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:
On 15 Dec 2018, at 3:28 am, Daniel Miller <dmil...@amfes.com <mailto:dmil...@amfes.com>> wrote:

Ok - so you have Postfix listening.  There's a few different choices available to have Postfix forward to ASSP.  I would recommend using Postfix's before-queue content filter method.

The entries you've setup in master.cf already are for mail that has been processed by ASSP and now needs delivery.  Again - before proceeding further you need to verify things work - clients can connect and authenticate and send via your existing ASSP/Postfix/Dovecot chain.

Now in master.cf:

465      inet  n       -       n       -       20      smtpd
         -osmtpd_proxy_filter  
<http://www.postfix.org/postconf.5.html#smtpd_proxy_filter>=127.0.0.1:10025
         -osmtpd_client_connection_count_limit  
<http://www.postfix.org/postconf.5.html#smtpd_client_connection_count_limit>=10

Note the above address/port are arbitrary - pick what you want though the localhost address is appropriate given your setup.  The "smtpd_client_connection_count_limit" may be adjusted as needed.  It is also up to you whether or not to have additional validation checks in this Postfix listener (you should - let Postfix block out whatever it can before it touches ASSP otherwise there's not much point in this approach).

The "smtpd_proxy_filter" tells Postfix to forward mail to another server for processing prior to delivery.  So ASSP needs to be listening for that connection.  You can use the primary listeners listenPort, listenPort2, and listenPortSSL but probably a better choice is to configure ASSP with:

     relayPort=127.0.0.1:10025

That matches the setting in master.cf above - and that should do it.  To make it SSL - for the master.cf entry above for 465 add

     -o smtpd_tls_wrappermode=yes

and in ASSP make it

     relayPort=SSL:127.0.0.1:10025
Daniel

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?

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.


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.

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".

Daniel

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