SMTP PORT 25 or 465 ! Please Help !

  • Hi,

    It took me a while to figure out a problem with my new Zimbra Mail server. It was able to send out emails on SMTP server using port 465, and i'm using pfsense as my firewall.
    But a biggest problem is, whenever i try to send an attachment, it gives out a request timed out error message. i thought it was the problem with the server, then i figured out that i can send any attachment of any size out of my firewall.

    I don't know what settings i need to prioritize in the Rules table.

    As for LAN, i have

    TCP  LAN net  *  postal  25 (SMTP)  *      LAN SMTP to Postal

    TCP LAN net * postal 465 (SMTP/S) *   LAN SMTP/S to Postal 
    TCP LAN net * postal 443 (HTTPS) *   LAN HTTPS to Postal 
    TCP LAN net * postal 80 (HTTP) *   LAN HTTP to Postal

    For DMZ,

    TCP  postal  *  *  25 (SMTP)  *      Allow Mail Going Out 
    TCP postal * * 7071 *   Allow Admin Console 
    TCP postal * * 443 (HTTPS) *   Allow HTTPS Out 
    TCP postal * * 80 (HTTP) *   Allow HTTP Out 
    TCP postal 143 (IMAP) * 143 (IMAP) *   Allow IMAP Out 
    TCP postal * * 110 (POP3) *   Allow POP3 Out 
    TCP postal 993 (IMAP/S) * 993 (IMAP/S) *   Allow IMAPS Out 
    TCP postal 995 (POP3/S) * 995 (POP3/S) *   Allow POP3/S Out 
    TCP postal * * 22 (SSH) *         Allow SSH Out 
    TCP/UDP postal * * 53 (DNS) *   Allow DNS Out

    For WAN

    *  *  *  postal  *  *      Postal Any

    Please help if you could find any error in my settings which is causing the time out in the network.

    Thank you for all your help.

    let me know if i need to provide any more details.
    Like i said, i can send out text emails, none with attachments because it is timed out. I tried to increase the time out from the mail server but that doesn't seems to change anything because i can use the mail server outside pfsense to send the attachments.
    Also, the telnet does connect to port 25.
    But, SSH connection too times out very often, probably in about 30 seconds of its connection.

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