There's actually a couple issues in the present version of Chrome that could keep the CIP/EAP from working. Building off what tim_841 and mateuszd have contributed, I was able to put together a set of instructions to work around these issues:
req_extentions = v3_reqAdd the following section and entry at the end of the file:
[ v3_req ]EAPsubjectAltName = DNS:vmware-localhost
subjectAltName = @alt_namesAdd the following section and entry at the end of the file:
[ alt_names ]
DNS.1 = vmware-plugin
"C:\Program Files (x86)\VMware\Client Integration Plug-in 6.0\openssl.exe" req -new -config C:\ProgramData\VMware\CIP\csd\ssl\csd-openssl.cfg -key C:\ProgramData\VMware\CIP\csd\ssl\key.pem -out C:\ProgramData\VMware\CIP\csd\ssl\server.csrEAP
"C:\Program Files (x86)\VMware\Plug-in Service\openssl.exe" req -new -config C:\ProgramData\VMware\CIP\csd\ssl\csd-openssl.cfg -key C:\ProgramData\VMware\CIP\csd\ssl\key.pem -out C:\ProgramData\VMware\CIP\csd\ssl\server.csr
"C:\Program Files (x86)\VMware\Client Integration Plug-in 6.0\openssl.exe" x509 -req -days 3650 -in C:\ProgramData\VMware\CIP\csd\ssl\server.csr -signkey C:\ProgramData\VMware\CIP\csd\ssl\key.pem -out C:\ProgramData\VMware\CIP\csd\ssl\cert.pem -extfile C:\ProgramData\VMware\CIP\csd\ssl\csd-openssl.cfg -extensions v3_reqEAP
"C:\Program Files (x86)\VMware\Plug-in Service\openssl.exe" x509 -req -days 3650 -in C:\ProgramData\VMware\CIP\csd\ssl\server.csr -signkey C:\ProgramData\VMware\CIP\csd\ssl\key.pem -out C:\ProgramData\VMware\CIP\csd\ssl\cert.pem -extfile C:\ProgramData\VMware\CIP\csd\ssl\csd-openssl.cfg -extensions req_x509_extensions
copy /b C:\ProgramData\VMware\CIP\csd\ssl\cert.pem+C:\ProgramData\VMware\CIP\csd\ssl\key.pem C:\ProgramData\VMware\CIP\csd\ssl\server.pem
"C:\Program Files (x86)\VMware\Client Integration Plug-in 6.0\openssl.exe" x509 -outform der -in C:\ProgramData\VMware\CIP\csd\ssl\cert.pem -out C:\ProgramData\VMware\CIP\csd\ssl\cert.derEAP
"C:\Program Files (x86)\VMware\Plug-in Service\openssl.exe" x509 -outform der -in C:\ProgramData\VMware\CIP\csd\ssl\cert.pem -out C:\ProgramData\VMware\CIP\csd\ssl\cert.der
C:\Windows\System32\icacls.exe C:\ProgramData\VMware\CIP\csd\ssl\cert.der /inheritance:r /grant:r *S-1-5-11:R /grant:r *S-1-5-32-544:F /grant:r "SYSTEM":F C:\Windows\System32\icacls.exe C:\ProgramData\VMware\CIP\csd\ssl\cert.pem /inheritance:r /grant:r *S-1-5-11:R /grant:r *S-1-5-32-544:F /grant:r "SYSTEM":F C:\Windows\System32\icacls.exe C:\ProgramData\VMware\CIP\csd\ssl\server.pem /inheritance:r /grant:r *S-1-5-11:R /grant:r *S-1-5-32-544:F /grant:r "SYSTEM":FEAP
C:\Windows\System32\icacls.exe C:\ProgramData\VMware\CIP\csd\ssl\cert.der /inheritance:r /grant:r "LOCAL SERVICE":R /grant:r "SERVICE":R /grant:r "SYSTEM":F /grant:r *S-1-5-32-544:F C:\Windows\System32\icacls.exe C:\ProgramData\VMware\CIP\csd\ssl\cert.pem /inheritance:r /grant:r "LOCAL SERVICE":R /grant:r "SERVICE":R /grant:r *S-1-5-11:R /grant:r "SYSTEM":F /grant:r *S-1-5-32-544:F C:\Windows\System32\icacls.exe C:\ProgramData\VMware\CIP\csd\ssl\server.pem /inheritance:r /grant:r "LOCAL SERVICE":R /grant:r "SERVICE":R /grant:r "SYSTEM":F /grant:r *S-1-5-32-544:F
Some notes: