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SSL handshake failure after ClientHello in Ubuntu 20.04 and Debian 10 (works in Ubuntu 18.04 and Debian 9)

I have been trying to use Oracle Cloud Email Delivery Service. Once configured it provides SMTP credentials which you can use to send email from approved senders.

I am stuck with few interesting scenarios.
It works in Ubuntu 18.04 but fails in docker container(running Debian 10) running on same machine.

I was testing handshake with openssl s_client

echo QUIT | openssl s_client -starttls smtp -crlf -connect smtp.email.ap-mumbai-1.oci.oraclecloud.com:587

This command works fine in Ubuntu 18.04 but fails with handshake failure in docker container running Debian 10

Output from Docker Container

root@06369bfe7c16:/var/www/html# echo QUIT | openssl s_client -starttls smtp -crlf -connect smtp.email.ap-mumbai-1.oci.oraclecloud.com:587
CONNECTED(00000003)
140491098481792:error:14094410:SSL routines:ssl3_read_bytes:sslv3 alert handshake failure:../ssl/record/rec_layer_s3.c:1544:SSL alert number 40
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 199 bytes and written 367 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
root@06369bfe7c16:/var/www/html#

I tried to check openssl versions in both.

18.04 is having openssl version OpenSSL 1.1.1 11 Sep 2018

Docker container is having openssl version OpenSSL 1.1.1d 10 Sep 2019

Can it be something related to versions?

I tried to debug more via Wireshark to see how ClientHello messages are sent –

ClientHello from Ubuntu 18.04 ( which returns in success)

TLSv1.2 Record Layer: Handshake Protocol: Client Hello
    Content Type: Handshake (22)
    Version: TLS 1.0 (0x0301)
    Length: 339
    Handshake Protocol: Client Hello
        Handshake Type: Client Hello (1)
        Length: 335
        Version: TLS 1.2 (0x0303)
        Random: e595f987b8d92387f7114d9dee4df7bc3f00b5b082ba0ec8…
        Session ID Length: 32
        Session ID: 74c873d7894514a047e0763cd14c01fb19a4f238cb9085f2…
        Cipher Suites Length: 62
        Cipher Suites (31 suites)
            Cipher Suite: TLS_AES_256_GCM_SHA384 (0x1302)
            Cipher Suite: TLS_CHACHA20_POLY1305_SHA256 (0x1303)
            Cipher Suite: TLS_AES_128_GCM_SHA256 (0x1301)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 (0xc02c)
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (0xc030)
            Cipher Suite: TLS_DHE_RSA_WITH_AES_256_GCM_SHA384 (0x009f)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca9)
            Cipher Suite: TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca8)
            Cipher Suite: TLS_DHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (0xccaa)
            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_DHE_RSA_WITH_AES_128_GCM_SHA256 (0x009e)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384 (0xc024)
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 (0xc028)
            Cipher Suite: TLS_DHE_RSA_WITH_AES_256_CBC_SHA256 (0x006b)
            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_DHE_RSA_WITH_AES_128_CBC_SHA256 (0x0067)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA (0xc00a)
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (0xc014)
            Cipher Suite: TLS_DHE_RSA_WITH_AES_256_CBC_SHA (0x0039)
            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_DHE_RSA_WITH_AES_128_CBC_SHA (0x0033)
            Cipher Suite: TLS_RSA_WITH_AES_256_GCM_SHA384 (0x009d)
            Cipher Suite: TLS_RSA_WITH_AES_128_GCM_SHA256 (0x009c)
            Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA256 (0x003d)
            Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA256 (0x003c)
            Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA (0x0035)
            Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA (0x002f)
            Cipher Suite: TLS_EMPTY_RENEGOTIATION_INFO_SCSV (0x00ff)
        Compression Methods Length: 1
        Compression Methods (1 method)
            Compression Method: null (0)
        Extensions Length: 200
        Extension: server_name (len=47)
            Type: server_name (0)
            Length: 47
            Server Name Indication extension
        Extension: ec_point_formats (len=4)
            Type: ec_point_formats (11)
            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)
        Extension: supported_groups (len=12)
            Type: supported_groups (10)
            Length: 12
            Supported Groups List Length: 10
            Supported Groups (5 groups)
        Extension: session_ticket (len=0)
            Type: session_ticket (35)
            Length: 0
            Data (0 bytes)
        Extension: encrypt_then_mac (len=0)
            Type: encrypt_then_mac (22)
            Length: 0
        Extension: extended_master_secret (len=0)
            Type: extended_master_secret (23)
            Length: 0
        Extension: signature_algorithms (len=48)
            Type: signature_algorithms (13)
            Length: 48
            Signature Hash Algorithms Length: 46
            Signature Hash Algorithms (23 algorithms)
                Signature Algorithm: ecdsa_secp256r1_sha256 (0x0403)
                Signature Algorithm: ecdsa_secp384r1_sha384 (0x0503)
                Signature Algorithm: ecdsa_secp521r1_sha512 (0x0603)
                Signature Algorithm: ed25519 (0x0807)
                Signature Algorithm: ed448 (0x0808)
                Signature Algorithm: rsa_pss_pss_sha256 (0x0809)
                Signature Algorithm: rsa_pss_pss_sha384 (0x080a)
                Signature Algorithm: rsa_pss_pss_sha512 (0x080b)
                Signature Algorithm: rsa_pss_rsae_sha256 (0x0804)
                Signature Algorithm: rsa_pss_rsae_sha384 (0x0805)
                Signature Algorithm: rsa_pss_rsae_sha512 (0x0806)
                Signature Algorithm: rsa_pkcs1_sha256 (0x0401)
                Signature Algorithm: rsa_pkcs1_sha384 (0x0501)
                Signature Algorithm: rsa_pkcs1_sha512 (0x0601)
                Signature Algorithm: SHA224 ECDSA (0x0303)
                Signature Algorithm: ecdsa_sha1 (0x0203)
                Signature Algorithm: SHA224 RSA (0x0301)
                Signature Algorithm: rsa_pkcs1_sha1 (0x0201)
                Signature Algorithm: SHA224 DSA (0x0302)
                Signature Algorithm: SHA1 DSA (0x0202)
                Signature Algorithm: SHA256 DSA (0x0402)
                Signature Algorithm: SHA384 DSA (0x0502)
                Signature Algorithm: SHA512 DSA (0x0602)
        Extension: supported_versions (len=9)
            Type: supported_versions (43)
            Length: 9
            Supported Versions length: 8
            Supported Version: TLS 1.3 (0x0304)
            Supported Version: TLS 1.2 (0x0303)
            Supported Version: TLS 1.1 (0x0302)
            Supported Version: TLS 1.0 (0x0301)
        Extension: psk_key_exchange_modes (len=2)
            Type: psk_key_exchange_modes (45)
            Length: 2
            PSK Key Exchange Modes Length: 1
            PSK Key Exchange Mode: PSK with (EC)DHE key establishment (psk_dhe_ke) (1)
        Extension: key_share (len=38)
            Type: key_share (51)
            Length: 38
            Key Share extension

ClientHello message from Docker Container (which results in handshake failure SSL alert number 40)

TLSv1.2 Record Layer: Handshake Protocol: Client Hello
    Content Type: Handshake (22)
    Version: TLS 1.0 (0x0301)
    Length: 234
    Handshake Protocol: Client Hello
        Handshake Type: Client Hello (1)
        Length: 230
        Version: TLS 1.2 (0x0303)
        Random: 20375888f578157f3989533cc8d2c6e5b1db2795dba56ff2…
        Session ID Length: 0
        Cipher Suites Length: 56
        Cipher Suites (28 suites)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 (0xc02c)
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (0xc030)
            Cipher Suite: TLS_DHE_RSA_WITH_AES_256_GCM_SHA384 (0x009f)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca9)
            Cipher Suite: TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca8)
            Cipher Suite: TLS_DHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (0xccaa)
            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_DHE_RSA_WITH_AES_128_GCM_SHA256 (0x009e)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384 (0xc024)
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 (0xc028)
            Cipher Suite: TLS_DHE_RSA_WITH_AES_256_CBC_SHA256 (0x006b)
            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_DHE_RSA_WITH_AES_128_CBC_SHA256 (0x0067)
            Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA (0xc00a)
            Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA (0xc014)
            Cipher Suite: TLS_DHE_RSA_WITH_AES_256_CBC_SHA (0x0039)
            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_DHE_RSA_WITH_AES_128_CBC_SHA (0x0033)
            Cipher Suite: TLS_RSA_WITH_AES_256_GCM_SHA384 (0x009d)
            Cipher Suite: TLS_RSA_WITH_AES_128_GCM_SHA256 (0x009c)
            Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA256 (0x003d)
            Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA256 (0x003c)
            Cipher Suite: TLS_RSA_WITH_AES_256_CBC_SHA (0x0035)
            Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA (0x002f)
            Cipher Suite: TLS_EMPTY_RENEGOTIATION_INFO_SCSV (0x00ff)
        Compression Methods Length: 1
        Compression Methods (1 method)
            Compression Method: null (0)
        Extensions Length: 133
        Extension: server_name (len=47)
            Type: server_name (0)
            Length: 47
            Server Name Indication extension
        Extension: ec_point_formats (len=4)
            Type: ec_point_formats (11)
            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)
        Extension: supported_groups (len=12)
            Type: supported_groups (10)
            Length: 12
            Supported Groups List Length: 10
            Supported Groups (5 groups)
        Extension: session_ticket (len=0)
            Type: session_ticket (35)
            Length: 0
            Data (0 bytes)
        Extension: encrypt_then_mac (len=0)
            Type: encrypt_then_mac (22)
            Length: 0
        Extension: extended_master_secret (len=0)
            Type: extended_master_secret (23)
            Length: 0
        Extension: signature_algorithms (len=42)
            Type: signature_algorithms (13)
            Length: 42
            Signature Hash Algorithms Length: 40
            Signature Hash Algorithms (20 algorithms)
                Signature Algorithm: ecdsa_secp256r1_sha256 (0x0403)
                Signature Algorithm: ecdsa_secp384r1_sha384 (0x0503)
                Signature Algorithm: ecdsa_secp521r1_sha512 (0x0603)
                Signature Algorithm: ed25519 (0x0807)
                Signature Algorithm: ed448 (0x0808)
                Signature Algorithm: rsa_pss_pss_sha256 (0x0809)
                Signature Algorithm: rsa_pss_pss_sha384 (0x080a)
                Signature Algorithm: rsa_pss_pss_sha512 (0x080b)
                Signature Algorithm: rsa_pss_rsae_sha256 (0x0804)
                Signature Algorithm: rsa_pss_rsae_sha384 (0x0805)
                Signature Algorithm: rsa_pss_rsae_sha512 (0x0806)
                Signature Algorithm: rsa_pkcs1_sha256 (0x0401)
                Signature Algorithm: rsa_pkcs1_sha384 (0x0501)
                Signature Algorithm: rsa_pkcs1_sha512 (0x0601)
                Signature Algorithm: SHA224 ECDSA (0x0303)
                Signature Algorithm: SHA224 RSA (0x0301)
                Signature Algorithm: SHA224 DSA (0x0302)
                Signature Algorithm: SHA256 DSA (0x0402)
                Signature Algorithm: SHA384 DSA (0x0502)
                Signature Algorithm: SHA512 DSA (0x0602)

This is ServerHello message from Ubuntu 18.04

TLSv1.2 Record Layer: Handshake Protocol: Multiple Handshake Messages
    Content Type: Handshake (22)
    Version: TLS 1.2 (0x0303)
    Length: 4345
    Handshake Protocol: Server Hello
        Handshake Type: Server Hello (2)
        Length: 81
        Version: TLS 1.2 (0x0303)
        Random: 5ecea16938ffb32685dee0d46241ab4533820a178f3766e6…
        Session ID Length: 32
        Session ID: 5ecea169972b4c49269218eb6d64fbdeedb76539703d48e5…
        Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f)
        Compression Method: null (0)
        Extensions Length: 9
        Extension: renegotiation_info (len=1)
        Extension: extended_master_secret (len=0)
    Handshake Protocol: Certificate
    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: 048f81fb0fcd06c8f1d50620af144965cae3dd3804df3454…
            Signature Algorithm: rsa_pkcs1_sha256 (0x0401)
            Signature Length: 256
            Signature: 76bf06d1a887440d01be65938a92094510ae52e031463d58…
    Handshake Protocol: Server Hello Done

Server seems to use CipherSuite TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 which happens to be present in Docker Container ClientHello as well.

So What I am missing in this case. I am new to SSL debugging.

If Ciphersuites are matching what could be different so that servers returns handshake failure?

Please provide me directions what can I investigate next.

I have uploaded wireshark captures at https://gofile.io/d/ERJXNe

There is one capture from docker container running Debian-9,(openssl 1.1.0l) which results in handshake success.

Update:
I tried to use openssl s_client in latest Ubuntu 20.04 VM, it fails with handshake failure.

Tags:

2

Answers


  1. 0

    This is one of the issues described in this github comment by David Benjamin:

    https://github.com/openssl/openssl/issues/11438#issuecomment-606927855

    Basically it is a buggy server. Even though it is perfectly capable of signing signatures using a SHA-2 hash, it will fail if SHA-1 is not in the list of supported signature algorithm hashes supported by the client.

    To test this I first tried this:

    $ openssl s_client -starttls smtp -crlf -connect smtp.email.ap-mumbai-1.oci.oraclecloud.com:587 -no_tls1_3 -trace -sigalgs "RSA+SHA256"

    I received the handshake failure alert that you got. I then retried the same command, but added an additional SHA1 based sigalg:

    $ openssl s_client -starttls smtp -crlf -connect smtp.email.ap-mumbai-1.oci.oraclecloud.com:587 -no_tls1_3 -trace -sigalgs "RSA+SHA256:RSA+SHA1"

    This second connection succeeds.

    You will notice in your traces that your docker contained based version of OpenSSL is not sending any SHA1 based signature algorithms. To work around the problem you need to additionally configure these.

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  2. 0

    FYI, the server was updated to use a SHA-2 root certificate to resolve this issue. But here’s an analysis of the issue and underlying standards:

    The actual issue is that the certificate chain for this server has a SHA-1 root certificate, and the client has stated that it doesn’t support validation of SHA-1 certificates in the certificate chain. Reading the TLS 1.2 specification (https://www.rfc-editor.org/rfc/rfc5246#section-7.4.1.4.1), the server’s behavior is correct under a reasonable interpretation:

       The client uses the "signature_algorithms" extension to indicate to
   the server which signature/hash algorithm pairs may be used in   
   digital signatures.

    The TLS 1.3 specification has more to say about this situation (https://www.rfc-editor.org/rfc/rfc8446#section-4.4.2.2):

       All certificates provided by the server MUST be signed by a signature
   algorithm advertised by the client if it is able to provide such a
   chain (see Section 4.2.3).  Certificates that are self-signed or
   certificates that are expected to be trust anchors are not validated
   as part of the chain and therefore MAY be signed with any algorithm.

   If the server cannot produce a certificate chain that is signed only
   via the indicated supported algorithms, then it SHOULD continue the
   handshake by sending the client a certificate chain of its choice
   that may include algorithms that are not known to be supported by the
   client.  This fallback chain SHOULD NOT use the deprecated SHA-1 hash
   algorithm in general, but MAY do so if the client's advertisement
   permits it, and MUST NOT do so otherwise.

    With this text, the interpretation depends on the word "use". If it means "use in certificate chain", the server’s behavior is correct and the TLS 1.3 spec is self-contradictory. If it means "use to validate certificate chain", then the server’s behavior is wrong (under TLS 1.3 rules) and the TLS 1.3 spec is consistent. I’m going to assume the latter is the better interpretation.

    So the server follows the TLS 1.2 rules but has not been updated to follow TLS 1.3 rules. As one of the engineers working on the server in question, I consider this a bug since TLS 1.3 supersedes TLS 1.2 but as it’s a behavior change between two versions of the standard, it’s not a particularly serious bug.

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