Thanks so much for your help.  It changed the bahavior but has not eliminated 
my issue.  Sorry to be such a pain!  A knowledgable person like you should be 
able to see what’s going on. It looks like It is not doing what the server 
expects yet.  Something in my config is still saying “do not send a password.”  
Is there a verbose option or something I can use to help troubleshoot?  

When I made the change you propose, I now get the following messages in my 
mail.log: 

 
------------------------------------------------------------------------------------------

Aug 16 09:20:11 RichCookHomeMac postfix/pickup[40015]: 6524929C83DF: uid=0 
from=<root>
Aug 16 09:20:11 RichCookHomeMac postfix/cleanup[40031]: 6524929C83DF: 
message-id=<20140816162011.6524929c8...@richcook.net>
Aug 16 09:20:11 RichCookHomeMac postfix/qmgr[40016]: 6524929C83DF: 
from=<r...@richcook.net>, size=332, nrcpt=1 (queue active)
Aug 16 09:20:11 RichCookHomeMac postfix/smtp[40033]: Untrusted TLS connection 
established to smtp.comcast.net[76.96.40.155]:587: TLSv1 with cipher 
DHE-RSA-AES256-SHA (256/256 bits)
Aug 16 09:20:12 RichCookHomeMac postfix/smtp[40033]: 6524929C83DF: 
to=<wealthyc...@gmail.com>, relay=smtp.comcast.net[76.96.40.155]:587, 
delay=0.64, delays=0.02/0.03/0.52/0.07, dsn=5.1.0, status=bounced (host 
smtp.comcast.net[76.96.40.155] said: 550 5.1.0 Authentication required (in 
reply to MAIL FROM command))
Aug 16 09:20:12 RichCookHomeMac postfix/bounce[40035]: 6524929C83DF: sender 
non-delivery notification: 152B329C83E1
Aug 16 09:20:12 RichCookHomeMac postfix/qmgr[40016]: 6524929C83DF: removed

 
------------------------------------------------------------------------------------------
Plus a bounce email from comcast, which is no surprise of course given the 
above.  

> This is the mail system at host richcook.net.
> 
> I'm sorry to have to inform you that your message could not
> be delivered to one or more recipients. It's attached below.
> 
> For further assistance, please send mail to postmaster.
> 
> If you do so, please include this problem report. You can
> delete your own text from the attached returned message.
> 
>                   The mail system
> 
> <wealthyc...@gmail.com>: host smtp.comcast.net[76.96.40.155] said: 550 5.1.0
>    Authentication required (in reply to MAIL FROM command)
> Reporting-MTA: dns; richcook.net
> X-Postfix-Queue-ID: F39D529C8122
> X-Postfix-Sender: rfc822; r...@richcook.net
> Arrival-Date: Sat, 16 Aug 2014 09:11:33 -0700 (PDT)
> 
> Final-Recipient: rfc822; wealthyc...@gmail.com
> Action: failed
> Status: 5.1.0
> Remote-MTA: dns; smtp.comcast.net
> Diagnostic-Code: smtp; 550 5.1.0 Authentication required
> 
> From: r...@richcook.net (System Administrator)
> Subject: test
> Date: August 16, 2014 at 9:11:33 AM PDT
> To: wealthyc...@gmail.com
> 
> 
> Sat Aug 16 09:11:33 PDT 2014

 
------------------------------------------------------------------------------------------

Here is the new main.cf configuration: 

#======================================================================
# Apple additions: 
mydomain_fallback = localhost
recipient_delimiter = +
smtpd_tls_ciphers = medium
inet_protocols = all
inet_interfaces = loopback-only
#======================================================================
relayhost=[smtp.comcast.net]:587
smtp_sasl_auth_enable=yes
smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
smtp_use_tls = yes 

smtpd_sasl_auth_enable=yes
smtpd_use_pw_server=yes
enable_server_options=yes
smtpd_pw_server_security_options=plain, login
smtp_tls_loglevel=1
smtpd_sasl_security_options=noanonymous
broken_sasl_auth_clients=yes
smtpd_sasl_local_domain=$mydomain
smtp_sasl_mechanism_filter =


# OLD
# Rich Cook mods: 
message_size_limit = 0
mydomain = richcook.net
myhostname = richcook.net
mynetworks=192.168.0.0/16,rcmac.llnl.gov,localhost,mom.richcook.net
smtpd_client_restrictions = permit_mynetworks permit_sasl_authenticated reject

 
------------------------------------------------------------------------------------------

Thanks again for any help.  
— Rich 

On Aug 16, 2014, at 3:24 AM, Patrick Ben Koetter <p...@sys4.de> wrote:

> The other side offers only PLAIN and LOGIN:
> 
> $ telnet 76.96.40.155 25
> Trying 76.96.40.155...
> Connected to 76.96.40.155.
> Escape character is '^]'.
> 220 omta20.emeryville.ca.mail.comcast.net comcast ESMTP server ready
> EHLO foo
> 250-omta20.emeryville.ca.mail.comcast.net hello [37.5.251.161], pleased to
> meet you
> 250-HELP
> 250-AUTH LOGIN PLAIN
> 250-SIZE 36700160
> 250-ENHANCEDSTATUSCODES
> 250-8BITMIME
> 250-STARTTLS
> 250 OK
> QUIT
> 221 2.0.0 omta20.emeryville.ca.mail.comcast.net comcast closing connection
> 
> 
> PLAIN and LOGIN are disabled on Postfix smtp client side by default, because
> their usage may be insecure over an unencrypted transport - PLAIN and LOGIN do
> not crypt, but only encode username and password:
> 
> smtp_sasl_security_options = noplaintext, noanonymous
> smtp_sasl_tls_security_options = $smtp_sasl_security_options
> smtp_sasl_tls_verified_security_options = $smtp_sasl_tls_security_option
> 
> Change Postfix' SASL policy for TLS shielded connections and it will work:
> 
> smtp_sasl_security_options = noplaintext, noanonymous
> smtp_sasl_tls_security_options = noanonymous
> 
> p@rick
> 
> 
> 
> * Rich Cook <wealthyc...@gmail.com>:
>> Hello, I am having a maddening problem.  I have googled of course for 
>> answers, but I cannot figure out exactly what the issue is.  
>> I am trying to put the final touches on my postfix/fetchmail setup.  Mostly 
>> it's working but the crucial piece I'm missing is the ability to send mail 
>> to other hosts through my comcast relay from the command line.
>> 
>> I can send mail from my mail client but not from the command line via 
>> sendmail, which I would like very much to be able to do.  There is just some 
>> little SASL detail or something going on here that I'm missing.  I could use 
>> a good pair of eyes for help!
>> 
>> To put it in a nutshell, here is what I'm seeing in the logs when I do  
>> "postfix flush":
>> Note that I can telnet to  smtp.comcast.net 587 and make a connection, so I 
>> am ignoring "no route to host" messages at the moment.  Especially since you 
>> can see it does connect.  Config logs are below.  Sorry for the long 
>> message, but I'm hopefully anticipating the questions a knowledgable expert 
>> might ask of me.  :-)
>> 
>> I can ramp up the verbosity but you probably get the idea.  
>> Warm thanks for any help! 
>> 
>> ================================================================================
>>  =============
>> # LOG FILE CONTENTS:
>> Aug 15 12:48:27 RichCookHomeMac postfix/qmgr[60944]: 810762983FD0: 
>> from=<***>, size=332, nrcpt=1 (queue active)
>> Aug 15 12:48:27 RichCookHomeMac postfix/qmgr[60944]: AED65298168E: 
>> from=<***>, size=327, nrcpt=1 (queue active)
>> Aug 15 12:48:27 RichCookHomeMac postfix/qmgr[60944]: AF585298168F: 
>> from=<***>, size=327, nrcpt=1 (queue active)
>> Aug 15 12:48:27 RichCookHomeMac postfix/qmgr[60944]: C873A29816BA: 
>> from=<***>, size=306, nrcpt=1 (queue active)
>> Aug 15 12:48:27 RichCookHomeMac postfix/qmgr[60944]: CFE0E2983B7C: 
>> from=<***>, size=302, nrcpt=1 (queue active)
>> Aug 15 12:48:27 RichCookHomeMac postfix/qmgr[60944]: D71C029816E8: 
>> from=<***>, size=307, nrcpt=1 (queue active)
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61130]: connect to 
>> smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61133]: connect to 
>> smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61132]: connect to 
>> smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61132]: CFE0E2983B7C: to=<***>, 
>> relay=smtp.comcast.net[76.96.40.155]:587, delay=1844, delays=1844/0/0.09/0, 
>> dsn=4.0.0, status=deferred (host smtp.comcast.net[76.96.40.155] refused to 
>> talk to me: 421 omta14.emeryville.ca.mail.comcast.net comcast Too many 
>> sessions opened)
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61130]: Untrusted TLS 
>> connection established to smtp.comcast.net[76.96.40.155]:587: TLSv1 with 
>> cipher DHE-RSA-AES256-SHA (256/256 bits)
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61133]: Untrusted TLS 
>> connection established to smtp.comcast.net[76.96.40.155]:587: TLSv1 with 
>> cipher DHE-RSA-AES256-SHA (256/256 bits)
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61131]: Untrusted TLS 
>> connection established to smtp.comcast.net[76.96.40.155]:587: TLSv1 with 
>> cipher DHE-RSA-AES256-SHA (256/256 bits)
>> Aug 15 12:48:27 RichCookHomeMac postfix/smtp[61134]: Untrusted TLS 
>> connection established to smtp.comcast.net[76.96.40.155]:587: TLSv1 with 
>> cipher DHE-RSA-AES256-SHA (256/256 bits)
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61130]: warning: SASL 
>> authentication failure: No worthy mechs found
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61130]: AED65298168E: to=<***>, 
>> relay=smtp.comcast.net[76.96.40.155]:587, delay=190442, 
>> delays=190441/0/0.39/0, dsn=4.7.0, status=deferred (SASL authentication 
>> failed; cannot authenticate to server smtp.comcast.net[76.96.40.155]: no 
>> mechanism available)
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61133]: warning: SASL 
>> authentication failure: No worthy mechs found
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61133]: 810762983FD0: to=<***>, 
>> relay=smtp.comcast.net[76.96.40.155]:587, delay=1162, delays=1161/0/0.4/0, 
>> dsn=4.7.0, status=deferred (SASL authentication failed; cannot authenticate 
>> to server smtp.comcast.net[76.96.40.155]: no mechanism available)
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61131]: warning: SASL 
>> authentication failure: No worthy mechs found
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61131]: AF585298168F: SASL 
>> authentication failed; cannot authenticate to server 
>> smtp.comcast.net[76.96.40.155]: no mechanism available
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61134]: warning: SASL 
>> authentication failure: No worthy mechs found
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61134]: C873A29816BA: SASL 
>> authentication failed; cannot authenticate to server 
>> smtp.comcast.net[76.96.40.155]: no mechanism available
>> Aug 15 12:48:28 RichCookHomeMac postfix/error[61137]: D71C029816E8: 
>> to=<***>, relay=none, delay=190645, delays=190645/0.41/0/0, dsn=4.7.0, 
>> status=deferred (delivery temporarily suspended: SASL authentication failed; 
>> cannot authenticate to server smtp.comcast.net[76.96.40.155]: no mechanism 
>> available)
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61131]: connect to 
>> smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61131]: AF585298168F: to=<***>, 
>> relay=none, delay=190350, delays=190349/0/0.42/0, dsn=4.4.1, status=deferred 
>> (connect to smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host)
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61134]: connect to 
>> smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host
>> Aug 15 12:48:28 RichCookHomeMac postfix/smtp[61134]: C873A29816BA: to=<***>, 
>> relay=none, delay=190865, delays=190864/0/0.43/0, dsn=4.4.1, status=deferred 
>> (connect to smtp.comcast.net[2001:558:fe2d:70::30]:587: No route to host)
>> 
>> 
>> ================================================================================
>>  =============
>> # main.cf:
>> mydomain_fallback = localhost
>> # message_size_limit = 10485760 # commented out by Rich
>> biff = no
>> #mynetworks = 127.0.0.0/8, [::1]/128
>> #smtpd_client_restrictions = permit_mynetworks permit_sasl_authenticated 
>> permit
>> recipient_delimiter = +
>> smtpd_tls_ciphers = medium
>> inet_protocols = all
>> inet_interfaces = loopback-only
>> #======================================================================
>> # Rich Cook mods:
>> message_size_limit = 0
>> 
>> relayhost=[smtp.comcast.net]:587
>> smtp_sasl_auth_enable=yes
>> smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
>> smtp_use_tls = yes 
>> 
>> smtpd_sasl_auth_enable=yes
>> smtpd_use_pw_server=yes
>> enable_server_options=yes
>> smtpd_pw_server_security_options=plain, login
>> smtp_tls_loglevel=1
>> smtpd_sasl_security_options=noanonymous
>> smtp_tls_security_level=encrypt
>> broken_sasl_auth_clients=yes
>> # commented out as I do not fully understand yet, but does not fix to put it 
>> back in.
>> # smtpd_recipient_restrictions=check_sender_access hash:/etc/postfix/access, 
>> check_client_access hash:/etc/postfix/access, permit_mynetworks, 
>> permit_sasl_authenticated, reject_unauth_destination, check_recipient_access 
>> hash:/etc/postfix/access
>> smtpd_sasl_local_domain=$mydomain
>> smtp_sasl_mechanism_filter =
>> 
>> # =========================================================================
>> root@RichCookHomeMac (postfix ): ls -l /etc/postfix/
>> total 392
>> -rw-r--r--  1 root  wheel  11942 Feb  8  2014 LICENSE
>> -rw-r--r--  1 root  wheel   1629 Feb  8  2014 TLS_LICENSE
>> -rw-r--r--  1 root  wheel  20876 Feb  8  2014 access
>> -rw-r--r--  1 root  wheel  16384 Aug 15 12:17 access.db
>> -rw-r--r--  1 root  wheel   8830 Aug 15 12:28 aliases
>> -rw-r--r--  1 root  wheel   8829 Jun  1 14:57 aliases.desktop
>> -rw-r--r--  1 root  wheel   3548 Feb  8  2014 bounce.cf.default
>> -rw-r--r--  1 root  wheel  11681 Feb  8  2014 canonical
>> -rw-r--r--  1 root  wheel     44 Feb  8  2014 custom_header_checks
>> -rw-------  1 root  wheel    157 Aug 15 11:37 fetchmailrc
>> -rw-r--r--  1 root  wheel   9904 Feb  8  2014 generic
>> -rw-r--r--  1 root  wheel  21535 Feb  8  2014 header_checks
>> -rw-r--r--  1 root  wheel  28864 Aug 15 12:43 main.cf
>> -rw-r--r--  1 root  wheel  26970 Feb  8  2014 main.cf.default
>> -rw-r--r--  1 root  wheel  26155 Jun  1 15:04 main.cf.upgradedMtnLion
>> -rw-r--r--  1 root  wheel  27430 Feb  8  2014 main.cf~orig
>> -rw-r--r--  1 root  wheel   1441 Feb  8  2014 makedefs.out
>> -rw-r--r--  1 root  wheel   7443 Feb  8  2014 master.cf
>> -rw-r--r--  1 root  wheel   7443 Feb  8  2014 master.cf.default
>> -rw-r--r--  1 root  wheel  18473 Feb  8  2014 postfix-files
>> -rw-r--r--  1 root  wheel   6816 Feb  8  2014 relocated
>> -rw-r-----  1 root  wheel     44 Aug 15 10:56 sasl_passwd
>> -rw-r-----  1 root  wheel  16384 Aug 15 12:18 sasl_passwd.db
>> -rw-r--r--  1 root  wheel  12549 Feb  8  2014 transport
>> -rw-r--r--  1 root  wheel  12494 Feb  8  2014 virtual
>> 
>> Rich Cook
>> wealthyc...@gmail.com
>> 
>> ----------------------------------------------
>> If you don't laugh enough, you might have humorrhoids, which is an 
>> enlargement of the onus, and the only thing you can pass then is heavy 
>> judgment.  -- Swami Beyondananda
>> 
>> 
>> 
>> 
>> 
> 
> -- 
> [*] sys4 AG
> 
> https://sys4.de, +49 (89) 30 90 46 64
> Franziskanerstraße 15, 81669 München
> 
> Sitz der Gesellschaft: München, Amtsgericht München: HRB 199263
> Vorstand: Patrick Ben Koetter, Marc Schiffbauer
> Aufsichtsratsvorsitzender: Florian Kirstein
> 

Rich Cook
wealthyc...@gmail.com

----------------------------------------------
If you don't laugh enough, you might have humorrhoids, which is an enlargement 
of the onus, and the only thing you can pass then is heavy judgment.  -- Swami 
Beyondananda





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