Blog: Outlook

We recently encountered a terminal server user who said they were in Outlook and accidentally hit some keyboard combination that caused it to close.  When they tried to get back into Outlook it kept giving an error message.

When I connected and tried to run Outlook, it kept displaying an error message that there was no Outlook Profile setup.  However, when I checked the profiles there were in fact several profiles listed.  I tried creating a brand new profile, but still received the error message.

I had the user log off and back on to the terminal server, checked outlook from my account to make sure it wasn’t something server wide, and then I checked the actual outlook.exe under the Program Files directory.  I did not see anything checked for compatibility with my account, but when I checked the outlook.exe from her account, it had Compatibility Mode for Windows 95 checked. [more]

My assumption on what happened is that outlook crashed, came back up, and asked if it should be run in compatibility mode.  I am assuming the user said yes at this point, and it turned the option on which caused outlook to not work anymore.


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.


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.


One of the new features in Outlook 2010 that I absolutely love is the ability to create “Quick Steps.” At home, I’ve got several email accounts that download into Outlook. From those separate inboxes, I file them into folders kept completely offline. A problem that I run into is that when using the preview pane, the email isn’t marked as read (intentionally) unless I click off and back onto it. When I click-drag the email to a folder to file it, it keeps its unread status unless, once again, I click off and on. This is not a very efficient way for me to work and Quick Steps fix that.

When you create a new Quick Step, you can define a set of actions that this one button performs. [more]

As can be seen below, the following Quick Step will ask you which folder to move your email to and mark it as read.

You can create a shortcut and tooltips for these and add as many actions as you would like. Very helpful!


Setting up additional accounts in Outlook is handy to get email from different servers.  You can use additional accounts to send email from those different mailboxes also.  But did you know that you can use this feature to send email from different email addresses that are set up on your Exchange server?  For example, if email messages you send come from, but you also want to be able to send email from  Here is a step by step guide on how to do this in Outlook 2007:

  • Go to Tools->Account Settings
  • E-mail tab
  • New...
  • Next >
  • Manually configure server settings...
  • Next >
  • Internet E-mail
  • Next >
  • Enter your name, email address such as
  • Account type POP3
  • Incoming mail server
  • Outgoing mail server (SMTP)
  • Enter username as <your domain>\<your username> and your domain password
  • If you save the password, you will have to update it here when you change it
  • You can choose the Test Account Settings...
  • It will get an error retrieving email using POP3, but we don't need that
  • Next >
  • Finish

At the bottom of the Accounts Settings window, be sure it is using your inbox for receiving messages. [more]

Go to Tools->Send/Receive->Send/Receive Settings->Define Send/Receive Groups
Edit the All Accounts group (and possibly any other groups) to exclude this account
This will prevent it from trying to retrieve email using POP3 all the time

Now, to send email from that email address, select that account from the Account dropdown under the Send button.


I’ve been running the Office 2010 beta for a while, although I’ve seen this problem occur on Office 2007 as well. Periodically, I’ll lose my ability to select text with the mouse inside Outlook. It just simply won’t work. Closing and restarting Outlook always fixes the problem, but it’s an annoying problem to have to deal with. After some searching on the internet, a solution from Microsoft popped up. From [more]

Problem Description:

You install an automatic update for Microsoft Office Word 2007 on a Windows Vista-based computer and then restart the computer. If Word 2007 was running when the computer was restarted, you experience one or more of the following symptoms:

  • The mouse does not work when you use Word.
  • You cannot open a Word document from the Search window in Windows Vista.
  • You cannot open a Word document from Windows Desktop Search.
  • Word crashes when you try to start or exit Word.
  • Word crashes when you open the Open dialog box.
  • Word crashes when you save a document.
  • Word crashes when you close a document.

The fix is simply to open the registry, browse to and delete the following registry subkey: HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Word\Data

Then close and restart your Word applications (Word, Outlook, etc.). So far, this seems to have fixed my problem, although I’m going to give it another week or two before I call it comfirmed.


Email usability: Best Practices for Microsoft Outlook 2007.  Here are three things that I would like to mention to help manage email.

1)  Set up a search folder and include many folders – inbox, rss feeds, mailing lists, Communicator conversations, etc.  This will put all items you need to consider in one place.

2)  Set up a rule to flag for follow up for all items.  Use the 4 D's for handling email: Delete it, Do it (respond, take action, file), Delegate it (forward it), or Defer it.  Once the email it taken care of, mark it complete.

3)  Use sorting and searching to find items.  You can click on the column headers to sort, then start typing the contents of the field and it will jump to those items.  An even better way (but requiring more typing) is searching.  Since our Exchange server indexes these items, searching is really fast.  You can enter search terms in the format keyword:value to find items.  For example, subject:"sql account" from:john, will find that email from John about that sql account.  To find the available keywords, search for help on “narrow your search” to find the topic “Learn to narrow your search criteria for better searches in Outlook”.  You can also search contacts and calendars. [more]

These ideas came from an article by Melissa MacBeth called Best Practices for Microsoft Outlook 2007, available at  This is a long article, but it has many good ideas.


While investigating why only some Outlook events showed up on a users iPhone calendar. I found that items created by the user or accept as meeting invitations were on both the iPhone and Outlook. But if it was created by another organizer, such as an assistant, on behalf of the user the event did not show on the iPhone calendar.  [more]

The user was running an older firmware version 3.0.1, which was before the calendar invitation fix. I downloaded and installed the latest firmware version 3.1.2 and installed it on the iPhone. Once installed the iPhone resynchronized and all calendar events including those created by an organizer were present on the iPhone and Outlook.

So… installing firmware 3.1 or newer, breaks the free tethering option that can be installed on the iPhone. Not installing the latest firmware does not allow for the new calendar invitation options. Therefore a choice must be made.


If you’ve ever wanted to restore the original Outlook shortcut to the desktop, you’ve probably found that a normal shortcut that points to outlook.exe (the kind with an arrow on the icon) lacks some of the functionality that the original Outlook icon had (for instance the ability to edit your machines “Mail” settings by right clicking and choosing properties). To restore the Outlook original icon to the desktop, edit the registry as outlined in the following KB article:


Progress. Innovation. One small step for man. Call it what you will but the advancement of software usually comes at a price with some bumps along the way. Apple, while a good company that puts out a good product, is mortal like the rest of us and as such is subject to the same development bumps and bruises. That was my experience this week when an executive assistant at one of our clients came to me in a panicked state saying “Help! I just sent out a meeting invite to over 30 executives and it keeps sending the invitation over and over and over again! People are getting upset!” [more]

Immediately I put together a lineup of potential offenders and began working my way through:

  1. Exchange message queues
  2. Online spam filter reinjection
  3. Notification of meeting change/update
  4. Corrupt/Malformed meeting event
  5. Possible wrong address in the list (we’ve seen this happen before) 
  6. MAPI profile/client issues.


  1. An inspection of the Exchange queues revealed nothing out of the ordinary, and the Exchange logs showed that each repeated meeting request appeared to be a new/separate message that was being received (and dutifully sent out) by the Exchange server. Nope, that’s not it.
  2. Online spam filter reinjection into Exchange was not a possibility since every recipient was internal… the spam service never saw the message. Innocent.
  3. Since the same meeting was supposedly being re-sent, I thought that it may be possible that the meeting would re-send whenever a user would update/respond to/propose a new meeting time for the calendar event. After looking at the executive assistant’s sent items as well as the inboxes of several attendees, none of this was true… the meetings were actually being re-sent. Strike three. 
  4. Thinking that there may be some oddity in the meeting event such as a reoccurring event, I had the user delete the meeting then recreate it while I watched. I noticed the user used a distribution list when inviting attendees.
  5. Some of our engineers have seen some quirks when using a distribution list with incorrect/invalid email addresses. I had the user recreate the distribution list from scratch, populating it only by clicking on addresses in the Global Address List. Re-created the meeting with new distribution list. Same behavior.
  6. Thinking that the problem may be a MAPI profile issue due to the Exchange logs indicating that each message was a separate submission from the client, I went to the user’s office to rebuild their MAPI profile. In doing so I realized that the user was on a thin client. Before building her Terminal Server MAPI profile I asked the user what time she had left the previous day. She said she left right at 5:00pm and had logged off of the Terminal Server at that time. The last meeting that was resent went out at 5:14pm. Hmmm…


At this point I had seemingly ruled out the client aspect as well as the server aspect of the problem, what could be left? Blackberry! I asked the executive assistant if she had a Blackberry, thinking that surely the Blackberry Enterprise Server was the guilty party since the problem was happening when she was logged out. “No, I don’t have a Blackberry… a couple of months ago I got an iPhone instead.” At this point I was getting desperate so I asked her to power off her phone for the remaining 6 hours of the workday. Magically not a single meeting invite was sent out. After that I asked her to power it on. Immediately a repeated meeting invite was sent! I asked her if anything had changed on her phone recently to which she replied ,”actually, I just upgraded my phone this weekend to the new 3.0 iPhone OS”. A quick Google confirmed that other users who had upgraded to the 3.0 Apple iPhone OS and had sent meeting requests to a distribution groups had experienced the same problem. A call to Apple support yielded no help as a “Product Specialist” (referred to as “iPhone Ninjas” by Apple Tier 1 support, no joke) told me that they don’t have any record of that happening to anyone else, call Microsoft since it’s an Exchange account.  So, until iPhone OS 3.1, it looks like users will not be able to use distribution groups when creating meeting requests. Isn’t there an App for that?