?
Solved

Postfix relay to Office 365 external recipients not delivered

Posted on 2013-01-29
1
Medium Priority
?
1,213 Views
Last Modified: 2013-02-19
I have an issue with Postfix relay to MS Office 365. I can send to internal addresses, but not external. I receive the following error message:

550 5.7.1 Client does not have permissions to send as this sender (in reply to end of DATA command))

I have setup a Microsoft SMTP server and it works fine, both internal and external, but Postfix will not deliver to external addresses. I know it has to be a configuration issue. I just can't pinpoint what it is. I really would prefer to use Postfix. I've used it before and never had any issues, but if I don't figure this out, I will have to go with MS

Here is my main.cf:

# See /usr/share/postfix/main.cf.dist for a commented, more complete version


# Debian specific: Specifying a file name will cause the first
# line of that file to be used as the name. The Debian default
# is /etc/mailname.
myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# TLS parameters
smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
smtpd_use_tls=yes
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for
# information on enabling SSL in the smtp client.

myhostname = mailrelay.mydomain.com
mydomain=mydomain.com
relay_domains=*
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
myorigin = /etc/mailname
mydestination = mailrelay.mydomain.com, localhost.mydomain.com, , localhost
relayhost = [pod51019.outlook.com]:587
mynetworks = 192.168.86.178, 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +

inet_interfaces = all

smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_tls_CAfile = /etc/postfix/cacert.pem

smtp_generic_maps = hash:/etc/postfix/generic
smtp_sasl_mechanism_filter = login
smtp_tls_loglevel = 1
smtp_tls_security_level = may
smtp_send_dummy_mail_auth = yes
0
Comment
Question by:shart68
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
1 Comment
 
LVL 37

Accepted Solution

by:
ArneLovius earned 1500 total points
ID: 38833680
I would guess that you had a username and password for the smarthost in the Microsoft SMTP relay.

Rather than relay through Office 365, why not just add your exit address to your SPF record and send direct ?
0

Featured Post

Get real performance insights from real users

Key features:
- Total Pages Views and Load times
- Top Pages Viewed and Load Times
- Real Time Site Page Build Performance
- Users’ Browser and Platform Performance
- Geographic User Breakdown
- And more

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Sometimes clients can lose connectivity with the Lotus Notes Domino Server, but there's not always an obvious answer as to why it happens.   Read this article to follow one of the first experiences I had with Lotus Notes on a client's machine, my…
New style of hardware planning for Microsoft Exchange server.
Get a first impression of how PRTG looks and learn how it works.   This video is a short introduction to PRTG, as an initial overview or as a quick start for new PRTG users.
Established in 1997, Technology Architects has become one of the most reputable technology solutions companies in the country. TA have been providing businesses with cost effective state-of-the-art solutions and unparalleled service that is designed…
Suggested Courses
Course of the Month11 days, 13 hours left to enroll

752 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question