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An encrypted connection to your mail server is not available

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I have one client computer that does not want to connect through Outlook 2010.  I get "An encrypted connection to your mail server is not available"  then it tries a unencrypted and fails.


Several other computers work with the same account, on the same connection.  


Its just one computer that keeps getting this error.   I have uninstalled outlook 2010, and used MS Fixit tool to remove anything extra.   I reinstalled, and same error.  "An encrypted connection to your mail server is not available"


Maybe the connector is not install correctly???  I don't know


Outlook 2010 full updated, on windows 7 sp1 fully updated. 




1 out of 2 people found this post helpful.

All Replies
  • Hello Curtis,

    One thing that you may need to check is the system date and time.  If there is a variance of 5 minutes this can cause issues with establishing a secure connection.

    Thank you, Jeff McDonald, O365 Forum Moderator

  • Hello Curtis,


    To fix the issue, please re-run the Setup office desktop apps through download page from portal. 

    If the issue persists, you can refer the 3rd method in KB 2404385 to configure Outlook manually.



  • CurtisD,

    I have this EXACT same issue. I've been on the phone with MS support for the past 3 hours and no luck. I've uninstalled Outlook 2010 three times and even cleared the registry. I too am running WIndows 7 SP1 fully updated and Outlook 2010 fully updated. Like you, I have another machine that can connect via Outlook 2010 without any issues, but my main laptop simply cannot.

    I tried BOTH Jeff's and Lester's recommendations below and no luck.

    If anyone has a solution, please advise!


  • For what it is worth, the Mailbox Server Name with my account is:

    Hostname is:

  • Uh is this a problem? I found this in the About... menu when logged into the portal:

    Client Access server time zone: ‎(UTC)‎ Monrovia, Reykjavik

    Why is this the timezone?

  • Same here

    Exchange Client Access server name:

    Exchange Client Access server .NET Framework version: 2.0.50727.5662

    Client Access server operating system version: Microsoft Windows NT 6.1.7600.0

    Client Access server operating system language: en-US

    Client Access server version:

    Client Access server language: en-US

    Client Access server time zone: (UTC) Monrovia, Reykjavik

    Client Access server platform: 64bit

    Mailbox server name:

    Mailbox server Microsoft Exchange version:

  • Hi Curtis and Fibreraid,


    The Client Access Server time zone is set to UTC for all users.

    Since you are able to connect on other machines, it’s not a server side issue.

    Could you provide some information about the working and non-working machine, like system service pack, Outlook add-ons, anti-virus, etc.?

    Has the connection ever worked on the effected machine, or just stopped recently?



    I have sent a private message to you, you can click the private messages on the right side of cummunity to check.

  • Hello,


    How is the thing going? Have you been able to connect through Outlook?



  • Hi Lester,

    I'm having this exact same problem.

    My issue occurs on Office 2007 and Office 2010 - seems to be the case that the solution can't connect to the autodiscovery service to setup the account?

    But manual configuration fails, and i cannot login to lync (service is unavailable) also.

    For reference - webapps work fine :)



    Ok so looks like the CNAME for auto-discover hasn't migrated so i guess it's a waiting game :)

  • I am still facing this issue and it apparently has no resolution. Sorry.

  • Hi Fibreraid,


    Your post was responded to in a private message.

    Go to the Your details section on the right side of the community site.
    Click Private messages.
    Click the subject title of the response to read the message.
    You can reply by using the form in this display.
    Click Submit Reply.

  • CNAME for auto-discover was just taking time to resolve/propagate - all seems fine now :)

  • Thanks Scott,

    Since the manually configuraion was not working at the first time, it's not autodiscover realted issue.



    Is there any update of this issue?



  • I am having the same issue here.  It is only impacting one of my computers so far.  

    I have tried the manual configuration, which fails, the automatic Outlook configuration and the configuration tool.  


  • [Skip down to ***WAIT*** to see what ended up working for me]

    I'm having this same issue (Win7 x64, Outlook 2010 x32).  I'm pretty certain it's client-side - especially since I *had* it working with the O365 email as a secondary email address.  (I want to delete the old locally-hosted email address which is the primary email on the profile.  The only way I know to do that is to create a new profile.)  My CNAME records don't seem to be an issue for a typical user configuration.

    Things I've tried

    After initial failures I deleted the O365 secondary email on my original profile.  

    I tried my usual procedure for adding.  No luck.

    I tried the manual procedure referenced above.  No luck.  It ended in: "The action cannot be completed.  The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."  I then started Outlook 2010 and tried again.  Same message.

    Sadly I now can't even add O365 email back to the original profile.  The procedure that added it in the first place now fails in the same way.

    Other information

    *We're doing a staged migration, as such I expect <user>@<domain>.com to autodiscover to my local server.  We use <user>@<domain> to access Office 365.  I am *not* using the onmicrosoft during the manual configuration.  I am using <user>@<domain>.com.

    *Since I unwittingly added O365 email to all existing user Outlook profiles, I will have to go back an create a new profile where O365 is the primary email address so that I can delete the original profile (and thus the local email).  Based on the experience with my own Outlook connection I'm very concerned that I resolve this configuration issue *before* doing trying this for other users.


    I just had success.  It looks like the manual configuration article (referenced by Lester above) is somewhat out of date or incomplete.  When Check Name fails, a different server/user dialog comes up asking for the "Exchange Server".  On a whim, I tried the entering the FQDN labeled "Exchange Client Access server name" in OWA About (instead of the one for "Mailbox server name").  In this case Check Name succeeded.  And the new email and profile were created.  Curiously, the original server is still listed by "Server".  This new connection appears to be work fine.

    I'm not sure if this matters, but I chose to create the new profile during Outlook startup.  I thought that might get around the message I listed above.  This may have been a necessary step, but it was not sufficient.

    Obviously a better solution would be to understand why to automatic technique I typically use didn't work, but at least I have Outlook connected to O365 again.

    Good Luck.