Hi, can you manually use commands to test the U/P are working from your postfix 
server ?

1. Run this to test connectivity to your server 
openssl s_client -starttls smtp -connect your.host.name:587
        Typical OUTPUT =
                250 DSN
                quit
                221 2.0.0 Bye
                closed

2. Run this to create a hash
python -c 'import base64,sys; u,p=sys.argv[1:3]; print 
base64.encodestring("%s\x00%s\x00%s" % (u,u,p))' username password
        OUTPUT = dXNlcm5hbWUAdXNlcm5hbWUAcGFzc3dvcmQ=
Replace username and password with real ones


Once Steps 1 and 2 work, you can test authentication with the hash in Step 3

3. Run the openssl commands and connect to your server.
        A. do and "ehlo domain" to see commands supported
                EXAMPLE :
                ehlo domain
                250-localpart.domain.part
                250-PIPELINING
                250-SIZE 31457280
                250-VRFY
                250-ETRN
                250-AUTH PLAIN LOGIN
                250-ENHANCEDSTATUSCODES
                250-8BITMIME
                250 DSN
        B. execute the AUTH PLAIN LOGIN command option using the HASH you made 
in Step 3
                AUTH PLAIN dXNlcm5hbWUAdXNlcm5hbWUAcGFzc3dvcmQ=         

        C. look for output
                235 2.7.0 Authentication successful


-ANGELO FAZZINA

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-----Original Message-----
From: owner-postfix-us...@postfix.org <owner-postfix-us...@postfix.org> On 
Behalf Of Michael
Sent: Monday, January 14, 2019 1:00 PM
To: postfix-users@postfix.org
Subject: Re: New SASL error when relaying through gmail

On 1/14/19 10:42 AM, Christopher van de Sande wrote:
> Just a guess, but are you using App passwords for GMail?  It's 
> possible Gmail is enforcing some 2FA/MFA or otherwise some kind of 
> "enhanced" authentication.
>
> Even if you aren't using 2FA, it might be worth giving a shot.
>
>> I thought this might be the case as well.   I reset the password the 
>> account password and also re-setup the application password on the 
>> gmail account for postfix (in my my sasl password file). That didn't 
>> seem to make a difference.   Is there an easy way to test the app 
>> password on google?
>>
>>
>> Michael
>>
>>


I went back into my account and turned on less secure apps and turned 
off 2FA.    I tried again with the regular password and the app 
password.   Still the same error.     I hate when things work and then 
suddenly break :(


Michael


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