Mailer Transports to SMTP Cannot Establish Secure Connections #34846

brandonsavage · 2019-12-06T02:03:50Z

Symfony version(s) affected: 5.0.1

Description
When using the Transport out of the box, the Transport is unable to establish a secure connection. This issue looks similar to #34064

I am using OpenSSL 1.1.1d and PHP 7.4. I've reproduced the issue on PHP 7.3 as well.

The exact error message I receive is:

Connection could not be established with host "ssl://smtp.postmarkapp.com:587": stream_socket_client(): SSL operation failed with code 1. OpenSSL Error messages: error:1408F10B:SSL routines:ssl3_get_record:wrong version number

How to reproduce

$transport = new PostmarkSmtpTransport($key);
$mailer = new Mailer($transport);
$mail = (new Email)->to('[email protected]')
->from('[email protected]')
->subject('Test Email')
->html('Test Email');
$mailer->send($mail);

The text was updated successfully, but these errors were encountered:

fabpot · 2019-12-07T14:17:12Z

maybe fixed by #34760?

brandonsavage · 2019-12-08T01:37:00Z

I applied the patch in #34760 without success in resolving this bug.

kbsanders · 2019-12-11T03:17:15Z

I am experiencing this exact same issue using the following SMTP transport:

$transport = new EsmtpTransport('smtp.office365.com',587,true);

The error received is:

Connection could not be established with host "ssl://smtp.office365.com:587": stream_socket_client(): SSL operation failed with code 1. OpenSSL Error messages: error:1408F10B:SSL routines:ssl3_get_record:wrong version number.

I am using Symfony version 5.0.1 and PHP version 7.3.11.
I am also using the localhost Symfony web server for development.

The patch mentioned above did not help to correct the issue.

kbsanders · 2019-12-11T04:15:03Z

Update:

I ran my code again, but this time with the TLS option set to false and the patch above applied and the transport actually succeeded.

$transport = new EsmtpTransport('smtp.office365.com',587,false);

However, when the patch is not applied, and TLS = false, I receive the following error:

Warning: fgets(): SSL: An existing connection was forcibly closed by the remote host. in C:\arwa\site-alruralwater\vendor\symfony\mailer\Transport\Smtp\Stream\AbstractStream.php (line 77)

Does this working with TLS = false perhaps have something to do with TLS vs STARTTLS?

toooni · 2019-12-22T17:04:50Z

@kbsanders But is the mail actually being sent? I can confirm that the error persists even with #34760. Setting TLS to false does indeed not result in the mentioned error and everything seems fine at first. But no mail is sent (no incoming mail on gmail nor activity visible on postmark).

kbsanders · 2019-12-26T16:09:07Z

@toooni I believe it was working for me, but I ended up switching to Swift Mailer for the time being until Mailer matures a bit more. I could never get Mailer to work with TLS. Swift Mailer has no issues with TLS.

fabpot · 2020-01-30T10:33:24Z

To be clear, you should use 465, true to use SSL to connect or 587, false to connect withou SSL and upgrade via STARTTLS. Any other combination won't work. The code was buggy, fixing it here:

…abpot) This PR was merged into the 4.4 branch. Discussion ---------- [Mailer] Fix STARTTLS support for Postmark and Mandrill | Q | A | ------------- | --- | Branch? | 4.4 | Bug fix? | yes | New feature? | no  | Deprecations? | no  | Tickets | Fix #34846  | License | MIT | Doc PR | n/a Commits ------- 44b27c6 [Mailer] Fix STARTTLS support for Postmark and Mandrill

cengizgoren · 2020-06-11T20:37:53Z

To be clear, you should use 465, true to use SSL to connect or 587, false to connect withou SSL and upgrade via STARTTLS. Any other combination won't work. The code was buggy, fixing it here: @fabpot you're a genius. ..

this solved my problem. i even told this solution to one.com support . thanks again

bestvayne · 2020-07-28T07:33:49Z

To be clear, you should use 465, true to use SSL to connect or 587, false to connect without SSL and upgrade via STARTTLS. Any other combination won't work. The code was buggy, fixing it here:

yes, 465 is right , I use mailgun service in Laravel 7.X, the error is "Connection could not be established with host smtp.mailgun.org:stream_socket_client(): SSL operation failed with code 1. OpenSSL Error messages: error:1408F10B:SSL routines:ssl3_get_record:wrong version number"

and I use 465 replace Laravel init 587, the mistake was solved.

This will make the mailer "auto-discover" the encryption capabilities of the SMTP server, allowing us to use port 587 with STARTTLS negotiation. Another solution would be to use port 465 with TLS set to `true`, but the [recommended way][1] is to use port 587 and let the library negotiate the encryption. See also symfony/symfony#34846 (comment) [1]: https://sendgrid.com/blog/whats-the-difference-between-ports-465-and-587/

hanzallahmsd · 2022-08-27T08:12:17Z

To be clear, you should use 465, true to use SSL to connect or 587, false to connect withou SSL and upgrade via STARTTLS. Any other combination won't work. The code was buggy, fixing it here:

I am also getting the same error. Where I will put these values?

hanzallahmsd · 2022-08-27T08:24:06Z

My SMTP Settings look like this

MAIL_MAILER=smtp
MAIL_HOST=smtpout.secureserver.net
MAIL_PORT=587
MAIL_USERNAME=[email protected]
MAIL_PASSWORD=MyPassword
MAIL_ENCRYPTION=tls
MAIL_FROM_ADDRESS=[email protected]
MAIL_FROM_NAME="${APP_NAME}"

hanzallahmsd · 2022-08-27T08:26:26Z

Pasting some part of the error.

[2022-08-27 08:05:13] local.ERROR: Connection could not be established with host "ssl://smtpout.secureserver.net:465": stream_socket_client(): Unable to connect to ssl://smtpout.secureserver.net:465 (Connection timed out) {"exception":"[object] (Symfony\Component\Mailer\Exception\TransportException(code: 0): Connection could not be established with host "ssl://smtpout.secureserver.net:465": stream_socket_client(): Unable to connect to ssl://smtpout.secureserver.net:465 (Connection timed out) at /var/www/mysite.com/vendor/symfony/mailer/Transport/Smtp/Stream/SocketStream.php:154)
[stacktrace]
#0 [internal function]: Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream->Symfony\Component\Mailer\Transport\Smtp\Stream\{closure}()
#1 /var/www/mysite.com/vendor/symfony/mailer/Transport/Smtp/Stream/SocketStream.php(157): stream_socket_client()
#2 /var/www/mysite.com/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(253): Symfony\Component\Mailer\Transport\Smtp\Stream\SocketStream->initialize()
#3 /var/www/mysite.com/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(192): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->start()
#4 /var/www/mysite.com/vendor/symfony/mailer/Transport/AbstractTransport.php(68): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->doSend()
#5 /var/www/mysite.com/vendor/symfony/mailer/Transport/Smtp/SmtpTransport.php(136): Symfony\Component\Mailer\Transport\AbstractTransport->send()
#6 /var/www/mysite.com/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(521): Symfony\Component\Mailer\Transport\Smtp\SmtpTransport->send()
#7 /var/www/mysite.com/vendor/laravel/framework/src/Illuminate/Mail/Mailer.php(285): Illuminate\Mail\Mailer->sendSymfonyMessage()

bitfactory-edo-freriks · 2023-01-03T10:07:29Z

@hanzallahmsd did you try

MAIL_ENCRYPTION=starttls

maynor96 · 2023-02-23T21:16:31Z

starttls

it worked for me!

prodev711 · 2023-02-25T20:19:42Z

MAIL_MAILER=smtp
MAIL_HOST=smtp.mailtrap.io
MAIL_PORT=587
MAIL_USERNAME=myuser
MAIL_PASSWORD=mypass
MAIL_ENCRYPTION=STARTTLS

When I set env values like this, there is no error. but email not send to target email.

…e STARTTLS (RFreij) This PR was merged into the 6.4 branch. Discussion ---------- [Mailer] [Mailjet] Disable tls for mailjet as it should use STARTTLS | Q | A | ------------- | --- | Branch? | 6.4  | Bug fix? | yes | New feature? | no  | Deprecations? | no  | Issues |  | License | MIT #52560 updates the default mailjet port and references the same change for mailgun. Similar to #51042 and with the same error message, the mailjet connection doesn't work now. The PR above already has a reference, but for completion sake: Ref #34846 (comment) for more explanation Commits ------- 709d56f fix(mailjet-smtp): disable tls for mailjet as it should use starttls instead

javiereguiluz added Bug Mailer labels Dec 6, 2019

carsonbot added the Status: Needs Review label Dec 6, 2019

fabpot mentioned this issue Jan 30, 2020

[Mailer] Fix STARTTLS support for Postmark and Mandrill #35518

Merged

fabpot closed this as completed Jan 30, 2020

dereks mentioned this issue Aug 17, 2020

Cannot connect to SMTP with SSL on port 465 roundcube/roundcubemail#7552

Closed

DaneEveritt mentioned this issue Sep 15, 2020

Gmail SMTP SSL error pterodactyl/panel#2348

Closed

driesvints mentioned this issue Feb 10, 2022

[9.x] Connection could not be established with host smtp and a different port from 465 with tls enabled laravel/framework#40887

Closed

joelwurtz mentioned this issue Jul 20, 2023

[Mailer] [Mailgun] Disable tls for mailgun as it should use STARTTLS #51042

Merged

samdark mentioned this issue Jul 25, 2023

cannot send email yiisoft/yii2-symfonymailer#57

Closed

RFreij mentioned this issue Dec 13, 2023

[Mailer] [Mailjet] Disable tls for mailjet as it should use STARTTLS #53061

Merged

Hlavtox mentioned this issue Apr 2, 2025

PS 9 Symfony mailer not working with port 587 (only 465) PrestaShop/PrestaShop#36663

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Mailer Transports to SMTP Cannot Establish Secure Connections #34846

Mailer Transports to SMTP Cannot Establish Secure Connections #34846

brandonsavage commented Dec 6, 2019

fabpot commented Dec 7, 2019

brandonsavage commented Dec 8, 2019

kbsanders commented Dec 11, 2019

kbsanders commented Dec 11, 2019

toooni commented Dec 22, 2019

kbsanders commented Dec 26, 2019

fabpot commented Jan 30, 2020

cengizgoren commented Jun 11, 2020

bestvayne commented Jul 28, 2020

hanzallahmsd commented Aug 27, 2022

hanzallahmsd commented Aug 27, 2022

hanzallahmsd commented Aug 27, 2022

bitfactory-edo-freriks commented Jan 3, 2023

maynor96 commented Feb 23, 2023 •

edited

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prodev711 commented Feb 25, 2023

Mailer Transports to SMTP Cannot Establish Secure Connections #34846

Mailer Transports to SMTP Cannot Establish Secure Connections #34846

Comments

brandonsavage commented Dec 6, 2019

fabpot commented Dec 7, 2019

brandonsavage commented Dec 8, 2019

kbsanders commented Dec 11, 2019

kbsanders commented Dec 11, 2019

toooni commented Dec 22, 2019

kbsanders commented Dec 26, 2019

fabpot commented Jan 30, 2020

cengizgoren commented Jun 11, 2020

bestvayne commented Jul 28, 2020

hanzallahmsd commented Aug 27, 2022

hanzallahmsd commented Aug 27, 2022

hanzallahmsd commented Aug 27, 2022

bitfactory-edo-freriks commented Jan 3, 2023

maynor96 commented Feb 23, 2023 • edited Loading

prodev711 commented Feb 25, 2023

maynor96 commented Feb 23, 2023 •

edited

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