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asp .net could not establish trust relationship for the SSL/TLS secure channel

A quick google search revealed multiple reported resolutions, however, after following the steps in the MSDN blog reference listed below, the issue was still unresolved in my situation.

Additional details in the stack trace will reveal another similar message: “The remote certificate is invalid according to the validation procedure.”

In this specific scenario, the site in question is either not configured with a wildcard certificate for a subdomain of the parent site or the operation system I am working on does not support SNI. In the meantime, a workaround is needed to continue testing and development.

Additional reading on google revealed another solution which was more suitable and utilized a code based approach, as opposed to a server configuration based solution.

To make it more dynamic, I added a key into the app/web config to control if SSL errors should be ignored. Please note that it is also possible to replace the code based approach solely with an app/web config entry listed in the west-wind blog referenced below, but I personally prefer to go with code whenever possible.

<?xml version="1.0"?>
    <add name="ConnectionString"
      connectionString="Data Source=servername;Initial Catalog=databasename;"
      providerName="System.Data.SqlClient" />
    <add key="ignoresslerrors" value="true"/>
<startup><supportedRuntime version="v4.0" sku=".NETFramework,Version=v4.0"/></startup></configuration>
 public class ConfigValues
        public static string IgnoreSSLErrors { get { return getval("ignoresslerrors"); } }

public function main() {

public function connect(string url, string ignoresslerrors) {
HttpWebRequest request = (HttpWebRequest)WebRequest.Create(url);

                if (Convert.ToBoolean(ignoresslerrors))
                    System.Net.ServicePointManager.ServerCertificateValidationCallback +=
            delegate(object sender, System.Security.Cryptography.X509Certificates.X509Certificate certificate,
                                    System.Security.Cryptography.X509Certificates.X509Chain chain,
                                    System.Net.Security.SslPolicyErrors sslPolicyErrors)
                return true; //will always accept the cert and ignore errors. this is not good common practice unless you are sure of the destination you are connecting to. needed in this scenario to continue development until issue with cert is resolved.
            catch (Exception ex)


Create Custom and Self Signed SSL Certificate in IIS 6 (Windows Server 2003)

Single domain


Note: Foremost, in order to access your site over HTTPS, the HTTP SSL Service will need to be running. This service binds to port 443 and filters HTTP traffic to IIS.

Relatively easy to do in never versions of IIS , but a few more steps in previous.

First, download SSL Diagnostics from MS:;displaylang=en&id=674

Make sure if you are on 32bit you install the x86 version above or the x64 version if you are on 64 bit.

Once installed, open a cmd prompt.

cd C:\Program Files\IIS Resources\SSLDiag
ssldiag /selfssl /N:CN=( /V:365 /S:(ID)

This will create a self signed cert with ( which is good for 365 days. See link below for additional information on other parameters you may need to pass in such as site identifier and key length (default 1024).

If you try to test it right now, you will likely get a “Page Cannot Be Displayed”, “Cannot Find Server”, “Server Cannot be Found” or something to this effect. This is because the port 443 bindings are not yet in place.

To add the port 443 bindings to your site, run adsutil:

cscript.exe "C:\inetpub\AdminScripts\adsutil.vbs" set w3svc/(site id in iis)/SecureBindings ""

To confirm the certificate was added, navigate to your site in IIS and go to:
(right click domain)->Properties->Directory Security->Secure Communications->View Certificate

Multi domain wildcard


Configuring the wildcard certificate, is essentially the same as above, however simply use * for sub domain in your cert creation and binding, and export and add this cert to your other sub domains which will be using it.

Multi domain SAN or UCC


Subject alternative name certificates a.k.a unified communications certificates can get very expensive when issued by third parties.. To create your own, there are three approaches to consider:

– Certificate Enrollment wizard with an enterprise CA (Using Advanced->Custom Request or New Request->Template)

– Certificate Enrollment wizard with a standalone CA

– Certreq.exe

For more information on configuring your own SAN cert, reference MS Kbase article


On Linux, the process is IMO a bit easier and simply requires openssl. Since this utility is also available for windows, this method can be used on IIS as well.

SAN Cert/Custom Request,
Page Cannot be Display,
Debug SSL Connectivity on Intermediary Device,
Cannot Find Server,
IIS forums,
Server 03 pre SP1 HTTP 1.1 host headers bug with SSL,
Configuring Host Headers (IIS6.0),
Configuring Server Bindings for SSL Host Headers,
Obtaining/Installing Wildcard certificate (IIS6),
SSL Host Headers in IIS 6,
UCC Certificate Partners,
How to Create SAN Certificate for Web Server,
OpenSSL SAN Cert,
How to Request a Certificate With a Custom Subject Alternative Name,