SSL certificate working in chrome but not openssl s_client or curl

Found a clearer tutorial that had a much simpler openssl.conf. In my original attempts to add SANs I must have un-commented extra lines in the conf that were adding extra info to the certs causing conflicts. Followed this template and my certificate is working all round:

[req]
distinguished_name = req_distinguished_name
req_extensions = v3_req

[req_distinguished_name]
countryName = Country Name (2 letter code)
countryName_default = US
stateOrProvinceName = State or Province Name (full name)
stateOrProvinceName_default = MN
localityName = Locality Name (eg, city)
localityName_default = Minneapolis
organizationalUnitName  = Organizational Unit Name (eg, section)
organizationalUnitName_default  = Domain Control Validated
commonName = Internet Widgits Ltd
commonName_max  = 64

[ v3_req ]
# Extensions to add to a certificate request
basicConstraints = CA:FALSE
keyUsage = nonRepudiation, digitalSignature, keyEncipherment
subjectAltName = @alt_names

[alt_names]
DNS.1 = kb.example.com
DNS.2 = helpdesk.example.org
DNS.3 = systems.example.net
IP.1 = 192.168.1.1
IP.2 = 192.168.69.14

Thanks for your comments @garethTheRed. Your comments helped me re-think my approach to debugging this issue.

Even starting a post here helps me lay out what I've tried and helps the brain think up more possible solutions.