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What determines the combination of ciphers available on an SSL server?

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I have a site that has been bound to a new SSL certificate with SAN (4 additional names). The certificate has a 2048-bit key.

The problem is that it works on some browser/OS combinations but not on others.

  • IE7 / Win XP - fail
  • IE6 / Win 2003 - fail
  • IE8 / Win XP / Corporate proxy - OK
  • IE8 / Win 7 / OTHER Corporate proxy - fail
  • IE9/10 / Win 7 - OK
  • Chrome / Win 7 - OK
  • Firefox / Win 7 - OK
  • Chrome / Android - OK

Note: The two corporate proxies are very different organisations, in two separate countries.

I have installed Fiddler on the IE6 / Win 2003 (2nd on the list) and have captured this from the Inspectors\Raw tab:

IE6:

CONNECT sorry.site.not.disclosed:443 HTTP/1.0User-Agent: Mozilla/4.0 (compatible; MSIE 6.0; Windows NT 5.2; SV1; .NET CLR 1.1.4322; .NET CLR 2.0.50727; .NET CLR 3.0.4506.2152; .NET CLR 3.5.30729; FDM; .NET4.0C; .NET4.0E)Host: sorry.site.not.disclosedContent-Length: 0Connection: Keep-AlivePragma: no-cacheA SSLv2-compatible ClientHello handshake was found. Fiddler extracted the parameters below.Major Version: 2Minor Version: 0Random: EA AE EB C5 20 0C 46 90 7F C1 E0 EE 47 BE 05 63SessionID: emptyCiphers:     [10080] SSL2_RC4_128_WITH_MD5    [700C0] SSL2_DES_192_EDE3_WITH_MD5    [30080] SSL2_RC2_128_WITH_MD5    [60040] SSL2_DES_64_WITH_MD5    [20080] SSL2_RC4_128_EXPORT40_WITH_MD5    [40080] SSL2_RC2_128_EXPORT40_WITH_MD5    [00FF]  TLS_EMPTY_RENEGOTIATION_INFO_SCSVCompression: (not specified)Extensions:     none

Chrome:

CONNECT sorry.site.not.disclosed:443 HTTP/1.1Host: sorry.site.not.disclosedConnection: keep-aliveUser-Agent: Mozilla/5.0 (Windows NT 5.2) AppleWebKit/537.22 (KHTML, like Gecko) Chrome/25.0.1364.172 Safari/537.22A SSLv3-compatible ClientHello handshake was found. Fiddler extracted the parameters below.Major Version: 3Minor Version: 2Random: 51 4A 0D 68 FE C4 50 A9 26 43 9E 1A C2 E9 05 5C FE 5F CF 37 4D 20 96 FF 0E 2F 5E EB 16 C1 F2 20SessionID: emptyCiphers:     [C014]  TLS1_CK_ECDHE_RSA_WITH_AES_256_CBC_SHA    [0088]  TLS_DHE_RSA_WITH_CAMELLIA_256_CBC_SHA    [0087]  TLS_DHE_DSS_WITH_CAMELLIA_256_CBC_SHA    [0039]  TLS_DHE_RSA_WITH_AES_256_SHA    [0038]  TLS_DHE_DSS_WITH_AES_256_SHA    [C00F]  TLS_ECDH_RSA_WITH_AES_256_CBC_SHA    [0084]  TLS_RSA_WITH_CAMELLIA_256_CBC_SHA    [0035]  TLS_RSA_AES_256_SHA    [C011]  TLS_ECDHE_RSA_WITH_RC4_128_SHA    [C013]  TLS1_CK_ECDHE_RSA_WITH_AES_128_CBC_SHA    [0045]  TLS_DHE_RSA_WITH_CAMELLIA_128_CBC_SHA    [0044]  TLS_DHE_DSS_WITH_CAMELLIA_128_CBC_SHA    [0066]  TLS_DHE_DSS_WITH_RC4_128_SHA    [0033]  TLS_DHE_RSA_WITH_AES_128_SHA    [0032]  TLS_DHE_DSS_WITH_AES_128_SHA    [C00C]  TLS_ECDH_RSA_WITH_RC4_128_SHA    [C00E]  TLS_ECDH_RSA_WITH_AES_128_CBC_SHA    [0096]  TLS_RSA_WITH_SEED_CBC_SHA    [0041]  TLS_RSA_WITH_CAMELLIA_128_CBC_SHA    [0005]  SSL_RSA_WITH_RC4_128_SHA    [0004]  SSL_RSA_WITH_RC4_128_MD5    [002F]  TLS_RSA_AES_128_SHA    [C012]  TLS_ECDHE_RSA_WITH_3DES_EDE_CBC_SHA    [0016]  SSL_DHE_RSA_WITH_3DES_EDE_SHA    [0013]  SSL_DHE_DSS_WITH_3DES_EDE_SHA    [C00D]  TLS_ECDH_RSA_WITH_3DES_EDE_CBC_SHA    [FEFF]  SSL_RSA_FIPS_WITH_3DES_EDE_SHA    [000A]  SSL_RSA_WITH_3DES_EDE_SHACompression:     [00]    NO_COMPRESSIONExtensions:     server_name sorry.site.not.disclosed    renegotiation_info  00    elliptic_curves 00 06 00 17 00 18 00 19    ec_point_formats    01 00    SessionTicket TLS   empty    NextProtocolNegotiation empty    channel_id(GoogleDraft) empty    status_request  01 00 00 00 00

When testing using SSLLabs, e.g. https://www.ssllabs.com/ssltest/analyze.html?d=mail.google.com

The site shows ONLY two options under cipher suites, and supports only TLS 1.0:

ProtocolsTLS 1.2 NoTLS 1.1 NoTLS 1.0 YesSSL 3.0 No          SSL 2.0 NoCipher Suites (SSLv3+ suites in server-preferred order, then SSLv2 suites where used)TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA (0xc013)   ECDH 256 bits (eq. 3072 bits RSA)                                128         TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (0xc014)   ECDH 256 bits (eq. 3072 bits RSA)                                

I have contacted Verisign (Australia) and the chap claims that all Verisign certificates support SSLv1, v2, v3, TLS.

So why does the IIS server not present it? Using a SELF-SIGNED wildcard certificate, I was able to get the same IIS server to report on SSLLabs:

ProtocolsTLS 1.2  No TLS 1.1  No TLS 1.0  Yes SSL 3.0  YesSSL 2.0   INSECURE           YesCipher Suites (SSLv3+ suites in server-preferred order, then SSLv2 suites where used)TLS_RSA_WITH_AES_128_CBC_SHA (0x2f)          128         TLS_RSA_WITH_AES_256_CBC_SHA (0x35)          256         TLS_RSA_WITH_RC4_128_SHA (0x5)      128         TLS_RSA_WITH_3DES_EDE_CBC_SHA (0xa)         168         TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA (0xc013)   ECDH 256 bits (eq. 3072 bits RSA)                128         TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (0xc014)   ECDH 256 bits (eq. 3072 bits RSA)                256         TLS_RSA_WITH_RC4_128_MD5 (0x4)     128         SSL_DES_192_EDE3_CBC_WITH_MD5 (0x700c0)                168         SSL_RC4_128_WITH_MD5 (0x10080)       128         

Where to look next?


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