Turn on Outlook Logging
Tools--Options-Others-Advanced Options-Select "Enable Logging (troubleshooting)
Log file Locations
MAPI(Exchange)
Vista/Windows7
C:\Users\userName\AppData\Local\temp
olkdisk.log
7268 111383621 04/29/11 10:07:06 Autodiscover to https://1ask2.com/autodiscover/autodiscover.xml starting
7268 111383824 04/29/11 10:07:06 Autodiscover to https://1ask2.com/autodiscover/autodiscover.xml FAILED (0x800C8203)
7268 111383824 04/29/11 10:07:06 Autodiscover to https://autodiscover.1ask2.com/autodiscover/autodiscover.xml starting
7268 111386788 04/29/11 10:07:09 Autodiscover XML Received
---BEGIN XML---
<?xml version="1.0" encoding="utf-8"?>
<Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
<Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
<User>
<DisplayName>Q1</DisplayName>
<LegacyDN>/o=1ASK2Company/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Q1</LegacyDN>
<AutoDiscoverSMTPAddress>Q1@1ask2.com</AutoDiscoverSMTPAddress>
<DeploymentId>3ef94938-efc0-4c8b-8086-d4bacebab292</DeploymentId>
</User>
<Account>
<AccountType>email</AccountType>
<Action>settings</Action>
<Protocol>
<Type>EXCH</Type>
<Server>Exserver.1ask2.com</Server>
<ServerDN>/o=1ASK2Company/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=Exserver.1ask2.com</ServerDN>
<ServerVersion>738180DA</ServerVersion>
<MdbDN>/o=1ASK2Company/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=Exserver.1ask2.com/cn=Microsoft Private MDB</MdbDN>
<AD>king.1ask2.com</AD>
<ASUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</ASUrl>
<EwsUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</EwsUrl>
<EcpUrl>https://exserver.1ask2.com/ecp/</EcpUrl>
<EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
<EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr>
<EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt>
<EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
<EcpUrl-sms>?p=sms/textmessaging.slab&exsvurl=1</EcpUrl-sms>
<EcpUrl-publish>customize/calendarpublishing.slab?exsvurl=1&FldID=<FldID></EcpUrl-publish>
<OOFUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</OOFUrl>
<UMUrl>https://exserver.1ask2.com/EWS/UM2007Legacy.asmx</UMUrl>
<OABUrl>https://exserver.1ask2.com/oab/b3aa16f2-b6ab-4abd-8320-27efc3d04575/</OABUrl>
<ServerExclusiveConnect>off</ServerExclusiveConnect>
</Protocol>
<Protocol>
<Type>EXPR</Type>
<Server>mail.1ask2.com</Server>
<SSL>On</SSL>
<AuthPackage>Ntlm</AuthPackage>
<ASUrl>https://mail.1ask2.com/EWS/EXchange.asmx</ASUrl>
<EwsUrl>https://mail.1ask2.com/EWS/EXchange.asmx</EwsUrl>
<EcpUrl>https://mail.1ask2.com/ecp/</EcpUrl>
<EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
<EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr>
<EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt>
<EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
<EcpUrl-sms>?p=sms/textmessaging.slab&exsvurl=1</EcpUrl-sms>
<EcpUrl-publish>customize/calendarpublishing.slab?exsvurl=1&FldID=<FldID></EcpUrl-publish>
<OOFUrl>https://mail.1ask2.com/EWS/EXchange.asmx</OOFUrl>
<UMUrl>https://mail.1ask2.com/EWS/UM2007Legacy.asmx</UMUrl>
<OABUrl>https://mail.1ask2.com/oab/b3aa16f2-b6ab-4abd-8320-27efc3d04575/</OABUrl>
<ServerExclusiveConnect>on</ServerExclusiveConnect>
<CertPrincipalName>msstd:*.1ask2.com</CertPrincipalName>
</Protocol>
<Protocol>
<Type>WEB</Type>
<Internal>
<OWAUrl AuthenticationMethod="Basic, Fba">https://exserver.1ask2.com/owa/</OWAUrl>
<OWAUrl AuthenticationMethod="Basic, Fba">https://fw.1ask2.com/owa/</OWAUrl>
<Protocol>
<Type>EXCH</Type>
<ASUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</ASUrl>
</Protocol>
</Internal>
<External>
<OWAUrl AuthenticationMethod="Fba">https://mail.1ask2.com/owa/</OWAUrl>
<Protocol>
<Type>EXPR</Type>
<ASUrl>https://mail.1ask2.com/EWS/EXchange.asmx</ASUrl>
</Protocol>
</External>
</Protocol>
</Account>
</Response>
</Autodiscover>
----END XML----
7268 111386788 04/29/11 10:07:09 Autodiscover to https://autodiscover.1ask2.com/autodiscover/autodiscover.xml succeeded (0x00000000)
Why failed?
https://1ask2.com/autodiscover/autodiscover.xml FAILED (0x800C8203)
Reason:

The certificate does not include the 1ask2.com.
Solution:

8176 117230960 04/29/11 11:44:33 Autodiscover to https://1ask2.com/autodiscover/autodiscover.xml starting
8176 117233971 04/29/11 11:44:36 Autodiscover XML Received
---BEGIN XML---
<?xml version="1.0" encoding="utf-8"?>
<Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
<Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
<User>
<DisplayName>Q1</DisplayName>
<LegacyDN>/o=1ASK2Company/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=Q1</LegacyDN>
<AutoDiscoverSMTPAddress>Q1@1ask2.com</AutoDiscoverSMTPAddress>
<DeploymentId>3ef94938-efc0-4c8b-8086-d4bacebab292</DeploymentId>
</User>
<Account>
<AccountType>email</AccountType>
<Action>settings</Action>
<Protocol>
<Type>EXCH</Type>
<Server>Exserver.1ask2.com</Server>
<ServerDN>/o=1ASK2Company/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=Exserver.1ask2.com</ServerDN>
<ServerVersion>738180DA</ServerVersion>
<MdbDN>/o=1ASK2Company/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=Exserver.1ask2.com/cn=Microsoft Private MDB</MdbDN>
<AD>king.1ask2.com</AD>
<ASUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</ASUrl>
<EwsUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</EwsUrl>
<EcpUrl>https://exserver.1ask2.com/ecp/</EcpUrl>
<EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
<EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr>
<EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt>
<EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
<EcpUrl-sms>?p=sms/textmessaging.slab&exsvurl=1</EcpUrl-sms>
<EcpUrl-publish>customize/calendarpublishing.slab?exsvurl=1&FldID=<FldID></EcpUrl-publish>
<OOFUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</OOFUrl>
<UMUrl>https://exserver.1ask2.com/EWS/UM2007Legacy.asmx</UMUrl>
<OABUrl>https://exserver.1ask2.com/oab/b3aa16f2-b6ab-4abd-8320-27efc3d04575/</OABUrl>
</Protocol>
<Protocol>
<Type>EXPR</Type>
<Server>mail.1ask2.com</Server>
<SSL>On</SSL>
<AuthPackage>Ntlm</AuthPackage>
<ASUrl>https://mail.1ask2.com/EWS/EXchange.asmx</ASUrl>
<EwsUrl>https://mail.1ask2.com/EWS/EXchange.asmx</EwsUrl>
<EcpUrl>https://mail.1ask2.com/ecp/</EcpUrl>
<EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
<EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr>
<EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt>
<EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
<EcpUrl-sms>?p=sms/textmessaging.slab&exsvurl=1</EcpUrl-sms>
<EcpUrl-publish>customize/calendarpublishing.slab?exsvurl=1&FldID=<FldID></EcpUrl-publish>
<OOFUrl>https://mail.1ask2.com/EWS/EXchange.asmx</OOFUrl>
<UMUrl>https://mail.1ask2.com/EWS/UM2007Legacy.asmx</UMUrl>
<OABUrl>https://mail.1ask2.com/oab/b3aa16f2-b6ab-4abd-8320-27efc3d04575/</OABUrl>
<CertPrincipalName>msstd:*.1ask2.com</CertPrincipalName>
</Protocol>
<Protocol>
<Type>WEB</Type>
<Internal>
<OWAUrl AuthenticationMethod="Basic, Fba">https://exserver.1ask2.com/owa/</OWAUrl>
<OWAUrl AuthenticationMethod="Basic, Fba">https://fw.1ask2.com/owa/</OWAUrl>
<Protocol>
<Type>EXCH</Type>
<ASUrl>https://exserver.1ask2.com/EWS/Exchange.asmx</ASUrl>
</Protocol>
</Internal>
<External>
<OWAUrl AuthenticationMethod="Fba">https://mail.1ask2.com/owa/</OWAUrl>
<Protocol>
<Type>EXPR</Type>
<ASUrl>https://mail.1ask2.com/EWS/EXchange.asmx</ASUrl>
</Protocol>
</External>
</Protocol>
</Account>
</Response>
</Autodiscover>
----END XML----
8176 117234002 04/29/11 11:44:36 Autodiscover to https://1ask2.com/autodiscover/autodiscover.xml succeeded (0x00000000)
From Internal computer, the Auto Discover Service URL is https://ex2.1ask2.com/autodiscover/autodiscover.xml.
Get-ClientAccessServer | fl name,auto*
Name : EX2
AutoDiscoverServiceCN : ex2
AutoDiscoverServiceClassName : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri : https://ex2.1ask2.com/Autodiscover/Autodiscover.xml
AutoDiscoverServiceGuid : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope : {Default-First-Site-Name}
Name : FW
AutoDiscoverServiceCN : FW
AutoDiscoverServiceClassName : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri : https://fw.1ask2.com/Autodiscover/Autodiscover.xml
AutoDiscoverServiceGuid : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope : {Default-First-Site-Name}