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RemcoViFlag for Netherlands

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Exchange 2007 & Outlook 2007 - Can't connect anymore / Password prompts

I got a weird problem and hopefully you could help me with it.

On last saturday the Small Business server 2008 was moved to an other location and while we at it, we updated the server with alot of updates. This wasn't done for a while.
Updates where installed great and server was shutdown.

When starting up the server again, it starts bleeping and the memory failed, so we replaced the memory and everything works fine again.

Now on sunday everything looks good.

Company started working on monday and yes the problems starts here. A user started Outlook and received a Username and Password prompt. In the mean while other users are also experience these issues.

I tested the OWA connection and i can login and receive and send e-mail messages
I tested the ping command to the server and it looks good
Checked the event viewer and no weird errors found for as far i can tell

Because i couldn't find any solutions, in a desperate attempt i installed every update in Windows update.
Next thing i did is installing SP3
After installing SP3 i installed the Rollup 8 ( latest update )
I restarted the SBS 2008 server and after it was done booting, i restarted the Terminal Server also.

But still no connection when creating a new profile.

This company uses Terminal Server Solution with Office 2007 installed on it. When i log in as a user and want to create a new e-mail profile i receive the following message ( translated from dutch to english )

"Can't complete the action. The name cannot be found in the address list"

One thing i noticed is that the C:\ drive has 10,8 Gb free. It should be enough, but this is one thing i will change in the future.

Sidenote: The clients uses a multi domain certificate wich is still valid.

Does anyone know any solution to this problem wich suddenly comes up?
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Larry Struckmeyer MVP
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SOLUTION
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@fl_flyfishing
Can't find a good solution. Did change this:

The last few days have been a nightmare of complaints. This month's update definately broke a perfectly working SBS 2008/Exchange 2007/Outlook 2007 authentication system, both over RPC and regular. Just keeps asking for password! Tried a million things just like the others, no joy. Went into IIS Manager, opened SBS Web Applications, Select Autodiscover, double click SSL settings (you have to scroll down to see it), check Accept instead of ignore or require, and Apply. I repeated for owa, remote, Rpc, RpcWithCert (possibly don't have to do all these). Restarted Web Publishing and Joy Joy Joy!!!

Restarted IIS but no change

@Exchange_Geek
Tried to compare the settings in your first link and it says that SSL is REQUIRED on the default website, but this option is greyed out for. Next step is the command and this is the result:
The last few days have been a nightmare of complaints. This month's update definately broke a perfectly working SBS 2008/Exchange 2007/Outlook 2007 authentication system, both over RPC and regular. Just keeps asking for password! Tried a million things just like the others, no joy. Went into IIS Manager, opened SBS Web Applications, Select Autodiscover, double click SSL settings (you have to scroll down to see it), check Accept instead of ignore or require, and Apply. I repeated for owa, remote, Rpc, RpcWithCert (possibly don't have to do all these). Restarted Web Publishing and Joy Joy Joy!!!




AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule, System.Securi
                     ty.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {remote.Domainname.nl, Domainname.nl, SERVER.Domainname.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=Domainname-SERVER-CA
NotAfter           : 6-11-2014 0:45:56
NotBefore          : 6-11-2012 0:45:56
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 615A7B0A00010000000D
Services           : IMAP, POP, IIS, SMTP
Status             : Valid
Subject            : CN=remote.Domainname.nl
Thumbprint         : 0CCA8100D0E985BFCA93BCFB152893002FE8CE09

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {Domainname-SERVER-CA}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=Domainname-SERVER-CA
NotAfter           : 6-11-2017 0:55:40
NotBefore          : 6-11-2012 0:45:41
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 2FDEC95C4EAA3F854DB2941CB8581BDD
Services           : None
Status             : Valid
Subject            : CN=Domainname-SERVER-CA
Thumbprint         : FD4394329A77AE4D13249B9232FA702A43B7CD3F

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule, System.Securi
                     ty.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {Domainname.nl, www.Domainname.nl, autodiscover.Domainname.nl, remote.
                     Domainname.nl, SERVER, SERVER.Domainname.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : SERIALNUMBER=07969287, CN=Go Daddy Secure Certification Au
                     thority, OU=http://certificates.godaddy.com/repository, O=
                     "GoDaddy.com, Inc.", L=Scottsdale, S=Arizona, C=US
NotAfter           : 21-7-2013 21:57:42
NotBefore          : 19-7-2012 20:22:09
PublicKeySize      : 2048
RootCAType         : ThirdParty
SerialNumber       : 2B0837DC3F9C83
Services           : IMAP, POP, SMTP
Status             : Valid
Subject            : CN=Domainname.nl, OU=Domain Control Validated, O=Domainname.nl
Thumbprint         : 57DD83C40B77CD0ACDFCB7A9CC620FF5320F95B0

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule, System.Securi
                     ty.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {SERVER.Domainname.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=Domainname-SERVER-CA
NotAfter           : 13-3-2013 19:38:08
NotBefore          : 13-3-2012 19:38:08
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 79E24C2C000000000008
Services           : SMTP
Status             : Valid
Subject            : CN=SERVER.Domainname.local
Thumbprint         : 5EEDA53C77DA66A7652CA60967896F0B10307408

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule, System.Securi
                     ty.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {Domainname.nl, www.Domainname.nl, autodiscover.Domainname.nl, remote.
                     Domainname.nl, SERVER, SERVER.Domainname.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : SERIALNUMBER=07969287, CN=Go Daddy Secure Certification Au
                     thority, OU=http://certificates.godaddy.com/repository, O=
                     "GoDaddy.com, Inc.", L=Scottsdale, S=Arizona, C=US
NotAfter           : 21-7-2012 21:57:42
NotBefore          : 21-7-2011 21:57:42
PublicKeySize      : 2048
RootCAType         : ThirdParty
SerialNumber       : 2B81456745FB29
Services           : IMAP, POP, SMTP
Status             : DateInvalid
Subject            : CN=Domainname.nl, OU=Domain Control Validated, O=Domainname.nl
Thumbprint         : F2710D14C75820F8C7DA7EEB5DE3C17EAFC9716F

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule, System.Securi
                     ty.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {remote.Domainname.nl, Domainname.nl, SERVER.Domainname.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=Domainname-SERVER-CA
NotAfter           : 18-7-2011 11:52:35
NotBefore          : 18-7-2009 11:52:35
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 61196299000000000004
Services           : IMAP, POP, SMTP
Status             : DateInvalid
Subject            : CN=remote.Domainname.nl
Thumbprint         : C3F6EA8DDE60E2ECC2FFC290770B41C9B1DA61D9

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule, System.Securi
                     ty.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {Sites, SERVER.Domainname.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=Domainname-SERVER-CA
NotAfter           : 18-7-2011 9:46:06
NotBefore          : 18-7-2009 9:46:06
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 6104BE6E000000000002
Services           : SMTP
Status             : DateInvalid
Subject            : CN=Sites
Thumbprint         : 5F744BF794017EBCFE7EB6113673FBB5E36E214F

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {Domainname-SERVER-CA}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=Domainname-SERVER-CA
NotAfter           : 18-7-2014 9:54:13
NotBefore          : 18-7-2009 9:44:14
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 4AF2F68B8CA1A9864537EE325023BC2E
Services           : None
Status             : Valid
Subject            : CN=Domainname-SERVER-CA
Thumbprint         : 412FA0ECB8039898134051E847B4CA9A9EC66A7C

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System
                     .Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {WMSvc-WIN-N3UOKR7ZP53}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=WMSvc-WIN-N3UOKR7ZP53
NotAfter           : 16-7-2019 9:11:41
NotBefore          : 18-7-2009 9:11:41
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 9761B268EE0F148544D6F3DB85049FE5
Services           : None
Status             : Valid
Subject            : CN=WMSvc-WIN-N3UOKR7ZP53
Thumbprint         : A7C4B027955EF231712C49443E0BE2456E6DD95F

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I still see some old certificates. How do i remove them and is that important enough? because the services are attached to the GoDaddy certificate wich is still valid.

I will try the last step now, but because the important of this issue i want to post this part already.
Avatar of RemcoVi

ASKER

I followed this link:
http://my.opera.com/RavenOverride/blog/2009/06/17/how-to-recreate-all-virtual-directories-for-exchange-2007

It looks good now. No password prompts anymore, but yesterday it also happens after some while.

So i will wait for 1 hour to check again.
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Fair enough, wait for a day and confirm if the issue is resolved.

Regards,
Exchange_Geek
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ASKER

Wait a day...... it took longer than that, but it is solved right now and the problems are gone after looking at this site and follow each step: http://my.opera.com/RavenOverride/blog/2009/06/17/how-to-recreate-all-virtual-directories-for-exchange-2007

So thanks.

The only thing i would like to know, and that would be the finishing touch, that would be cleaning up the certificates. Wich one could i delete and how?
Aight, some good news to read :) :)

Now, which cert to delete - you can read them out by running cmdlet

Get-ExchangeCertificate | FL

Points to note:
1) Services related to each certificate
2) Expiry Date of each certificate
3) Issuer details (if the cert is issued internally or externally)

Regards,
Exchange_Geek
Avatar of RemcoVi

ASKER

For some reasons i don''t get a reply that you answered my question, sorry for the late response, but it looks good. Maybe you could also mention the best command to delete the right certificate?
Avatar of RemcoVi

ASKER

@Exchange_Geek or someone else
Do you have the command to delete the certificates wich are expired?
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