TLS v1.3 error with certain endpoints - Description: Illegal Parameter (47) - ssl

I am working with IBM on trying to find the cause for some handshake errors we are receiving randomly when connecting with certain endpoints. This is happening on an IBM i system using the GSKit SSL APIs. The IBM is acting as the client.
The error we are receiving during the handshake is 415 (Bad Peer).
In the trace we show this response from the remote server:
TLSv1.2 Record Layer: Alert (Level: Fatal, Description: Illegal Parameter)
Content Type: Alert (21)
Version: TLS 1.2 (0x0303)
Length: 2
Alert Message
Level: Fatal (2)
Description: Illegal Parameter (47)
If we remove TLS 1.3 from the communications, the errors do not occur. If we add it back in, then the errors pop up communicating with Google and GoDaddy.
This only seemed to start happening recently after new SSL Certificates were installed at the endpoints. And, as I said, it's random. If I encounter the error, I can make the same request again without any error.
We weren't sure if it was because of how certain servers on their farms are configured differently from others, or if updates are propagating through them... but it's very odd.
We have isolated 2 ciphers that seem to be the issue. When removed, the errors seem to stop. They are:
*ECDHE_RSA_AES_256_GCM_SHA384 - this one seems to cause problems with Google
*AES_256_GCM_SHA384 - this one seems to cause problems with GoDaddy
The tech at IBM said that if we could somehow get in touch with someone at either place and recreate the issue, it would be a great help to figure out what is going on. Just hoping we can make that happen... if anyone knows anyone on the SSL support side of GoDaddy or Google that would be willing to work with myself and IBM to resolve this, it would be great.
Or, if anyone knows why it's happening, we're all ears. Right now the only option we have is turning off TLS v1.3 or removing these two ciphers. (and there may be more that affect other endpoints that we just don't know about yet).
TIA!
UPDATE
According to my tech, they are not following the RFC properly:
RFC 5246 (the last sentence):
The cipher suite list, passed from the client to the server in the
ClientHello message, contains the combinations of cryptographic
algorithms supported by the client in order of the client's
preference (favorite choice first). Each cipher suite defines a key
exchange algorithm, a bulk encryption algorithm (including secret key
length), a MAC algorithm, and a PRF. The server will select a cipher
suite or, if no acceptable choices are presented, return a handshake
failure alert and close the connection. If the list contains cipher
suites the server does not recognize, support, or wish to use, the
server MUST ignore those cipher suites, and process the remaining
ones as usual.
UPDATE 2
Here is a handshake that fails:
TLSv1.2 Record Layer: Handshake Protocol: Client Hello
Content Type: Handshake (22)
Version: TLS 1.2 (0x0303)
Length: 549
Handshake Protocol: Client Hello
Handshake Type: Client Hello (1)
Length: 545
Version: TLS 1.2 (0x0303)
Random: 16ab36ccafcb18074cf7ce0296745cb87a4ef732402fbdc273790f082d4844d1
Session ID Length: 0
Cipher Suites Length: 18
Cipher Suites (9 suites)
Cipher Suite: TLS_AES_128_GCM_SHA256 (0x1301)
Cipher Suite: TLS_AES_256_GCM_SHA384 (0x1302)
Cipher Suite: TLS_CHACHA20_POLY1305_SHA256 (0x1303)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256 (0xc02b)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384 (0xc02c)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 (0xc02f)
Cipher Suite: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 (0xc030)
Cipher Suite: TLS_ECDHE_ECDSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca9)
Cipher Suite: TLS_ECDHE_RSA_WITH_CHACHA20_POLY1305_SHA256 (0xcca8)
Compression Methods Length: 1
Compression Methods (1 method)
Extensions Length: 486
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: renegotiation_info (len=1)
Type: renegotiation_info (65281)
Length: 1
Renegotiation Info extension
Extension: ec_point_formats (len=2)
Type: ec_point_formats (11)
Length: 2
EC point formats Length: 1
Elliptic curves point formats (1)
EC point format: uncompressed (0)
Extension: signature_algorithms (len=22)
Type: signature_algorithms (13)
Length: 22
Signature Hash Algorithms Length: 20
Signature Hash Algorithms (10 algorithms)
Signature Algorithm: ecdsa_secp521r1_sha512 (0x0603)
Signature Algorithm: ecdsa_secp384r1_sha384 (0x0503)
Signature Algorithm: ecdsa_secp256r1_sha256 (0x0403)
Signature Algorithm: rsa_pss_rsae_sha512 (0x0806)
Signature Algorithm: rsa_pss_rsae_sha384 (0x0805)
Signature Algorithm: rsa_pss_rsae_sha256 (0x0804)
Signature Algorithm: rsa_pkcs1_sha512 (0x0601)
Signature Algorithm: rsa_pkcs1_sha384 (0x0501)
Signature Algorithm: rsa_pkcs1_sha256 (0x0401)
Signature Algorithm: rsa_pkcs1_sha1 (0x0201)
Extension: signature_algorithms_cert (len=20)
Type: signature_algorithms_cert (50)
Length: 20
Signature Hash Algorithms Length: 18
Signature Hash Algorithms (9 algorithms)
Signature Algorithm: ecdsa_secp521r1_sha512 (0x0603)
Signature Algorithm: ecdsa_secp384r1_sha384 (0x0503)
Signature Algorithm: ecdsa_secp256r1_sha256 (0x0403)
Signature Algorithm: rsa_pss_rsae_sha512 (0x0806)
Signature Algorithm: rsa_pss_rsae_sha384 (0x0805)
Signature Algorithm: rsa_pss_rsae_sha256 (0x0804)
Signature Algorithm: rsa_pkcs1_sha512 (0x0601)
Signature Algorithm: rsa_pkcs1_sha384 (0x0501)
Signature Algorithm: rsa_pkcs1_sha256 (0x0401)
Extension: supported_groups (len=12)
Type: supported_groups (10)
Length: 12
Supported Groups List Length: 10
Supported Groups (5 groups)
Supported Group: secp256r1 (0x0017)
Supported Group: secp384r1 (0x0018)
Supported Group: x25519 (0x001d)
Supported Group: secp521r1 (0x0019)
Supported Group: x448 (0x001e)
Extension: key_share (len=71)
Type: key_share (51)
Length: 71
Key Share extension
Client Key Share Length: 69
Key Share Entry: Group: secp256r1, Key Exchange length: 65
Group: secp256r1 (23)
Key Exchange Length: 65
Key Exchange: 047fbc26145d5067052eff17103285a7bdc30952cdbcea601491a6a08eca7d424484a9cb…
Extension: server_name (len=20)
Type: server_name (0)
Length: 20
Server Name Indication extension
Extension: extended_master_secret (len=0)
Type: extended_master_secret (23)
Length: 0
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: pre_shared_key (len=283)
Type: pre_shared_key (41)
Length: 283
Pre-Shared Key extension
Identities Length: 230
PSK Identity (length: 224)
Identity Length: 224
Identity: 000017719425bdded0ac21c8cd61318334f131527b4ef48f21ba8116523cf71681ae51fa…
Obfuscated Ticket Age: 68965835
PSK Binders length: 49
PSK Binders
The server then responds with
TLSv1.2 Record Layer: Alert (Level: Fatal, Description: Illegal Parameter)
Content Type: Alert (21)
Version: TLS 1.2 (0x0303)
Length: 2
Alert Message
Level: Fatal (2)
Description: Illegal Parameter (47)

IBM released an APAR with PTF for V7R3 and V7R4.
The APAR number is MA49492
Regards Michael

You can review encryption protocols that Google Front End supports when communicating with clients in this whitepaper.
In this whitepaper, you will find more detail on encryption in transit for Google Cloud, including Google Cloud Platform and Google Workspace.
From table 1, you can check that the cipher ECDHE_RSA_AES_256_GCM_SHA384, which is having trouble connecting with Google, is not listed as compatible.
I have found this documentation from IBM that lists the supported CipherSpecs (I’m not quite sure if this applies to your IBM product). Also, there’s a troubleshooting TLS guide from IBM.
It is important to understand this information is not a comprehensive source for troubleshooting information, but rather a guide to aid in common problem resolution.
UPDATE
It's unclear if IBM's GSKit SSL APIs are generating the error, or if it is allowing the user to send invalid packets and then reporting the error.
Unsupported TLS 1.2 ciphers would be ignored in the handshake as stated here, but I believe there is just 5 ciphers in TLS 1.3 (see RFC 8446 - Cipher Suites and OpenSSL - Ciphersuites), and ECDHE_RSA_AES_256_GCM_SHA384 is not in them, so it would be strange if IBM's product allowed an invalid cipher to be requested.
The 1.3 cipher specs work fine with Google servers, like:
echo | openssl s_client -tls1_3 -connect SERVER:443 -ciphersuites TLS_CHACHA20_POLY1305_SHA256 | grep "New, TLSv1.3, Cipher"
As mentioned above, ECDHE_RSA_AES_256_GCM_SHA384 is not in the list of TLS 1.2 cipher specifications.
UPDATE 2
From the whitepaper, I noted:
TLS in the GFE is implemented with BoringSSL. Table 1 shows the encryption protocols that GFE supports when communicating with clients.
Protocols
Authentication
Key exchange
Encryption
Hash Functions
TLS 1.34
RSA 2048
Curve25519
AES-128-GCM
SHA384
TLS 1.2
ECDSA P-256
P-256 (NIST secp256r1)
AES-256-GCM
SHA256
The supported values above don't match with the Cipher Suite list provided shown on the handshake packet capture, note the different SHA values:
TLS_AES_128_GCM_SHA256 (0x1301)
TLS_AES_256_GCM_SHA384 (0x1302)
The values used are AES128 with SHA256, and AES256 with SHA384 but BoringSSL supports AES128 with SHA384 for TLS 1.3 and AES256 with SHA256 for TLS 1.2.
Looking at some more IBM docs for z/OS, I'm seeing a discrepancy with 0x1302 which showcases AES256 with SHA256.
For TLS V1.3, the following is allowed in the evaluated configurations:
Ciphers:
1301 - TLS_AES_128_GCM_SHA256
1302 - TLS_AES_256_GCM_SHA256
How are the SSL certificates used? Is it possible to share the link for those docs?
Throubleshoot
I would recommend to try the following:
Find out what is causing the randomness. Maybe there could be some propagation delay on your IBM system or the SSL distribution management.
Try changing 1302 from TLS_AES_256_GCM_SHA384 to TLS_AES_256_GCM_SHA256 and verify if matching z/OS docs works
Try changing 1301 from TLS_AES_128_GCM_SHA256 to TLS_AES_128_GCM_SHA384 and verify if matching BoringSSL works

Related

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.
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.
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.

Enovy error - The following ciphers were rejected when tried individually: TLS_AES_128_GCM_SHA256

In istio 1.5.1, when I tried to add a particular cipher suit to the gateway's tls section using this syntax:
minProtocolVersion: TLSV1_3
mode: SIMPLE
cipherSuites: [TLS_AES_128_GCM_SHA256]
I got the following error in the istio-ingress pod's logs:
[Envoy (Epoch 0)] [2020-06-08 15:15:44.033][22][warning][config] [external/envoy/source/common/config/grpc_subscription_impl.cc:87]
gRPC config for type.googleapis.com/envoy.api.v2.Listener rejected:
Error adding/updating listener(s) 0.0.0.0_443: Failed to initialize cipher suites TLS_AES_128_GCM_SHA256.
The following ciphers were rejected when tried individually: TLS_AES_128_GCM_SHA256
If I remove the cipherSuites line from the tls section, there is no errors, and the same cipher suit appears in the list of valid cipher suits.
Any advise? Thanks
As far as I checked in envoy documentation And BoringSSL documentation
TLS 1.3 ciphers do not participate in this mechanism and instead have a
built-in preference order. Functions to set cipher lists do not affect TLS
1.3, and functions to query the cipher list do not include TLS 1.3
ciphers.
cipher_suites
If specified, the TLS listener will only support the specified cipher list when negotiating TLS 1.0-1.2 (this setting has no effect when negotiating TLS 1.3). If not specified, the default list will be used.
In non-FIPS builds, the default cipher list is:
[ECDHE-ECDSA-AES128-GCM-SHA256|ECDHE-ECDSA-CHACHA20-POLY1305]
[ECDHE-RSA-AES128-GCM-SHA256|ECDHE-RSA-CHACHA20-POLY1305]
ECDHE-ECDSA-AES128-SHA
ECDHE-RSA-AES128-SHA
AES128-GCM-SHA256
AES128-SHA
ECDHE-ECDSA-AES256-GCM-SHA384
ECDHE-RSA-AES256-GCM-SHA384
ECDHE-ECDSA-AES256-SHA
ECDHE-RSA-AES256-SHA
AES256-GCM-SHA384
AES256-SHA
In builds using BoringSSL FIPS, the default cipher list is:
ECDHE-ECDSA-AES128-GCM-SHA256
ECDHE-RSA-AES128-GCM-SHA256
ECDHE-ECDSA-AES128-SHA
ECDHE-RSA-AES128-SHA
AES128-GCM-SHA256
AES128-SHA
ECDHE-ECDSA-AES256-GCM-SHA384
ECDHE-RSA-AES256-GCM-SHA384
ECDHE-ECDSA-AES256-SHA
ECDHE-RSA-AES256-SHA
AES256-GCM-SHA384
AES256-SHA
Additionally take a look at this github issue.

The difference between ECDH-ECDSA-AES128-SHA256 and ECDHE-ECDSA-AES128-SHA256?

I am using ECC certificate to observe how TLS works,Can someone helps me the difference between ECDH-ECDSA-AES128-SHA256 and ECDHE-ECDSA-AES128-SHA256.
When use ECDHE-ECDSA-AES128-SHA256,client and server works fine.
New, TLSv1/SSLv3, Cipher is ECDHE-ECDSA-AES128-SHA256
Server public key is 256 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
Protocol : TLSv1.2
Cipher : ECDHE-ECDSA-AES128-SHA256
When use ECDH-ECDSA-AES128-SHA256 ,the SERVER_HELLO fails:
140344027961248:error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure:s23_clnt.c:769:
The difference is the key exchange algorithm.
ECDH - Elliptic Curve Diffie-Hellman Key Exchange
ECDHE - ECDH in ephemeral mode
ECDH in static mode uses a long term ECDH key.
In ephemeral mode, a ECDH key pair is generated every time and then thrown away, so it's only used with the length of the ECDH key exchange.
Update:
The server is rejecting the ECDH version because it'b been configured to do so.
All SSL implementations allow user to setup what ciphers are allowed or not.
In openssl we have a API like SSL_CTX_set_cipher_list to setup what ciphers are allowed or not. This is normally exposed through a application specific configuration.
There are a lot of web sites like this one that gives advice on what to set the cipher list too that gives the best security for that current situation now.
For information on cipher string see the openssl ciphers command.

Is it possible to use TLSv1.3 ciphers in TLSv1.2 session?

I'm reversing an Android application and I noticed, while sniffing, that something weird happens.
TLSv1.3 introduces few new ciphers such as
TLS_AES_256_GCM_SHA384
TLS_CHACHA20_POLY1305_SHA256
TLS_AES_128_GCM_SHA256
TLS_AES_128_CCM_8_SHA256
TLS_AES_128_CCM_SHA256
And, from what I've read on OpenSSL documentation (https://wiki.openssl.org/index.php/TLS1.3),
There are new ciphersuites that only work in TLSv1.3. The old ciphersuites cannot be used for TLSv1.3 connections and the new ones cannot be used in TLSv1.2 and below.
Now, this application does something very strange: .
It is using TLSv1.2 with new TLSv1.3 ciphers during "Client Hello" and server, which also supports TLSv1.3, allows it and they start the communication for some reason.
How is that possible? Thank you.
No, you are missing an important new aspect I think ( I can not see your linked image, you should post all relevant data inside the question itself).
For compatibility reasons, TLSv1.3 try to mask itself as TLSv1.2 during ClientHello, see https://www.rfc-editor.org/rfc/rfc8446#section-4.1.2 :
4.1.2. Client Hello
When a client first connects to a server, it is REQUIRED to send the
ClientHello as its first TLS message.
Structure of this message:
uint16 ProtocolVersion;
opaque Random[32];
uint8 CipherSuite[2]; /* Cryptographic suite selector */
struct {
ProtocolVersion legacy_version = 0x0303; /* TLS v1.2 */
Random random;
opaque legacy_session_id<0..32>;
CipherSuite cipher_suites<2..2^16-2>;
opaque legacy_compression_methods<1..2^8-1>;
Extension extensions<8..2^16-1>;
} ClientHello;
Note the legacy_version being TLSv1.2 in fact, and then the explanation:
legacy_version: In previous versions of TLS, this field was used for
version negotiation and represented the highest version number
supported by the client. Experience has shown that many servers
do not properly implement version negotiation, leading to "version
intolerance" in which the server rejects an otherwise acceptable
ClientHello with a version number higher than it supports. In
TLS 1.3, the client indicates its version preferences in the
"supported_versions" extension (Section 4.2.1) and the
legacy_version field MUST be set to 0x0303, which is the version
number for TLS 1.2. TLS 1.3 ClientHellos are identified as having
a legacy_version of 0x0303 and a supported_versions extension
present with 0x0304 as the highest version indicated therein.
(See Appendix D for details about backward compatibility.)
As for cipher suites and TLS versions, the situation is more complicated. TLSv1.3 standardized only a few of them as mandatory, for reasons explained in the specification.
However that does not strictly forbid other TLS versions to use them either.
See:
ChaCha20-Poly1305 Cipher Suites for Transport Layer Security (TLS): This document describes the use of the ChaCha stream cipher and
Poly1305 authenticator in version 1.2 or later of the Transport Layer
Security (TLS) protocol
TLS 1.2 Update for Long-term Support with AES+SHA
The "AES GCM" family was defined 10 years ago in https://www.rfc-editor.org/rfc/rfc5116
TLSv1.3 standardized on only perfect forward privacy so that meant only (EC)DHE key exchanges, if not using PSK (see section 2 of RFC8446)
Have a look at https://security.stackexchange.com/a/77018/137710 and https://github.com/ssllabs/research/wiki/SSL-and-TLS-Deployment-Best-Practices#23-use-secure-cipher-suites
But the TLSv1.3 ciphers suite is defined differently, using new names, because previous ones were not relevant anymore, as TLS 1.3 made some choices about algorithms to use, etc. that removes volatility in some parts.
Hence you will see this warning in OpenSSL changelog:
Separated TLSv1.3 ciphersuite configuration out from TLSv1.2 ciphersuite
configuration. TLSv1.3 ciphersuites are not compatible with TLSv1.2 and
below. Similarly TLSv1.2 ciphersuites are not compatible with TLSv1.3.
In order to avoid issues where legacy TLSv1.2 ciphersuite configuration
would otherwise inadvertently disable all TLSv1.3 ciphersuites the
configuration has been separated out. See the ciphers man page or the
SSL_CTX_set_ciphersuites() man page for more information.
(https://github.com/openssl/openssl/pull/5392)
CloudFlare documentation on https://support.cloudflare.com/hc/en-us/articles/200933580-What-cipher-suites-does-CloudFlare-use-for-SSL- says below table:
Although TLS 1.3 uses the same cipher suite space as previous versions of TLS, TLS 1.3 cipher suites are defined differently, only specifying the symmetric ciphers, and cannot be used for TLS 1.2. Similarly, TLS 1.2 and lower cipher suites cannot be used with TLS 1.3 (IETF TLS 1.3 draft 21).

Unserstanging the Wireshark SSL record

I am trying to troubleshoot an issue where connection is reset.
When i captured the TCP packets in wireshark, I see that Version is shown as SSL2.0 and then after Handshake Message Type, it shows TLS 1.2.
Actually my server only accepts TLS 1.2.
Please help me to understand if client initiated SSL v2.0 or TLS 1.2?
SSLv2 Record Layer: Client Hello
[Version: SSL 2.0 (0x0002)]
Length: 257
Handshake Message Type: Client Hello (1)
Version: TLS 1.2 (0x0303)
Cipher Spec Length: 216
Session ID Length: 0
Challenge Length: 32
Cipher Specs (72 specs)
Challenge