This is one of those "after banging my head on the desk more times than I care to admit, I finally got x and y to play nice together; here's how you do it" posts.
I was trying to set up a test environment with a single-server deployment of SharePoint Portal Server (SPS) using an MSDE database. I also wanted to enable SSL on the server.
So — and this was my mistake — I started off by creating my own certificate with SelfSSL and installing it for the default virtual server in IIS. In theory, this virtual server would then be extended with WSS when I installed SPS, with the SSL certificate remaining in place. Didn't quite work that way, though.
In case you haven't heard about it, SelfSSL is one of the excellent free tools provided by Microsoft in the IIS 6.0 Resource Kit. It lets you quickly create self-published test certificates, allowing you to use SSL in your test environments. Great tool, but since it's a free (unsupported?) tool, it has some rough edges. It doesn't always play nice with other applications — in this case, MSDE.
MSDE is another useful, free product. It's the poor man's version of SQL Server 2000. Unless you're using it's the full SQL Server, SPS relies on MSDE to hold its data. When you install SPS with MSDE, it creates an MSDE instance named SharePointPortal.
However, the MSDE installation will fail if you have any SelfSSL certificates installed! Both WSS and SPS will install just fine, but MSDE will fail with several of these in the setup logs:
SSL Security error :ConnectionOpen (SECDoClientHandshake())
KB 309398 explains this in more detail, and tells you how to temporarily uninstall your certificates while you install MSDE. Alternately, I could have avoided all of this mess by waiting to install the SelfSSL certificate until
after the SPS installation.
And one more thing...
The issue I described above will not affect you if you're just installing WSS (not SPS) with WMSDE on a server with a SelfSSL certificate.
WSS without SQL Server 2000 — essentially the poor man's version of SPS — installs WMSDE, which is a specialized version of MSDE that is, in some ways, actually more powerful than MSDE. For one thing, it isn't affected by the SSL issue. :-)
Apparently, upgrading from WSS to SPS actually downgrades (crossgrades?) your WMSDE database to MSDE. Check out Graham Tyler's SharePoint Storage Overview - MSDE vs WMSDE vs SQL Server 2000 post for more on the strange world that is SharePoint storage.
