Outlook Security Popup - Exchange Certificate Message
Hi,
My certificate recently expired so I recreated a new one:
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule, System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAcc
essRule}
CertificateDomains : {hubcas.hostname.co.uk, webmail.hostname.co.uk, autodiscover.hostname.co.uk, mail1.hostname.co.uk, mail2.hostname
.co.uk, hubtransport1.hostname.co.uk, hubtransport2.hostname.co.uk, exchange.hostname.co.uk, exchange1.hostname.co.uk, exchange2.hostname.co.uk}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=hubcas.hostname.co.uk
NotAfter : 04/04/2016 11:20:02
NotBefore : 04/04/2011 11:20:02
PublicKeySize : 2048
RootCAType : None
SerialNumber : 7D0DA6EFBE87BDB34B55D8A6921AADA0
Services : IMAP, POP, IIS, SMTP
Status : Valid
Subject : CN=hubcas.hostname.co.uk
Thumbprint : B1755D84F81335D1E58789C3C9239E7C4AD48909
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule}
CertificateDomains : {hostname-HUBTRANSPORT1-CA}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=hostname-HUBTRANSPORT1-CA, DC=hostname, DC=co, DC=uk
NotAfter : 30/03/2014 16:21:05
NotBefore : 30/03/2009 16:11:06
PublicKeySize : 2048
RootCAType : Registry
SerialNumber : 476CA49ECE8EA490460329CAEDC97D72
Services : None
Status : Valid
Subject : CN=hostname-HUBTRANSPORT1-CA, DC=hostname, DC=co, DC=uk
Thumbprint : C2541573C2D1E8CBF943F3D34A69C878A8AB296A
But when the users use outlook they get this security popup.
files.me.com/phil.pearce/ld8gg3
If i look at the details, it is the old certificate as the date has expired.
I have to admit its been around 4 years since I did this last so I may have forgotten the next steps.
Can anyone point me in the right direction?
Thanks
Phil
April 8th, 2011 5:36am
Hi,
I will explain the whole renewing stuff in step-by step for Exchange 2007. So you may follow the required steps and can remember for the next time :)
If you are in Exchange 2010, follow the article published by myself in my forums here:
http://windowsadmin.info/viewtopic.php?f=20&t=180
1. Run in shell: New-ExchangeCertificate -GenerateRequest -Path c:\mynewssl.csr -KeySize 1024 -SubjectName “c=IN, s=KER, l=MyCompany, ou=IT, cn=mail.mydomain.com” -PrivateKeyExportable $True
c-Country name, s-State, I-Coumpany Name, ou- Ou in company which handles certificate, cn-identical name to the mail url
2. Check c:\mynewssl.csr for the CSR and send this file to the SSL provider. The company will send you the CRF file, may be some alphanemeric text. Copy the entire text in to a text file, say newssl.txt and rename it as newssl.cer
3. Copy the file to CAS server
4. Remove the existing certificate: Run the cmdlet:
Get-ExchangeCertficate |fl and copy the Thumbprint of the existing one
5. Run Remove-ExchangeCertificate -thumbprint "%THUMBPRINT%" and remove the existing one
6. Import the new one: Import-ExchangeCertificate -path
newssl.cer –FriendlyName “mail.mydomain.com”
7. Notedown the thumbprint
8. Run Enable-exchangecertificate -services IMAP, POP, UM, IIS, SMTP -Thumbprint "%THUMBPRINT%" to enable it for the services listed here
9. Check the Autodiscovery is okay: Get-ClientAccessServer -Identity CASServer | FL . If it lists something wrong, set the autodiscovery: Set-ClientAccessServer -Identity CASServer -AutoDiscoverServiceInternalUri https://mail.mydomain.com/Autodiscover/Autodiscover.xml
10. Run the following commands to fix your internalURLs so your Outlook client can successfully take advantage of your web distribution services:
Set-WebServicesVirtualDirectory -Identity “CASServer\EWS (Default Web Site)” -InternalURL
https://mail.mydomain.com/EWS/Exchange.asmx -BasicAuthentication:$true
Set-OABVirtualDirectory -Identity “CASServer\OAB (Default Web Site)” -InternalURL
https://mail.mydomain/OABRegards from www.windowsadmin.info
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April 8th, 2011 6:20am
Thanks
I am using 2007.
Dont I need to have all the domains like in the example? Also I dont have an SSL provider so I must have done this another way?Phil
April 8th, 2011 6:24am
Hi,
These are actually the required domain names for Exchange 2K7. Try it as per your requirement.
Regards from www.windowsadmin.info
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April 8th, 2011 6:32am
Ok, I assume this is all one line
New-ExchangeCertificate -GenerateRequest -Path c:\mynewssl.csr -KeySize 1024 -SubjectName “c=IN, s=KER, l=MyCompany, ou=IT, cn=mail.mydomain.com” -PrivateKeyExportable $True c-Country name, s-State, I-Coumpany Name, ou- Ou in company which handles
certificate, cn-identical name to the mail url
I have to admit I cant remember doing this before. What should I do about the SSL part as we dont use anyone for this?Phil
April 8th, 2011 6:36am
Run this much New-ExchangeCertificate -GenerateRequest -Path c:\mynewssl.csrRegards from www.windowsadmin.info
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April 8th, 2011 7:44am
Thanks
Ok, I'm going to start this shortly..
In this part:
2. Check c:\mynewssl.csr for the CSR and send this file to the SSL provider. The company will send you the CRF file, may be some alphanemeric text. Copy the entire text in to a text file, say newssl.txt and rename it as newssl.cer
I generate the csr via the above post, but how do I get the CRF file?Phil
April 8th, 2011 8:45am
Hi,
Next is all about purchasing an SSL certificate. Find a suitable root certification authirity like verisign,twate, godaddy etc..and purchase CRF after submitting the CSRRegards from www.windowsadmin.info
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April 8th, 2011 12:18pm
I have a question, this is for my internal users, why do i need to by a SSL certificate provided by an authority? Im sure I didnt do this before and its been working fine. Just expired on the 01/04/11.
Phil
April 8th, 2011 12:20pm
Hi Phil,
Then you may use a self signed certificate.
1. Remove the existing certificate: Run the cmdlet:
Get-ExchangeCertficate |fl and copy the Thumbprint of the existing one
2. Run Remove-ExchangeCertificate -thumbprint "%THUMBPRINT%" and remove the existing one
3. Run in shell: New-ExchangeCertificate . This will create a self signed certificate. Run
Get-ExchangeCertficate |fl and copy the Thumbprint
4. Run Enable-ExchangeCertificate -thumbprint “"%THUMBPRINT%” -services IIS to enable it
Regards from www.windowsadmin.info
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April 8th, 2011 12:31pm
This is the exact process I did. But still the messagebox appears.
:(Phil
April 8th, 2011 12:33pm
Hi,
Are you using EDGE Servers? In this case, you need a EDGE sync between CAS and EDGE as there is new stuffRegards from www.windowsadmin.info
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April 8th, 2011 12:40pm
No edge servers.
2 clustered mailbox servers, 2 hub / cas servers
infront of that is an ironport mail appliance.
Do i have to import this certificate into the root authority?Phil
April 8th, 2011 3:09pm
Hi Phil,
Please do "Test E-Mail AutoConfiguration" on client (select "Use AutoDiscover") .
The clients are domain-joined ones, right?
What's the results of Get-ExchangeCertificate | fl now?
Please also try to delete the old certificates in the IIS or Certificate MMC on the Exchange server.
If you create a new mailbox or renew Outlook profile, does it work?
Frank Wang
TechNet Subscriber Support
in forum
If you have any feedback on our support, please contact
tngfb@microsoft.com
Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
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April 11th, 2011 3:53am
Test E-Mail Auto Configuration =Unable to determine settings
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule, System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAcc
essRule}
CertificateDomains : {hubcas.hostname.co.uk, webmail.hostname.co.uk, autodiscover.hostname.co.uk, mail1.hostname.co.uk, mail2.hostname
.co.uk, hubtransport1.hostname.co.uk, hubtransport2.hostname.co.uk, exchange.hostname.co.uk, exchange1.lcpl
c.co.uk, exchange2.hostname.co.uk}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=hubcas.hostname.co.uk
NotAfter : 04/04/2016 11:20:02
NotBefore : 04/04/2011 11:20:02
PublicKeySize : 2048
RootCAType : None
SerialNumber : 7D0DA6EFBE87BDB34B55D8A6921AADA0
Services : IMAP, POP, IIS, SMTP
Status : Valid
Subject : CN=hubcas.hostname.co.uk
Thumbprint : B1755D84F81335D1E58789C3C9239E7C4AD48909
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule}
CertificateDomains : {hostname-HUBTRANSPORT1-CA}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=hostname-HUBTRANSPORT1-CA, DC=hostname, DC=co, DC=uk
NotAfter : 30/03/2014 16:21:05
NotBefore : 30/03/2009 16:11:06
PublicKeySize : 2048
RootCAType : Registry
SerialNumber : 476CA49ECE8EA490460329CAEDC97D72
Services : None
Status : Valid
Subject : CN=hostname-HUBTRANSPORT1-CA, DC=hostname, DC=co, DC=uk
Thumbprint : C2541573C2D1E8CBF943F3D34A69C878A8AB296A
This is the only entry as I removed the old one.
THe certificates on IIS server
files.me.com/phil.pearce/5w5iiw
Phil
April 11th, 2011 3:59am
Certificate dialogue box, when I try to connect
files.me.com/phil.pearce/o1kc95
Also I should have mentioned that I have 2 Hubcas servers in a NLB. the above was to do with one. the below is for the 2nd.
When I went onto the 2nd hubtransport I found these certificates
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.Crypto
KeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {hubcas.hostname.co.uk, webmail.hostname.co.uk, autodiscover.hostname.co.uk, mail1.hostname.co.uk, m
ail2.hostname.co.uk, hubtransport1.hostname.co.uk, hubtransport2.hostname.co.uk, exchange.hostname.c
o.uk, exchange1.hostname.co.uk, exchange2.hostname.co.uk}
HasPrivateKey : True
IsSelfSigned : False
Issuer : CN=hostname-HUBTRANSPORT1-CA, DC=hostname, DC=co, DC=uk
NotAfter : 01/04/2011 11:59:44
NotBefore : 01/04/2009 11:59:44
PublicKeySize : 2048
RootCAType : Unknown
SerialNumber : 19A2B01E000000000007
Services : IMAP, POP, IIS, SMTP
Status : Invalid
Subject : CN=hubcas.hostname.co.uk, OU=IT, O=hostname, L=Bath, S=Avon, C=GB
Thumbprint : D91CEAD0BA826467DA8CDD7044B0EEEDBF2F88DA
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.Crypto
KeyAccessRule}
CertificateDomains : {hubtransport1.hostname.co.uk, hubtransport2.hostname.co.uk, HUBCAS.hostname.co.uk, autodiscover.
hostname.co.uk}
HasPrivateKey : True
IsSelfSigned : False
Issuer : CN=hostname-HUBTRANSPORT1-CA, DC=hostname, DC=co, DC=uk
NotAfter : 31/03/2011 14:42:43
NotBefore : 31/03/2009 14:42:43
PublicKeySize : 2048
RootCAType : Unknown
SerialNumber : 15119334000000000005
Services : IMAP, POP
Status : Invalid
Subject : CN=hubtransport1.hostname.co.uk
Thumbprint : 9C02373FD9BB87826F1615E3727EEE93B12521F7
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.Crypto
KeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule, System.Security.Access
Control.CryptoKeyAccessRule}
CertificateDomains : {HubTransport2, HubTransport2.hostname.co.uk}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=HubTransport2
NotAfter : 15/01/2010 13:12:15
NotBefore : 15/01/2009 13:12:15
PublicKeySize : 2048
RootCAType : Unknown
SerialNumber : 100126D6A2C6FCA549F5E2B3B79724CE
Services : SMTP
Status : Invalid
Subject : CN=HubTransport2
Thumbprint : D95EB7BFBB295DBB768D403C55FE897191B3C053
Phil
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April 11th, 2011 5:27am
Certificate dialogue box, when I try to connect
files.me.com/phil.pearce/o1kc95Phil
April 11th, 2011 5:27am
Would this be what i need to do from here
New-ExchangeCertificate -GenerateRequest -FriendlyName "ExchangeSSL2011" -domainName hubcas.hostname.co.uk, webmail.hostname.co.uk, autodiscover.hostname.co.uk, mail1.hostname.co.uk, mail2.hostname.co.uk, hubtransport1.hostname.co.uk, hubtransport2.hostname.co.uk,
exchange.hostname.co.uk, exchange1.hostname.co.uk, exchange2.hostname.co.uk -path c:\temp\exchangeSSL2011.txt
Remove existing thumbprint? Enable-ExchangeCertificate -thumbprint xxxxx -Services "POP,IMAP,SMTP,IIS"
On Second HubCas Server remove all certificates (as above post) Import the new one this 2nd Hubcas Server: Import-ExchangeCertificate -path
c:\temp\exchangeSSL2011.txt
Notedown the thumbprint
Run Enable-exchangecertificate -services IMAP, POP, UM, IIS, SMTP -Thumbprint "%THUMBPRINT%" to enable it for the services listed here
Check the Autodiscovery is okay: Get-ClientAccessServer -Identity CASServer | FL . If it lists something wrong, set the autodiscovery: Set-ClientAccessServer -Identity CASServer -AutoDiscoverServiceInternalUri https://mail.mydomain.com/Autodiscover/Autodiscover.xml
Run the following commands to fix your internalURLs so your Outlook client can successfully take advantage of your web distribution services:
Set-WebServicesVirtualDirectory -Identity “CASServer\EWS (Default Web Site)” -InternalURL
https://mail.mydomain.com/EWS/Exchange.asmx -BasicAuthentication:$true
Set-OABVirtualDirectory -Identity “CASServer\OAB (Default Web Site)” -InternalURL
https://mail.mydomain/OAB
????
Phil
Free Windows Admin Tool Kit Click here and download it now
April 12th, 2011 4:55am
Import the new one this 2nd Hubcas Server: Import-ExchangeCertificate -path
c:\temp\exchangeSSL2011.txt
Hi Phil,
I'm afraid this is not right. You can import an existing certificate and private key from a PKCS #12 (.pfx or .p12) file.
Import-ExchangeCertificate
http://technet.microsoft.com/en-us/library/bb124424(EXCHG.80).aspx
So please run the cmdlet on 1st hubcas:
New-ExchangeCertificate -FriendlyName "ExchangeSSL2011" -domainName hubcas.hostname.co.uk, webmail.hostname.co.uk, autodiscover.hostname.co.uk, mail1.hostname.co.uk, mail2.hostname.co.uk, hubtransport1.hostname.co.uk, hubtransport2.hostname.co.uk,
exchange.hostname.co.uk, exchange1.hostname.co.uk, exchange2.hostname.co.uk -PrivateKeyExportable $true
Enable the service, then remove any other valid/invalid certificates.
Export the certificate from the 1st hubcas to pfx file,
Export-ExchangeCertificate
http://technet.microsoft.com/en-us/library/aa996305(EXCHG.80).aspx
After that, import the pfx file to 2nd hubcas server. Remove any other valid/invalid certificates.
Frank Wang
TechNet Subscriber Support
in forum
If you have any feedback on our support, please contact
tngfb@microsoft.com
Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
April 12th, 2011 10:39pm
Sir,
You are a star.
Phil
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April 13th, 2011 4:02am
Many thanks, a further question, when i try and remove the existing certificate I get
Remove-ExchangeCertificate : The internal transport certificate cannot be removed because that would cause the Microsof
t Exchange Transport service to stop. To replace the internal transport certificate, create a new certificate. The new
certificate will automatically become the internal transport certificate. You can then remove the existing certificate.
Parameter name: Thumbprint
At line:1 char:27
this ok to proceed? I assume after the creation then I restart the transport service?Phil
April 13th, 2011 4:02am