Centos 7 - Sendmail google relay issue

Question

So since my isp's smtp servers didn't work i decided to use google's servers, with port 587 since it isn't blocked. So i followed this tutorial: https://linuxconfig.org/configuring-gmail-as-sendmail-email-relay. And now when i try to send i get this:

sudo /usr/sbin/sendmail -v -q

Running /var/spool/mqueue/u6TBoGKj027936 (sequence 1 of 3)
<jcoatanea@gmail.com>... Connecting to gmail-smtp-msa.l.google.com. port 587 via relay...
220 smtp.gmail.com ESMTP n128sm2730927lfb.45 - gsmtp
>>> EHLO dynavio.com
250-smtp.gmail.com at your service, [87.92.41.2]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
>>> STARTTLS
220 2.0.0 Ready to start TLS
>>> EHLO dynavio.com
250-smtp.gmail.com at your service, [87.92.41.2]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
>>> QUIT
221 2.0.0 closing connection n128sm2730927lfb.45 - gsmtp
<jcoatanea@gmail.com>... Deferred: Temporary AUTH failure

The mail still isn't getting sent, why does setting up sendmail have to be this hard?

Edit:

Ok, i made some changes and now am getting this:
jcoatanea@live.com... Connecting to gmail-smtp-msa.l.google.com. port 587 via relay...
220 smtp.gmail.com ESMTP g69sm5267646lji.44 - gsmtp
>>> EHLO dynavio.com
250-smtp.gmail.com at your service, [87.92.41.2]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
>>> STARTTLS
220 2.0.0 Ready to start TLS
>>> EHLO dynavio.com
250-smtp.gmail.com at your service, [87.92.41.2]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
>>> AUTH LOGIN
334 VXNlcm5hbWU6
>>> ZHluYXZpby5jb29wQGdtYWlsLmNvbQ==
334 UGFzc3dvcmQ6
>>> MTYwOWVlY2M=
534-5.7.14 <https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbuy
534-5.7.14 o2OFUpUafLjLSp0oOwV56X1PMcDOdU_NSJ-tIxcNg4eG05FIMmDPNp0lw6yyn8rt-2JPop
534-5.7.14 wrj3m4AoX4_RYtua4gpoJpBLGbEhdv8cYND0LB7zZFpXFEsZkSAl6Admnz7ocBgzgFmcFJ
534-5.7.14 AWgkWUrUC_TdY1rGh3-E54jrVPt8hkcrW-Kg5cgW10gI8GNgYGfSJcf_p7iS3jeFftT4Ij
534-5.7.14 ETjjxhxKR9Vfoh8TBvSX1W0o40YdA> Please log in via your web browser and
534-5.7.14 then try again.
534-5.7.14  Learn more at
534 5.7.14  https://support.google.com/mail/answer/78754 g69sm5267646lji.44 - gsmtp
>>> AUTH PLAIN cm9vdABkeW5hdmlvLmNvb3BAZ21haWwuY29tADE2MDllZWNj
534-5.7.14 <https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbv8
534-5.7.14 nN0UFd92qcwx3IrSgUlbzsnnHjlfZHm50wV-weu4xEYV8zyIJ4aaVHerzMekBa1o8ApYHO
534-5.7.14 EzwE6hUwDlC1boJKwkoinzqeWSgMLZiY6ki6fMeizSL_OnMcoUJdlva7dg7JUWpnyGiYco
534-5.7.14 l82HioM6NWMIgIdUE8wB35JNnNMOhlmkb0wuG2pffQfPqY6oZW_jR5VWkXl2c5UeOBYK_x
534-5.7.14 rAQNHWWuunvC1fvMbyDL67jtIY0wM> Please log in via your web browser and
534-5.7.14 then try again.
534-5.7.14  Learn more at
534 5.7.14  https://support.google.com/mail/answer/78754 g69sm5267646lji.44 - gsmtp
>>> MAIL From:<duser@dynavio.com> SIZE=67
530-5.5.1 Authentication Required. Learn more at
530 5.5.1  https://support.google.com/mail/answer/14257 g69sm5267646lji.44 - gsmtp
duser... Connecting to local...
duser... Sent
Closing connection to gmail-smtp-msa.l.google.com.
>>> QUIT
221 2.0.0 closing connection g69sm5267646lji.44 - gsmtp

Edit#2: So now it's working, but the from header doesn't work for some reason.

In general questions/problems regarding the usability of or inaccuracies in HOWTO's and manuals should be addressed to their author and not posted on ServerFault. - Alternatively read our [guide to writing good questions](http://meta.serverfault.com/a/3609/37681) and post an [on-topic](http://serverfault.com/help/on-topic) question that contains sufficient details/errors/configuration-settings about **your setup** to provide you with a good solution, rather than confusing the issue with potential issues in both that guide and/or how accurately it was followed. — HBruijn, Jul 29 '16 at 12:07
See for instance [this Q&A](http://serverfault.com/questions/360289/telling-sendmail-to-auth) — HBruijn, Jul 29 '16 at 12:28

score 2 · Accepted Answer · answered Jul 29 '16 at 12:21

As to your question:

why does setting up sendmail have to be this hard?

History.

The author of sendmail has written a nice piece in The Architecture of Open Source Applications about the design choices, the evolution of sendmail, lessons learned and:

17.8.1. Things I Would Do Differently
Perhaps my biggest mistake with sendmail was to not recognize early enough how important it was going to be. I had several opportunities to nudge the world in the correct direction but didn't take them; in fact, in some cases I did damage, e.g., by not making sendmail stricter about bad input when it became appropriate to do so. Similarly, I recognized that the configuration file syntax needed to be improved fairly early on, when there were perhaps a few hundred sendmail instances deployed, but decided not to change things because I didn't want to cause the installed user base undue pain. In retrospect it would have been better to improve things early and cause temporary pain in order to produce a better long-term result.

Centos 7 - Sendmail google relay issue

1 Answers1