Thanks Daniel.

> On 17 Dec 2018, at 2:29 am, Daniel Miller <dmil...@amfes.com 
> <mailto:dmil...@amfes.com>> wrote:
> 
> As I don't use Mail.app (but do use Thunderbird and AquaMail on Android) my 
> guess is different client configuration.  But a couple possibilities:
> 
> That shows me ASSP is connecting to Postfix via Postfix's listener on 10026.
> On 12/16/2018 4:38 AM, James Brown wrote:
>> 
>> Hi Daniel, thanks again for your help. I’ve been trying to get this working 
>> all weekend. Listening ports:
>> 
>> $sudo lsof -i :10025
>> COMMAND   PID USER   FD   TYPE             DEVICE SIZE/OFF NODE NAME
>> perl    68782 root   18u  IPv4 0x1117b83fd26dc88b      0t0  TCP 
>> localhost:10025 (LISTEN)
>> 
>> $ sudo lsof -i :10026
>> COMMAND   PID USER   FD   TYPE             DEVICE SIZE/OFF NODE NAME
>> master  89692 root   85u  IPv4 0x1117b83fdbb9d20b      0t0  TCP 
>> localhost:10026 (LISTEN)
>> 
>> $ sudo lsof -i :465
>> COMMAND   PID USER   FD   TYPE             DEVICE SIZE/OFF NODE NAME
>> master  89692 root  102u  IPv4 0x1117b83fab73ce8b      0t0  TCP *:urd 
>> (LISTEN)
>> 
>> If I try to send an email via Thunderbird I get:
>> 
>> 2018-12-16 23:00:32.330688+1100 0x40dc66   Activity    0x49b2e0             
>> 72070  0    smtpd: (libsystem_info.dylib) Retrieve User by Name
>> 2018-12-16 23:00:32.331438+1100 0x40dc66   Activity    0x49b2e1             
>> 72070  0    smtpd: (libsystem_info.dylib) Retrieve User by Name
>> 2018-12-16 23:00:32.332155+1100 0x40dc66   Activity    0x49b2e2             
>> 72070  0    smtpd: (libsystem_info.dylib) Retrieve Group by Name
>> 2018-12-16 23:00:32.342027+1100 0x40dc66   Activity    0x49b2e3             
>> 72070  0    smtpd: (libsystem_info.dylib) Resolve user group list
>> 2018-12-16 23:00:32.344741+1100 0x40dc66   Info        0x0                  
>> 72070  0    smtpd: connect from localhost[127.0.0.1]
>> 2018-12-16 23:02:08.138177+1100 0x40d37c   Info        0x0                  
>> 71932  0    smtpd: disconnect from localhost[127.0.0.1] ehlo=2 starttls=1 
>> mail=1 rcpt=1 data=1 quit=1 commands=7
>> 2018-12-16 23:03:43.607388+1100 0x40dc66   Info        0x0                  
>> 72070  0    smtpd: lost connection after UNKNOWN from localhost[127.0.0.1]
>> 2018-12-16 23:03:43.607455+1100 0x40dc66   Info        0x0                  
>> 72070  0    smtpd: disconnect from localhost[127.0.0.1] unknown=0/3 
>> commands=0/3
>> 
>> Nothing in mail.log and nothing from ASSP in maillog.txt. I tried with 
>> Microsoft Outlook for Mac and had the same situation.
> What is the above from if it's not from mail.log? 
> 
Running new version of macOS (Mojave) which has a different logging system. So 
running this in Terminal to display Postscript log:

$ log stream --predicate '(process == "smtpd") || (process == "smtp") || 
(process == "master") || (senderImagePath CONTAINS  "postfix")' -debug

Dovecot can log to mail.log OK, not sure why Postfix is different. 
> You should increase the log settings in ASSP working through this.  Set 
> ConnectionLog to verbose for a start.  If that doesn't show activity - next 
> I'd try would be ValidateSenderLog to verbose.
> 
ConnectionLog is already set to Diagnostic. ValidateSenderLog is already set to 
Verbose.
>> 
>> But using Mail.app again it works perfectly:
>> 
>> 2018-12-16 22:56:56.338582+1100 0x40d362   Info        0x0                  
>> 71926  0    smtpd: connect from localhost[127.0.0.1]
>> 2018-12-16 22:56:56.578031+1100 0x40d362   Info        0x0                  
>> 71926  0    smtpd: Anonymous TLS connection established from 
>> localhost[127.0.0.1]: TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 
>> (256/256 bits)
>> 2018-12-16 22:56:56.655063+1100 0x40d378   Default     0x0                  
>> 71931  0    trivial-rewrite: warning: database 
>> /usr/local/etc/postfix/transport.db is older than source file 
>> /usr/local/etc/postfix/transport
> Probably not the end of the world - but fix the easy stuff first.  Looks like 
> your /usr/local/etc/postfix/transport.db needs to be regenerated.
>> 2018-12-16 22:56:56.761289+1100 0x40d362   Activity    0x49ad34             
>> 71926  0    smtpd: (libsystem_info.dylib) Retrieve service by name
>> 2018-12-16 22:56:57.304324+1100 0x40d37c   Activity    0x49ad90             
>> 71932  0    smtpd: (libsystem_info.dylib) Retrieve User by Name
>> 2018-12-16 22:56:57.305045+1100 0x40d37c   Activity    0x49ad91             
>> 71932  0    smtpd: (libsystem_info.dylib) Retrieve User by Name
>> 2018-12-16 22:56:57.305746+1100 0x40d37c   Activity    0x49ad92             
>> 71932  0    smtpd: (libsystem_info.dylib) Retrieve Group by Name
>> 2018-12-16 22:56:57.312412+1100 0x40d37c   Activity    0x49ad93             
>> 71932  0    smtpd: (libsystem_info.dylib) Resolve user group list
>> 2018-12-16 22:56:57.315379+1100 0x40d37c   Info        0x0                  
>> 71932  0    smtpd: connect from localhost[127.0.0.1]
>> 2018-12-16 22:57:00.488720+1100 0x40d37c   Info        0x0                  
>> 71932  0    smtpd: Anonymous TLS connection established from 
>> localhost[127.0.0.1]: TLSv1.2 with cipher ECDHE-RSA-AES128-GCM-SHA256 
>> (128/128 bits)
>> 2018-12-16 22:57:01.263857+1100 0x40d362   Info        0x0                  
>> 71926  0    smtpd: NOQUEUE: client=localhost[127.0.0.1], sasl_method=PLAIN, 
>> sasl_username=jlbr...@bordo.com.au 
>> <mailto:sasl_username=jlbr...@bordo.com.au>
>> 2018-12-16 22:57:02.467839+1100 0x40d37c   Activity    0x49ad94             
>> 71932  0    smtpd: (libsystem_info.dylib) Retrieve service by name
>> 2018-12-16 22:57:02.548724+1100 0x40d37c   Info        0x0                  
>> 71932  0    smtpd: 854ED8E602D: client=localhost[127.0.0.1]
>> 2018-12-16 22:57:06.622777+1100 0x40d3d8   Info        0x0                  
>> 71933  0    cleanup: 854ED8E602D: 
>> message-id=<bf241d65-018c-458c-83bd-631f710b4...@bordo.com.au 
>> <mailto:bf241d65-018c-458c-83bd-631f710b4...@bordo.com.au>>
>> 2018-12-16 22:57:06.623801+1100 0x40181f   Info        0x0                  
>> 68623  0    qmgr: 854ED8E602D: from=<jlbr...@bordo.com.au 
>> <mailto:jlbr...@bordo.com.au>>, size=1096, nrcpt=1 (queue active)
>> 2018-12-16 22:57:06.767183+1100 0x40d3eb   Info        0x0                  
>> 71936  0    pipe: 854ED8E602D: to=<jlbr...@bordo.com.au 
>> <mailto:jlbr...@bordo.com.au>>, relay=dovecot, delay=5.9, 
>> delays=5.8/0.02/0/0.12, dsn=2.0.0, status=sent (delivered via dovecot 
>> service (lda(jlbr...@bordo.com.au <mailto:jlbr...@bordo.com.au>,)Error: 
>> net_connect_unix(/usr/local/var/run/dovecot/stats-writer) failed: P))
>> 2018-12-16 22:57:06.767634+1100 0x40181f   Info        0x0                  
>> 68623  0    qmgr: 854ED8E602D: removed
>> 2018-12-16 22:57:07.341530+1100 0x40d362   Info        0x0                  
>> 71926  0    smtpd: proxy-accept: END-OF-MESSAGE: 250 2.0.0 Ok: queued as 
>> 854ED8E602D; from=<jlbr...@bordo.com.au <mailto:jlbr...@bordo.com.au>> 
>> to=<jlbr...@bordo.com.au <mailto:jlbr...@bordo.com.au>> proto=ESMTP 
>> helo=<[127.0.0.1]> sasl_username=<jlbr...@bordo.com.au 
>> <mailto:jlbr...@bordo.com.au>>
>> 2018-12-16 22:58:07.428262+1100 0x40d362   Info        0x0                  
>> 71926  0    smtpd: disconnect from localhost[127.0.0.1] ehlo=2 starttls=1 
>> auth=1 mail=1 rcpt=1 data=1 quit=1 commands=8
>> 
>> And mail.log shows:
>> 
>> Dec 16 22:57:06 lda(jlbr...@bordo.com.au 
>> <mailto:jlbr...@bordo.com.au>)<71937><+K2AKZI9FlwBGQEAYBwt+A>: Info: 
>> msgid=<bf241d65-018c-458c-83bd-631f710b4...@bordo.com.au 
>> <mailto:bf241d65-018c-458c-83bd-631f710b4...@bordo.com.au>>: saved mail to 
>> INBOX
> Try setting "smtpd_tls_loglevel = 2" in main.cf
>> 
>> While ASSP shows:
>> 
>> Dec-16-18 22:56:57 [Worker_1] Info: try to connect to server at 
>> 127.0.0.1:10026
>> Dec-16-18 22:56:57 [Worker_1] Info: connected to server at 127.0.0.1:10026
>> Dec-16-18 22:56:57 [Worker_1] Connected: session:7FB6906A1160 
>> 127.0.0.1:63176 > 127.0.0.1:10025 > 127.0.0.1:63178 > 127.0.0.1:10026 , 21-22
>> Dec-16-18 22:56:59 [Worker_1] 127.0.0.1 info: injected '250-STARTTLS' offer 
>> in to EHLO reply
>> Dec-16-18 22:56:59 [Worker_1] 127.0.0.1 info: send '250-STARTTLS' - injected 
>> for 127.0.0.1
>> Dec-16-18 22:56:59 [Worker_1] 127.0.0.1 info: removed '250-STARTTLS' - it 
>> was already injected
>> Dec-16-18 22:57:00 [Worker_1] 127.0.0.1 info: injected STARTTLS request to 
>> 127.0.0.1
> This tells me something is not right.  If you used the directives I gave you 
> - connections should be made via SSL and there would be no STARTTLS command 
> issued.  So I'm assuming you didn't exactly follow my config lines...or 
> Mail.app isn't connecting to port 465.  After you've enabled connection 
> logging in ASSP things might be clearer.
>> I really don’t know why only Mail.app works. 
> As a Thunderbird user I'm confident it's not a Thunderbird flaw - it's a 
> PEBKAC issue.  ;)  I have more than a few myself.
> 

I’m sure it is!

When I send from Thunderbird, Postfix says:

2018-12-17 10:42:27.126166+1100 0xbbbc     Info        0x0                  
5686   0    smtpd: connect from localhost[127.0.0.1]
2018-12-17 10:44:07.838129+1100 0xbbbc     Info        0x0                  
5686   0    smtpd: lost connection after UNKNOWN from localhost[127.0.0.1]
2018-12-17 10:44:07.838284+1100 0xbbbc     Info        0x0                  
5686   0    smtpd: disconnect from localhost[127.0.0.1] unknown=0/3 commands=0/3

> After enabling more logging, if things don't resolve themselves share your 
> new logs and also a full copy of assp.cfg and the result of "postconf -n”.
> 
$ sudo postconf -n
broken_sasl_auth_clients = yes
command_directory = /usr/local/sbin
compatibility_level = 2
daemon_directory = /usr/local/libexec/postfix
data_directory = /var/lib/postfix
debug_peer_level = 7
debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd 
$daemon_directory/$process_name $process_id & sleep 5
default_process_limit = 100
disable_vrfy_command = yes
dovecot_destination_recipient_limit = 1
html_directory = no
inet_protocols = ipv4
mail_owner = _postfix
mailbox_size_limit = 102400000
mailq_path = /usr/local/bin/mailq
manpage_directory = /usr/local/man
message_size_limit = 102400000
meta_directory = /usr/local/etc/postfix
mydomain = bordo.com.au <http://bordo.com.au/>
myhostname = mail.bordo.com.au <http://mail.bordo.com.au/>
newaliases_path = /usr/local/bin/newaliases
queue_directory = /var/spool/postfix
readme_directory = no
sample_directory = /usr/local/etc/postfix
sendmail_path = /usr/local/sbin/sendmail
setgid_group = _postdrop
shlib_directory = no
smtpd_client_connection_count_limit = 100
smtpd_command_filter = pcre:/etc/postfix/command_filter.regex
smtpd_data_restrictions = reject_unauth_pipelining
smtpd_enforce_tls = no
smtpd_etrn_restrictions = reject
smtpd_helo_required = yes
smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, 
reject_unauth_pipelining, reject_unauth_destination, permit
smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated 
defer_unauth_destination
smtpd_sasl_auth_enable = yes
smtpd_sasl_local_domain = $myhostname
smtpd_sasl_path = private/auth
smtpd_sasl_security_options = noanonymous
smtpd_sasl_type = dovecot
smtpd_tls_cert_file = /usr/local/etc/dovecot/mail.bordo.com.au.pem
smtpd_tls_key_file = /usr/local/etc/dovecot/mail.bordo.com.au.pem
smtpd_tls_loglevel = 2
smtpd_use_tls = yes
tls_random_source = dev:/dev/urandom
transport_maps = hash:/usr/local/etc/postfix/transport
unknown_local_recipient_reject_code = 550
vacation_destination_recipient_limit = 1
virtual_alias_maps = mysql:/usr/local/etc/postfix/mysql_virtual_alias_maps.cf
virtual_gid_maps = static:102
virtual_mailbox_base = /usr/local/virtual/
virtual_mailbox_domains = 
mysql:/usr/local/etc/postfix/mysql_virtual_domains_maps.cf
virtual_mailbox_limit = 512000000
virtual_mailbox_maps = 
mysql:/usr/local/etc/postfix/mysql_virtual_mailbox_maps.cf
virtual_minimum_uid = 102
virtual_transport = dovecot
virtual_uid_maps = static:102

I’m sure there’s a lot that could be improved with this!

master.cf (non-commented out stuff only):

pickup    unix  n       -       n       60      1       pickup
cleanup   unix  n       -       n       -       0       cleanup
qmgr      unix  n       -       n       300     1       qmgr
tlsmgr    unix  -       -       n       1000?   1       tlsmgr
rewrite   unix  -       -       n       -       -       trivial-rewrite
bounce    unix  -       -       n       -       0       bounce
defer     unix  -       -       n       -       0       bounce
trace     unix  -       -       n       -       0       bounce
verify    unix  -       -       n       -       1       verify
flush     unix  n       -       n       1000?   0       flush
proxymap  unix  -       -       n       -       -       proxymap
proxywrite unix -       -       n       -       1       proxymap
smtp      unix  -       -       n       -       -       smtp
relay     unix  -       -       n       -       -       smtp
        -o syslog_name=postfix/$service_name
showq     unix  n       -       n       -       -       showq
error     unix  -       -       n       -       -       error
retry     unix  -       -       n       -       -       error
discard   unix  -       -       n       -       -       discard
local     unix  -       n       n       -       -       local
virtual   unix  -       n       n       -       -       virtual
lmtp      unix  -       -       n       -       -       lmtp
anvil     unix  -       -       n       -       1       anvil
scache    unix  -       -       n       -       1       scache

127.0.0.1:10026    inet  n       -       n       -       -       smtpd
   -o smtpd_sasl_auth_enable=yes
127.0.0.1:126      inet  n       -       n       -       -       smtpd
  -o syslog_name=assptls
  -o smtpd_tls_wrappermode=yes
  -o smtpd_proxy_filter=
  -o myhostname=mail.bordo.com.au <http://mail.bordo.com.au/>
465    inet  n       -       n       -       20       smtpd
        -o smtpd_proxy_filter=127.0.0.1:10025
        -o smtpd_client_connection_count_limit=100

proxywrite unix -       -       n       -       1       proxymap
vacation        unix    -       n       n       -       -       pipe
        flags=DRhu user=_vacation argv=/var/spool/vacation/vacation.pl -f 
${sender} -- ${recipient}

dovecot unix - n n - - pipe
  flags=DRhu user=_vmail argv=/usr/local/libexec/dovecot/deliver -f ${sender} 
-d ${recipient}



James.
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