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SMTP SSL Error "Could not encrypt connection" #687

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opened 2026-02-04 22:13:30 +03:00 by OVERLORD · 6 comments
OVERLORD commented 2026-02-04 22:13:30 +03:00
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Originally created by @davidus05 on GitHub (Apr 15, 2020).

SMTP SSL Error "Could not encrypt connection"

Some days ago I generated a new SSL certificate with Let's Encrypt for our exchange server. I use it to connect via SMTP to send mails from bitwarden_rs. Now I wanted to log in to the vault on the Android app, but this doesn't work, because: "Could not send login notification email. Please contact your administrator.

Then I saw that sending emails in general does not work anymore.

Your environment

  • Bitwarden_rs version: 1.14.2
  • Install method: Docker image
  • Clients used: Android
  • Other relevant information: It worked before I generated the new SSL certifiate

Steps to reproduce

  1. Configure SMTP email settings
  2. Send SMTP test mail

Expected behaviour

I should get an email.

Actual behaviour

Sending an email did not work.

Relevant logs

[2020-04-15 20:32:12][request][INFO] POST /admin/test/smtp/
[2020-04-15 20:32:12][lettre::smtp][INFO] connection established to *******:587
[2020-04-15 20:32:12][error][ERROR] LetreErr.
[CAUSE] Client(
"Could not encrypt connection, aborting",
)

How to solve this problem or is there a way to ignore the certificate like in Bitwarden orig: (https://github.com/bitwarden/server/issues/451)

Originally created by @davidus05 on GitHub (Apr 15, 2020). <!-- Please fill out the following template to make solving your problem easier and faster for us. This is only a guideline. If you think that parts are unneccessary for your issue, feel free to remove them. Remember to hide/obfuscate personal and confidential information, such as names, global IP/DNS adresses and especially passwords, if neccessary. --> ### SMTP SSL Error "Could not encrypt connection" Some days ago I generated a new SSL certificate with Let's Encrypt for our exchange server. I use it to connect via SMTP to send mails from bitwarden_rs. Now I wanted to log in to the vault on the Android app, but this doesn't work, because: "Could not send login notification email. Please contact your administrator. Then I saw that sending emails in general does not work anymore. ### Your environment <!-- The version number, obtained from the logs or the admin page --> * Bitwarden_rs version: 1.14.2 <!-- How the server was installed: Docker image / package / built from source --> * Install method: Docker image * Clients used: <!-- if applicable --> Android * Other relevant information: It worked before I generated the new SSL certifiate ### Steps to reproduce 1. Configure SMTP email settings 2. Send SMTP test mail ### Expected behaviour I should get an email. ### Actual behaviour Sending an email did not work. ### Relevant logs [2020-04-15 20:32:12][request][INFO] POST /admin/test/smtp/ [2020-04-15 20:32:12][lettre::smtp][INFO] connection established to *******:587 [2020-04-15 20:32:12][error][ERROR] LetreErr. [CAUSE] Client( "Could not encrypt connection, aborting", ) How to solve this problem or is there a way to ignore the certificate like in Bitwarden orig: (https://github.com/bitwarden/server/issues/451)
OVERLORD commented 2026-02-04 22:13:43 +03:00
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@BlackDex commented on GitHub (Jun 4, 2020):

Do you use a self generated SSL Certificate?
What happens if you try executing:

openssl s_client -connect my-email-server.com:587

That should report with a certificate, but i doubt that it will on port 587, since that is by default a submission port which normally uses starttls instead of ssl.

For example, GMail uses SSL and that works using:

openssl s_client -connect smtp.gmail.com:465
@BlackDex commented on GitHub (Jun 4, 2020): Do you use a self generated SSL Certificate? What happens if you try executing: ```bash openssl s_client -connect my-email-server.com:587 ``` That should report with a certificate, but i doubt that it will on port 587, since that is by default a submission port which normally uses starttls instead of ssl. For example, GMail uses SSL and that works using: ```bash openssl s_client -connect smtp.gmail.com:465 ```
OVERLORD commented 2026-02-04 22:13:46 +03:00
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@davidus05 commented on GitHub (Jun 7, 2020):

Hey, thanks for your reply!
The first command gives following output:

CONNECTED(00000003)
139665375049088:error:1408F10B:SSL routines:ssl3_get_record:wrong version number                                                                                                                                                             :../ssl/record/ssl3_record.c:252:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 5 bytes and written 176 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : 0000
    Session-ID:
    Session-ID-ctx:
    Master-Key:
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1591552629
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
---

The second command:

CONNECTED(00000003)
140312739898752:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../ssl/record/ssl3_record.c:252:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 5 bytes and written 176 bytes
Verification: OK
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : 0000
    Session-ID:
    Session-ID-ctx:
    Master-Key:
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1591552747
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
---
@davidus05 commented on GitHub (Jun 7, 2020): Hey, thanks for your reply! _The first command gives following output:_ ``` CONNECTED(00000003) 139665375049088:error:1408F10B:SSL routines:ssl3_get_record:wrong version number :../ssl/record/ssl3_record.c:252: --- no peer certificate available --- No client certificate CA names sent --- SSL handshake has read 5 bytes and written 176 bytes Verification: OK --- New, (NONE), Cipher is (NONE) Secure Renegotiation IS NOT supported Compression: NONE Expansion: NONE No ALPN negotiated SSL-Session: Protocol : TLSv1.2 Cipher : 0000 Session-ID: Session-ID-ctx: Master-Key: PSK identity: None PSK identity hint: None SRP username: None Start Time: 1591552629 Timeout : 7200 (sec) Verify return code: 0 (ok) Extended master secret: no --- ``` _The second command:_ ``` CONNECTED(00000003) 140312739898752:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../ssl/record/ssl3_record.c:252: --- no peer certificate available --- No client certificate CA names sent --- SSL handshake has read 5 bytes and written 176 bytes Verification: OK --- New, (NONE), Cipher is (NONE) Secure Renegotiation IS NOT supported Compression: NONE Expansion: NONE No ALPN negotiated SSL-Session: Protocol : TLSv1.2 Cipher : 0000 Session-ID: Session-ID-ctx: Master-Key: PSK identity: None PSK identity hint: None SRP username: None Start Time: 1591552747 Timeout : 7200 (sec) Verify return code: 0 (ok) Extended master secret: no --- ```
OVERLORD commented 2026-02-04 22:13:47 +03:00
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@MichZipp commented on GitHub (Aug 27, 2020):

@davidus05 I currently have the same issue, did you solve it in the meantime?

@MichZipp commented on GitHub (Aug 27, 2020): @davidus05 I currently have the same issue, did you solve it in the meantime?
OVERLORD commented 2026-02-04 22:13:49 +03:00
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@BlackDex commented on GitHub (Sep 23, 2020):

@davidus05 & @MichZipp could you both try again with the latest testing image from docker? There are several items changed regarding emails maybe they fixed your issues.

@BlackDex commented on GitHub (Sep 23, 2020): @davidus05 & @MichZipp could you both try again with the latest testing image from docker? There are several items changed regarding emails maybe they fixed your issues.
OVERLORD commented 2026-02-04 22:13:55 +03:00
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@MichZipp commented on GitHub (Sep 23, 2020):

@BlackDex Issue is fixed, thanks a lot!

@MichZipp commented on GitHub (Sep 23, 2020): @BlackDex Issue is fixed, thanks a lot!
OVERLORD commented 2026-02-04 22:13:57 +03:00
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@siddjellali commented on GitHub (Mar 19, 2021):

Hi,

It seems the same issue appears again... Anyone Else has the issue ?

root@a38bd1710df0:/# openssl s_client -connect smtp.gmail.com:465
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
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
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 2638 bytes and written 386 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)
---
---
Post-Handshake New Session Ticket arrived:
SSL-Session:
    Protocol  : TLSv1.3
    Cipher    : TLS_AES_256_GCM_SHA384
    Session-ID: D1611E0C63D459F95D3E0F04C935A053E024AB82080A08DFDE9D1FD91493F89C
    Session-ID-ctx: 
    Resumption PSK: ABDB4DE7644B6C8BB45E59C3BBAA14BDE7E37BF083B011014ECBE6E233C2172AC19BC86ED51118830CFCD5DF5209515C
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 172800 (seconds)
    TLS session ticket:
    0000 - 01 41 e6 ab cb f9 5b fe-76 79 f3 e5 73 ad 10 d8   .A....[.vy..s...
    0010 - 1e 68 fb d9 56 fa 61 2f-1b 0c d0 7d 2c 9e b8 0b   .h..V.a/...},...
    0020 - cc e1 be a2 3f 36 92 93-df b2 20 12 0a f9 18 4b   ....?6.... ....K
    0030 - 4d 01 c2 60 41 4e 68 5c-d3 d6 21 cb b2 62 8c bf   M..`ANh\..!..b..
    0040 - 3b 4b 10 cb 25 d8 a4 77-34 d2 a8 ae f3 33 7e 3d   ;K..%..w4....3~=
    0050 - e2 f3 cf 71 01 1d bc e8-5e 4e 11 b3 5c 2a 3a bb   ...q....^N..\*:.
    0060 - 5b cc 93 b2 4c 46 e8 df-9d ee 37 d4 c9 a4 7f 84   [...LF....7.....
    0070 - 3b d4 98 3a ae 41 40 d1-56 cb 56 26 58 30 62 20   ;..:.A@.V.V&X0b 
    0080 - 63 f1 ad 91 7f 91 2d 59-0d f9 c5 ba 85 02 88 04   c.....-Y........
    0090 - b1 29 e6 00 67 c0 50 e8-36 e6 ac 1a 2c b0 69 94   .)..g.P.6...,.i.
    00a0 - b2 cd 79 65 29 5a 6f 32-2e 5a 4a 15 6d 26 48 09   ..ye)Zo2.ZJ.m&H.
    00b0 - 3a 93 99 b3 25 45 b4 25-2d d3 26 5d c4 44 3c 79   :...%E.%-.&].D<y
    00c0 - 00 72 06 6d 80 e3 89 c7-49 47 48 d0 a5 1e 4d dc   .r.m....IGH...M.
    00d0 - 0f 11 49 2f 34 53 76 db-d5 de 13 65 9d 60 1c 94   ..I/4Sv....e.`..
    00e0 - 4f 05 3d fd 2f bd 2c fe-1f 09 e8 63               O.=./.,....c

    Start Time: 1616150180
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
    Max Early Data: 0
---
read R BLOCK
---
Post-Handshake New Session Ticket arrived:
SSL-Session:
    Protocol  : TLSv1.3
    Cipher    : TLS_AES_256_GCM_SHA384
    Session-ID: 6C7BD7A939C1D185FF08B3503A9C2F534F4D9541E652494EAB2DDC687924B316
    Session-ID-ctx: 
    Resumption PSK: 443EDBAE67C3D510E2F5EB2870D099A720496B623269C5AA2CB1F166C97DDF9F9341EFD22336EB56514564DE59B084D2
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    TLS session ticket lifetime hint: 172800 (seconds)
    TLS session ticket:
    0000 - 01 41 e6 ab cb f9 5b fe-76 79 f3 e5 73 ad 10 d8   .A....[.vy..s...
    0010 - 02 d4 39 70 ea 0d d4 e5-7f c4 7f 9e e2 54 bc e2   ..9p.........T..
    0020 - 45 08 99 49 91 e0 00 41-43 53 d8 fb 9b 36 c2 1d   E..I...ACS...6..
    0030 - f6 c6 b3 90 9c d5 84 99-72 62 91 6a d6 1c 6f d6   ........rb.j..o.
    0040 - dc 85 82 34 4d 5d 34 58-b7 99 ee bc 31 d2 88 0d   ...4M]4X....1...
    0050 - a4 11 e6 9d fe fa 4f d1-52 16 81 08 4f a1 05 88   ......O.R...O...
    0060 - 74 db 0a 50 71 09 fc 2a-5c 8c 20 05 16 95 cf e0   t..Pq..*\. .....
    0070 - 3d f5 06 9c 6e 5f 54 67-65 df 07 1f 4e ea d9 e2   =...n_Tge...N...
    0080 - b5 78 5f 61 3f a8 08 64-cb 06 4f 35 cc 83 d2 b4   .x_a?..d..O5....
    0090 - 8a 2f 50 76 3b 95 37 b2-d9 aa 29 21 4e 01 3e ca   ./Pv;.7...)!N.>.
    00a0 - 49 fc bb 4d 13 ef 9b c5-37 31 2b 5a b7 74 e8 54   I..M....71+Z.t.T
    00b0 - ee c0 bd 3b d6 7c 73 a8-0e 2b 36 db f4 23 c5 e3   ...;.|s..+6..#..
    00c0 - 3d 57 93 a2 5b 08 e0 a4-b0 50 5f 1b ce 0e 3a a6   =W..[....P_...:.
    00d0 - 42 14 39 8c 8a f0 90 88-64 c9 38 29 67 c6 1f 8a   B.9.....d.8)g...
    00e0 - 0d 58 f5 15 01 04 2d 9f-4a 82 cd a8               .X....-.J...

    Start Time: 1616150180
    Timeout   : 7200 (sec)
    Verify return code: 0 (ok)
    Extended master secret: no
    Max Early Data: 0
---
read R BLOCK
220 smtp.gmail.com ESMTP c2sm5805947wme.15 - gsmtp
^C
root@a38bd1710df0:/# openssl s_client -connect smtp.gmail.com:587
CONNECTED(00000003)
140235754124416:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../ssl/record/ssl3_record.c:332:
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 5 bytes and written 306 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)
---
@siddjellali commented on GitHub (Mar 19, 2021): Hi, It seems the same issue appears again... Anyone Else has the issue ? ``` root@a38bd1710df0:/# openssl s_client -connect smtp.gmail.com:465 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 --- Server certificate -----BEGIN CERTIFICATE----- MIIExjCCA66gAwIBAgIQVaARneYUhJ4FAAAAAId/fDANBgkqhkiG9w0BAQsFADBC MQswCQYDVQQGEwJVUzEeMBwGA1UEChMVR29vZ2xlIFRydXN0IFNlcnZpY2VzMRMw EQYDVQQDEwpHVFMgQ0EgMU8xMB4XDTIxMDIyMzE1NDEyOFoXDTIxMDUxODE1NDEy N1owaDELMAkGA1UEBhMCVVMxEzARBgNVBAgTCkNhbGlmb3JuaWExFjAUBgNVBAcT DU1vdW50YWluIFZpZXcxEzARBgNVBAoTCkdvb2dsZSBMTEMxFzAVBgNVBAMTDnNt dHAuZ21haWwuY29tMFkwEwYHKoZIzj0CAQYIKoZIzj0DAQcDQgAEz5t6F4A0l3nC l+KAgd1NdLXCIU8oAmMPijon/g68gFbsViPZSlWXhrArCnqNlUT8GbEdcFj9icKy Bu3w4fRliqOCAlswggJXMA4GA1UdDwEB/wQEAwIHgDATBgNVHSUEDDAKBggrBgEF BQcDATAMBgNVHRMBAf8EAjAAMB0GA1UdDgQWBBRB4vZADwgT77UkdUlSQWDDbHLj 0DAfBgNVHSMEGDAWgBSY0fhuEOvPm+xgnxiQG6DrfQn9KzBoBggrBgEFBQcBAQRc MFowKwYIKwYBBQUHMAGGH2h0dHA6Ly9vY3NwLnBraS5nb29nL2d0czFvMWNvcmUw KwYIKwYBBQUHMAKGH2h0dHA6Ly9wa2kuZ29vZy9nc3IyL0dUUzFPMS5jcnQwGQYD VR0RBBIwEIIOc210cC5nbWFpbC5jb20wIQYDVR0gBBowGDAIBgZngQwBAgIwDAYK KwYBBAHWeQIFAzAzBgNVHR8ELDAqMCigJqAkhiJodHRwOi8vY3JsLnBraS5nb29n L0dUUzFPMWNvcmUuY3JsMIIBAwYKKwYBBAHWeQIEAgSB9ASB8QDvAHUAfT7y+I// iFVoJMLAyp5SiXkrxQ54CX8uapdomX4i8NcAAAF3z8RgtAAABAMARjBEAiBMVvzP 0VlhlUAQ2xdmgelVJRUkQQKQ3eU8JKrqC99TjwIgDvuhxAo6uoH6AjiI1/CDvcpN OANtGlBm5FX5SabqwfcAdgBElGUusO7Or8RAB9io/ijA2uaCvtjLMbU/0zOWtbaB qAAAAXfPxGGoAAAEAwBHMEUCIQD7FFCH3J3+yer1NThMYgOOGNqYEyoo1uHHTwiU HF1L8AIgfdngbodie3HDo0nx0n0JFPsEDvCx3j6AuPc8ACjZ9hgwDQYJKoZIhvcN AQELBQADggEBAB7fhKIaCwxGFROxc7mI2ZZHd0WYp0BWKEUqc7P3Khmr2skJ17bn vdmAI4SNwrVgLkVJyLUfwf9N2i1xRsymZGvonxwjSSlqjvuBJkwnMsnQxsCNXGNU UB9C1T/4EygpoeL9ed9912KsiHuaJE4Kkqobl0/TnDqzLY2IXyR3CMhLnbSzTxTu nlYB6n+CScYhnywHPnR89XW0i8RgcBHU6JIRdn0QyOxMQ8Yz3Xg56uPHkaXTIwLq o1BgdkkdUvlz4+13dqywVfl0FPkKDuYZ5dvcB7lAM84Fzot824BjoFGBVum5iaQi qU3C697yW0MvW+HRVM4CPirCZggWbiVru3Q= -----END CERTIFICATE----- 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 2638 bytes and written 386 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) --- --- Post-Handshake New Session Ticket arrived: SSL-Session: Protocol : TLSv1.3 Cipher : TLS_AES_256_GCM_SHA384 Session-ID: D1611E0C63D459F95D3E0F04C935A053E024AB82080A08DFDE9D1FD91493F89C Session-ID-ctx: Resumption PSK: ABDB4DE7644B6C8BB45E59C3BBAA14BDE7E37BF083B011014ECBE6E233C2172AC19BC86ED51118830CFCD5DF5209515C PSK identity: None PSK identity hint: None SRP username: None TLS session ticket lifetime hint: 172800 (seconds) TLS session ticket: 0000 - 01 41 e6 ab cb f9 5b fe-76 79 f3 e5 73 ad 10 d8 .A....[.vy..s... 0010 - 1e 68 fb d9 56 fa 61 2f-1b 0c d0 7d 2c 9e b8 0b .h..V.a/...},... 0020 - cc e1 be a2 3f 36 92 93-df b2 20 12 0a f9 18 4b ....?6.... ....K 0030 - 4d 01 c2 60 41 4e 68 5c-d3 d6 21 cb b2 62 8c bf M..`ANh\..!..b.. 0040 - 3b 4b 10 cb 25 d8 a4 77-34 d2 a8 ae f3 33 7e 3d ;K..%..w4....3~= 0050 - e2 f3 cf 71 01 1d bc e8-5e 4e 11 b3 5c 2a 3a bb ...q....^N..\*:. 0060 - 5b cc 93 b2 4c 46 e8 df-9d ee 37 d4 c9 a4 7f 84 [...LF....7..... 0070 - 3b d4 98 3a ae 41 40 d1-56 cb 56 26 58 30 62 20 ;..:.A@.V.V&X0b 0080 - 63 f1 ad 91 7f 91 2d 59-0d f9 c5 ba 85 02 88 04 c.....-Y........ 0090 - b1 29 e6 00 67 c0 50 e8-36 e6 ac 1a 2c b0 69 94 .)..g.P.6...,.i. 00a0 - b2 cd 79 65 29 5a 6f 32-2e 5a 4a 15 6d 26 48 09 ..ye)Zo2.ZJ.m&H. 00b0 - 3a 93 99 b3 25 45 b4 25-2d d3 26 5d c4 44 3c 79 :...%E.%-.&].D<y 00c0 - 00 72 06 6d 80 e3 89 c7-49 47 48 d0 a5 1e 4d dc .r.m....IGH...M. 00d0 - 0f 11 49 2f 34 53 76 db-d5 de 13 65 9d 60 1c 94 ..I/4Sv....e.`.. 00e0 - 4f 05 3d fd 2f bd 2c fe-1f 09 e8 63 O.=./.,....c Start Time: 1616150180 Timeout : 7200 (sec) Verify return code: 0 (ok) Extended master secret: no Max Early Data: 0 --- read R BLOCK --- Post-Handshake New Session Ticket arrived: SSL-Session: Protocol : TLSv1.3 Cipher : TLS_AES_256_GCM_SHA384 Session-ID: 6C7BD7A939C1D185FF08B3503A9C2F534F4D9541E652494EAB2DDC687924B316 Session-ID-ctx: Resumption PSK: 443EDBAE67C3D510E2F5EB2870D099A720496B623269C5AA2CB1F166C97DDF9F9341EFD22336EB56514564DE59B084D2 PSK identity: None PSK identity hint: None SRP username: None TLS session ticket lifetime hint: 172800 (seconds) TLS session ticket: 0000 - 01 41 e6 ab cb f9 5b fe-76 79 f3 e5 73 ad 10 d8 .A....[.vy..s... 0010 - 02 d4 39 70 ea 0d d4 e5-7f c4 7f 9e e2 54 bc e2 ..9p.........T.. 0020 - 45 08 99 49 91 e0 00 41-43 53 d8 fb 9b 36 c2 1d E..I...ACS...6.. 0030 - f6 c6 b3 90 9c d5 84 99-72 62 91 6a d6 1c 6f d6 ........rb.j..o. 0040 - dc 85 82 34 4d 5d 34 58-b7 99 ee bc 31 d2 88 0d ...4M]4X....1... 0050 - a4 11 e6 9d fe fa 4f d1-52 16 81 08 4f a1 05 88 ......O.R...O... 0060 - 74 db 0a 50 71 09 fc 2a-5c 8c 20 05 16 95 cf e0 t..Pq..*\. ..... 0070 - 3d f5 06 9c 6e 5f 54 67-65 df 07 1f 4e ea d9 e2 =...n_Tge...N... 0080 - b5 78 5f 61 3f a8 08 64-cb 06 4f 35 cc 83 d2 b4 .x_a?..d..O5.... 0090 - 8a 2f 50 76 3b 95 37 b2-d9 aa 29 21 4e 01 3e ca ./Pv;.7...)!N.>. 00a0 - 49 fc bb 4d 13 ef 9b c5-37 31 2b 5a b7 74 e8 54 I..M....71+Z.t.T 00b0 - ee c0 bd 3b d6 7c 73 a8-0e 2b 36 db f4 23 c5 e3 ...;.|s..+6..#.. 00c0 - 3d 57 93 a2 5b 08 e0 a4-b0 50 5f 1b ce 0e 3a a6 =W..[....P_...:. 00d0 - 42 14 39 8c 8a f0 90 88-64 c9 38 29 67 c6 1f 8a B.9.....d.8)g... 00e0 - 0d 58 f5 15 01 04 2d 9f-4a 82 cd a8 .X....-.J... Start Time: 1616150180 Timeout : 7200 (sec) Verify return code: 0 (ok) Extended master secret: no Max Early Data: 0 --- read R BLOCK 220 smtp.gmail.com ESMTP c2sm5805947wme.15 - gsmtp ^C root@a38bd1710df0:/# openssl s_client -connect smtp.gmail.com:587 CONNECTED(00000003) 140235754124416:error:1408F10B:SSL routines:ssl3_get_record:wrong version number:../ssl/record/ssl3_record.c:332: --- no peer certificate available --- No client certificate CA names sent --- SSL handshake has read 5 bytes and written 306 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) --- ```
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Reference: starred/vaultwarden#687
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