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Outlook 2010 "Trying to Connect" - Intermittent but Frequent

  • I was not encountering any issues connecting to Exchange Online.  I don't know if it's related or just a coincidence, but I recently added (2) other Exchange accounts to my Outlook desktop client that I need to be able to reply from.  Now the main default  account seems to have endless problems connecting to Exchange, though sometimes the problem seems to move to the other accounts.

    Other than the user names, all accounts are configured identically.   In case it's relevant the main account is the one with most of the data, about 3 GB, the others store virtually nothing.  The problem is occurring on BOTH my desktop and my laptop.


    Any suggestions?  This is impacting my ability to work rather severely.


    Thank You

    0 out of 1 people found this post helpful.

  • Hello David,

    Try accessing with OWA (Oulook Web Access) at  You may wish to use OWA while we troubleshoot the problem, especially if you have some work that must get done and OWA is not having the same issue.  Does the issue go away when using OWA?

    We already know that the issue isn't isolated to one computer since both your laptop and desktop are having the same issue. Is you laptop setup the same way with the 3 accounts?

    To troubleshoot:

    1) To test if adding the additional accounts created the issue, create a new Exchange profile.  Be sure to rename or copy the old profile first for backup, then create a new OL profile, and setup your original O365 account and test. If this works, then we have an issue with adding the additional accounts, or you have a corrupt Outlook profile or maybe a corrupt user profile. Add the two additional accounts again and see if the issue resurfaces.

    2) To test for a corrupt user profile, login to your computer with a different user profile (you can login as admin or create a new user profile) and then setup OL with just your one O365 account.  If this works, then we had a corrupt user profile. Add the two additional accounts again and see if the issue resurfaces.

    If you still have the connection problems then we will want to isolate to your network or not.  

    3) To test if you are having a network issue, try a computer that is NOT on the same network (for example from a home computer).  Also, do you have other users in your office using O365 and if so are any of them experiencing the same issue?  If the problem goes away when you are not on your network, then you have a network issue.

    Additional info that would be helpful:

    1) What version of Outlook are you using?

    2) What is your mail server (you should be able to get this from Outlook Account Settings -> Accounts.  Double click on the account and check the server (should be like

    3) How did you add the other two accounts?  

      a. Did you go to Account Settings, Add Account?  

      b. Did you use the Auto Account Setup feature (fill in your Name and Email Address) to add the accounts or did you set them up manually?  

      c. Did you select Cached Exchange mode for a manual configuration?

    Let's start with this and see what happens...

    Thank you,

    Todd Douglass

    MSFT Support Engineer

  • Todd, thank you for your thorough response.  It may take me a few days but I will investigate as soon as I am able to and report back.

  • Thanks Todd.

    1. Outlook 2010.


    3. I've done it multiple times both automatically and manually.  I close Outlook, go to control panel, and add the accounts.  Yes to cached exchange.

    I can also reproduce it 100%.  Remove the extra accounts, everything works.  Add the extra accounts, instant connectivity issues.  Remove them, instantly works.

  • David & Todd,

    I'm also having this same issue. Multiple exchange accounts (in my case, more than 3) from Office 365 in Outlook 2010 cause Send/Receive to hang.

  • David and nsideras,

    If you go into Outlook, File, Account Settings, Account Settings, are all three Office 365 accounts configured as Exchange or are any of them configured as POP/IMAP?  

    Are all three accounts in the Same Office 365 plan and same domain?  

  • Gabriel,

    They are all Exhange accounts, and are all in the same Office 365 plan. They are, however, spread across a handful of domains.

    I've been working with tech support over the phone, but so far we haven't come to any solutions. After running across David's similar issue, I've forwarded them this page in hopes that there might be a common fix.

  • I just received a call from support, and was informed that there is in fact some sort of limit with multiple accounts. I should be getting a call back Monday or Tuesday with additional information.

  • David and nsideras,

    What version of Office are you running?  If you open Outlook and go to File, Help, what is the version listed?

  • I'm running Outlook Professional 2010 (14.0.6023.1000) 32-bit on Windows 7, Vista, and XP. All versions of Windows and Office have all the current updates and meet the minimum system requirements as specified in the Office 365 system requirements.

  • When you installed Office did you install by downloading from the Microsoft Online Portal (MOP) and following the steps there or are you running with you own copy of Office 2010 Pro?  

    Connectivity issues can occur if special updates were not installed.  The updates are installed when you run the "Setup and Configure" from the Download page in the MOP or if you manually install the updates listed on this page,  

  • They are our own copies of Office 2010, but I did run the Office 365 set up utility from the Downloads page in the Office 365 portal. I believe this installs all of those updates.

  • I'd run through the Manually install updates section to make sure you have all the necessary updates. I had this exact issue and the client kept telling me they had all the updates, but in fact they were missing a pre-requisite (SP2 for Visio 2007) which was causing the Sign In Assistant to not run properly.

    Also make sure you are 100% up to date on all critical updates for Windows and to be safe install SP1 for Office 2010, that has a rollup of all required O365 updates.

  • David and nsideras,

    I did an exercise to help double check the Outlook version.  Please double check your version.  In Outlook click File, Help, Additional version and Copyright information.  

    The main thing I found to check is the version next to Outlook and not MSO.  Whether I started with my own copy of Office 2010 or installed from the Online Portal the correct Outlook version that you should be running is 14.0.6102.5000.  The MSO version varried but if you are up to date with SP 1 it is 14.0.6023.1000.

    I know David has a support case now but the Outlook team asked we verify the version because some of the updates are required when using multiple O365 accounts in Outlook.  Hopefully we can get a solution to this issue soon.

    All updates installed and SP 1 installed:

    Outlook 2010 Subscription 14.0.6102.5000

    MSO 14.0.6023.1000


    Initial install from Microsoft Online Portal Downloads:

    Outlook 2010 Subscription 14.0.4760.1000

    MSO 14.0.5128.5000

    Initial install from MOP and ran the Configuration updates:



    Initial install from MOP and ran the Configuration updates then add SP 1:



    SP 1 only without running the Configuration updates or manually installing them.  



  • Gabriel,

    Thanks for the additional information. We're running version 14.0.6023.1000.

    I'll also mention that we tried creating a new profile last week, but we're still seeing the same issue within two days of using the new profile.