Outlook 2007 does not connect to exchange at computer startup

Hi all :)
Here's the situation we're encountring: we are using exchange 2010 with outlook 2007 clients. The issue is that at the startup of the computer, outlook does not connect to exchange (it opens up but it marks that it's not connected to exchange). After trying
a few times it connects and stays stable (if I close outlook and I open it again, it connects normally).
This suggests that there's may be a DNS problem: The client is having an issue resolving the name, but once it does and the IP of exchange is available in the cache, outlook doesn't face any issues.
So I ran some nslookup commands and I noticed the following:
when I try to resolve the name of exchange, the request times out twice before providing the answer.
This issue occurs only for forward lookups (when I try to resolve the same IP for the hostname, there's no timeout)
I also noticed that this issue only occurs when I run nslookup from the client machines (no timeout when I run it from exchange for instance).
Any ideas about what the problem might be? Could it be something else other than DNS?
Thank you all for your help.

Hi all,
The problem seems not to be related to DNS. Our exchange 2010 organization was actually migrated from a 2007 one. Since then we noticed this issue of outlook taking too much time to connect and sometimes disconnects. I was messing around into adsiedit and
I noticed that a decomissioned Mailbox Server from our old exchange 2007 organization still exists among the new exchange 2010 objects.
To further look into it, I ran best practise analyser, the result (to my surprise) was that exchange is still trying to contact the old exchange 2007 server.
I ran some network trafic captures with Network Monitor, but I was not very successful interpreting anything.
I uploaded the .cap files with the best practise analyser report and a print screen of the old server into adsiedit objects. I hope you'll be able to help with it.
I took the network captures on the two CAS Servers (configured in a CAS array) and on a client machine. The IP addresses are as follow:
client 192.168.0.47
Domain Controller1 192.168.1.205
Domain Controller2 192.168.1.213
CAS1 192.168.2.216
CAS2 192.168.2.217
CAS Array 192.168.2.218
Download Link: https://onedrive.live.com/redir?resid=9360346C01880F58%21935
Thanks,

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        <EcpUrl-photo>PersonalSettings/E.testAccount.aspx?rfr=olk&chgPhoto=1&exsvurl=1&realm=name_domain.test</EcpUrl-photo>
        <EcpUrl-tm>?rfr=olk&ftr=TeamMailbox&exsvurl=1&realm=name_domain.test</EcpUrl-tm>
        <EcpUrl-tmCreating>?rfr=olk&ftr=TeamMailboxCreating&SPUrl=<SPUrl>&.testle=<.testle>&SPTMAppUrl=<SPTMAppUrl>&exsvurl=1&realm=name_domain.test</EcpUrl-tmCreating>
        <EcpUrl-tmE.testing>?rfr=olk&ftr=TeamMailboxE.testing&Id=<Id>&exsvurl=1&realm=name_domain.test</EcpUrl-tmE.testing>
        <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&exsvurl=1&realm=name_domain.test</EcpUrl-extinstall>
        <OOFUrl>https://webmail.name_domain.test/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://webmail.name_domain.test/ews/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://webmail.name_domain.test/OAB/e66d9a4a-6ed2-4512-b72f-522381524dd9/</OABUrl>
        <ServerExclusiveConnect>on</ServerExclusiveConnect>
        <CertPrincipalName>msstd:webmail.name_domain.test</CertPrincipalName>
        <EwsPartnerUrl>https://webmail.name_domain.test/ews/exchange.asmx</EwsPartnerUrl>
        <GroupingInformation>LAN</GroupingInformation>
      </Protocol>
      <Protocol>
        <Type>WEB</Type>
        <Internal>
          <OWAUrl AuthenticationMethod="Basic, Fba">https://webmail.name_domain.test/</OWAUrl>
          <Protocol>
            <Type>EXCH</Type>
            <ASUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</ASUrl>
          </Protocol>
        </Internal>
        <External>
          <OWAUrl AuthenticationMethod="Basic">https://webmail.name_domain.test/</OWAUrl>
          <Protocol>
            <Type>EXPR</Type>
            <ASUrl>https://webmail.name_domain.test/ews/exchange.asmx</ASUrl>
          </Protocol>
        </External>
      </Protocol>
      <Protocol>
        <Type>EXHTTP</Type>
        <Server>webmail.name_domain.test</Server>
        <SSL>On</SSL>
        <AuthPackage>Ntlm</AuthPackage>
        <ASUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</ASUrl>
        <EwsUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</EwsUrl>
        <EmwsUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</EmwsUrl>
        <EcpUrl>https://webmail.name_domain.test/ecp/</EcpUrl>
        <EcpUrl-um>?rfr=olk&p=customize/voicemail.aspx&exsvurl=1&realm=name_domain.test</EcpUrl-um>
        <EcpUrl-aggr>?rfr=olk&p=personalsettings/EmailSubscriptions.slab&exsvurl=1&realm=name_domain.test</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?rfr=olk&exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx>&realm=name_domain.test</EcpUrl-mt>
        <EcpUrl-ret>?rfr=olk&p=organize/retentionpolicytags.slab&exsvurl=1&realm=name_domain.test</EcpUrl-ret>
        <EcpUrl-sms>?rfr=olk&p=sms/textmessaging.slab&exsvurl=1&realm=name_domain.test</EcpUrl-sms>
        <EcpUrl-publish>customize/calendarpublishing.slab?rfr=olk&exsvurl=1&FldID=<FldID>&realm=name_domain.test</EcpUrl-publish>
        <EcpUrl-photo>PersonalSettings/E.testAccount.aspx?rfr=olk&chgPhoto=1&exsvurl=1&realm=name_domain.test</EcpUrl-photo>
        <EcpUrl-tm>?rfr=olk&ftr=TeamMailbox&exsvurl=1&realm=name_domain.test</EcpUrl-tm>
        <EcpUrl-tmCreating>?rfr=olk&ftr=TeamMailboxCreating&SPUrl=<SPUrl>&.testle=<.testle>&SPTMAppUrl=<SPTMAppUrl>&exsvurl=1&realm=name_domain.test</EcpUrl-tmCreating>
        <EcpUrl-tmE.testing>?rfr=olk&ftr=TeamMailboxE.testing&Id=<Id>&exsvurl=1&realm=name_domain.test</EcpUrl-tmE.testing>
        <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&exsvurl=1&realm=name_domain.test</EcpUrl-extinstall>
        <OOFUrl>https://webmail.name_domain.test/EWS/Exchange.asmx</OOFUrl>
        <UMUrl>https://webmail.name_domain.test/EWS/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://webmail.name_domain.test/OAB/e66d9a4a-6ed2-4512-b72f-522381524dd9/</OABUrl>
        <ServerExclusiveConnect>On</ServerExclusiveConnect>
        <CertPrincipalName>msstd:webmail.name_domain.test</CertPrincipalName>
      </Protocol>
      <Protocol>
        <Type>EXHTTP</Type>
        <Server>webmail.name_domain.test</Server>
        <SSL>On</SSL>
        <AuthPackage>Basic</AuthPackage>
        <ASUrl>https://webmail.name_domain.test/ews/exchange.asmx</ASUrl>
        <EwsUrl>https://webmail.name_domain.test/ews/exchange.asmx</EwsUrl>
        <EmwsUrl>https://webmail.name_domain.test/ews/exchange.asmx</EmwsUrl>
        <EcpUrl>https://webmail.name_domain.test/ecp/</EcpUrl>
        <EcpUrl-um>?rfr=olk&p=customize/voicemail.aspx&exsvurl=1&realm=name_domain.test</EcpUrl-um>
        <EcpUrl-aggr>?rfr=olk&p=personalsettings/EmailSubscriptions.slab&exsvurl=1&realm=name_domain.test</EcpUrl-aggr>
        <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?rfr=olk&exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx>&realm=name_domain.test</EcpUrl-mt>
        <EcpUrl-ret>?rfr=olk&p=organize/retentionpolicytags.slab&exsvurl=1&realm=name_domain.test</EcpUrl-ret>
        <EcpUrl-sms>?rfr=olk&p=sms/textmessaging.slab&exsvurl=1&realm=name_domain.test</EcpUrl-sms>
        <EcpUrl-publish>customize/calendarpublishing.slab?rfr=olk&exsvurl=1&FldID=<FldID>&realm=name_domain.test</EcpUrl-publish>
        <EcpUrl-photo>PersonalSettings/E.testAccount.aspx?rfr=olk&chgPhoto=1&exsvurl=1&realm=name_domain.test</EcpUrl-photo>
        <EcpUrl-tm>?rfr=olk&ftr=TeamMailbox&exsvurl=1&realm=name_domain.test</EcpUrl-tm>
        <EcpUrl-tmCreating>?rfr=olk&ftr=TeamMailboxCreating&SPUrl=<SPUrl>&.testle=<.testle>&SPTMAppUrl=<SPTMAppUrl>&exsvurl=1&realm=name_domain.test</EcpUrl-tmCreating>
        <EcpUrl-tmE.testing>?rfr=olk&ftr=TeamMailboxE.testing&Id=<Id>&exsvurl=1&realm=name_domain.test</EcpUrl-tmE.testing>
        <EcpUrl-extinstall>Extension/InstalledExtensions.slab?rfr=olk&exsvurl=1&realm=name_domain.test</EcpUrl-extinstall>
        <OOFUrl>https://webmail.name_domain.test/ews/exchange.asmx</OOFUrl>
        <UMUrl>https://webmail.name_domain.test/ews/UM2007Legacy.asmx</UMUrl>
        <OABUrl>https://webmail.name_domain.test/OAB/e66d9a4a-6ed2-4512-b72f-522381524dd9/</OABUrl>
        <ServerExclusiveConnect>On</ServerExclusiveConnect>
        <CertPrincipalName>msstd:webmail.name_domain.test</CertPrincipalName>
      </Protocol>
    </Account>
</Response>
</Autodiscover>
Get-OwaVirtualDirectory | fl name,*auth*,*url*
Name                          : owa (Default Web Site)
ClientAuthCleanupLevel        : High
InternalAuthenticationMethods : {Basic, Fba}
BasicAuthentication           : True
WindowsAuthentication         : False
DigestAuthentication          : False
FormsAuthentication           : True
LiveIdAuthentication          : False
AdfsAuthentication            : False
OAuthAuthentication           : False
ExternalAuthenticationMethods : {Basic}
Url                           : {}
SetPhotoURL                   :
Exchange2003Url               :
FailbackUrl                   :
InternalUrl                   : https://webmail.name_domain.test/
ExternalUrl                   : https://webmail.name_domain.test/

Follow the results of the test
Outlook Anywhere (RPC over HTTP).
Has been used an account for which
outlook anywhere works. The account
for which the outlook anywhere does not work is
an administrative account and therefore
can not be used in the test.
Autodiscovery returns the
same result for both mailbox.
I'm testing RPC/HTTP connectivity.
Testing RPC over HTTP has not been exceeded.
Test steps
Microsoft connectivity Analyzer is attempting to test the Autodiscover service for user_test@domain_name.test.
Test the Autodiscover service has not been exceeded.
Test steps
I'm trying to contact the Autodiscover service with each method available.
I was not able to contact the Autodiscover service with no method.
Test steps
I'm trying to test the possible URL for the Autodiscover service https://domain_name.test/AutoDiscover/AutoDiscover.xml
The test of this potential URL for the Autodiscover service has not been exceeded.
Test steps
I'm trying to resolve the host name domain_name. DNS test.
I was able to resolve the host name.
IP addresses are returned: xxx.yyy.zzz.www
I'm testing the TCP port 443 on the host domain_name. tests to check that is open and listening.
The door has been opened properly.
I'm testing the validity of your SSL certificate.
The SSL certificate has not exceeded one or more validation controls.
Test steps
Microsoft connectivity Analyzer is attempting to obtain the SSL certificate from the remote server domain_name. test on port 443.
Microsoft connectivity Analyzer got the remote SSL certificate.
Remote certificate subject: E = it_staff@domain_name.test, CN = * domain_name. test, OU = it staff, O = domain_name, L = city, S = state, C = test issuer: E = it_staff@domain_name.test, CN = * domain_name. test, OU = it staff, O = domain_name,
L = city, S = state, C = test.
I am validating the certificate name.
I could not validate the certificate name.
More info about this issue and how to resove it
The host name domain_name. testing does not match any name found on the certificate and server = it_staff@domain_name.test, CN = * domain_name. test, OU = it staff, O = domain_name, L = city, S = state, C = test.
I'm trying to test the possible URL for the Autodiscover service https://autodiscover.domain_name.test/AutoDiscover/AutoDiscover.xml
The test of this potential URL for the Autodiscover service has not been exceeded.
Test steps
I'm trying to resolve the host name autodiscover. domain_name. DNS test.
I was able to resolve the host name.
IP addresses are returned: xxx.yyy.zzz.kkk
I'm testing the TCP port 443 on the host autodiscover. domain_name. tests to check that is open and listening.
The door has been opened properly.
I'm testing the validity of your SSL certificate.
The SSL certificate has not exceeded one or more validation controls.
Test steps
Microsoft connectivity Analyzer is attempting to obtain the SSL certificate from the remote server autodiscover. domain_name. test on port 443.
Microsoft connectivity Analyzer got the remote SSL certificate.
Other details
Remote certificate subject: CN = webmail. domain_name. test, OU = it staff, O = domain_name, L = city, S = city, C = test issuer: CN = domain_name-DC1-CA, DC = domain_name, DC = test.
I am validating the certificate name.
I validated the certificate name.
Other details
I found the host name autodiscover. domain_name. test in the voice of the alternative name of the certificate object.
Elapsed time: 1 ms.
I am validating the reliability of certificates.
I was not able to validate the reliability of the certificate.
Test steps
Microsoft connectivity Analyzer is attempting to generate certificate chains to a certificate CN = webmail. domain_name. test, OU = it staff, O = domain_name, L = city, S = city, C = test.
I failed to build a certificate chain for the certificate.
Other details
Failed to generate the certificate chain.
May be missing the required intermediate certificates.
I'm trying to contact the Autodiscover service using the HTTP redirect method.
I was not able to contact the Autodiscover service using the HTTP redirect method.
Test steps
I'm trying to resolve the host name autodiscover. domain_name. DNS test.
I was able to resolve the host name.
IP addresses are returned: xxx.yyy.zzz.kkk
I'm testing the TCP port 80 on the host autodiscover. domain_name. tests to check that is open and listening.
The specified port is blocked, is not listening or doesn't produce the expected response.
More info about this issue and how to resove it
I encountered a network error while communicating with the remote host.
I'm trying to
find the
SRV DNS record _audiscover._tcp.domain_name.test.
I failed to find
the SRV record of the
Autodiscover service
in DNS.
Some clarifications:
1 - xxx.yyy.zzz.www and xxx.yyy.zzz.kkk
are two static public addresses
of which only the latter exposes Exchange services;
2 - The certificate
*. Domain_name.test is not related
to Exchange services;
3 -I imported the certificate
of the issuing CA on the standalone test PC to validate the certificate.
3- The port 80 is not open and are not published SRV records.
Best regards.

Outlook 2007 does not connect to exchange at computer startup

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