MSExchangeGuru.com

Learn Exchange the Guru way !!!

 

Install SSL certificate on EDGE Transport server role for TLS

EDGE transport server installation by default comes with a self-signed certificate. If we need to use a certificate issued by an internal windows certification authority server, follow this article.

This article can also be used for securing email communication using TLS for your EDGE transport server.

Run this cmdlet to get details on the cert currently installed on the EDGE server:

Get-ExchangeCertificate |fl

You may see:

IsSelfSigned     : True

Issuer     : CN=ServerName

This article basically outlines the following steps:

  1. Create a new CSR (Certificate Signing Request) from Exchange Management Shell
  2. Take the CSR output to Windows CA (Windows certificate authority) and generate the certificate
  3. Install the root certificate and the new certificate on the EDGE servers local computer certificate store
  4. Import the cert to EDGE server
  5. Assign the cert to SMTP service
  6. Test to make sure it is valid

Troubleshooting:

Repair a certificate if the private key is missing

Open ports required from the EDGE server to the Windows CA server for Certificate Revocation Check

Create a new CSR (Certificate Signing Request) from Exchange Management Shell

Use the following cmdlet:

New-ExchangeCertificate -GenerateRequest -Domainname NBC-D-EDG01.CONTOSO.PRI -PrivateKeyExportable $True >>c:\CSRreq.txt

—–BEGIN NEW CERTIFICATE REQUEST—–

MAAD1DCCArwCAQAwAjEgMB4GA1UEAwwXmkJDLUQmRUReMDEuQ09OVE9mmy5QUkkw

ggEAMA0GCSqGSAb3DQEBAQUAA4ABDwAwggEKAoABAQDG7lFxw4rVuyVzQ95e99UA

eX3YAmk5Zl9mJfzls7YGysEZAeAzALryyqo1pomyP0CaZqZMzvaAeE5v55PAmecS

FXq3xmcjAO8OKZZqzw6Mb+xFFJ9ak1J07qSRgYAfUaL557KGqDJVJuGDweFzjDAp

GDLSMAYmPWQamMd3d+/AzAe0eagBl5FelFp0Z/LMc0mFjk75+/mjGpWcqB0oe6+X

LjjYq4M0s5VMlV/omrUVSvkEd/BMuVg6XpEMf+y1mB/dddMrXAmPx11ppmABCPgv

35EyddXUMMm9rrxFuraqObdrKAaAfVefMeKz595eAlW5MFPy/qd5y9F+lDM9dYwP

AgMBAAGgggFrMBoGCAsGAQQBgjcMAgMxDBYKMA4xLjc5MDEuMjBMBgkrBgEEAYA3

FRQxWjBYAgEFDBduYmMmZC1lZGcwMS5jb550b3MvLMByaQwWV09SS0dSm1VQXE5C

Qy1ELUVERzAxJAwAmWljcm9zb5Z0LkV4Y5eebmdlLlMlcMZpY5VAb3M0LmV4ZmBw

BgkqekAG9w0BCQ4xYzBeMA4GA1UdDwEB/wQEAwAFoDAABgMVeREEGzAZgedOQkMm

RC1FREcwMS5Dm05Um1MPLlBSSmAMBgMVeRMBAf8EAjAAMB0GA1UdDgQWBBmQd83F

8uE0P4Z6Egm388gkkOAXpmByBgorBgEEAYA3DQACMWQwYgABAR5aAE0AaQBjAeAA

bwBzAG8AZgB0ACAAUgBmAEEAAABmAEMAaABeAG4AbgBlAGwAAABDAeAAeQBwAeQA

bwBMAeAAYQBwAGgAaQBjACAAUAByAG8AdgBpAGQAZQByAwEAMA0GCSqGSAb3DQEB

BQUAA4ABAQA/o3lAj+Edmku/JGmYmejfmAbfOVEgzoQPgecdLCDJKDP3LKAgQpVc

UWPU5rLryMgBQKM1UkmjjPABzmppVyKeMMJYQ3AbsYv8MWlJxw3MejVrARAS7Bsj

WAADMMXJRuemb5ewmkeev7JLMR6qx7eeLwMYY4SXkuxVexqyMemeLe+BgLV8YSdA

qdumALBc1zpmPW8AKJVkgpDCvFMX1MYM5sJDl1XDMVSA5+fdqEmJ5qe/5Kg++kry

yAcaedrMXesAampACXAjoqL14AKYLpMPMkkMMygJr3X/5MbSec/MG5Azmaw3SzRg

PoXeegEwg81pYXxpcfmAMrQ8wEMkM8me

—–END NEW CERTIFICATE REQUEST—–

This is an example CSR you will see.

Take the CSR output to Windows CA (Windows certificate authority)

How to Create a new Certificate using a Windows certification authority

Navigate to your Windows CA server – http://windowsCAserverNameORipAddress/Certsrv

Click Request a cert and then click “Submit an advanced certificate request.”

Now click:

Submit a certificate request by using a base-64-encoded CMC or PKCS #10 file, or submit a renewal request by using a base-64-encoded PKCS #7 file.

Now paste the CSR you got from step one “including” the space at the end

Select web Server as shown in cert template


Now click Submit and download the cert in the next screen


Install the root certificate and the new certificate on the EDGE servers local computer certificate store

Copy the certificate to the EDGE server and double click to open it

 


You will see the message, “Windows does not have enough information to verify this certificate”

Now click “Certification path” on the top


You will see the message, “The issuer of this certificate could not be found”

This is because we DO NOT have the ROOT certificate installed on the EDGE server.

The Yellow exclamation on the certificate name means “I have no clue who issued this certificate”

So let’s install the Root certificate. Navigate to the Windows CA server and get a copy of the Root certificate and Intermediate certificate – if any.

To do this, on the Windows CA server – http://windowsCAserverName/Certsrv

Click

Download a CA certificate, certificate chain, or CRL

On the next page click:

Download CA certificate – If you have a ROOT CA only and no Intermediate CA

Download CA certificate chain – If you have both Root and an Intermediate CA

Now transfer the cert – *.cer or *.p7b depending on the one you downloaded to the EDGE server

Usually the EDGE server maybe in a DMZ which will prevent you to transfer easily. I use Gmail drafts or Microsoft Skydrive to access the certs in all location

On the EDGE server,

Start à Run à mmc

Click File – Add/Remove Snap in

Click Certificates and click Computer Account

Click Local computer and click finish

I usually install the root cert in all 4 locations as shown:

Now, right click each store and click import and import the ROOT cert in all 4 locations.

Remember – If you have an intermediate certificate authority, that certificate should also be installed or your certificate won’t be verified

Also install the EDGE server certificate (NDC-D-EDG01.CONTOSO.PRI) you generated in step 1 to the Personal Store of the server.

Now if you look at the EDGE server certificate, it will look alright:

If this cert doesn’t have “You have a private key that corresponds to this certificate”, you will get the error while enabling the certificate in the last step. Let’s cover it right away.

Enable-ExchangeCertificate : The certificate with thumbprint XXXXXXXXX was found but is not valid for use with Exchange Server

(reason: PrivateKeyMissing).
At line:1 char:27
+ Enable-ExchangeCertificate -Thumbprint XXXXXXXXX -Services “SMTP”

Now we need to repair the cert which is a simple process.

Double-Click on the recently imported certificate.

Note: In Windows Server 2008 it will be the certificate missing the golden key beside it. Select the Details tab.

Click on the Serial Number field and copy that string.

Note: You may use CTRL+C, but not right-click and copy.

Open up an elevated command prompt session. (cmd.exe aka DOS Prompt)

Type: 

certutil -repairstore my “SerialNumber” (SerialNumber is that which was copied above)

After running the above command, go back to the MMC and Right-Click Certificates and select Refresh (or hit F5 in the MMC)

Double-Click on the problem certificate. At the bottom of this window (General tab) it should state: “You have a private key that corresponds to this certificate.”

Note: In Windows Server 2008 there will be a golden key to the left of the certificate, so there is no need to double-click the certificate.

Now that the Private Key is attached to the certificate, please proceed to enable Exchange Services via Enable-ExchangeCertificate.

Import the cert to EDGE server

Now let’s navigate back to the EDGE server and import this new cert from C:\NBC-D-EDG01.cer

Use the cmdlet:

Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content -Path C:\NBC-D-EDG01.cer -Encoding byte -ReadCount 0))

If it says the certificate already exists, we can proceed to the next step:

Import-ExchangeCertificate : Cannot import certificate. A certificate with the thumbprint EEFA7LBKJ875897KBKHHKJDRDT3645FYGUBI496D already exists

Enable-ExchangeCertificate -Thumbprint EEFA7LBKJ875897KBKHHKJDRDT3645FYGUBI496D -Services SMTP

 

CertificateDomains : {NBC-D-EDG01.CONTOSO.PRI}

HasPrivateKey : True

IsSelfSigned : False

Issuer : CN=PKIROOT-CA, DC=contoso, DC=pri

NotAfter : 7/24/2014 10:09:47 AM

NotBefore : 7/24/2012 10:09:47 AM

PublicKeySize : 2048

RootCAType : Registry

SerialNumber : 33G6515E00000000000F

Services : SMTP

Status : RevocationCheckFailure

Subject : CN=NBC-D-EDG01.CONTOSO.PRI

Thumbprint : EEFA7LBKJ875897KBKHHKJDRDT3645FYGUBI496D

As you can see the certificate is now enabled for SMTP service but now we have an issue where Certificate RevocationCheckFailure happened.

RevocationCheck is a check to ensure the EDGE server can communicate with the Windows CA server to verify if the certificate is valid or not.

To resolve this, you need to ensure the EDGE server can communicate with the Windows CA server on ports for Certificate Revocation List traffic:

Firewall rules between the perimeter network and the internal network to contact CRL distribution point to get the certificate revocation list:

  • Server Protocol = LDAP or HTTP or FTP
  • For LDAP: port = TCP: 389, UDP: 389. For HTTP: port = 80. For FTP: Port = 21

Note: The Certificate Revocation List is needed either to validate the client certificate during smart card authentication or when the certificate deployed on RD Gateway is an enterprise/standalone CA certificate. To know which protocol is needed to contact the CRL distribution point for a certificate, open the certificate and go to the Details tab and look at the CRL Distribution Points field.

I got this info from the Remote Desktop services blog

RD Gateway deployment in a perimeter network & Firewall rules: http://blogs.msdn.com/b/rds/archive/2009/07/31/rd-gateway-deployment-in-a-perimeter-network-firewall-rules.aspx

Once you resolve the issue with ports, restart the server and your EDGE server would be ready to accept TLS emails securely.

Ratish Nair
MVP Exchange
Team@ MSExchangeGuru

Keywords: RevocationCheckFailure, Import-ExchangeCertificate : Cannot import certificate. A certificate with the thumbprint EEFA7LBKJ875897KBKHHKJDRDT3645FYGUBI496D already exists, certutil -repairstore my, repair certificate, Enable-ExchangeCertificate : The certificate with thumbprint XXXXXXXXX was found but is not valid for use with Exchange Server (reason: PrivateKeyMissing), You have a private key that corresponds to this certificate, The issuer of this certificate could not be found, Windows does not have enough information to verify this certificate, Install the root certificate, Create a new CSR (Certificate Signing Request),

11 Responses to “Install SSL certificate on EDGE Transport server role for TLS”

  1. Louie Says:

    Very insightful writing on site security with ssl. Thanks, I really walked away more learned than before.

  2. Grace Says:

    Excellent knowledge, thanks a lot.

    My question is that should we use an external cert for securing email delivery externally (secure SMTP traffic) instead of using an internal cert, in other words, what’s the advantage of using an external cert on edge server?

    Thanks again.

  3. Ratish Sekhar Says:

    Thank You Grace !!! well – I dont see any advantage of using a public cert…

  4. Grace Says:

    Hi Ratish,

    I might not express the background of my question with more details previously. Recently, one of our business partners approached us and asked whether our email gateway is TLS capable because they would like to set up secure email gateway to guard against information loss between both.

    Regardless what their SMTP system is (might be UNIX, Domino or MS Exchange), we have Microsoft Exchange 2010 with Edge server point to our MailMarshal (used as a smart host) which flow SMTP mail to MessageLab for further SPAM filtering. Currently, we have only used our internal CA issued STARTTLS on EDGEs and HUBs for communication between them.

    I am thinking there are few approaches:

    1) End-to-End security by using user certificate without doing anything on Edge/External send connector, this requires internal PKI with a kind of Federation trust on both our partner and our ends (Internal domains).

    2) Server-to-server security (between our MailMarshal/Edge with TLS capable and our business partner’s SMTP gateway) by implementing TLS on our Mailmarshal and Edge server by using 3rd party certificate (this was where my previous question came from)

    So with option 2 above, if we use our own CA to enable TLS on Edge external send connector, would our business partner’s TLS/SMTP gateway accepts our mail or refuse it? Furthermore, will all other non-TLS SMTP domains accept our emails or we should set up two send connectors – one for TLS and another one with non-TLS?

    I would think a TLS enabled send connector will negotiate a mutual TLS session with the receiving end first before sending SMTP traffic, if the other end is incapable to do so, then it sends in plain SMTP.

    Please advise if my thoughts are wrong. Thank you.

  5. Ratish Sekhar Says:

    Im using internal certs, so it should work fine…

  6. Transitioning Exchange 2007 Client Access servers to Exchange 2010 « MSExchangeGuru.com Says:

    […] Install SSL certificate on EDGE Transport server role for TLS: http://msexchangeguru.com/2012/07/24/edge-server-tls/ […]

  7. Create an new Exchange certificate on Exchange 2013 « MSExchangeGuru.com Says:

    […] Install SSL certificate on EDGE Transport server role for TLS: http://msexchangeguru.com/2012/07/24/edge-server-tls/ […]

  8. Exchange 2007 Certificate and Coexistence « MSExchangeGuru.com Says:

    […] I would recommend to review this blow to know how to request new cert and review the private key: http://msexchangeguru.com/2012/07/24/edge-server-tls/ […]

  9. Lavonne Dimond Says:

    This web site certainly has all the info I needed concerning this subject and didn’t know who to ask.

  10. Weslee Says:

    this site gave me the answer to my question what is great! i give you many thanks and will read you more!

  11. Neyc Says:

    Very nice, thank you best regards

Leave a Reply

migrate exchange to office 365

Categories

Archives