Failed to connect to smtp-relay.gmail.com:25

neok

Hi, I am testing from the terminal of my osTicket to send mails via SMTP relay from Gmail with telnet and I can do it without problems. The emails arrive.

telnet smtp-relay.gmail.com 25

HELO somedomain.com
MAIL FROM: <hello@somedomain.com>
RCPT TO: <some@somedomain.com>
DATA
From: hello@somedomain.com
To: some@somedomain.com
Subject: Test smtp-relax
Test mail
.

But when configuring osTicket I have this error:

Where else could I look for the cause of the problem?
I found nothing in the PHP logs even if I activate the logs to file.

Thanks in advance for your help
Regards

Gabriel

Server Information
osTicket Version v1.14.2 (cba6035)
— v1.14.7 is available
Web Server Software Apache/2.4.6 (CentOS) OpenSSL/1.0.2k-fips PHP/7.2.31
MySQL Version 10.2.32
PHP Version 7.2.31
PHP Extensions
gdlib Used for image manipulation and PDF printing
imap Used for email fetching
xml XML API
xml-dom Used for HTML email processing
json Improves performance creating and processing JSON
mbstring Highly recommended for non western european language content
phar Highly recommended for plugins and language packs
intl Highly recommended for non western european language content
fileinfo Used to detect file types for uploads
zip Used for ticket and task exporting
APCu Improves overall performance
Zend Opcache Improves overall performance
PHP Settings
cgi.fix_pathinfo "1" is recommended if AJAX is not working
date.timezone America/Argentina/Buenos_Aires
Database Information and Usage
Schema osticketdb (localhost)
Schema Signature 4bd47d94b10bd8a6bab35c119dadf41f
Space Used 92.64 MiB
Space for Attachments 11.52 MiB
Timezone -03 (Interpreted as America/Argentina/Buenos_Aires)

neok

I want to add that the account I am using is a paid Google Workspace account. And I have IP authentication enabled. I mean Google only lets me send if my mail comes from the IPs I declare in the Google Workspace console. So I tried to send by telnet and I was able to do it. So the configuration on the Google side is already working. I still need to make it work from osTicket.

Daedalus01

a Failed HELO means that the outgoing IP address that is being used by your server that connects to the world does not have a public DNS 'A' record tied to it, is not resolvable to the same connecting IP address, or is not a fully qualified host-name. Google is blocking it because it thinks its a bogus Mail Server. Your Telnet session also appears bogus since it doesnt have legit information in it.

neok

Daedalus01
First, my public IP does have an associated A record.
Second, the telnet session is legitimate. I initiated it myself and as I said I was able to send an email that reached its destination. I just changed my domain in the post for privacy reasons.
Third BYE.

Daedalus01

neok
SMTP: HELO was not accepted. --- I just replied based on the error message in your pictures. The IP address might have a 'A' record, but its possible it might still have an issue. For legit tests you don't use "somedomain". If you edited out your actual domain, put a disclaimer.

Third -- Don't be rude to people trying to help you. best of luck in resolving your issue.

ntozier

@neok I would say that you probably want to take a look at the helpful Gmail Configuration video that they put a while ago on the docs site, and the verbiage after the video for google apps/gSuite to make sure that you didnt miss anything.

https://docs.osticket.com/en/latest/Getting%20Started/Email%20Settings.html

Since you are running CentOS are you also running SELinux? (enabled by default) If so then you would likely need to look at the SELinux logs to see if there is anything being logged about this. Alternatively you can try disabling SELinux and re-testing, you can always turn it back on after.

Lastly you might want to take a look at this thread:
https://forum.osticket.com/d/96708-failed-to-connect-to-mail-server-smtp-helo-was-not-accepted/6

neok

ntozier thanks for reply. All Gmail configurations are set up and SElinux is disabled. I think that may some PHP mailer function thats still need to be configured.

elvisfreb

Some apps and email clients doesn't meet Gmail security standards , they use less secure technologies to log you into Gmail account , and servers blocks these requests by default. In order to resolve this issue, log in to your Gmail account through a web browser and enable access through less secure apps.

To enable "less secure" email programs to access Gmail:

Log into your GMAIL account.
Navigate to the 'Less secure apps' page.
Toggle to turn this feature 'ON'.

Less secure apps can make your account more vulnerable, Google will automatically turn this setting off if it's not being used. However, bypass this security setting with a configuration tweak within your Google Email Account .

How "more secure apps" help to protect your account?

Which level of access you're giving the client before you connect your Account.
Client access only a relevant part of your Account, like your email or calendar.
Connect your Google Account to the client without exposing your password.
Disconnect your Google Account from the client at any time.