received, the IP address of the email server, and the email software that was used.

An administrator can test for potential problems by following the steps below:

1. Send email messages to test email account and request receipts
2. Next, move those email messages to a junk email folder
3. Synchronize with your IMAP server
4. Update all folders
5. Close Outlook
6. From a different email client empty the junk email folder
7. Reopen Outlook.

The administrator should note that he will receive read receipts when email is emptied out of the junk email folder. This will occur even though the Tracking settings may indicate the opposite and are thus ignored.

If you wish to avoid this problem then you can mark the junk email messages with a status showing that they have been read. Do this before closing Outlook or before synchronizing with the IMAP email server. The result will be that your tracking settings will not get ignored and your read receipt request will get processed accordingly. Another option is to empty out the junk email folder.

As a precaution, administrators should notify end users to always mark their email messages as having been read before emptying the junk email folder. An administrator might also like to create a wrapper or script that is then installed or linked on each client’s account such that whenever a user attempts to empty out their junk email folder the script would mark all messages with a read status. Furthermore, the junk email folder should always be emptied out from Outlook.

Another workaround is to configure Outlook to neither ask nor send read receipts. If that’s not an option then an administrator can at least configure Outlook to always ask before sending read receipts.

From the Tools menu, choose Options, then email options and then tracking options to configure Outlook for the appropriate tracking settings.

Now another problem that can occur when using read receipts is just the opposite from above: not receiving read receipts.

This can happen for a number of reasons:

1. The recipient has chosen not to acknowledge receipt of the email message.
2. The recipient has disabled the read receipt feature.
3. The email message was not marked as having been read.
4. If the email software the recipient uses does not support read receipts then the sender will not receive an acknowledgement.
5. Exchange mail server has not yet been configured to forward read receipts.

Lastly, a junk email filter on the server might be causing read receipts to be dropped and placed into a junk email folder before Outlook can download the receipts. If using POP3 then you can log into a web based mailbox and check for those receipts.

Read Receipt Requests and Junk Email

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Having the ability to recall email messages in Outlook can be a very useful feature. Many a time have I sent email messages and then almost immediately wanted them back. This can happen to any user especially when messages are written in the heat of the moment only to have the sender cringe later after realizing that his or her message was sent in haste or was “poorly” worded.

Luckily for end users of Outlook there is a functionality that exists which administrators can implement for the benefit of their end users. That embarrassment saving feature is the “Recall” function of Outlook. Specifically it is the Recall function available if you have installed Outlook option called the Corporate Workgroup/Other option.

If you are in a corporate environment then this has probably already been implemented as you are most likely using the Messaging Application Programming Interface (MAPI) services to communicate with the Exchange server. If you need to determine if a predecessor has already done this for you then you can go to the Help menu and click on the About Microsoft Outlook choice. If you have the corporate option installed then you will see the title “Corporate Workgroup”.

Also, for Recall to work both the sender and the receiver must be using Microsoft Exchange Server as their email server.

First let me give you the basics of how to use the Recall feature and then I’ll discuss some of the problems that can happen with Recall and the solutions to fix those problems.

To recall or replace a message, follow these steps:

1. Bring up the View menu and then click on the Folder List item.
2. From the Folder list you should then click on Sent Items.
3. Locate the message that you want to recall, replace or delete.
4. From the Actions menu click “Recall This Message”.
5. Next you have the choice of recalling or replacing the email message. Either choice will effectively delete the message. If you want to recall the message then click on “Delete unread copies of this message”. If you want to replace the message then click on “Delete unread copies and replace with a new message”. After either selection click OK or hit enter and then type your new message. Then send your new message.
6. If you want to be notified – as in get a receipt – that your message has successfully been recalled or replaced then click on the “Tell me if recall succeeds or fails for each recipient” check box.
7. Lastly, click OK or hit enter.

Now let’s discuss the possible reasons why recall will not work.

Unfortunately not everyone is using Outlook with the MAPI communications service. There are installations that are using Simple Mail Transfer Protocol (SMTP) as their email communications service. Others may be using the Post Office Protocol (POP) or the Internet Message Access Protocol (IMAP) to access their mail box accounts on a mail server. If you find that your end users are unable to recall messages then you’ll need to verify which protocols are being used by the Outlook clients for both the sender and the receiver.

And if the receiver of the email in question is not using Outlook then the sender will probably need to start writing his “mea culpa” follow-up email to correct any misunderstandings created from his first email.

When a recall of a message does not work it can also be the case that the message has already been moved out of the recipients Inbox. The most obvious reason is that the receiver has already read or viewed the email. Even viewing the message in a preview mode will cause the mail message to be marked as having been read by the recipient. It is also possible that the receiver has created a filter for their email client which automatically moves or deletes incoming email messages that meet certain guidelines. Such messages to be automatically moved to specific folder could include messages based on who the sender is, where (what domain) the message came from and maybe even based on the recipients listed on the CC list.

Another reason for recall to not work is if the receiver is not logged on to their email service provider.

There are some situations where a recalled message can result in multiple notification emails reporting failed recalls. Again, an administrator will need to verify that the mail server is Microsoft Exchange server. But it is also possible that the number of failed recall notifications coincides with the number of recipients who have already opened the sent message. Another possibility is that the message is stuck in a queue and the server continues to send out the failed notification messages. An administrator should be able to check the queue for any failed messages.

Of course, the best way to protect users from having to recall messages is to encourage them to use some kind of time delay filter mechanism for questionably messages.

Troubleshooting the Recall Function in Outlook

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Email attachments must be sent, received, opened and closed on a daily basis. When a user cannot open an attachment you can be sure that an administrator is going to hear about it. Sometimes there are problems with saving attachments; other times the problems show up when a user attempts to open an attachment.

Some error messages are related to Outlook’s attachment security settings. Other times the error message might be a result of a suspected virus as reported by the user’s anti-virus software.

The most common error message displayed will be something like:

“Cannot create file: file name. Right-click the folder you want to create the file in and click Properties on the shortcut menu to check your permissions for the folder.”

This error message can be an indication of a lack of sufficient permissions of the Temporary Internet Files folder stored on a server. You can fix this problem by configuring Outlook to use a specific folder for temporary internet files.

If Outlook 2000 is being used then you’ll have to make changes to the Registry. As always, before making any edits to the Registry you should always make a backup. That way if any errors are made then you will have a good working backup point that you can restore to.

The change is fairly easy. Just go down to the lower left corner of the screen on most Windows systems and click on the Start button. Then locate the Run program and click again. In the Open text field type in the word “regedit” and hit enter or click OK. This will start the Registry Editor. Next, locate and click on the registry key:
HKEY_CURRENT_USER\Software\Microsoft\Office\9.0\Outlook\Security\OutlookSecureTempFolder

Depending on your version of Outlook you may have to look under a different folder instead of the 9.0 subfolder. It might be under 11.0 or 10.0 – you will need to check this. Now if the registry key does not exist on the system then you will have to manually create it.

Your next step is to double-click on OutlookSecureTempFolder. Then in the Value Data field, type in the new directory name of an existing folder such as C:\newtemp\ and then hit the enter key or click OK. Lastly exit the Registry Editor and then restart the system. After restart, verify that you are able to open the attachment.

Another reason for being unable to open attachments can be caused by how temporary files are opened in Outlook. When an attachment is opened Outlook will save a copy of the attachment in a hidden Temporary Internet Files sub-folder. Outlook then appends the same file name with a sequence number. The problem occurs if Outlook tries to open a file more than ninety-nine times. Every time the file is opened the sequence number is incremented but after ninety-nine times it is no longer incremented. And this is where the error happens. The solution is to delete all files within that sub-folder.

The temp folder is created with a name that starts with the letters OLK and is followed by a random number. You will need to search for this folder under the local user’s profile path. If you try to locate this folder using Windows Explorer you will be unable to find it. Even if you have “show hidden folders” turned on it will not help because Windows Explorer prevents the folder from being seen. So what you will have to do is locate this folder manually.

You can start your manual search by clicking on the Start button, then on the Run program and then type in “CMD” in the Open field and hit enter or click OK. This will bring up an MS-DOS command prompt window. From here you’ll need to CD to the “Local Settings\Temporary Internet Files” folder. From inside this folder you can run the command “dir *.” and look for the directory (folder) that starts with OLK. You will need to delete all files in the “Temporary Internet Files” folder.

Now that you know the folder name you can go back into Windows Explorer and navigate to the parent directory and add the newly found folder name such as “OLK(somerandomnumber)”. Then from Windows Explorer you’ll be able to delete all the files inside the newly added directory. If you want to perform a manual delete then cd into that specific folder, OLK(somerandomnumber) and then run the command “del *.*” to delete all the files inside. Be absolutely certain you are in the OLK(somerandomnumber) folder before performing any deletes.

After deleting the files you can then restart Microsoft Outlook. After Outlook has restarted verify that you are able to open your attachment.

Outlook Cannot Create or Open Attachment

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It seems that the more you try to keep someone out of your life or your house the more they want in. It’s the same with unauthorized access to your corporate email accounts. But what’s worse than someone trying to gain unauthorized access to your email accounts is some “thing” trying to gain access to your email accounts. The “something” that I am talking about is the following warning message:

“A program is trying to access e-mail addresses stored in Outlook. Do you want to allow this?”

If you have Outlook 2002 deployed in your environment then you can implement some security features that will prompt a user or notify an administrator of attempted unauthorized access to email.

Some security features will notify you if an application attempts to access the Outlook address book. Such security features can also be configured so that access must be granted by a user or an administrator’s role. Logging of such events can also be turned on for historical purposes.

Some applications can be added as a trusted source and will require the Outlook Email Security Administrator Package from Microsoft. Other applications may need to be configured as trusted COM add-ins. Administrator assistance will most likely be needed as some changes will need to be performed on the Exchange server.

If you still have users who are running Outlook 2000 then there was an Outlook Email Security Update that came out to address most of the issues surrounding access to email by software applications.

That particular Email Security Update affected how email attachments were handled by Outlook. It also impacted how applications were allowed access to email. Always a scary thought that you’re opening up access to email components by software applications. The good news is that warnings and popup messages would result in more immediate notifications about attempts to gain access to your email. Some of the software components affected by the Security Update include: email attachments, the Outlook object model and the Simple Messaging Application Programming Interface (Simple MAPI).

Upon an attempt to access email a warning message will appear that will ask a user for confirmation. They then must confirm the action to allow email access or access to an email component. It is possible for an administrator to override the default settings. Some users may experience multiple popups asking for confirmation more than once depending on how the incoming application was written.

You may find that after having implemented the security update and after a couple of months that some users will become annoyed with what will seem to them the many interruptions of their work day by having to constantly click through these multiple warning popup windows.

Email components and features that may be affected by the Security Update include: Mail Merge, Mail Merge to Email or Fax, Team Folders, Digital Dashboards, New Folder Invitations, and “Unsafe” attachment forwarding.

You will probably hear from users who notice that blank spaces in some of their email messages. This can be caused by the fact that attachments to email messages using the rich text format are filled by a blank space where the attachments would normally be prior to the security update being implemented.

If you find that storage space is a concern then you can advise your users to forward any emails which contained unsafe attachments to themselves. You, the administrator, or the user can delete the original message once it has been forwarded so that you can free up your storage space. The reason why this works is because the forwarded message does not contain the unsafe attachment.

There are other areas affected by the security update that you will run into. For instance, warning messages may not be observed that are at the top of journal items or custom Outlook forms. So if Outlook has blocked access to an attachment you may not be able to see the visual warning message.

You should note that there are some drawbacks to the standard security system. One of those drawbacks is that it doesn’t you the ability to determine the source of the threat. Another drawback already mentioned is that some earlier applications can inadvertently cause multiple confirmation windows to popup. All of this can result in a user who manages to disable these security features – which is not what any administrator wants to happen in an environment that they are trying to keep secure.

To help out in this situation there are add-in products available in the marketplace that will allow you to identify and categorize potential email access violations. After an application has been identified then its status can be preset so that on future occasions the application can have its access either blocked or allowed. It could even have the default Outlook handler set to run for future access attempts. All of these handling actions can be set to run automatically. Just remember that you are overriding security features set by a Security Update.

Unauthorized Access to Email

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Email administration should be just one of the duties of a typical administrator for any large company. Most often email administration is performed by network administrators and sometimes by operating system administrators. Most day to day email administration consists of pretty routine activities.

However, you’ll sometimes find yourself with a never before seen problem. One such problem is that of duplicate emails. Thankfully, this is an infrequent occurrence.

Email inboxes use up a lot of space as it is and having limits on the amount of inbox space a user can use can be helpful as an alert mechanism for spotting trouble with duplicate email messages. A lot of duplicate emails can use up a lot of space and fill up your end users’ inboxes almost overnight. And these duplicate email messages can certainly cause confusion and negatively impact a company’s productivity.

Some administrators have noticed this problem when they’ve downloaded email messages using Microsoft Office Outlook 2003 from a POP3 (Post Office Protocol) email server and then on their next download they notice that duplicate email messages have been downloaded as well.

There are a couple of different reasons why this can happen. There is an option called, “Leave a copy of messages on the server” which if enabled can create an environment that allows duplicate emails to be downloaded. Luckily, this problem was fixed in a hotfix. That hotfix has been included as of Service Pack 2. The latest Office 2003 service pack corrects this problem.

If you’ve just installed the hotfix then you will see duplicate email messages the first time you download but the duplicate downloads will stop occurring after that initial download.

If you wish to enable the “Leave a copy of messages on the server” option then you can start by opening up the Tools menu and clicking on “E-mail Accounts”. Then click on “View or change existing e-mail accounts” and then click on Next. Locate your POP3 email account and click “Change”. You’ll next have to click on “More Settings” which will allow you to choose the “Advanced” tab. Here you will want to check mark the “Leave a copy of messages on the server” check box. Then click OK or hit the enter key.

There are other circumstances that allow for duplicate email messages to get downloaded. One such circumstance that allows this to happen is if there are multiple POP3 email accounts associated with the same profile in Outlook.  When your end user logs on to Outlook they may be prompted for their password for one of their accounts and that is the point when they will receive duplicate email messages. Those two accounts are likely pointing to the same POP3 email server which results in an end user getting duplicate emails.

You can fix this by turning off email reception for one of those accounts. Bring up Outlook and bring up the Tools menu. Locate “Send/Receive Settings” and click on “Define Send/Receive Groups”. You’ll have to determine which group contains the two POP3 email accounts. Once you know which group that is then double-click that group and under Accounts select the POP3 email account that you want to stop receiving duplicate email messages and click on it. Then clear the “Return mail items” check box. This will disable that particular email account from receiving any further emails and hence stop the duplicate emails from appearing.

Another situation that results in duplicate email messages is if the email server contains corrupt email messages in the users’ inbox. As the administrator you’ll have to check the logs for possible error messages related to corrupt email. If you determine that there are corrupt email messages on the server then you’ll have to log in to the server and delete them.

There are times when you have reinstalled the system software and also needed to reinstall Outlook. Sometimes, after an Outlook reinstall, your users will receive duplicate email messages. Other times duplicate messages may result after a user has synchronized Outlook with one of their mobile devices such as a PDA, Palm, a smart phone or other Windows mobile device.

If necessary, before any settings are changed – such as the ones mentioned above – it would be a good idea to have an end user scan and identify duplicate email messages. Obviously this is a non-productive use of their time. So having a tool in your toolbox that can scan for, identify and delete duplicate email messages can be a great time saver. There are many tools on the market that can help you with this activity.

Managing Duplicate Email Messages in Outlook

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I’ve written in the past about various issues involving Outlook and security, third-party software, add-ins, etc. But there are also less email specific issues that can affect the basic working functionality of Outlook. These basic issues can be addressed with some standard troubleshooting procedures.

If you have installed Outlook with the Corporate or Workgroup option – which supports the Messaging Application Programming Interface (MAPI) services -  then here are some areas that can have a negative impact on the operation of Outlook when mis-configured: TCP/IP settings, Domain Naming and Exchange server configurations. Configuration problems can affect such Transport services as: Internet email, Microsoft Exchange Server, Address Book and Personal Folders.

If you want to find out what Outlook option is installed you can click About Microsoft Outlook, on the Help menu and then verify the installation as “Corporate or Workgroup”.

Sometimes you may get an end user who is having problems with their folders in Outlook. When they click on any of their folders such as Sent Items, personal folders or their Inbox, they get the following error message:

“Unable to display the folder. Network problems are preventing connection to the exchange server computer.”

It’s possible that shutting down Outlook and then restarting it might correct the problem. Maybe some process didn’t exit correctly or memory was stepped on that caused this problem. But as an admin you want to step through the process of diagnosing the cause of the problem and then making the appropriate corrections as needed.

As an admin, you always want to ensure that your network connection is working properly. One way to do this is by using the “ping” command. If you are able to issue the “ping” command to a known server using an IP address then you’ll know that the TCP/IP connection is working properly.

You can issue the command by opening an MS DOS prompt window by clicking on the Start menu button in the lower left corner and then pulling right on All Programs and then pulling right on Accessories. Once you have the Accessories open then select on Command Prompt to bring up an MS DOS prompt window. Then type in this command:

ping 209.131.36.158

You should see the following results if you have a successful connection:

C:\Documents and Settings\Administrator>ping 209.131.36.158

Pinging 209.131.36.158 with 32 bytes of data:

Reply from 209.131.36.158: bytes=32 time=39ms TTL=54

Reply from 209.131.36.158: bytes=32 time=25ms TTL=54

Reply from 209.131.36.158: bytes=32 time=31ms TTL=54

Reply from 209.131.36.158: bytes=32 time=24ms TTL=54

Ping statistics for 209.131.36.158:

Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),

Approximate round trip times in milli-seconds:

Minimum = 24ms, Maximum = 39ms, Average = 29ms

C:\Documents and Settings\Administrator>

Now that you’ve established that there’s nothing wrong with your TCP/IP connection you should verify that your domain configuration is working. By this I mean that you should try to ping a server using the “servername.com” reference instead of the IP address.

Well known servers include www.google.com and www.yahoo.com. After the window opens up just type in one of these commands:

ping www.google.com

Or

ping www.yahoo.com

You should get something like the following:

C:\Documents and Settings\Administrator>ping www.google.com

Pinging www.l.google.com [74.125.19.99] with 32 bytes of data:

Reply from 74.125.19.99: bytes=32 time=25ms TTL=51

Reply from 74.125.19.99: bytes=32 time=44ms TTL=51

Reply from 74.125.19.99: bytes=32 time=28ms TTL=51

Reply from 74.125.19.99: bytes=32 time=60ms TTL=51

Ping statistics for 74.125.19.99:

Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),

Approximate round trip times in milli-seconds:

Minimum = 25ms, Maximum = 60ms, Average = 39ms

C:\Documents and Settings\Administrator>ping www.yahoo.com

Pinging www-real.wa1.b.yahoo.com [209.131.36.158] with 32 bytes of data:

Reply from 209.131.36.158: bytes=32 time=26ms TTL=54

Reply from 209.131.36.158: bytes=32 time=24ms TTL=54

Reply from 209.131.36.158: bytes=32 time=24ms TTL=54

Reply from 209.131.36.158: bytes=32 time=26ms TTL=54

Ping statistics for 209.131.36.158:

Packets: Sent = 4, Received = 4, Lost = 0 (0% loss),

Approximate round trip times in milli-seconds:

Minimum = 24ms, Maximum = 26ms, Average = 25ms

C:\Documents and Settings\Administrator>

If you are able to ping successfully then your Domain Name Server (DNS) settings have been set up correctly and are working as expected.

Lastly, if you are working with Dynamic Host Configuration Protocol (DHCP) then that can add an extra layer of complexity to your diagnostic procedures. It’s possible that you might have to include the Exchange server domain in the Search Domains field in the Network System Preferences. And, at the same time, you might also have to remove domain name server entries in the DNS Servers field.

These are just some of the problems you may encounter when setting up your systems and servers for Outlook and Exchange.

Troubleshooting Outlook Configuration Issues – Part 1

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Sending secure email often involves the process of also having to troubleshoot error messages related to TLS and SMTP in Outlook.

Transport Layer Security (TLS) is a cryptographic protocol used to encrypt traffic over networks such as the Internet. Use TLS encryption for servers that require basic authentication. With so much critical information such as usernames and passwords passing through your network, why take the risk that someone snooping could eavesdrop and pull out important corporate information? Implementing encryption and other security measures can help to protect your corporate jewels. The enforcement of security will require users to use the same encryption level that you set when they try to negotiate access to your network and servers. Without the same level of security, messages will be returned and non-delivery reports (NDR) will be generated.

Simple Mail Transfer Protocol (SMTP) is used for sending outgoing mail for both POP and IMAP clients and is well known for its vulnerabilities such as spoofing of emails.

To minimize your security exposure and to ensure that your corporate SMTP communications are protected you can start by implementing the Transport Layer Security protocol in the Exchange Server.

If you are like most email or system administrators you will be supporting both end users who work at corporate offices and also end users working from remote locations such as out of state offices or home offices.

Occasionally you will get a complaint from end users who are unable to send email but they can still receive email. After changing the SMTP addresses in their outgoing email servers you find that they are still not able to send email and that they are getting an error message such as the following:

“Verify the email address in your account properties. Server responded: 530
5.7.0. Issue a STARTTLS command first.”

The STARTTLS command takes plain text communications and provides a secure connection without having to use a separate port for encrypted communication. It is an extension to plain text communication protocols and makes a plain text connection become an encrypted connection such as a TLS or SSL connection.

The benefits to using STARTTLS include the ability to verify the identity of the client and/or server in an e-mail transmission. It can also be used to encrypt mail transmissions with or without the identity verified between two mail servers. And it provides the capability to authenticate a user for relaying through a mail server.

Now as previously mentioned, if for some reason a client is not able to send email and they are receiving an error message about having to issue a STARTTLS command first then a solution is to enable an encrypted Secure Socket Layer (SSL) connection for the SMTP server. You make this change in the account setup. Look for the advanced tab of the More Settings dialog box.

Another troubleshooting mechanism you can use is to turn on transport logging in Microsoft Outlook. This will allow you to log all communications between Outlook and many of the email servers that are out there. By reviewing the logs you will be able to identify any communication problems that might occur when using Outlook and email servers.

• You can turn on logging in Outlook by going to the Tools menu and clicking Options.
• Next, select the Other tab and then click on the Advanced Options button.
• You will get a check box labeled “Enable mail logging”.
• Put a check mark in the box by clicking on it.
• Then save your changes by clicking OK.
• Click OK again after you have returned to the main options.
• Finally exit Outlook and then restart it.

If your problem is that you are having trouble establishing a secure connection to Microsoft Exchange server it might be because you are trying to use a different port other than the default (SMTP) port 25. This may have happened if another administrator or an end user changed the default port by selecting the check box labeled, “This server requires a secure connection”. This will also affect other email servers that require a STARTTLS negotiation.

When Outlook 2000 is used to create a secure connection for SMTP it will issue a STARTTLS command which then starts the TLS handshake process for a connection using the default port 25. But this is not the same process for ports other than port 25.

A solution to this kind of problem is to upgrade to Microsoft Outlook 2002. After the upgrade the email client will be able to issue the STARTTLS command and initiate the negotiation process for a secure socket on a different port number that is not port 25.

Debugging SMTP and TLS errors in Outlook

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