Exchange 2013 + Outlook 2010, Security Alert

A small customer has Outlook 2010 connecting to Exchange Server 2013 on a Windows 2008
R2 server at a remote site. Recently, the users began receiving a security
alert ("The identity of this web site or the integrity of this connection
cannot be verified", "The name on the security certificate is invalid
or does not match the name of the site"). This occurs every time a user
opens Outlook, and when they click on "Yes" they are able to use
Outlook normally. <o:p></o:p>
This problem began not long after 1) the wildcard ssl certificate was renewed and 2)
Exchange 2013 was updated to the most recent SP and CU. It is noteworthy that
the PCs being used are not members of the domain. The users also receive this
error if they use Outlook to connect from their home PCs. <o:p></o:p>
The Exchange server passes connectivity and autodiscover tests. I have checked all the URLs
in Exchange Server. I have tried changing authentication, re-enabling the the
*.domain.ca certificate, I have not been able to reproduce the error on my own
laptop from the customer's site. <o:p></o:p>
This problem is not critical, but it is annoying for the users, and I have tried
just about everything I can find on the Internet to resolve it. <o:p></o:p>
Any suggestions? <o:p></o:p>

Hi,
Please run the following command to set the CertPrincipalName parameter which specifies the Secure Sockets Layer (SSL) certificate principal name required for connecting to Exchange from an external location to have a try:
Set-OutlookProvider EXPR -CertPrincipalName msstd:*.domain.ca
If the issue persists, please follow the steps below to check Exchange services for the problematic users :
Open Outlook - press CTRL key - right click on the Outlook icon from right bottom corner taskbar -
Test Email AutoConfiguration. Put your email address - uncheck use guessmart and secure guessmart authentication - click Test to check your Autodiscover service.
Please collect the information in the Log tab and Results tab.
Regards,
Winnie Liang
TechNet Community Support

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    Carl
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    Hi,
    Please try to enable FBA for external and internal OWA 2010 users by the methods in the blog below.
     There are several ways to accomplish this:
    Have internal users pointed to the internal interface of the Forefront TMG and utilize the forms-based authentication logon page offered by Forefront TMG. 
    Deploy Forefront UAG instead of Forefront TMG. Forefront UAG allows you to have FBA enabled on both the Exchange 2010 Client Access Servers and on the Forefront UAG solution itself. 
    Publish Exchange 2010 to the Internet using Forefront TMG but do not configure pre-authentication. This way the users need to go through the Forefront TMG solution, but will authenticate directly against the Exchange 2010 Client Access servers. 
    Configure an additional OWA and ECP virtual directory on the Exchange 2010 Client Access Servers.
    Reference:http://www.msexchange.org/articles-tutorials/exchange-server-2010/management-administration/enabling-forms-based-authentication-external-internal-owa-2010-users-exchange-2010-published-using-forefront-tmg-2010-part1.html
    Then check the blog
    - Creating a custom Forefront TMG 2010 OWA FBA logon page
    Note:
    Microsoft provides third-party contact information to help you find technical support. This contact information may change without notice. Microsoft does not guarantee the accuracy of this third-party contact information.
    Best Regards,
    Joyce
    Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Subscriber Support, contact [email protected]

  • Migration to Exchange 2013 from 2010 - Client side issues

    Hi Everyone, 
       I've been having issues with clients connecting to an existing Exchange server (Getting login prompt- but not usual reason).  
    We currently run Exchange 2010 with approx 200 mailboxes on the server.  Last night I renewed the certificate on the 2010 server (go daddy SAN cert, all ok) and added the cert to my new Exchange 2013 server.  I tested it with my account, and a
    test account approx 12 times, and had not login prompt when launching Outlook. All seemed ok, until this morning.....
    This morning, most (not all) users are getting the login prompt.  We are able to get by this by inputting domain\username and Outlook opens fine and is able to connect.  No users are on the Exchange 2013 server yet (only 1 test account) 
    I've been googling all morning and I'm not seeing anything directly relating to my issue.  I've read about the Anon vs Negotiate issues (KB2834139) - But - the strange thing is all clients are set to negotiate network security (And encrypt data) This
    is opposite of what the MS article says.  CLients are all Outlook 2010 
    Here are my outlook anywhere settings: 
    ServerName               : exchange2010
    IISAuthenticationMethods : {Basic}
    ServerName               : exchange2013A
    IISAuthenticationMethods : {Basic, Ntlm}
    ServerName               : exchange2013B
    IISAuthenticationMethods : {Basic, Ntlm}
    Identity                          ClientAuthenticationMethod IISAuthenticationMethods
    exchange2010\Rpc (Default Web Site)                        Basic {Basic}
    exchange2013a\Rpc (Default Web Site)                       Ntlm {Basic, Ntlm}
    exchange2013b\Rpc (Default Web Site)                       Ntlm {Basic, Ntlm}
    If I change the Exchange 2010 server to NTLM, will this resolve what I'm seeing? And do I need to restart RPC Client Access and Transport Service to make changes take effect? Or reboot the whole server? 
    If you need more info or logs please let me know
    Thank you for any help! 
    -Jeff

    Hi,
    Please confirm if the Login prompt issue occurs when users open the Outlook client at first time after renewing Exchange certificate or happens when opening the Outlook every time.
    I noticed that the user can connect to Exchange server after inputting domain\username. Please confirm if the issue happens to external users who use Outlook Anywhere. For Outlook Anywhere coexistence,
    please choose NTLM for IIS authentication.
    Set-OutlookAnywhere -Identity "exchange2010\Rpc (Default Web Site)" -IISAuthenticationMethods Basic,Ntlm
    Regards,
    Winnie Liang
    TechNet Community Support

  • The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action. Error while connecting to exchange through Outlook 2010

    Hi,
    I have set up Exchange Server 2013 on Windows Server 2008 R2. Everything is working fine except I am unable to configure Exchange account in Outlook 2010 or any other version. It says 
    "The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." 
    Error screenshot is attached. Even, I am able to configure exchange active sync on my adroid and ipad which is working perfect. Please let me know if any body have any idea about it. Searched many blog and forum but still now solution till now.
    Thanks in advance
    Regards,
    Manoj

    Hi Manoj,
    Can you ping your Exchange server? It would hlep us isolate the fault from network releated issue.
    Is there a trusted certificate installed on Exchange 2013 server?
    If you run the test of RPC over HTTP in
    https://www.testexchangeconnectivity.com/, is there any error returned?
    For more information, please refer to :
    http://technet.microsoft.com/en-us/library/bb123741(v=exchg.150).aspx
    http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/1b4dc21c-c745-4699-8eee-423105608dcd/
    Thanks.
    Fiona Liao
    TechNet Community Support

  • Exchange 2013 - Outlook 2007 - Server name GUID

    Hi Guys.
    I am hoping someone can shine some light on something for me.
    Right now I have the following with roles.
    1 x Exchange 2010 - MBX & CAS
    1x Exchange 2013 - MBX
    1 x Exchange 2013 - CAS
    Mix of Outlook 2007 & 2010
    I migrated a user from Exchange 2010 over to Exchange 2013 and the process went fine. Email flow is working, OWA and Active Sync again working ok.
    However when we opened Outlook 2007 it displayed a message to say an Administrator had made changes and we needed to restart Outlook. No issues there.
    Outlook connected up fine and everything works. However when you look in the mail profile for the Exchange server name i see something like
    [email protected]
    Also Outlook Anywhere is ticked and when you untick it from the client and then open it again it comes back.
    Are the above items of migration?

    Hi,
    RPC is no longer a supported direct access protocol. This means that all Outlook connectivity must take place using RPC over HTTP (also known as Outlook Anywhere).
    Outlook clients no longer connect to a server FQDN as they have done in all previous versions of Exchange. Outlook uses Autodiscover to create a new connection point comprised of mailbox GUID, @ symbol, and the domain portion of the user’s primary SMTP
    address.
    To expand on this a little bit, I worked an issue with a new Exchange 2013 environment for 3 days before figuring out that you do NOT specify a server name where it asks for it in Outlook, you use the format mentioned above.  
    For reference, I received a very particular error from testconnectivity.microsoft.com that made no sense until I discovered the server name format.  If a test fails with a 404 HTTP Not Found error and an X-CasErrorCode of MailboxGuidWithDomainNotFound,
    this is most likely your problem.  Its very frustrating that Microsoft does not have it documented anywhere exactly what this error means, would have saved me a lot of time and energy.

  • Exchange 2013 and 2010 co-existance

    We will have 2013 and 2010 exist together for a while...we plan to move away from using Unified Access Gateway for HTTP redirection to our Exchange services and implement Kemp
    load balancers...two at our HQ site and two at our DR stie...
    We plan to have a one arm configuration...from what I gathered...each load balancer will have a network connection and only one network connection and be on the same network as
    our new Exchange 2013 servers.  Can someone take a look at my config and give some input whether or not this will work and some suggestion on Ex13 urls, cert SAN names, etc.
    HQKemp 2400 A    
    HQKemp 2400 B               
    DCKemp 2400 A        DCKemp 2400 B
    172.16.1.104        
    172.16.1.105                     
    172.25.1.104          
    172.25.1.10
    Virtual IP   172.16.1.106          
                             Virtual IP 
    172.25.1.104
    From the video I’ve watched for Kemp install…we’ll create the following internal DNS records for the Exchange services that will be configured on balancers.
    OWA/ECP   
        mail.corp.local.com
                  172.16.1.107
    EWS               ews.corp.local.com          
    172.16.1.108
    OAB               oab.corp.local.com           
    172.16.1.109
    ActiveSync      mobile.corp.local.co         
    172.16.1.110
    OA                 oa.corp.local.com            
    172.16.1.111
    Autodiscover   autodiscover.corp.local.com 172.16.1.112
    Question: 
    We will configure the Exchange services with these ip addresses linked to each service on all four load balancers? 
    Or will DR site load balancers have different IPs configured for same Exchange services?
    Exchange services are split between our two sites…meaning Outlook Anywhere is configured for our CAS servers at our DR site and ActiveSync comes to HQ CAS servers as an example…so
    I want all Exchange services to come through the newly installed load balancers at HQ and if they don’t respond…the Exchange services get redirected to the load balancers at our DR site. 
    Can you give some insight on the config of load balancers as to how we can do that?
    I have a question about the cert we will have. 
    Our Microsoft rep says we should get a new wildcard cert…currently we have a UCC cert with the following SANs attached.
    Will this new cert have to be installed on load balancers? 
    If so…can you suggest some ideas as to what new SANs I need if any of the new cert with Exchange 2010 and 2013 co-existing for a while. 
    Below are the SANs on our current UCC cert.
    Outside resolvable SANs
    Webmail.corp.local.com          
    205.223.19.25           portal.corp.local.com     205.223.27.78
    Portal2.corp.local.com             
    205.223.19.25         
    Autodiscover.corp.local.com     
    205.223.19.25
    Internal SANs  
    Hqcas1.corp.local.com              
    Hqcas2.corp.local.com              
    Dccas1.corp.local.com              
    Dccas2.corp.local.com              
    Owamail.corp.local.com     
    (this CAS Array server name that HQ CAS servers create)
    What do you suggest we use for the external urls on Exchange 2013 for these services?
    Our firewall guy says we’ll use same names, 
    but I’m not sure if we try to use same name if we’ll get an error? 
    Active Directory may say name already in use?
    We plan to have firewall to just redirect requests for external urls to load balancers…sound correct? 
    Meaning load balancer won’t have an external NIC defined…which makes it a one arm config…correct?

    Hi Techy,
    According to your description, I am still not quite sure about your environment. Could you please provide more information about it, such as:
    1. How many Exchange servers in your coexistence environment? One Exchange 2010 with all roles and one Exchange 2013 with all roles? Or several Exchange 2010 and multiple Exchange 2013?
    2. Are there two sites in your environment? What’s the Exchange deployment in different sites?
    3. Please confirm if both Exchange 2010 and Exchange 2013 are Internet-facing.
    Additionally, if you are using different namespaces for different services for internal access and external accessing, we need to include all service namespaces in your certificate with IIS service. Personal suggestion, we can follow ED Crowley’s suggestion
    to use split-brain DNS in your environment and only use the same namespace for Exchange service URLs.
    The following article described the details about how to configure different namespace for Exchange services by using Load Balance in Exchange 2013:
    http://www.msexchange.org/articles-tutorials/exchange-server-2013/high-availability-recovery/introducing-load-balancing-exchange-server-2013-part2.html
    Regards,
    Winnie Liang
    TechNet Community Support

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