E-MailRelay / Support Requests / #68 Gmail relay set up

Graeme Walker - 2022-05-02

Your emailrelay server is not configured to do authentication because you have not used --server-auth. It does not advertise that it can do authentication in the EHLO response but the remote client tries anyway.

You should just add --server-auth pointing at a secrets file containing whatever account details the client is trying to use. Or stop the client from trying to authenticate.

If you would like to refer to this comment somewhere else in this project, copy and paste the following link:

There is nothing in your log snippet that suggests any interaction with gmail. 10.10.10.16 is a local IP address and I can't tell what's trying to authenticate from there. If it's an e-mail client then you need to explore its account settings.

FWIW, you can stop emailrelay from trying to authenticate by removing the --client-auth option.

Note that if you are using emailrelay to send to and also receive from gmail then you will need to run two instances, one upstream and one downstream, with different spool directories and listening addresses.

So I made some changes and this is the error I am receiving at this time, I
definitely feel I've made significant progress and I am close to resolving
this. I just need to be pointed in the right direction.

Any advice is greatly appreciated!
Thank you for your time!

emailrelay: 20220504.112326.393: info: 10.10.10.16; rx<<: "534-5.7.14
emailrelay: 20220504.111803.080: info: forwarding address xxx.xxx.xxx.xx:587
emailrelay: 20220504.111803.084: warning: using --immediate can result in client timeout errors: try --forward-on-disconnect instead
emailrelay: 20220504.111803.086: info: smtp server on 0.0.0.0:25
emailrelay: 20220504.111803.086: info: smtp server on ::.25
emailrelay: 20220504.112324.112: info: 10.10.10.16; smtp connection from 10.10.10.16:57088
emailrelay: 20220504.112324.112: info: 10.10.10.16; tx>>: "220 SERVER.example.local -- E-MailRelay V2.2 -- Service ready"
emailrelay: 20220504.112324.366: info: 10.10.10.16; rx<<: "HELO SASPDM01"
emailrelay: 20220504.112324.367: info: 10.10.10.16; tx>>: "250 OK"
emailrelay: 20220504.112324.632: info: 10.10.10.16; rx<<: "MAIL FROM:<SOLIDWORKS_PDM@email.com>"
emailrelay: 20220504.112324.632: info: 10.10.10.16; content file: C:\ProgramData\E-MailRelay\spool\emailrelay.2092.1651520826.2.content
emailrelay: 20220504.112324.632: info: 10.10.10.16; tx>>: "250 OK"
emailrelay: 20220504.112324.897: info: 10.10.10.16; rx<<: "RCPT TO:<xxxxxxxx@email.com>"
emailrelay: 20220504.112324.898: info: 10.10.10.16; tx>>: "250 OK"
emailrelay: 20220504.112325.163: info: 10.10.10.16; rx<<: "DATA"
emailrelay: 20220504.112325.163: info: 10.10.10.16; tx>>: "354 start mail input -- end with <CRLF>.<CRLF>"
emailrelay: 20220504.112325.429: info: 10.10.10.16; rx<<: [message content not logged]
emailrelay: 20220504.112325.429: info: 10.10.10.16; rx<<: "."
emailrelay: 20220504.112325.429: info: 10.10.10.16; envelope file: C:\ProgramData\E-MailRelay\spool\emailrelay.2092.1651520826.2.envelope.new
emailrelay: 20220504.112325.431: info: 10.10.10.16; locking file "emailrelay.2092.1651520826.2.envelope"
emailrelay: 20220504.112325.436: info: 10.10.10.16; processing message "emailrelay.2092.1651520826.2"
emailrelay: 20220504.112325.491: info: 10.10.10.16; smtp connection to 172.253.115.28:587
emailrelay: 20220504.112325.606: info: 10.10.10.16; rx<<: "220 smtp-relay.gmail.com ESMTP h7-20020a170902f70700b0015e8d4e8673sm693305plo.63 - gsmtp"
emailrelay: 20220504.112325.607: info: 10.10.10.16; tx>>: "EHLO SERVER.example.local"
emailrelay: 20220504.112325.701: info: 10.10.10.16; rx<<: "250-smtp-relay.gmail.com at your service, [172.241.25.231]"
emailrelay: 20220504.112325.701: info: 10.10.10.16; rx<<: "250-SIZE 157286400"
emailrelay: 20220504.112325.701: info: 10.10.10.16; rx<<: "250-8BITMIME"
emailrelay: 20220504.112325.701: info: 10.10.10.16; rx<<: "250-STARTTLS"
emailrelay: 20220504.112325.702: info: 10.10.10.16; rx<<: "250-ENHANCEDSTATUSCODES"
emailrelay: 20220504.112325.702: info: 10.10.10.16; rx<<: "250-PIPELINING"
emailrelay: 20220504.112325.702: info: 10.10.10.16; rx<<: "250-CHUNKING"
emailrelay: 20220504.112325.702: info: 10.10.10.16; rx<<: "250 SMTPUTF8"
emailrelay: 20220504.112325.702: info: 10.10.10.16; tx>>: "STARTTLS"
emailrelay: 20220504.112325.791: info: 10.10.10.16; rx<<: "220 2.0.0 Ready to start TLS"
emailrelay: 20220504.112325.906: info: 10.10.10.16; tls: certificate verification: [peer certificate not signed by a trusted ca]
emailrelay: 20220504.112325.906: info: 10.10.10.16; tls protocol established with 172.253.115.28:587 protocol TLSv1.2 cipher TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256
emailrelay: 20220504.112325.906: info: 10.10.10.16; tx>>: "EHLO SERVER.example.local"
emailrelay: 20220504.112325.996: info: 10.10.10.16; rx<<: "250-smtp-relay.gmail.com at your service, [172.241.25.231]"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250-SIZE 157286400"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250-8BITMIME"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250-ENHANCEDSTATUSCODES"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250-PIPELINING"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250-CHUNKING"
emailrelay: 20220504.112325.997: info: 10.10.10.16; rx<<: "250 SMTPUTF8"
emailrelay: 20220504.112325.997: info: 10.10.10.16; tx>>: "AUTH PLAIN XXX="
emailrelay: 20220504.112326.393: info: 10.10.10.16; rx<<: "534-5.7.14 XXX
emailrelay: 20220504.112326.393: info: 10.10.10.16; rx<<: "534-5.7.14 XXX"
emailrelay: 20220504.112326.393: info: 10.10.10.16; rx<<: "534-5.7.14 XXX"
emailrelay: 20220504.112326.393: info: 10.10.10.16; rx<<: "534-5.7.14 Please log in via your web browser and then try again."
emailrelay: 20220504.112326.393: info: 10.10.10.16; rx<<: "534-5.7.14 Learn more at"
emailrelay: 20220504.112326.394: info: 10.10.10.16; rx<<: "534 5.7.14 https://support.google.com/mail/answer/XXX - gsmtp"
emailrelay: 20220504.112326.394: info: 10.10.10.16; smtp error: authentication failed using mechanism [plain] and plaintext secret for [xxxx@gmail.com] from line 10: [XXX]"
emailrelay: 20220504.112326.394: info: 10.10.10.16; tx>>: "AUTH LOGIN XXX=="
emailrelay: 20220504.112326.483: info: 10.10.10.16; rx<<: "334 UGFzc3dvcmQ6"
emailrelay: 20220504.112326.483: info: 10.10.10.16; tx>>: [response not logged]
emailrelay: 20220504.112326.767: info: 10.10.10.16; rx<<: "534-5.7.14 https://accounts.google.com/signin/XXX"
emailrelay: 20220504.112326.768: info: 10.10.10.16; rx<<: "534-5.7.14 XXX"
emailrelay: 20220504.112326.768: info: 10.10.10.16; rx<<: "534-5.7.14 XXX"
emailrelay: 20220504.112326.768: info: 10.10.10.16; rx<<: "534-5.7.14 Please log in via your web browser and then try again."
emailrelay: 20220504.112326.768: info: 10.10.10.16; rx<<: "534-5.7.14 Learn more at"
emailrelay: 20220504.112326.768: info: 10.10.10.16; rx<<: "534 5.7.14 https://support.google.com/mail/answer/XXX"
emailrelay: 20220504.112326.768: info: 10.10.10.16; smtp client error: smtp error: authentication failed using mechanism [login] and plaintext secret for [xxxx@gmail.com] from line 10: [XXX]
emailrelay: 20220504.112326.769: info: 10.10.10.16; failing file: "emailrelay.2092.1651520826.2.envelope.busy" -> "emailrelay.2092.1651520826.2.envelope.bad"
emailrelay: 20220504.112326.769: info: 10.10.10.16; tx>>: "452 forwarding failed"
emailrelay: 20220504.112326.985: info: 10.10.10.16; rx<<: "QUIT"
emailrelay: 20220504.112326.985: info: 10.10.10.16; tx>>: "221 OK"
emailrelay: 20220504.112326.985: info: 10.10.10.16; smtp connection closed: smtp protocol done: 10.10.10.16:57088

Carlos Garcia
Carlos@xpertekit.com daniel@xpertekit.com | 972.591.6019 <9725916019>
XPERTEK IT
3044 Old Denton Rd Ste 111-262
Carrollton, TX 75007

Last edit: Graeme Walker 2022-05-05

alternate

Graeme Walker - 2022-05-05

I've sanitied your log snippet so that it's more readable through this web interface, but the log just shows that you have authentication errors when connecting to gmail.

Note that the error response from google says 'please log in via your web browser' and it also contains a link to one of their help pages. Have you tried following that link?

If you would like to refer to this comment somewhere else in this project, copy and paste the following link:
- Carlos Garcia - 2022-05-05
  
  Graeme,
  
  Thank you so much! That's exactly what I needed. Since gmail is forcing
  2FA, this particular account (which had 2FA disabled) was not allowing me
  to sign in to gmail because of that. I used the app password & voila!
  
  Thank you again, I appreciate your swift responses.
  You've been a great help!
  
  Carlos Garcia
  Carlos@xpertekit.com daniel@xpertekit.com | 972.591.6019 <9725916019>
  XPERTEK IT
  3044 Old Denton Rd Ste 111-262
  Carrollton, TX 75007
  www.xpertekit.com
  [image: twitter icon] https://twitter.com/xpertekit [image: linkedin icon]
  https://www.linkedin.com/company/xpertek/
  
  On Wed, May 4, 2022 at 9:32 PM Graeme Walker graeme_walker@users.sourceforge.net wrote:
  
  I've sanitied your log snippet so that it's more readable through this web
  interface, but the log just shows that you have authentication errors when
  connecting to gmail.
  
  Note that the error response from google says 'please log in via your web
  browser' and it also contains a link to one of their help pages. Have you
  tried following that link?
  
  [support-requests:#68]
  https://sourceforge.net/p/emailrelay/support-requests/68/ Gmail relay set
  up *
  
  Status: open
  Group: v1.0 (example)
  Created: Mon May 02, 2022 02:08 PM UTC by Carlos Garcia
  Last Updated: Mon May 02, 2022 06:49 PM UTC
  Owner: nobody
  
  I am attempting to establish gmail relay and and I can see messages making
  it thru on incoming but they do not make it to outgoing thus, they never
  get sent via gmail.
  
  The following are the logs. Please advise if something looks out of the
  regular.
  
  emailrelay: 20220429.110638.517: info: 10.10.10.16; smtp connection from
  10.10.10.16:54218
  emailrelay: 20220429.110638.517: info: 10.10.10.16; tx>>: "220
  PCNAME.exaple.local -- E-MailRelay V2.2 -- Service ready"
  emailrelay: 20220429.110638.777: info: 10.10.10.16; rx<<: "EHLO SASPDM01"
  emailrelay: 20220429.110638.778: info: 10.10.10.16; tx>>:
  "250-PCNAME.exmple.local says hello\r\n250-VRFY\r\n250 8BITMIME"
  emailrelay: 20220429.110639.042: info: 10.10.10.16; rx<<: "AUTH LOGIN"
  emailrelay: 20220429.110639.042: warning: 10.10.10.16; client protocol
  error: AUTH requested but not advertised
  emailrelay: 20220429.110639.042: info: 10.10.10.16; tx>>: "502 command not
  implemented"
  emailrelay: 20220429.110639.292: info: 10.10.10.16; rx<<: "QUIT"
  emailrelay: 20220429.110639.292: info: 10.10.10.16; tx>>: "221 OK"
  emailrelay: 20220429.110639.292: info: 10.10.10.16; smtp connection
  closed: smtp protocol done: 10.10.10.16:54218
  
  Sent from sourceforge.net because you indicated interest in
  https://sourceforge.net/p/emailrelay/support-requests/68/
  
  To unsubscribe from further messages, please visit
  https://sourceforge.net/auth/subscriptions/
  
  Related
  
  Support Requests: ~~#68~~
  
  alternate
  
  If you would like to refer to this comment somewhere else in this project, copy and paste the following link:

Description has changed:

Diff:

--- old
+++ new
@@ -1,4 +1,3 @@
-
 I am attempting to establish gmail relay and and I can see messages making it thru on incoming but they do not make it to outgoing thus, they never get sent via gmail. 

 The following are the logs. Please advise if something looks out of the regular.

status: open --> closed

Gmail relay set up

SMTP email proxy and relay server

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Searches

Help

#68 Gmail relay set up

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