Could not start TLS connection encryption protocol

[jcarver]

HESK version: 2.7.5 - HESK is up to date
PHP version: 7.1.7 (MySQLi)
MySQL version: 5.1.73-community
/hesk_settings.inc.php Exists, Writable
/attachments Exists, Writable
/cache Exists, Writable
Windows server 2016
IIS version 10

Hello, I recently started having issues with Hesk sending emails to our smtp server. Nothing changed the day it stopped working. We have since updated Hesk to 2.7.5 but this did not change the error.
smtp.gmail.com
Port: 587
SSL: Off
TLS: On

The error I receive is:
Could not start TLS connection encryption protocol
Resolving SMTP server domain "smtp.gmail.com"...
Connecting to SMTP server "smtp.gmail.com" port 587...
Connected to SMTP server "smtp.gmail.com".
S 220 smtp.gmail.com ESMTP q12sm2516044oti.48 - gsmtp
C EHLO xx.xx.local
S 250-smtp.gmail.com at your service, [x.x.x.x]
S 250-SIZE 35882577
S 250-8BITMIME
S 250-STARTTLS
S 250-ENHANCEDSTATUSCODES
S 250-PIPELINING
S 250-CHUNKING
S 250 SMTPUTF8
C STARTTLS
S 220 2.0.0 Ready to start TLS
Starting TLS cryptograpic protocol

I've tried to update the openssl cert bundle like in this thread but I can't find the correct php files to get it to work.
https://www.softaculous.com/board/index ... nd_PHP_5.6

Thanks!

[Klemen]

See my 3rd response here: viewtopic.php?f=13&t=6060#25866

[iolay]

Hello. I have the same error as in 1 post. Did everything under the link of the 2 posts. The error has remained.

[Klemen]

This means a SSL certificate error is occurring; it's a PHP/server configuration thing and not something that can be fixed within Hesk (SSL certificate validation will fail with any PHP script, not just Hesk).

[pinhoone]

Hello folks!
So... recently my company is migrating our e-mail to Office365, so I'm having some issues integrating my systems to O365... So now I'm dealing with HESK... I'm doing some tests on e-mail configuration, I set to:
use SMPT Server
on SMTP address smtp.office365.com
SMTP Port 587
SSL: OFF
TLS: ON
user@domain.com/password


When I use the Test SMTP connection I got this error: Could not start TLS connection encryption protocol
And this results: Resolving SMTP server domain "smtp.office365.com"...
Connecting to SMTP server "smtp.office365.com" port 587...
Connected to SMTP server "smtp.office365.com".
S 220 CP0PR00CA0000.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 10 Jul 2020 18:07:55 +0000
C EHLO ticket.domain.com
S 250-CP0PR00CA0000.outlook.office365.com Hello [xxx.xxx.xxx.xxx]
S 250-SIZE 157286400
S 250-PIPELINING
S 250-DSN
S 250-ENHANCEDSTATUSCODES
S 250-STARTTLS
S 250-8BITMIME
S 250-BINARYMIME
S 250-CHUNKING
S 250 SMTPUTF8
C STARTTLS
S 220 2.0.0 SMTP server ready
Starting TLS cryptograpic protocol

And on POP3 configuration
POP3 Server: outlook.office365.com
POP3 Port: 995
TLS: ON
user POP3: user@domain.com / password

And when I test connection POP3 I got this error: establishing TLS connections requires the OpenSSL extension enabled

And no message on the box below...

Does anyone have any idea why this happen?
I already put exception all the ports on my firewall to the server where Hesk is installed.
Currently, I'm using Hesk version: 2.8.4

[Klemen]

You'll probably need to contact your host and ask them to enable OpenSSL support for PHP.