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I have a really old piece of industrial equipment that connects from windows professional to a sql server 2008r2 on win 2008R2, not completely patched. We cannot replace the windows 2000, but would like to connect to a sql server 2016.

This is the connection string in the udl file [oledb] ; Everything after this line is an OLE DB initstring Provider=SQLOLEDB.1;Password=blabla;Persist Security Info=True;User ID=LVD;Initial Catalog=LVDLASER;Data Source=someserver

It works if I point to the old server. If I change the servername, test it on a win 10 machine, it works. On the win2000 I get this: enter image description here

Test connection failed because of an error in initializing provider. [DBNETLIB]ConnectionOpen (SECDoClientHandshake()).SSL Security error.

Any suggestion is very much appreciated.

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    I cannot tell you exactly how to rectify this, but an idea you may follow: Probably the protocol version or ciphers the 2016 offers are too new and not supported by the 2000.
    – sticky bit
    Feb 4 at 11:59
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    Which client do you have installed on the Windows 2000 machine? I think the latest version that works on Windows 2000 is the SQL Server Native Client(SQL Server 2005). Whether or not it can connect to SQL Server 2016 I don't know. Also suggest trying to connect without SSL, if possible. I know it's not secure but I guess in your case functionality trumps security. Feb 4 at 12:46
  • I wonder if there is some way of proxying a connection via another PC. But my first line of thinking would be to get rid of Windows 2000, it must have a huge amount of security holes by now. I'd be interested to know why it cannot be replaced with Windows 10 or Server 2016+ Feb 5 at 9:30
  • To add to sticky bit's comment, the newest version of SSL/TLS that works on Windows 2000 is TLS 1.0. SQL 2016 on a modern OS can talk TLS 1.0. But it is possible that TLS 1.0 and 1.1 were disabled on your SQL 2016 server for security/compliance purposes. If so, the two machines can't agree on a TLS version, and that would give an error like you are seeing.
    – Doug Deden
    Feb 5 at 15:52
  • The 2000 cannot be replaced because it is part of a laser cutting machine that has a built in computer. That computer runs windows 2000, is +15 yrs old. Feb 5 at 17:28
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Colin's suggestion fixed it. Installed windows installer 3.1 and found the native client 2005 somewhere and now it is ok. Works also for sql server 2019 on windows 2019.

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