We've recently gotten our SS2005 system running over our intranet using both the Lan and Remote Access Http services. The HTTP service was initally setup without SSL as recommended in the following article...
http://alinconstantin.dtdns.net/WebDocs/SCC/_VSS_Internet.htm
During our initial attempts to setup SSL (as described in Setting up SourceSafe and VisualStudio for Secure Internet access (HTTPS / SSL) in the article above), Internet Explorer kept prompting us with a security alert dialog every time we navigated to the https address - https://vesta.companyname.ca:81/SourceSafe/VssService.asmx even though it said we had installed the certificate. Also, after attempting to enable SSL within SourceSafe administrator we received the error saying that SSL could not be enforced and the service was going to be disabled.
I've done some research in this forum and I found the following post by Alin(http://forums.microsoft.com/MSDN/ShowPost.aspx PostID=152546&SiteID=1) where he answered a questions regarding SSL and manually created sites...
"> If I set remote access manually, how do I set "require SSL" on the server
See this for how to assign the vertificate in IIS http://msdn2.microsoft.com/library/ms181053%28en-us,vs.80%29.aspx
Then, in IIS Manager right click SourceSafe folder, select Properties. In the tab DirectorySecurity, click Edit button. Check the 'Require Secure channel' and '128 bits encryption' checkboxes, then ok all the dialogs."
Therefore, I logged back into the server and removed all certificates and recreated the certificate using SELFSSL. However, when I now attempt to navigate to https://vesta.companyname.ca:81/SourceSafe/VssService.asmx I no longer receive the security alert as the "page cannot be displayed" error appears! If I try the non-secure address (ie Http://...) then I receive the normal "Server Error in '/SourceSafe' Application." error which tells me that the service is running properly. Any ideas what might be happening here
Thanks in advance.

SSL
Eric Latham
I don't know if this helps but I ran Microsoft's SSL Diagnostics tool and when I attempt to simulate a SSL handshake with the sourcesafe website I receive the following message...
#WARNING:Connecting to server: wrong IP address
DroopyMsdn
I've just noticed that if I try the following address in IE without the port number...
https://vesta.companyname.ca/SourceSafe/VssService.asmx
...the IE Security Alert dialog box opens. I even deleted the "default" SourceSafe virtual directory from the Default Web Site and this still opens. Can the above address be mapping to vesta.companyname.ca:81 somehow
Andrew Thorpe
Make sure a couple of things happened here: