Blog: Outlook

Starting with Microsoft Outlook 2010, a new feature called “Suggested Contacts” automatically keeps track of everyone you send a message to, but isn’t in your Outlook contacts.  By default, when you sync Contacts with an iPhone, both “Contacts” and “Suggested Contacts” are copied over.

To Turn off the Suggested Contacts feature: in Outlook, click File > Options > Contacts, and uncheck “Automatically create Outlook contacts...”  Note: you will still need to remove any existing “Suggested Contacts” for them to be removed your iPhone contacts.

e recently had a client who was receiving the following error message in Microsoft Outlook: "Your automatic reply settings cannot be deployed because the server is currently unavailable. Try again later."

The reason this error message is displaying is because Outlook can’t see your Client Access Server. [more]

To get Out-of-Office to work you need to add a bypass to your proxy server for your CAS. To do this you need the name of your CAS (typically the exchange server).

Open up your Internet Options settings in Control Panel and click on the “Connections” tab.  Make sure that the “Bypass proxy server for local addresses” is ticked then click on “Advanced”.

In the “Exceptions” panel type in your CAS server name followed by .* then press OK->OK -> OK to close all of the windows.

Close and reopen Outlook and out of Office settings options should now work.

One of our users was having trouble opening an e-mail attachment that was sent from one of our software applications.  It looked like some kind of permission problem.  When he tried to preview it, it would just say the file cannot be previewed because of an error in the PDF Preview Handler.  If he tried to open it, it would say that it could not save the attachment.  He was previously able to open them without receiving the error.  I found that when you open Outlook attachments, it usually saves them in a randomly named folder under this path:

%userprofile%\AppData\Local\Microsoft\Windows\Temporary Internet Files\Content.Outlook

This location can be changed with a registry edit.  Since that Temporary Internet Files folder is a special folder, you cannot drill down to this; you must paste or type it into explorer (or your favorite command prompt).

I'm sure you've seen how Windows will create a file with a number in parentheses if a file by that name already exists?  The problem in Grant’s case is that the attachments being e-mailed to him were all named Attachment.pdf, so they were being named Attachment.pdf(1), Attachment.pdf(2), etc.  It seems like the limit was 199 of these renamed files on Grant’s machine.  I have not been able to determine how this limit is determined, and it does not seem to be the same everywhere.  Cleaning out that folder solved his issue (at least until he gets the 200th e-mail again).

This applies to any e-mail accounts setup to get e-mail using POP3. 

A customer that uses an e-mail account provided by their ISP for work was frequently having new e-mail rejected because the mailbox was full.  Looking at the storage space on the ISP’s website, they were limited to only 20 MB of e-mail storage.  They usually would have to delete e-mails on the ISPs website in order to receive new e-mails again.  The customer also had been setup to connect to the ISP’s server using POP3 in Microsoft Outlook, and Microsoft Outlook was configured to save e-mails to a local PST file on the hard drive.

In Microsoft Outlook, open the “Account Settings” for your e-mail account.  Click on “More Options” to view more settings and select the “Advanced” tab. [more]

With POP3, you can give Microsoft Outlook the option to “Leave a copy of messages on the server”.  If this is unchecked, new e-mails received at the ISP remain there until Microsoft Outlook downloads them.  After it downloads the e-mail, the e-mail is deleted on the ISP’s mail account.

An important thing to remember is that the local PST file needs to be backed up regularly because all e-mails will be lost if the PC crashes, PST file becomes corrupt, or you want to change PCs.

You can edit existing emails, although usually this would not be a good idea since you probably want to preserve the exact email you received.  You can add something to the subject line without even choosing to edit it.  Categories are fine for a preset list, but sometimes I like to make a comment and save it with the email to make it easier to find later.  Sometimes the subject is blank or created programmatically with little relevance (like voicemails).  So I add something to the subject, marking it with something identifiable so I can clearly see what was added.  It was pointed out in the meeting that changing the subject line will break the default behavior for the built in search for “messages in this conversation” since it has to match the subject exactly (well, except for RE:, etc.).  Keep this in mind if you use that feature.  I usually just use the regular search feature, which just finds anything that includes that string.

When opening an attachment directly from within Outlook you could get an error message saying that it can’t create the file and to that you need check the permissions on the folder you want to save it in. In most cases the permissions on the folder isn’t the issue but the fact that the folder is “full”. When you open an attachment directly from within Outlook it will first save a copy to a subfolder of the Temporary Internet Files folder. Cleaning out the folder will solve the issue.

How to Empty Outlook Secure Temp folder

The subfolder name Outlook creates (on installation of Outlook) in the Temporary Internet Files folder is quite random. In Outlook 2003 and previous, the name starts with OLK and is followed by up to 4 random numbers or letters. In Outlook 2007 and Outlook 2010, this folder is called Content.Outlook and then has a subfolder which is named with 8 random numbers and letters. Getting to the Temporary Outlook Folder can still be accomplished in 2 easy steps though. [more]

Step 1: Locate the folder
The folder location is stored in the registry in the following key;
• Outlook 97
HKEY_CURRENT_USER\Software\Microsoft\Office\8.0\Outlook\Security
• Outlook 98
HKEY_CURRENT_USER\Software\Microsoft\Office\8.5\Outlook\Security
• Outlook 2000
HKEY_CURRENT_USER\Software\Microsoft\Office\9.0\Outlook\Security
• Outlook 2002/XP
HKEY_CURRENT_USER\Software\Microsoft\Office\10.0\Outlook\Security
• Outlook 2003
HKEY_CURRENT_USER\Software\Microsoft\Office\11.0\Outlook\Security
• Outlook 2007
HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\Security
• Outlook 2010
HKEY_CURRENT_USER\Software\Microsoft\Office\14.0\Outlook\Security

Step 2: Get to the folder and delete content
1. Open the OutlookSecureTempFolder registry key from the location provided in Step 1.
2. Copy the path from the key.
3. Open Explorer.
4. Paste the address in the Address Bar and press Enter.
5. Delete the content of the Outlook Secure Temp Folder.

One of our customers was having problems connecting Outlook to exchange accounts hosted with Microsoft through their Office365 program. The machines in the domain running Windows XP with Office 2007 had no problem connecting, but none of the Windows 7 machines with Office 2010 were able to connect. Since the email accounts were hosted at Microsoft, Outlook was using port 80 web traffic to establish a connection. After exempting the source IP of the test machine from filtering in the Barracuda, the connection immediately worked. This proved that something was not working correctly inside the Barracuda.

The domain outlook.com was whitelisted prior to these changes. After talking to Barracuda tech support, they found several IP addresses that Outlook was trying to contact. They suggested adding those IP addresses to the list of IP addresses that bypass the Barracuda, which is the proxy server, and opening port 80 for those IP addresses on the firewall. We made the suggested changes and it worked correctly. The Barracuda engineering department found that the traffic to outlook.com was being redirected to live.com, and therefore being dropped by the Barracuda. Barracuda suggested we add an expression to the Barracuda to allow port 443 traffic to live.com, but they later said we would probably have to whitelist live.com for this to work properly. We chose to just leave port 80 open to those IP address on the firewall and have clients bypass the proxy for those addresses.
 
When troubleshooting issues that might be related to the Barracuda, it is often helpful to temporarily exempt the source IP of the machine on which you are working. When the Barracuda is in Forward Proxy mode, this can be done by going to Advanced > Proxy. Add the IP to the Source IP group under the Proxy Authentication Exemptions.

We recently became aware of a problem with Exchange 2010 users being unable to set their out of office settings.  With their legacy Exchange 2003 mailboxes, they could set out of office.

When trying to set out of office within Outlook, users would get an error message that the Exchange server could not be contacted.  Performing the “Test e-mail autoconfiguration” kept failing to connect to the server with HTTP status code 401 Unauthorized.  It was also noted that OWA would not allow logins because the login credentials would not work for anyone.

After trying to troubleshoot permission problems within IIS of the mail server, I eventually came across this thread:[more] http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/36662e7c-8c4a-44dc-85d9-eb7fab1d8b49/

I ran powershell as an administrator on the server, and typed in the following:

• Import-Module ServerManager
• Add-WindowsFeature NET-Framework,RSAT-ADDS,Web-Server,Web-Basic-Auth,Web-Windows-Auth,Web-Metabase,Web-Net-Ext,Web-Lgcy-Mgmt-Console,WAS-Process-Model,RSAT-Web-Server,Web-ISAPI-Ext,Web-Digest-Auth,Web-Dyn-Compression,NET-HTTP-Activation,RPC-Over-HTTP-Proxy

It appears that this command re-imports many IIS modules.  In the article, it has a –restart at the end, but I left it off to prevent the server from rebooting.  It was not necessary in my case in order to resolve all of the issues with OWA/OOF/Autoconfiguration.

After some updates were installed on an SBS 2008 server, Outlook started prompting for credentials from time to time.  Searching the Internet for this was futile.  Many incidents of this happening with many different solutions exist, but none of these worked.  A $99 case with Microsoft was opened and the tech that called back knew exactly what the cause of the problem was.  This update (http://support.microsoft.com/kb/973917) enabled kernel mode authentication with IIS and it was causing Outlook’s user mode authentication to fail. This article:

http://blogs.technet.com/b/sbs/archive/2010/02/16/outlook-2007-credential-prompts-in-small-business-server-2008.aspx

explains what broke and how to fix it by running this command as an admin:

%windir%\System32\inetsrv\appcmd.exe set config -section:windowsAuthentication /useKernelMode:false