I installed MIAB on a cloud VM and it works fine for sending email directly to another email account (e.g., MIAB > Gmail works perfectly).
I am trying to run a helpldesk application on another cloud VM and set it up to send email through MIAB using a specific username/password. I have tried a couple different helpdesk web applications (osTicket and Hesk) and every time I try to enable email sending, i get an SMTP error that looks something like this:
SMTP ERROR: Failed to connect to server: Connection timed out (110)
(the exact wording varies by application, but it’s always a 110 time out).
I have tried the following:
-Connecting via SSL and TLS on ports 25, 465 and 587 using the MIAB’s FQDN
-Verifying the ports are open on the MIAB server
-Changing the email address/password used to connect
I am able to use Outlook on a PC to connect/send email using IMAP/SMTP (over 465) without issue, but the web server seems to be unable to connect with any combo.
I can use other web servers (different FQDN and IP address) with no issue.
MIAB is up to date and the host VM is Ubuntu 24.04 and up to date as well.
Is there any reason why a specific host wouldn’t be able to send? What else could I check to see why this specific server times out on sending?
The instructions are listed in the Admin Panel MailAndUsers>Instructions. PORT 587 is not listed there but it does work.
I have used MIAB with an SMTP plugin for WordPress and it does work.
You are doing something wrong. Check authentication Config in OSTicket and play with SSL TLS
Also please note if your tickets are improperly HTML formatted you will get blacklisted pretty soon by GMAIL and OUTLOOK. Send gradually and test. Not a good idea to use MIAB as bulk sender. Use a relay.
Test the VM containing the web app via telnet to connect to the MIAB see if any ports are closed:
I followed the instructions in the Admin Panel:
I copied the FQDN listed (just to make sure I didn’t mistype it).
I have tried using port 25, 465 and 587 each with both SSL and TLS.
I have a separate web server running NextCloud and it can use MIAB without problem. This leads me to think this one VM’s public IP address could possibly be “blacklisted” by some filter in MIAB for some reason?
Please try to manually connect from the VM with the app to the VM with MIAB as per the instructions in my previous post. SSH to VM with tha app and telnet to MIAB to connect to it. Read above how to do that. Please report if this was successful. The syntax is
telnet yourMIABip 587
Also see if the mail log reports any refused connections originating from the VM with the app or any error messages. The log is stored here
/var/log/mail.log
Lookup here to see if that IP is blacklisted but I doubt that MIAB would refuse any connections.
Haven’t had a lot of time to look at this issue in-depth, but my ultimate guess is that the osTicket VM was blocked from SMTP logins after a few attempts switching ports and SSL/TLS. I ended up erasing the osTicket VM and am rebuilding a new one with Hesk (different helpdesk software). So far, Hesk connects on this VM with no issue (SSL/TLS/Port combo figured out). I do need osTicket on this VM for a different application use-case, so I will try that as well and report back with my findings.
Since I was able to use SMTP from another VM (nextcloud - different IP address) this further leads me to think MIAB had some blocklist feature or maybe Ubuntu had a rate-limiting feature I don’t know about.
In addition, I discovered I had my SPF DNS record messed up defining which servers could send mail (this has been fixed), but I doubt this would result in SMTP tiemout errors.
osTicket is now working with MIAB using SMTP. In case anyone runs into this issue, these are the settings I used:
For the “Remote Mailbox” (fetching new emails) tab:
Configuring the hostname as “ssl://your.fqdn.address”
Port 993
Basic authentication with username (full email address) and password.
(I haven’t tested receiving emails as ticket, but these settings allow successful connection.)
For the “Outgoing (SMTP)” tab:
Hostname is “ssl://your.fqdn.address”
Port 465
Authentication is Same as Remote Mailbox
These settings work to successfully send email, and emails sent are delivered to an Inbox instead of Spam/Junk with the correct public DNS records.
Thanks for everyone’s help! MIAB and its community are awesome.
