Blog: Outlook 2010

We recently encountered a strange issue with a customer running Outlook 2010 in an Exchange 2007 environment. Some users (not all) would randomly get certificate warning pop-ups in Outlook. The certificate warnings indicated the Fully Qualified Domain Name (FQDN) "" wasn’t on the certificate. The certificate warning was legitimate; that FQDN was not on the certificate because this customer didn't have a UCC certificate.

However, all the autodiscover SCP records had been changed via Powershell to point the autodiscover URL to "" which WAS on the certificate. All the PCs were joined to the Active Directory domain so the SCP lookup should have had precedence over any other autodiscover method. Doing an autodiscover check via the Outlook system tray icon indicated the certificate warning pop-up and all the values returned by the test were all correct.

The question was why were these PC's even contacting ""? After much troubleshooting, we found that even though the domain SCP records were correct, some Outlook clients were also doing DNS lookups for "" in parallel with the SCP lookup. Checking DNS there was an "" A record and pointed to the IP address of the Exchange server; however, since that FQDN wasn’t a subject alternate name on the certificate, it would have legitimately generated the certificate warning.

The resolution was to simply remove the "" A record from DNS and we added SRV records for good measure. It doesn’t seem like having that A record in DNS would have mattered since the autodiscover priority shouldn’t have ever used it, but from now on we will use DNS SRV records and SCP exclusively for Exchange autodiscover.


I came across a weird issue with a user running Windows 7 with Outlook 2010.  Tif attachments opened from an e-mail launched Windows Photo Viewer.  When the document was printed, it was cutting off a good portion of the bottom from all of the pages. 

While troubleshooting printer settings, I had saved the tif attachment to the user’s desktop and it printed correctly after opening it from there.  There were no changes between opening the document from Outlook vs. the desktop, but something was causing the printer to cut off the bottom area. [more]

It was suggested that we try using the Microsoft Office Document Imaging (MODI) application to handle tif files instead of the Windows Photo Viewer in Windows 7.  Upon trying to install the feature from Office 2010, it is not available. Microsoft has the following workarounds listed in this article

I chose to go with option 2 which was to download the free SharePoint Designer 2007 which includes the MODI tool.  Beware that this download is 295 MB, so it took me about 30 minutes to download just to get this little utility. 

After performing the custom install for MODI, it does not show up in the list when you right click the tif file and choose what program to open tif files with.  I had to right click on the shortcut in the start menu and get the file path from the properties.  Then I added MODI to the list of applications to open tifs with and checked “always use”.

The Microsoft Office Document Imaging utility printed out the user’s tif documents without any issues.


Recently, I was working with someone who receives a lot of email. Because of the sheer amount of email she receives, she must prioritize what messages she can read in order to continue working effectively. The request came in to see if it were possible to auto-categorize emails in Outlook based on the sender of the email so that one could simply glance through the inbox and see (by color) what emails had come in. After looking at it for a bit, we set up a Outlook Rule to color categorize an email as soon as it came in if the email was on a list of senders manually added to the rule. This worked fine until we reached the size limit of the Outlook Rule.

The fix is quite simple. Create a new local Address Book with all the recipients you’d like to color code. Then, set your Outlook Rule to scan the address book for a sender to color code the email. [more]


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
• Outlook 98
• Outlook 2000
• Outlook 2002/XP
• Outlook 2003
• Outlook 2007
• Outlook 2010

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.


If you forward a meeting invitation, Exchange will notify the meeting Organizer that the meeting notice has been forwarded, and to who it was forwarded.  So, if you don’t want the Organizer to know that their meeting was forwarded, you can forward the meeting as an attachment.


  • When you forward a meeting request, it will not include the organizers name in the “To” or “CC”  fields; however, there is a small note above the “To” section that says “When you forward this meeting, a meeting forward notification will be sent to the organizer.”
  • If you look at the forwarded message (from your sent items), it does not show it was sent to the organizer; however, it does state in the From: Your Name on behalf of Person You Forwarded To.


When I am away from the office I often set Outlook to “Work Offline.”  This allows me to have Outlook open for access to the cached information and it doesn’t try to connect and update all the folders whenever I establish a VPN back to the office.

At some point, Outlook started resorting to Work Offline every time it started.  This was troublesome as I might go for hours at a time not realizing I was Working Offline and as a result, not receiving email messages.  Before this problem, Outlook would start in whatever state (Connected or Work Offline) it was in whenever it was shut down.

In researching the problem I found many references to this problem which go all the way back to Outlook 2003. [more]

Microsoft’s solution is to create a new Outlook profile, as the existing profile has somehow become corrupted.  I really wanted to find a “cause and effect” fix, but never did.  So ultimately, I created a new profile and the problem is solved.  It seems as though this is a work around rather than a solution, but I am now Online.

To create a new Outlook profile go to Mail (32 bit) in the Control Panel (Windows 7).

  • Click on the Show Profiles button under Profiles.
  • Click on the Add button.
  • Give the new profile a different name from your existing profile.
  • Follow the instructions and Outlook will connect to the Exchange server and automatically create a new profile.
  • With a new profile, you can now have Outlook prompt you regarding which profile you want to use when Outlook starts.  You can also specify one of the profiles for Outlook to use automatically.
  • If you specify a profile, be sure you specify the new one you just created.  This will ensure Outlook will start up and look for a connection to the Exchange server rather than ignore the Exchange server and Work Offline.


For several months I would try to open Outlook 2010 and nothing would happen. When I checked the Task Manager I would see two Outlook.exe processes running. If I killed the process with the most memory, Outlook would open and all would be well.

One day I decided to fix the problem. My first guess was that Outlook was not starting correctly. When I searched for "Outlook startup problems", I didn't find anything useful. After a little research I found that when I closed Outlook, the process did not go away. A quick search for "Outlook shutdown problems" immediately returned the most common problem is a third party Add-Ins. When I checked the list of Outlook Add-Ins, the most likely suspect was "Outlook Change Notifier" that was in an Apple subdirectory. I removed the Add-In and Outlook would open and close like a champ.  [more]

I found a forum discussion,, that said opening iTunes will reinstall the add-in. It tried it and iTunes acted like it was reinstalling and the Outlook Add-In was back.

Instead of removing the Add-In, just uncheck the box next to the Add-In to disable it. This will allow Outlook to close correctly and iTunes won't try to reinstall it. An alternative method is to rename the file that contains the Add-In: Although Apple claims it's not a problem with Outlook 2010, it is.


I recently upgraded my laptop to Windows 7 with Office 2010. After getting everything setup I was experiencing a problem with Outlook not reopening after I had previously had closed it. I would check the task manager and it would show to instances of Outloo.exe running. I would kill the one with the highest memory usage and Outlook would open. I began disabling and enabling Outlook add-ins until I found that the problem was caused by “OutlookChangeNotifier” which is installed with iTunes. Once that was disabled Outlook opened and closed without any problems.


Recently a user at a customers site was having trouble sending email.  I ran a script that connected to each mail server and specified the sender and recipient to see if any would get errors.  One refused to accept the email because the reverse DNS lookup on the source IP failed.  So the lesson to learn here is this.  If something does not work, try to figure out where it is broken and try to see exactly what is going on in that part that is broken.  But wait - that's not the end of the story because the user was sending email to 27 recipients and none of the messages were being delivered.

Mr. Peabody, set the WABAC machine to February 2004.  Microsoft has just published a paper "The Coordinated Spam Reduction Initiative". [more]

Section 11 is about Computational Puzzles For Spam Deterrence.  The idea is to have the computer sending email solve a puzzle that require a lot of resources, usually CPU time, but verifying that solution is fast.  The idea was to make it expensive for spammers to send out spam.  I know this sounds silly now with botnets having 1000s of machines sending spam.  But did you know Microsoft actually implemented this in Outlook 2003?  And did you know it is still in Outlook 2007?  And did you know it is still in Outlook 2010?  It's called postmarking now, but it is still the same computational puzzle.  This is only used when it thinks your email might look like spam.

Ok, so the way this works is that Outlook or your Exchange server generates the puzzle solution and adds it to the email headers.  It uses the header "x-cr-hashedpuzzle".  RFC 2821 (Simple Mail Transfer Protocol) states "The maximum total length of a text line including the <CRLF> is 1000 characters".  This x-cr-hashedpuzzle is quite long, so it is broken up into several lines.  The first line is 1000 characters, but the continuation lines have a <tab> inserted at the front, causing them to be 1001 characters long.  If this happens to be going through an ASA with ESMTP inspection enabled, it will send out resets to close the connection because it violates the RFC.

This is why the user I was working with could not send email to a list of 27 recipients. I removed the SMTP inspection on our ASA (which I have been wanting to do anyway) to work around this.


If you have any programs that use Outlook to script objects in Exchange, you need to  be aware that the folder name for root public folder changed with Outlook 2010.  In previous versions of Outlook the root public folder is named “\Public Folders”.  Starting with Outlook 2010 the root public folder is named “\Public Folders –” where is the connected user’s primary email address.  Fortunately you can use the GetDefaultFolder() method on the Outlook NameSpace object to get common folders without hard coding the name of it.  For example you could call GetDefaultFolder(olPublicFoldersAllPublicFolders) to get the "All Public Folders" folder in the Exchange Public Folders store if you're using Exchange.