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We are SaaS & IaaS provider that predominantly use Windows 2012 (R2) for hosting. We have started evaluating Windows 2016 OS and noticed our sites are no longer accessible via Chrome / Firefox (works via IE / Edge). It throws:

This site can’t be reached

The webpage at https://gemini-ci.dev.company.com.au/ might be temporarily down or it may have moved permanently to a new web address. ERR_SPDY_INADEQUATE_TRANSPORT_SECURITY

Below is the Fiddler output:

    A SSLv3-compatible ClientHello handshake was found. Fiddler extracted the parameters below.

Version: 3.3 (TLS/1.2)
Random: F6 42 DD 5A 96 11 36 5C DD 6C 85 43 1D 9C 29 48 D4 E5 62 05 66 A6 14 6F 4B B8 D7 C4 02 2B 86 85
"Time": 23/04/2018 12:20:38 PM
SessionID: D2 44 00 00 BF 88 16 FA BC 63 84 AC DD 57 4C 7E A0 15 AA 84 9A BA DF DD 03 0C E6 FC E1 D3 F1 E9
Extensions: 
    0xdada      empty
    renegotiation_info  00
    server_name gemini-ci.dev.company.com.au
    extended_master_secret  empty
    SessionTicket   empty
    signature_algs  sha256_ecdsa, Unknown[0x8]_Unknown[0x4], sha256_rsa, sha384_ecdsa, Unknown[0x8]_Unknown[0x5], sha384_rsa, Unknown[0x8]_Unknown[0x6], sha512_rsa, sha1_rsa
    status_request  OCSP - Implicit Responder
    SignedCertTimestamp (RFC6962)   empty
    ALPN        h2, http/1.1
    channel_id(GoogleDraft) empty
    ec_point_formats    uncompressed [0x0]
    elliptic_curves unknown [0x4A4A), unknown [0x1D), secp256r1 [0x17], secp384r1 [0x18]
    0x5a5a      00
    padding 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00
Ciphers: 
    [FAFA]  Unrecognized cipher - See http://www.iana.org/assignments/tls-parameters/
    [C02B]  TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256
    [C02F]  TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256
    [C02C]  TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384
    [C030]  TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384
    [CCA9]  TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256
    [CCA8]  TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256
    [C013]  TLS1_CK_ECDHE_RSA_WITH_AES_128_CBC_SHA
    [C014]  TLS1_CK_ECDHE_RSA_WITH_AES_256_CBC_SHA
    [009C]  TLS_RSA_WITH_AES_128_GCM_SHA256
    [009D]  TLS_RSA_WITH_AES_256_GCM_SHA384
    [002F]  TLS_RSA_AES_128_SHA
    [0035]  TLS_RSA_AES_256_SHA
    [000A]  SSL_RSA_WITH_3DES_EDE_SHA

Compression: 
    [00]    NO_COMPRESSION

and

    This is a CONNECT tunnel, through which encrypted HTTPS traffic flows.
To view the encrypted sessions inside this tunnel, enable the Tools > Options > HTTPS > Decrypt HTTPS traffic option.

A SSLv3-compatible ServerHello handshake was found. Fiddler extracted the parameters below.

Version: 3.3 (TLS/1.2)
SessionID:  D2 44 00 00 BF 88 16 FA BC 63 84 AC DD 57 4C 7E A0 15 AA 84 9A BA DF DD 03 0C E6 FC E1 D3 F1 E9
Random:     59 81 38 EA 88 E4 DA 94 9C 2F 59 86 38 92 D3 42 B8 59 6F F7 F3 08 EF D6 CC 8E 76 CF E3 99 36 EE
Cipher:     TLS_RSA_WITH_AES_256_GCM_SHA384 [0x009D]
CompressionSuite:   NO_COMPRESSION [0x00]
Extensions:
        ALPN        h2
        extended_master_secret  empty
        renegotiation_info  00
        server_name empty

All relevant configurations for Hashes, Key-Exchange Algorithms, TLS / SSL support, Cipher Suite orders are automated and gets managed via Puppet, which works well on 2012 R2 VMs but not so much on 2016 OS.

Below is what I've done so far:

Disabled PCT 1.0, SSL 2.0, SSL 3.0
Enabled TLS 1.0, TLS 1.1, TLS 1.2
Enabled Ciphers AES 128/128, AES 256/256, Triple DES 168/168
Enabled Hashes MD5, SHA, SHA256, SHA384, SHA512 
Enabled Key-Exchange algorithms Diffie-Hellman, PKCS, ECDH

Cipher Suites Order:

'TLS_DHE_RSA_WITH_AES_256_GCM_SHA384',
'TLS_DHE_RSA_WITH_AES_128_GCM_SHA256',
'TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384_P521',
'TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384_P384',
'TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P521',
'TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P384',
'TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P256',
'TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384_P521',
'TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384_P384',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P521',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P384',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P256',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P256',
'TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P521',
'TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P384',
'TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P256',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P521',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P384',
'TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P256',
'TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P521',
'TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384',
'TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P256',
'TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P521',
'TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P384',
'TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P256',
'TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P521',
'TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P384',
'TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P256',
'TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P521',
'TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P384',
'TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P256',
'TLS_RSA_WITH_AES_256_GCM_SHA384',
'TLS_RSA_WITH_AES_128_GCM_SHA256',
'TLS_RSA_WITH_AES_256_CBC_SHA256',
'TLS_RSA_WITH_AES_128_CBC_SHA256',
'TLS_RSA_WITH_AES_256_CBC_SHA',
'TLS_RSA_WITH_AES_128_CBC_SHA'

Why does it complain that extended_master_secret is empty? I understand it's an issue with the Cipher Suite order but I can't seem to find a perfect forward-secrecy order. Any suggestions would be of great help, thanks.

Karthik

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