Re: What does this error mean? sslv3 alert certificate unknown:state 23

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On 4/24/17, 7:26 PM, "openssl-users on behalf of Viktor Dukhovni" <openssl-users-bounces@xxxxxxxxxxx on behalf of openssl-users@xxxxxxxxxxxx> wrote:

    I get slightly annoyed when I take the time to help, but my response is
    skimmed over and not read carefully.  Upthread I said:
    
    See my recent post: https://www.spinics.net/lists/openssl-users/msg05623.html
    for instructions on how to extract SSL info from PCAP files in a way that
    mostly trims away endpoint details...

My apologies. Please find attached the tshark-processed (as instructed) PCAPNG file. I’d love to learn what one can glean from it.


    If the alert is from the application to the proxy, then most likely the
    application does not trust the proxy MiTM root CA.
    
Thanks!  

Secure Sockets Layer
    SSL Record Layer: Handshake Protocol: Client Hello
        Content Type: Handshake (22)
        Version: TLS 1.2 (0x0303)
        Length: 228
        Handshake Protocol: Client Hello
            Handshake Type: Client Hello (1)
            Length: 224
            Version: TLS 1.2 (0x0303)
            Random
                GMT Unix Time: Apr 24, 2017 17:59:40.000000000 EDT
                Random Bytes: 010124d7b6a3fcc51f5495bfaeb11c0be284472c54217e63...
            Session ID Length: 0
            Cipher Suites Length: 58
            Cipher Suites (29 suites)
                Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256 (0xc023)
                Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256 (0xc027)
                Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA256 (0x003c)
                Cipher Suite: TLS_ECDH_ECDSA_WITH_AES_128_CBC_SHA256 (0xc025)
                Cipher Suite: TLS_ECDH_RSA_WITH_AES_128_CBC_SHA256 (0xc029)
                Cipher Suite: TLS_DHE_RSA_WITH_AES_128_CBC_SHA256 (0x0067)
                Cipher Suite: TLS_DHE_DSS_WITH_AES_128_CBC_SHA256 (0x0040)
                Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA (0xc009)
                Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA (0xc013)
                Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA (0x002f)
                Cipher Suite: TLS_ECDH_ECDSA_WITH_AES_128_CBC_SHA (0xc004)
                Cipher Suite: TLS_ECDH_RSA_WITH_AES_128_CBC_SHA (0xc00e)
                Cipher Suite: TLS_DHE_RSA_WITH_AES_128_CBC_SHA (0x0033)
                Cipher Suite: TLS_DHE_DSS_WITH_AES_128_CBC_SHA (0x0032)
                Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 (0xc02b)
                Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f)
                Cipher Suite: TLS_RSA_WITH_AES_128_GCM_SHA256 (0x009c)
                Cipher Suite: TLS_ECDH_ECDSA_WITH_AES_128_GCM_SHA256 (0xc02d)
                Cipher Suite: TLS_ECDH_RSA_WITH_AES_128_GCM_SHA256 (0xc031)
                Cipher Suite: TLS_DHE_RSA_WITH_AES_128_GCM_SHA256 (0x009e)
                Cipher Suite: TLS_DHE_DSS_WITH_AES_128_GCM_SHA256 (0x00a2)
                Cipher Suite: TLS_ECDHE_ECDSA_WITH_3DES_EDE_CBC_SHA (0xc008)
                Cipher Suite: TLS_ECDHE_RSA_WITH_3DES_EDE_CBC_SHA (0xc012)
                Cipher Suite: TLS_RSA_WITH_3DES_EDE_CBC_SHA (0x000a)
                Cipher Suite: TLS_ECDH_ECDSA_WITH_3DES_EDE_CBC_SHA (0xc003)
                Cipher Suite: TLS_ECDH_RSA_WITH_3DES_EDE_CBC_SHA (0xc00d)
                Cipher Suite: TLS_DHE_RSA_WITH_3DES_EDE_CBC_SHA (0x0016)
                Cipher Suite: TLS_DHE_DSS_WITH_3DES_EDE_CBC_SHA (0x0013)
                Cipher Suite: TLS_EMPTY_RENEGOTIATION_INFO_SCSV (0x00ff)
            Compression Methods Length: 1
            Compression Methods (1 method)
                Compression Method: null (0)
            Extensions Length: 125
            Extension: elliptic_curves
                Type: elliptic_curves (0x000a)
                Length: 52
                Elliptic Curves Length: 50
                Elliptic curves (25 curves)
                    Elliptic curve: secp256r1 (0x0017)
                    Elliptic curve: sect163k1 (0x0001)
                    Elliptic curve: sect163r2 (0x0003)
                    Elliptic curve: secp192r1 (0x0013)
                    Elliptic curve: secp224r1 (0x0015)
                    Elliptic curve: sect233k1 (0x0006)
                    Elliptic curve: sect233r1 (0x0007)
                    Elliptic curve: sect283k1 (0x0009)
                    Elliptic curve: sect283r1 (0x000a)
                    Elliptic curve: secp384r1 (0x0018)
                    Elliptic curve: sect409k1 (0x000b)
                    Elliptic curve: sect409r1 (0x000c)
                    Elliptic curve: secp521r1 (0x0019)
                    Elliptic curve: sect571k1 (0x000d)
                    Elliptic curve: sect571r1 (0x000e)
                    Elliptic curve: secp160k1 (0x000f)
                    Elliptic curve: secp160r1 (0x0010)
                    Elliptic curve: secp160r2 (0x0011)
                    Elliptic curve: sect163r1 (0x0002)
                    Elliptic curve: secp192k1 (0x0012)
                    Elliptic curve: sect193r1 (0x0004)
                    Elliptic curve: sect193r2 (0x0005)
                    Elliptic curve: secp224k1 (0x0014)
                    Elliptic curve: sect239k1 (0x0008)
                    Elliptic curve: secp256k1 (0x0016)
            Extension: ec_point_formats
                Type: ec_point_formats (0x000b)
                Length: 2
                EC point formats Length: 1
                Elliptic curves point formats (1)
                    EC point format: uncompressed (0)
            Extension: signature_algorithms
                Type: signature_algorithms (0x000d)
                Length: 28
                Signature Hash Algorithms Length: 26
                Signature Hash Algorithms (13 algorithms)
                    Signature Hash Algorithm: 0x0603
                        Signature Hash Algorithm Hash: SHA512 (6)
                        Signature Hash Algorithm Signature: ECDSA (3)
                    Signature Hash Algorithm: 0x0601
                        Signature Hash Algorithm Hash: SHA512 (6)
                        Signature Hash Algorithm Signature: RSA (1)
                    Signature Hash Algorithm: 0x0503
                        Signature Hash Algorithm Hash: SHA384 (5)
                        Signature Hash Algorithm Signature: ECDSA (3)
                    Signature Hash Algorithm: 0x0501
                        Signature Hash Algorithm Hash: SHA384 (5)
                        Signature Hash Algorithm Signature: RSA (1)
                    Signature Hash Algorithm: 0x0403
                        Signature Hash Algorithm Hash: SHA256 (4)
                        Signature Hash Algorithm Signature: ECDSA (3)
                    Signature Hash Algorithm: 0x0401
                        Signature Hash Algorithm Hash: SHA256 (4)
                        Signature Hash Algorithm Signature: RSA (1)
                    Signature Hash Algorithm: 0x0402
                        Signature Hash Algorithm Hash: SHA256 (4)
                        Signature Hash Algorithm Signature: DSA (2)
                    Signature Hash Algorithm: 0x0303
                        Signature Hash Algorithm Hash: SHA224 (3)
                        Signature Hash Algorithm Signature: ECDSA (3)
                    Signature Hash Algorithm: 0x0301
                        Signature Hash Algorithm Hash: SHA224 (3)
                        Signature Hash Algorithm Signature: RSA (1)
                    Signature Hash Algorithm: 0x0302
                        Signature Hash Algorithm Hash: SHA224 (3)
                        Signature Hash Algorithm Signature: DSA (2)
                    Signature Hash Algorithm: 0x0203
                        Signature Hash Algorithm Hash: SHA1 (2)
                        Signature Hash Algorithm Signature: ECDSA (3)
                    Signature Hash Algorithm: 0x0201
                        Signature Hash Algorithm Hash: SHA1 (2)
                        Signature Hash Algorithm Signature: RSA (1)
                    Signature Hash Algorithm: 0x0202
                        Signature Hash Algorithm Hash: SHA1 (2)
                        Signature Hash Algorithm Signature: DSA (2)
            Extension: server_name
                Type: server_name (0x0000)
                Length: 27
                Server Name Indication extension
                    Server Name list length: 25
                    Server Name Type: host_name (0)
                    Server Name length: 22
                    Server Name: cs.visual-paradigm.com

Secure Sockets Layer
    TLSv1.2 Record Layer: Handshake Protocol: Server Hello
        Content Type: Handshake (22)
        Version: TLS 1.2 (0x0303)
        Length: 89
        Handshake Protocol: Server Hello
            Handshake Type: Server Hello (2)
            Length: 85
            Version: TLS 1.2 (0x0303)
            Random
                GMT Unix Time: Jan 12, 2043 21:01:43.000000000 EST
                Random Bytes: 74befd6060b40803a1f2eeee81de721667ea45ac751fb7cd...
            Session ID Length: 32
            Session ID: c07a259d71e9906c44632f6f9e885d40a647d514ef5deb8b...
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f)
            Compression Method: null (0)
            Extensions Length: 13
            Extension: renegotiation_info
                Type: renegotiation_info (0xff01)
                Length: 1
                Renegotiation Info extension
                    Renegotiation info extension length: 0
            Extension: ec_point_formats
                Type: ec_point_formats (0x000b)
                Length: 4
                EC point formats Length: 3
                Elliptic curves point formats (3)
                    EC point format: uncompressed (0)
                    EC point format: ansiX962_compressed_prime (1)
                    EC point format: ansiX962_compressed_char2 (2)

Secure Sockets Layer
    TLSv1.2 Record Layer: Handshake Protocol: Certificate
        Content Type: Handshake (22)
        Version: TLS 1.2 (0x0303)
        Length: 2017
        Handshake Protocol: Certificate
            Handshake Type: Certificate (11)
            Length: 2013
            Certificates Length: 2010
            Certificates (2010 bytes)
                Certificate Length: 1038
                Certificate (id-at-commonName=cs.visual-paradigm.com)
                    signedCertificate
                        version: v3 (2)
                        serialNumber : 0x1c3d07eea2d576e83c60613e5f3c2a18e518b8a0
                        signature (sha256WithRSAEncryption)
                            Algorithm Id: 1.2.840.113549.1.1.11 (sha256WithRSAEncryption)
                        issuer: rdnSequence (0)
                            rdnSequence: 6 items (id-at-commonName=McAfee Web Gateway,id-at-countryName=US,...
                                RDNSequence item: 1 item (id-at-organizationName=MIT Lincoln Laboratory)
                                    RelativeDistinguishedName item (id-at-organizationName=MIT Lincoln Laboratory)
                                        Id: 2.5.4.10 (id-at-organizationName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: MIT Lincoln Laboratory
                                    . . . . .
                                RDNSequence item: 1 item (id-at-commonName=McAfee Web Gateway)
                                    RelativeDistinguishedName item (id-at-commonName=McAfee Web Gateway)
                                        Id: 2.5.4.3 (id-at-commonName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: McAfee Web Gateway
                        validity
                            notBefore: utcTime (0)
                                utcTime: 17-04-24 18:35:25 (UTC)
                            notAfter: utcTime (0)
                                utcTime: 18-04-24 18:35:25 (UTC)
                        subject: rdnSequence (0)
                            rdnSequence: 1 item (id-at-commonName=cs.visual-paradigm.com)
                                RDNSequence item: 1 item (id-at-commonName=cs.visual-paradigm.com)
                                    RelativeDistinguishedName item (id-at-commonName=cs.visual-paradigm.com)
                                        Id: 2.5.4.3 (id-at-commonName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: cs.visual-paradigm.com
                        subjectPublicKeyInfo
                            algorithm (rsaEncryption)
                                Algorithm Id: 1.2.840.113549.1.1.1 (rsaEncryption)
                            Padding: 0
                            subjectPublicKey: 3082010a02820101009a686b8a742ec2e4341a6f43e20f71...
                        extensions: 5 items
                            Extension (id-ce-basicConstraints)
                                Extension Id: 2.5.29.19 (id-ce-basicConstraints)
                                BasicConstraintsSyntax [0 length]
                            Extension (id-ce-subjectKeyIdentifier)
                                Extension Id: 2.5.29.14 (id-ce-subjectKeyIdentifier)
                                SubjectKeyIdentifier: 749037cb5eef9dc9b52ade1c2c465c61f1a63206
                            Extension (id-ce-authorityKeyIdentifier)
                                Extension Id: 2.5.29.35 (id-ce-authorityKeyIdentifier)
                                AuthorityKeyIdentifier
                                    authorityCertIssuer: 1 item
                                        GeneralName: directoryName (4)
                                            directoryName: rdnSequence (0)
                                                rdnSequence: 6 items (id-at-commonName=McAfee Web Gateway,...
                                                    RDNSequence item: 1 item (id-at-organizationName=MIT Lincoln Laboratory)
                                                        RelativeDistinguishedName item (id-at-organizationName=MIT Lincoln Laboratory)
                                                            Id: 2.5.4.10 (id-at-organizationName)
                                                            DirectoryString: uTF8String (4)
                                                                uTF8String: MIT Lincoln Laboratory
                                                            . . . . .
                                                    RDNSequence item: 1 item (id-at-commonName=McAfee Web Gateway)
                                                        RelativeDistinguishedName item (id-at-commonName=McAfee Web Gateway)
                                                            Id: 2.5.4.3 (id-at-commonName)
                                                            DirectoryString: uTF8String (4)
                                                                uTF8String: McAfee Web Gateway
                                    authorityCertSerialNumber: 1
                            Extension (id-ce-keyUsage)
                                Extension Id: 2.5.29.15 (id-ce-keyUsage)
                                Padding: 5
                                KeyUsage: a0 (digitalSignature, keyEncipherment)
                                    1... .... = digitalSignature: True
                                    .0.. .... = contentCommitment: False
                                    ..1. .... = keyEncipherment: True
                                    ...0 .... = dataEncipherment: False
                                    .... 0... = keyAgreement: False
                                    .... .0.. = keyCertSign: False
                                    .... ..0. = cRLSign: False
                                    .... ...0 = encipherOnly: False
                                    0... .... = decipherOnly: False
                            Extension (id-ce-extKeyUsage)
                                Extension Id: 2.5.29.37 (id-ce-extKeyUsage)
                                KeyPurposeIDs: 1 item
                                    KeyPurposeId: 1.3.6.1.5.5.7.3.1 (id-kp-serverAuth)
                    algorithmIdentifier (sha256WithRSAEncryption)
                        Algorithm Id: 1.2.840.113549.1.1.11 (sha256WithRSAEncryption)
                    Padding: 0
                    encrypted: 76a83746f5faf96fe7911ad7fd57c7240262fcec5439075e...
                Certificate Length: 966
                Certificate (id-at-commonName=McAfee Web Gateway,. . .
                    signedCertificate
                        version: v3 (2)
                        serialNumber: 1
                        signature (shaWithRSAEncryption)
                            Algorithm Id: 1.2.840.113549.1.1.5 (shaWithRSAEncryption)
                        issuer: rdnSequence (0)
                            rdnSequence: 6 items (id-at-commonName=McAfee Web Gateway,...
                                RDNSequence item: 1 item (id-at-organizationName=MIT Lincoln Laboratory)
                                    RelativeDistinguishedName item (id-at-organizationName=MIT Lincoln Laboratory)
                                        Id: 2.5.4.10 (id-at-organizationName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: MIT Lincoln Laboratory
                                        . . . . .
                                RDNSequence item: 1 item (id-at-commonName=McAfee Web Gateway)
                                    RelativeDistinguishedName item (id-at-commonName=McAfee Web Gateway)
                                        Id: 2.5.4.3 (id-at-commonName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: McAfee Web Gateway
                        validity
                            notBefore: utcTime (0)
                                utcTime: 12-08-07 21:51:05 (UTC)
                            notAfter: utcTime (0)
                                utcTime: 22-08-07 21:51:05 (UTC)
                        subject: rdnSequence (0)
                            rdnSequence: 6 items (id-at-commonName=McAfee Web Gateway,. . .
                                RDNSequence item: 1 item (id-at-organizationName=MIT Lincoln Laboratory)
                                    RelativeDistinguishedName item (id-at-organizationName=MIT Lincoln Laboratory)
                                        Id: 2.5.4.10 (id-at-organizationName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: MIT Lincoln Laboratory
                                        . . . . .
                                RDNSequence item: 1 item (id-at-commonName=McAfee Web Gateway)
                                    RelativeDistinguishedName item (id-at-commonName=McAfee Web Gateway)
                                        Id: 2.5.4.3 (id-at-commonName)
                                        DirectoryString: uTF8String (4)
                                            uTF8String: McAfee Web Gateway
                        subjectPublicKeyInfo
                            algorithm (rsaEncryption)
                                Algorithm Id: 1.2.840.113549.1.1.1 (rsaEncryption)
                            Padding: 0
                            subjectPublicKey: 3082010a028201010085b3b7c94a1150fdde952428b6a343...
                        extensions: 4 items
                            Extension (ns_cert_exts.comment)
                                Extension Id: 2.16.840.1.113730.1.13 (ns_cert_exts.comment)
                                BER Error: String with tag=22 expected but class:UNIVERSAL(0) primitive tag:12 was unexpected
                                    [Expert Info (Warn/Malformed): BER Error: String expected]
                                        [BER Error: String expected]
                                        [Severity level: Warn]
                                        [Group: Malformed]
                            Extension (id-ce-subjectAltName)
                                Extension Id: 2.5.29.17 (id-ce-subjectAltName)
                                GeneralNames: 1 item
                                    GeneralName: rfc822Name (1)
                                        rfc822Name: help@xxxxxxxxxx
                            Extension (id-ce-basicConstraints)
                                Extension Id: 2.5.29.19 (id-ce-basicConstraints)
                                BasicConstraintsSyntax
                                    cA: True
                            Extension (id-ce-keyUsage)
                                Extension Id: 2.5.29.15 (id-ce-keyUsage)
                                Padding: 1
                                KeyUsage: 06 (keyCertSign, cRLSign)
                                    0... .... = digitalSignature: False
                                    .0.. .... = contentCommitment: False
                                    ..0. .... = keyEncipherment: False
                                    ...0 .... = dataEncipherment: False
                                    .... 0... = keyAgreement: False
                                    .... .1.. = keyCertSign: True
                                    .... ..1. = cRLSign: True
                                    .... ...0 = encipherOnly: False
                                    0... .... = decipherOnly: False
                    algorithmIdentifier (shaWithRSAEncryption)
                        Algorithm Id: 1.2.840.113549.1.1.5 (shaWithRSAEncryption)
                    Padding: 0
                    encrypted: 408fc9a991e6cebbec05fa6b2463d89bcb8b2dc888c1a1b6...
Hypertext Transfer Protocol
    [Proxy-Connect-Hostname: cs.visual-paradigm.com]
    [Proxy-Connect-Port: 443]
Secure Sockets Layer
    TLSv1.2 Record Layer: Handshake Protocol: Server Key Exchange
        Content Type: Handshake (22)
        Version: TLS 1.2 (0x0303)
        Length: 333
        Handshake Protocol: Server Key Exchange
            Handshake Type: Server Key Exchange (12)
            Length: 329
            EC Diffie-Hellman Server Params
                Curve Type: named_curve (0x03)
                Named Curve: secp256r1 (0x0017)
                Pubkey Length: 65
                Pubkey: 04ddd74a3192f97d6c0285a4af7940263ec557207e9e2382...
                Signature Hash Algorithm: 0x0401
                    Signature Hash Algorithm Hash: SHA256 (4)
                    Signature Hash Algorithm Signature: RSA (1)
                Signature Length: 256
                Signature: 2e4a11ef3f32891a5cd389b99f556f83e1329e9d9d44da40...
    TLSv1.2 Record Layer: Handshake Protocol: Server Hello Done
        Content Type: Handshake (22)
        Version: TLS 1.2 (0x0303)
        Length: 4
        Handshake Protocol: Server Hello Done
            Handshake Type: Server Hello Done (14)
            Length: 0

Secure Sockets Layer
    TLSv1.2 Record Layer: Alert (Level: Fatal, Description: Certificate Unknown)
        Content Type: Alert (21)
        Version: TLS 1.2 (0x0303)
        Length: 2
        Alert Message
            Level: Fatal (2)
            Description: Certificate Unknown (46)

Secure Sockets Layer

Secure Sockets Layer

Attachment: smime.p7s
Description: S/MIME cryptographic signature

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