Problem with sending email in 9.1.0 after update

[izito]

After updating to version 9.1.0, there's an issue with sending emails.
Log:

[2025-05-08 10:56:58] ERROR: (0) Email sending error: Connection could not be established with host "ssl://mail.itys.ru:465": stream_socket_client(): SSL opera>
[2025-05-08 10:56:58] WARNING: Email sending:unknownError; 0

Has anyone encountered this problem and found a solution?

[victor]

Hi izito,

Try replacing SSL/TLS => STARTTLS in your SMTP settings.

If that doesn't work, please send a screenshot of your SMTP settings.

[izito]

Hello @victor

This is my settings:


I have a Exhange server and 465 port work only with STARTTLS.
"Before updating to 9.1.0, everything worked with the same settings, but after the update, it stopped.

In other applications, with similar settings, the connection goes through and emails are sent.

[victor]

Please try the following:

- Port: instead of "465" => "587"
- Security: instead of "SSL/TLS" => "STARTTLS"

[izito]

"Logs when attempting to connect on port 587:

[2025-05-09 09:57:33] ERROR: (451) Email sending error: Failed to authenticate on SMTP server with username "info-from-lgc@lgcaesthetic.com" using the followin>
[2025-05-09 09:57:33] WARNING: Email sending:unknownError; 0

Overall, this is an expected result, as port 587 is not used on our Exchange server since we use port 465 with STARTTLS.

Additional connection diagnostics:

openssl s_client -starttls smtp -connect mail.itys.ru:587

Connecting to 195.72.249.195
CONNECTED(00000005)
Didn't find STARTTLS in server response, trying anyway...

openssl s_client -starttls smtp -connect mail.itys.ru:465

Connecting to 195.72.249.195
CONNECTED(00000005)
depth=2 C=US, O=Internet Security Research Group, CN=ISRG Root X1
verify return:1
depth=1 C=US, O=Let's Encrypt, CN=R10
verify return:1
depth=0 CN=mail.itys.ru
verify return:1
---
Certificate chain
0 s:CN=mail.itys.ru
i:C=US, O=Let's Encrypt, CN=R10
a:PKEY: RSA, 3072 (bit); sigalg: sha256WithRSAEncryption
v:NotBefore: May 7 05:41:02 2025 GMT; NotAfter: Aug 5 05:41:01 2025 GMT
1 s:C=US, O=Let's Encrypt, CN=R10
i:C=US, O=Internet Security Research Group, CN=ISRG Root X1
a:PKEY: RSA, 2048 (bit); sigalg: sha256WithRSAEncryption
v:NotBefore: Mar 13 00:00:00 2024 GMT; NotAfter: Mar 12 23:59:59 2027 GMT
---
Server certificate
-----BEGIN CERTIFICATE-----​
*****
-----END CERTIFICATE-----
subject=CN=mail.itys.ru
issuer=C=US, O=Let's Encrypt, CN=R10
---
No client certificate CA names sent
Peer signing digest: SHA256
Peer signature type: rsa_pkcs1_sha256
Peer Temp Key: ECDH, secp384r1, 384 bits
---
SSL handshake has read 3882 bytes and written 1736 bytes
Verification: OK
---
New, TLSv1.2, Cipher is ECDHE-RSA-AES256-GCM-SHA384
Protocol: TLSv1.2
Server public key is 3072 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
Protocol : TLSv1.2
Cipher : ECDHE-RSA-AES256-GCM-SHA384
Session-ID: CD2D00000255EFB4FABC915FF0F3DFF6928DF4524EC44D8DF0 43D29A805DFCA5
Session-ID-ctx:
Master-Key: 91F9681C6BBC7CE49A2601AB14FDFC84B55F2A57A797BF5272 265E110A6CB6BE47258531BC4964BA87377D6A2049BE2D
PSK identity: None
PSK identity hint: None
SRP username: None
Start Time: 1746784545
Timeout : 7200 (sec)
Verify return code: 0 (ok)
Extended master secret: yes
---
250 SMTPUTF8​

As we can see, the connection via port 465 works perfectly.
And, once again, before updating to 9.1.0, everything worked great. It broke after the update.

[victor]

Please try the previous option, but before that create a duplicate of your Email Account, and re-enter the password (deactivate or delete the old Email Account).

Also try the option with 465 ssl/tls (re-enter the password).

[izito]

"I created a separate connector on the Exchange server on port 587 with STARTTLS support, and everything started working.

Exchange does not support SSL/TLS, as it considers such a connection insecure. Setting up a separate Postfix gateway felt like too much effort.

Overall, thanks for the consultations. This case turned out to be interesting.

[yuri]

In v9.1 we changed the email sending library. From laminas-mail (which is abandoned) to the Symfony Mailer. Not sure why it was working before and stopped now. Maybe the former had some fallback mechanism.