I am receiving HTTP 500 errors when running tests from testexchangeconnectivity.com/ I have already uninstalled and re-installed the RPC proxy twice. When I go tohttps://webmail.mydomain.org/rpc/rpcproxy.dll I get page cannot be displayed. I have checked and verified that my SSL settings are correct in IIS and I have checked the authentication settings are correct as according to http://technet.microsoft.com/en-us/library/gg263433(v=exchg.80).aspx. Please help. Webmail is working as an interim workaround but this has been happening since last week and users are getting restless. Testing RPC/HTTP connectivity. The RPC/HTTP test failed. Test Steps Attempting to resolve the host name webmail.mydomain.org in DNS. The host name resolved successfully. Additional Details IP addresses returned: MY IP Testing TCP port 443 on host webmail.mydomain.org to ensure it's listening and open. The port was opened successfully. Testing the SSL certificate to make sure it's valid. The certificate passed all validation requirements. Test Steps ExRCA is attempting to obtain the SSL certificate from remote server webmail.mydomain.org on port 443. ExRCA successfully obtained the remote SSL certificate. Additional Details Remote Certificate Subject: CN=webmail.mydomain.org, OU=Domain Control Validated, O=webmail.mydomain.org, Issuer: SERIALNUMBER=xxxxxxx, CN=Go Daddy Secure Certification Authority, OU=http://certificates.godaddy.com/repository, O="GoDaddy.com, Inc.", L=Scottsdale, S=Arizona, C=US. Validating the certificate name. The certificate name was validated successfully. Additional Details Host name webmail.mydomain.org was found in the Certificate Subject Common name. Certificate trust is being validated. The certificate is trusted and all certificates are present in the chain. Test Steps ExRCA is attempting to build certificate chains for certificate CN=webmail.mydomain.org, OU=Domain Control Validated, O=webmail.mydomain.org. One or more certificate chains were constructed successfully. Additional Details A total of 2 chains were built. The highest quality chain ends in root certificate OU=Go Daddy Class 2 Certification Authority, O="The Go Daddy Group, Inc.", C=US. Analyzing the certificate chains for compatibility problems with versions of Windows. No Windows compatibility problems were identified. Additional Details The certificate chain has been validated up to a trusted root. Root = E=info@valicert.com, CN=http://www.valicert.com/, OU=ValiCert Class 2 Policy Validation Authority, O="ValiCert, Inc.", L=ValiCert Validation Network. Testing the certificate date to confirm the certificate is valid. Date validation passed. The certificate hasn't expired. Additional Details The certificate is valid. NotBefore = 3/20/2012 7:10:03 PM, NotAfter = 3/20/2013 7:10:03 PM Checking the IIS configuration for client certificate authentication. Client certificate authentication wasn't detected. Additional Details Accept/Require Client Certificates isn't configured. Testing HTTP Authentication Methods for URL https://webmail.mydomain.org/rpc/rpcproxy.dll. The HTTP authentication test failed. Additional Details An HTTP 500 response was returned from Unknown.

There are a number of potential causes. http://www.lmgtfy.com/?q=http+500+outlook+anywhereEd Crowley MVP "There are seldom good technological solutions to behavioral problems."

I have been Google Searching for 3 days now. Most of the posts recommend things I have already tried (i.e re-install RPC proxy, Check SSL settings in IIS, verify correct name on SSL cert { comman and SAN}, check external URL, etc..... ) I am looking for something that I may be missing thanks for not helping and making fun of a situation I inherited. Thought this is where to go to post questions to a community to seek help when running into an issue outside your knowledge base.

Nothing in Event Viewer? Does this provide any information? Test-OutlookConnectivity Re-installing the RPC Proxy usually does the trick (from personal experience and from what I've been reading). I suppose you followed steps like those shown here and restarted the AD Topology Service and so forth? http://www.msdigest.net/2011/01/exchange-2010-outlook-anywhere-not-working-and-getting-http-500-response-error/Please mark as helpful if you find my contribution useful or as an answer if it does answer your question. That will encourage me - and others - to take time out to help you.

It would be helpful if you were to say that up front so people don't tell you what you've already tried.Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Sorry I failed to mention I am running Exchange 2007. I believe Test-OutlookConnectivty is a cmdlet introduced in Exchange 2010. I did follow the step in the article you referenced (actually that is the exact article I used) Checked event viewed and not seeing anything out of the ordinary.

The most common fix for this issue is to remove and reinstall Outlook Anywhere and all of its compnents, but you have to it in the correct order. Disable Outlook Anywhere in Exchange. Wait for the event log entry to say it has been disabled. Then remove the RPC proxy component. Ensure the two virtual directories have been removed from IIS manager. Run IISRESET to write the change to the IIS metabase. Reinstall the RPC Proxy component, and then enable Outlook Anywhere again. Wait for the event log entry to appear. When you browse to the address in the first question, you should get an authentication prompt. Nothing else. If you don't get a prompt, then something is still wrong. Simon.Simon Butler, Exchange MVP Blog | Exchange Resources | In the UK? Hire Me.

The most common fix for this issue is to remove and reinstall Outlook Anywhere and all of its compnents, but you have to it in the correct order. Disable Outlook Anywhere in Exchange. Wait for the event log entry to say it has been disabled. Then remove the RPC proxy component. Ensure the two virtual directories have been removed from IIS manager. Run IISRESET to write the change to the IIS metabase. Reinstall the RPC Proxy component, and then enable Outlook Anywhere again. Wait for the event log entry to appear. When you browse to the address in the first question, you should get an authentication prompt. Nothing else. If you don't get a prompt, then something is still wrong. Simon.Simon Butler, Exchange MVP Blog | Exchange Resources | In the UK? Hire Me.

Hi, Reset and reboot the server is a worth to try. If the issue continues, please collect the following information for further research: Do you have any firewall between exchange server and external clients? If you test the URL https://localhost/rpc/rpcproxy.dllon the CAS server, can you logon and get the blank page? Is there any error recorded in IIS log? Http error 500 might be caused by various factors, see http://support.microsoft.com/kb/318380or http://support.microsoft.com/kb/943891. However, if there is no any record in IIS log when the issue occurs, you might encounter configuration issue on the firewall or DNS settings. Thanks. Fiona Liao TechNet Community Support

Hi, Reset and reboot the server is a worth to try. If the issue continues, please collect the following information for further research: Do you have any firewall between exchange server and external clients? If you test the URL https://localhost/rpc/rpcproxy.dllon the CAS server, can you logon and get the blank page? Is there any error recorded in IIS log? Http error 500 might be caused by various factors, see http://support.microsoft.com/kb/318380or http://support.microsoft.com/kb/943891. However, if there is no any record in IIS log when the issue occurs, you might encounter configuration issue on the firewall or DNS settings. Thanks. Fiona Liao TechNet Community Support