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I can't seem to get Work Folders to serve using the correct certificate. I've bound it via netsh to a wild card certificate, and when I check "netsh http show sslcert" every binding uses the correct certificate.

C:\Users\Administrator>netsh http show sslcert

SSL Certificate bindings:
-------------------------

IP:port                      : 0.0.0.0:443
Certificate Hash             : d3228f2011af4142da58197d0ade82a7da37f519
Application ID               : {4dc3e181-e14b-4a21-b022-59fc669b0914}
Certificate Store Name       : My
Verify Client Certificate Revocation : Enabled
Verify Revocation Using Cached Client Certificate Only : Disabled
Usage Check                  : Enabled
Revocation Freshness Time    : 0
URL Retrieval Timeout        : 0
Ctl Identifier               : (null)
Ctl Store Name               : (null)
DS Mapper Usage              : Disabled
Negotiate Client Certificate : Disabled

IP:port                      : 192.168.51.2:443
Certificate Hash             : d3228f2011af4142da58197d0ade82a7da37f519
Application ID               : {4dc3e181-e14b-4a21-b022-59fc669b0914}
Certificate Store Name       : My
Verify Client Certificate Revocation : Enabled
Verify Revocation Using Cached Client Certificate Only : Disabled
Usage Check                  : Enabled
Revocation Freshness Time    : 0
URL Retrieval Timeout        : 0
Ctl Identifier               : (null)
Ctl Store Name               : (null)
DS Mapper Usage              : Disabled
Negotiate Client Certificate : Disabled

The thumbprints match the wildcard certificate. I've tried deleting & re-adding. Nothing works.

When I try to access the address internally "workfolders.domain.com" it works, no certificate problem. However externally the server is providing the self signed "SERVERNAME.AD.LOCAL"

The only difference is that the domain name points to the internal address and a NAT'd internet IP externally. It's definitely hitting the correct server.

Why would it do this?

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You cannot use a self signed certificate externally (and should not internally), since self signed certs are not automatically trusted by the Client.

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