On 12 Jun 2019, at 20:28, David Drum wrote:

Matus UHLAR wrote:

out from your postfix server? This looks like you have problems sending out to your postfix server

Yes, that is a better way to phrase it.

and this looks like your client IP is rejected.

Why would it be, when I am coming from mynetworks? In any case, given that

and this looks like your mail client did not authenticate to postfix.

I have double-checked my Mail.app client configuration and password. I still cannot send mail from my client to postfix for delivery locally or remotely. Is there anything about my postfix configuration telling it not to prompt clients for credentials? How would I go about fixing it?

I don't see anything that should be causing the rejection other than the possible lack of SASL authentication.

Since you're using Mail.app, you can get a detailed log of a test mail submission session with the "Connection Doctor" feature. That log will show whether you are getting the right responses to EHLO from Postfix before and after TLS establishment that would tell Mail.app to try to authenticate. The log should look something like the attached example.

--
Bill Cole
b...@scconsult.com or billc...@apache.org
(AKA @grumpybozo and many *@billmail.scconsult.com addresses)
INITIATING CONNECTION Jun 12 21:31:16.731 host:toaster.scconsult.com -- 
port:587 -- socket:0x0 -- thread:0x604000c61bc0

CONNECTED Jun 12 21:31:16.803 [kCFStreamSocketSecurityLevelNone] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0

READ Jun 12 21:31:16.842 [kCFStreamSocketSecurityLevelNone] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
220 toaster.scconsult.com ESMTP Postfix

WROTE Jun 12 21:31:16.853 [kCFStreamSocketSecurityLevelNone] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
EHLO [192.168.254.125]

READ Jun 12 21:31:16.905 [kCFStreamSocketSecurityLevelNone] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
250-toaster.scconsult.com
250-PIPELINING
250-SIZE 40960000
250-ETRN
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250-SMTPUTF8
250 CHUNKING

WROTE Jun 12 21:31:16.905 [kCFStreamSocketSecurityLevelNone] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
STARTTLS

READ Jun 12 21:31:16.916 [kCFStreamSocketSecurityLevelNone] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
220 2.0.0 Ready to start TLS

WROTE Jun 12 21:31:16.930 [kCFStreamSocketSecurityLevelTLSv1_2] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
EHLO [192.168.254.125]

READ Jun 12 21:31:16.969 [kCFStreamSocketSecurityLevelTLSv1_2] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
250-toaster.scconsult.com
250-PIPELINING
250-SIZE 40960000
250-ETRN
250-AUTH PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250-SMTPUTF8
250 CHUNKING

WROTE Jun 12 21:31:16.969 [kCFStreamSocketSecurityLevelTLSv1_2] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
AUTH PLAIN ********************

READ Jun 12 21:31:17.680 [kCFStreamSocketSecurityLevelTLSv1_2] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
235 2.7.0 Authentication successful

WROTE Jun 12 21:31:17.680 [kCFStreamSocketSecurityLevelTLSv1_2] -- 
host:toaster.scconsult.com -- port:587 -- socket:0x60c0008b5600 -- 
thread:0x604000c61bc0
QUIT

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