Using this command i'm using ipv6 connection
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echo QUIT | openssl s_client -debug -crlf -starttls smtp -connect smtp.gmail.com:587
and I get:
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CONNECTED(00000003)
read from 0x55979b0a2260 [0x55979b0abe90] (4096 bytes => 48 (0x30))
0000 - 34 32 31 20 34 2e 37 2e-30 20 54 72 79 20 61 67 421 4.7.0 Try ag
0010 - 61 69 6e 20 6c 61 74 65-72 2c 20 63 6c 6f 73 69 ain later, closi
0020 - 6e 67 20 63 6f 6e 6e 65-63 74 69 6f 6e 2e 0d 0a ng connection...
write to 0x55979b0a2260 [0x55979b0acea0] (23 bytes => 23 (0x17))
0000 - 45 48 4c 4f 20 6d 61 69-6c 2e 65 78 61 6d 70 6c EHLO mail.exampl
0010 - 65 2e 63 6f 6d 0d 0a e.com..
read from 0x55979b0a2260 [0x55979b0abe90] (4096 bytes => 0 (0x0))
Didn't find STARTTLS in server response, trying anyway...
write to 0x55979b0a2260 [0x7ffd650340a0] (10 bytes => 10 (0xA))
0000 - 53 54 41 52 54 54 4c 53-0d 0a STARTTLS..
read from 0x55979b0a2260 [0x55979afd4410] (8192 bytes => 0 (0x0))
write to 0x55979b0a2260 [0x55979b0ba610] (322 bytes => 322 (0x142))
0000 - 16 03 01 01 3d 01 00 01-39 03 03 99 34 b9 dc fd ....=...9...4...
0010 - 8f d1 fc 68 40 14 ab 46-eb fb 0b 9f 0c 02 10 e5 ...h@..F........
0020 - 04 ce 0d 70 60 b7 81 bd-54 47 56 20 81 98 61 4e ...p`...TGV ..aN
0030 - a9 e0 36 8a 71 52 3a eb-d4 55 ef dc c7 f9 d8 41 ..6.qR:..U.....A
0040 - 7c 64 30 14 9c 02 dc 6d-52 e8 ce 27 00 48 13 02 |d0....mR..'.H..
0050 - 13 03 13 01 13 04 c0 2c-c0 30 cc a9 cc a8 c0 ad .......,.0......
0060 - c0 2b c0 2f c0 ac c0 23-c0 27 c0 0a c0 14 c0 09 .+./...#.'......
0070 - c0 13 00 9d c0 9d 00 9c-c0 9c 00 3d 00 3c 00 35 ...........=.<.5
0080 - 00 2f 00 9f cc aa c0 9f-00 9e c0 9e 00 6b 00 67 ./...........k.g
0090 - 00 39 00 33 00 ff 01 00-00 a8 00 00 00 13 00 11 .9.3............
00a0 - 00 00 0e 73 6d 74 70 2e-67 6d 61 69 6c 2e 63 6f ...smtp.gmail.co
00b0 - 6d 00 0b 00 04 03 00 01-02 00 0a 00 0c 00 0a 00 m...............
00c0 - 1d 00 17 00 1e 00 19 00-18 00 23 00 00 00 16 00 ..........#.....
00d0 - 00 00 17 00 00 00 0d 00-30 00 2e 04 03 05 03 06 ........0.......
00e0 - 03 08 07 08 08 08 09 08-0a 08 0b 08 04 08 05 08 ................
00f0 - 06 04 01 05 01 06 01 03-03 02 03 03 01 02 01 03 ................
0100 - 02 02 02 04 02 05 02 06-02 00 2b 00 05 04 03 04 ..........+.....
0110 - 03 03 00 2d 00 02 01 01-00 33 00 26 00 24 00 1d ...-.....3.&.$..
0120 - 00 20 1c e0 83 0a 93 b4-95 26 77 5b 2e 45 bd 1d . .......&w[.E..
0130 - a6 0c 2a 84 17 cb f0 f6-92 cd f9 c6 71 16 a3 b1 ..*.........q...
0140 - 20 75 u
read from 0x55979b0a2260 [0x55979b0b13f3] (5 bytes => 0 (0x0))
write:errno=0
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 48 bytes and written 355 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)
---
read from 0x55979b0a2260 [0x55979afd4410] (8192 bytes => 0 (0x0))
But if i use the same command but on ipv4 connection
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echo QUIT | openssl s_client -4 -debug -crlf -starttls smtp -connect smtp.gmail.com:587
I get this:
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CONNECTED(00000003)
depth=2 OU = GlobalSign Root CA - R2, O = GlobalSign, CN = GlobalSign
verify return:1
depth=1 C = US, O = Google Trust Services, CN = GTS CA 1O1
verify return:1
depth=0 C = US, ST = California, L = Mountain View, O = Google LLC, CN = smtp.gmail.com
verify return:1
Certificate chain
0 s:C = US, ST = California, L = Mountain View, O = Google LLC, CN = smtp.gmail.com
i:C = US, O = Google Trust Services, CN = GTS CA 1O1
1 s:C = US, O = Google Trust Services, CN = GTS CA 1O1
i:OU = GlobalSign Root CA - R2, O = GlobalSign, CN = GlobalSign
subject=C = US, ST = California, L = Mountain View, O = Google LLC, CN = smtp.gmail.com
issuer=C = US, O = Google Trust Services, CN = GTS CA 1O1
---
No client certificate CA names sent
Peer signing digest: SHA256
Peer signature type: ECDSA
Server Temp Key: X25519, 253 bits
---
SSL handshake has read 2889 bytes and written 435 bytes
Verification: OK
---
New, TLSv1.3, Cipher is TLS_AES_256_GCM_SHA384
Server public key is 256 bit
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 0 (ok)
---
250 SMTPUTF8
DONE