I have set up postfix to receive email from one of my domain, roadpost.org

I have set up two mailboxes - supp...@roadpost.org and suppo...@roadpost.org

When I send email to the support2 account, postfix delivers the mail to a
local mailbox as is expected.

When I send email to the support account, postfix forwards the email to the
smtp server for roadpost.com

The configuration is such that the incoming mail is for the .org domain,
but outgoing email is set go out as though its coming from the .com domain.
This was done so that I can have individual email addresses for some of my
.com addresses on a different machine than where the primary .com email is
handled.

Email is forwarded from a microsoft outlook.com shared account handling the
.com account to an account at the .org machine.

There is outgoing email activity for supp...@roadpost.com - there was
speculation that because postfix has seen traffic from the support account,
it somehow thinks it should forward email that arrives from supp...@...org.
Does postfix track outbound activity such that inbound mail routing depends
on what email has arrived for a particular mailbox?

Any help would be most appreciated.

Here is the postconf output:

alias_database = hash:/etc/aliases
alias_maps = hash:/etc/aliases
command_directory = /usr/sbin
config_directory = /etc/postfix
daemon_directory = /usr/libexec/postfix
data_directory = /var/lib/postfix
debug_peer_level = 4
debug_peer_list = *
home_mailbox = Maildir/
html_directory = no
inet_interfaces = all
inet_protocols = all
mail_owner = postfix
mailbox_size_limit = 0
mailq_path = /usr/bin/mailq.postfix
manpage_directory = /usr/share/man
mydestination = roadpost.org, localhost, $mydomain, mail.roadpost.org,
www.$mydomain, ftp.$mydomain
mydomain = roadpost.org
myhostname = 3202184.roadpost.org
myorigin = roadpost.com
newaliases_path = /usr/bin/newaliases.postfix
queue_directory = /var/spool/postfix
readme_directory = /usr/share/doc/postfix-2.6.6/README_FILES
sample_directory = /usr/share/doc/postfix-2.6.6/samples
sendmail_path = /usr/sbin/sendmail.postfix
setgid_group = postdrop
unknown_local_recipient_reject_code = 550

Here are some fragments from the maillog:

Doesn't work - supp...@roadpost.org

Doesn't work - supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: C95771EE06CF: recipient limit
5000
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: C95771EE06CF: from=<
r...@roadpost.com>, size=438, nrcpt=1 (queue active)
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: start sorted recipient list
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_message_sort:
supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: end sorted recipient list
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: connect to subsystem
private/rewrite
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr request = resolve
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr sender =
r...@roadpost.com
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr address =
supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/rewrite socket: wanted
attribute: flags
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: flags
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute value: 0
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/rewrite socket: wanted
attribute: transport
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: transport
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute value: local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/rewrite socket: wanted
attribute: nexthop
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: nexthop
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute value:
3202184.roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/rewrite socket: wanted
attribute: recipient
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: recipient
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute value:
supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/rewrite socket: wanted
attribute: flags
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: flags
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute value: 256
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: resolve_clnt: `r...@roadpost.com'
-> `supp...@roadpost.org' -> transp=`local' host=`3202184.roadpost.org'
rcpt=`supp...@roadpost.org' flags= class=local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: start sorted recipient list
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_message_sort:
supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: end sorted recipient list
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: mail_flow_put: 1 1
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_transport_select: local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_active_drain: allocate
local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: connect to subsystem
private/local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: done incoming queue scan
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: transport_event: local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/local socket: wanted
attribute: status
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: status
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute value: 0
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: private/local socket: wanted
attribute: (list terminator)
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: input attribute name: (end)
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_peer_select: C95771EE06CF
local supp...@3202184.roadpost.org (1 of 2)
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_job_retire: C95771EE06CF
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr flags = 3
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr queue_name = active
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr queue_id =
C95771EE06CF
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr offset = 174
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr size = 438
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr nexthop =
3202184.roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr encoding =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr sender =
r...@roadpost.com
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr envelope_id =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr ret_flags = 0
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr time = [data 88 bytes]
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr log_client_name =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr log_client_address =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr log_client_port =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr log_protocol_name =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr log_helo_name =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr sasl_method =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr sasl_username =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr sasl_sender =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr rewrite_context =
local
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr recipient_count = 1
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr original_recipient =
supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr recipient =
supp...@roadpost.org
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr offset = 636
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr dsn_orig_rcpt =
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: send attr notify_flags = 0
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: qmgr_deliver: site `
supp...@3202184.roadpost.org'
Oct 10 09:19:27 3202184 postfix/cleanup[22991]: CF5501EE03FF: message-id=<
20141010131927.c95771ee0...@3202184.roadpost.org>
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: trigger_server_accept_fifo:
trigger arrived
Oct 10 09:19:27 3202184 postfix/qmgr[9316]: master_notify: status 0
Oct 10 09:19:27 3202184 postfix/local[22993]: C95771EE06CF: to=<
supp...@roadpost.org>, relay=local, delay=0.04, delays=0.03/0.01/0/0,
dsn=2.0.0, status=sent (forwarded as CF5501EE03FF)

Does Work:

Oct  9 17:06:28 3202184 postfix/qmgr[9316]: input attribute value: 0
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: private/local socket: wanted
attribute: (list terminator)
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: input attribute name: (end)
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: qmgr_peer_select: 59CC81EE06D0
localsuppo...@3202184.roadpost.org (1 of 2)
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: qmgr_job_retire: 59CC81EE06D0
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr flags = 3
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr queue_name = active
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr queue_id =
59CC81EE06D0
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr offset = 174
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr size = 439
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr nexthop =
3202184.roadpost.org
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr encoding =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr sender =
r...@roadpost.com
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr envelope_id =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr ret_flags = 0
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr time = [data 88 bytes]
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr log_client_name =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr log_client_address =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr log_client_port =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr log_protocol_name =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr log_helo_name =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr sasl_method =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr sasl_username =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr sasl_sender =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr rewrite_context =
local
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr recipient_count = 1
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr original_recipient =
suppo...@roadpost.org
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr recipient =
suppo...@roadpost.org
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr offset = 638
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr dsn_orig_rcpt =
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: send attr notify_flags = 0
Oct  9 17:06:28 3202184 postfix/qmgr[9316]: qmgr_deliver: site `
suppo...@3202184.roadpost.org'
Oct  9 17:06:28 3202184 postfix/local[6302]: 59CC81EE06D0: to=<
suppo...@roadpost.org>, relay=local, delay=0.03, delays=0.01/0.01/0/0.01,
dsn=2.0.0, status=sent (delivered to maildir)

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