Email not sending V5 selfhosted in Plesk

Self-Hosted | v5
1

Hi folks.
I have been having some issues with sending emails through V5, I can connect and send through Gmail which is fine… though when using email deliverability tools it gets flagged as spam because of a few reasons.

When connecting to my own mail server self-hosted through Plesk I am running into the same obstacle time and time again.

I have essentially copied my mail credentials into the env file

MAIL_DRIVER=smtp
MAIL_PORT=587
MAIL_ENCRYPTION=tls
MAIL_HOST=mail.URL.co.uk
MAIL_USERNAME="scott@URL.co.uk"
MAIL_FROM_ADDRESS="scott@URL.co.uk"
MAIL_FROM_NAME="Business Name"
MAIL_PASSWORD='something with special characters like ! and & and maybe a ^'

On Plesk my credentials are as follows:
### Manual setup

Mail server username
scott@URL.co.uk

Incoming mail server
URL.co.uk

Outgoing mail server
URL.co.uk
(server requires authentication)

Supported incoming mail protocols
POP3, POP3 over SSL/TLS, IMAP, IMAP over SSL/TLS
Supported outgoing mail protocols
SMTP
To connect via POP3 securely over SSL/TLS, use port 995.
To connect via IMAP securely over SSL/TLS, use port 993.
To send messages via SMTP securely, use port 465.

with the following option
Enable SMTP service on port 587 on all IP addresses enabled.

The error I keep getting is
"connection could not be established with host mail.URL.co.uk :stream_socket_client(): unable to connect to tcp://mail.URL.co.uk:587 (operation timed out)

Is there something that I am missing here at all?

2

Hi,

Are you sure the port is correct, you may want to run telnet mail.URL.co.uk 587 to check that it’s reachable.

3

Hi thanks for your response. Telnet from a remote source says that it can connect ok. Telnet from within the VM that contains Plesk and the container isn’t able to reach.

This then might be a DNS issue locally where it’s not getting resolved correctly?

4

It could be, you could try using the IP instead of the domain name to check

5

Ok, yes. doing telnet to the ip address works.
Having changed the env file to the following
MAIL_HOST=10.0.#.#

and putting " in the password as opposed to ’ is helping me move forward

New error message that comes from that is as follow:
*stream_socket_enable_crypto(): SSL operation failed with code 1. Open SSL Error message error:1416F086:SSL routine:tls_process_server_certificate:certificate verify failed

6

It looks like there’s a problem with the SSL certificate, sorry I can’t provide more help

7

No problem. I’m further forward than where I was. I appreciate your help.