Postfix problems sending mail to gmail addresses

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Can you reach any SMTP server beyond your ISP network?
Do you get SMTP greeting message using "telnet tests"?

telnet mx-host-name 25

NO => Maybe your ISP blocks outgoing connections to SMTP port to block outgoing spam.

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Joris Molnar
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Joris Molnar

Updated on September 18, 2022

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  • Joris Molnar
    Joris Molnar almost 2 years

    I have just installed Postfix and while recieving email seems to work fine, I have trouble sending email.

    When I send mail to an address provided by my ISP, the mail gets delivered successfully. The problems start when I send a mail to a gmail address.

    When I check the mail queue, I can see the email is stuck:

    myuser@My-Server:~$ mailq
    -Queue ID- --Size-- ----Arrival Time---- -Sender/Recipient-------
    7580BB40C58      551 Sat Apr 23 18:30:27  [email protected]
    (connect to alt2.gmail-smtp-in.l.google.com[64.233.189.26]:25: Connection timed out)
                                             [email protected]
    -- 0 Kbytes in 1 Request.
    

    You can see it says Connection timed out. The problems get confirmed when I check postfix.log:

    Apr 23 18:30:27 My-Server postfix/pickup[11208]: 7580BB40C58: uid=1000 from=<myuser>
    Apr 23 18:30:27 My-Server postfix/cleanup[12038]: 7580BB40C58: message-id=<[email protected]>
    Apr 23 18:30:27 My-Server postfix/qmgr[11209]: 7580BB40C58: from=<[email protected]>, size=551, nrcpt=1 (queue active)
    Apr 23 18:30:27 My-Server postfix/smtp[12040]: connect to gmail-smtp-in.l.google.com[2a00:1450:4013:c01::1a]:25: Network is unreachable
    Apr 23 18:30:57 My-Server postfix/smtp[12040]: connect to gmail-smtp-in.l.google.com[74.125.136.26]:25: Connection timed out
    Apr 23 18:31:27 My-Server postfix/smtp[12040]: connect to alt1.gmail-smtp-in.l.google.com[74.125.68.26]:25: Connection timed out
    Apr 23 18:31:27 My-Server postfix/smtp[12040]: connect to alt1.gmail-smtp-in.l.google.com[2404:6800:4003:c02::1b]:25: Network is unreachable
    Apr 23 18:31:57 My-Server postfix/smtp[12040]: connect to alt2.gmail-smtp-in.l.google.com[64.233.189.26]:25: Connection timed out
    Apr 23 18:31:58 My-Server postfix/smtp[12040]: 7580BB40C58: to=<[email protected]>, relay=none, delay=91, delays=0.17/0.01/90/0, dsn=4.4.1, status=deferred (connect to alt2.gmail-smtp-in.l.google.com[64.233.189.26]:25: Connection timed out)
    

    It says status=deffered and Connection timed out. It retries every few minutes automatically, and fails everytime.

    My mail.cf files looks like this:

    myhostname = mail.mydomain.nl
    
    alias_maps = hash:/etc/aliases
    alias_database = hash:/etc/aliases
    
    myorigin = /etc/mailname
    mydestination = mail.mydomain.nl, My-Server, , localhost, mydomain.nl
    
    relayhost = 
    mynetworks = 127.0.0.0/8 192.168.1.0/24 10.8.0.1/32 [::1]/128 [fe80::]/64
    mailbox_size_limit = 0
    recipient_delimiter = +
    inet_interfaces = all
    
    # Uncomment the next line to generate "delayed mail" warnings
    #delay_warning_time = 4h
    
    inet_protocols = all
    

    I have my own domain name and think I have configured its DNS settings correctly. I also think I have set the name correctly on my server, but I am not entirely sure. Please note I do not want to relay my mail through gmail servers, but just send mail to them.
    The server runs Ubuntu Server 14.04 LTS.

    If someone could help me with this problem, it would be greatly appreciated.

  • Joris Molnar
    Joris Molnar about 8 years
    Yes, this was the problem. When I tested this command using the gmail SMTP server it returned the same message. I did some googling (ironic) and found that my ISP was indeed blocking outgoing SMTP connections. I added relayhost = smtp.myisp.nl:25 and that solved everything.