Discussion:
reportbug and GMail SMTP servers
(too old to reply)
Sophoklis Goumas
2016-11-05 14:42:55 UTC
Permalink
Hello.

Anybody else having troubles when using GMails' SMTP servers?

Does one need to to enable adjust appropriately the "Allow less secure
apps" setting [1] ?

Excerpts from my ~/.reportbugrc:
smtphost "smtp.gmail.com:587"
smtpuser "***@gmail.com"
smtptls

Error messages received:
Enter SMTP password for ***@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed. Try again.
Connecting to smtp.gmail.com:587 via SMTP...
Enter SMTP password for ***@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed. Try again.
Connecting to smtp.gmail.com:587 via SMTP...
Enter SMTP password for ***@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed. Try again.
SMTP send failure: (534, '5.7.14
<https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbs-\n5.7.14
4KseUxkpnd4ZLZDr-do4jBwza3dZKvET3qBcCazVkiD2TVwsWeD1KwWbj4Cz_b8m7O7HE-\n5.7.14
-7ZjAjS6oxY5WVTKtlcKpofyX3HkQPsSkhhTsCnAiYgKPFD_fjiLUMCZnMe18bezc237Xq\n5.7.14
gUUazTO6tHljaGpzmXMhJdm8qLK_W5mm2cTE0gfSNKu6MrYwWAoTwT-3GzQBOl7XWRgDji\n5.7.14
s1KvnQqzHAr9ArBlw7aDzhVoSAQX0> Please log in via your web browser
and\n5.7.14
then try again.\n5.7.14 Learn more at\n5.7.14
https://support.google.com/mail/answer/78754 k2sm8729843wjv.11 -
gsmtp'). Do you want to retry (or else save the report and exit)?
[Y|n|q|?]? q

Thanks in advance,
Sophoklis

[1] https://support.google.com/accounts/answer/6010255
Henning Follmann
2016-11-05 15:47:24 UTC
Permalink
Post by Sophoklis Goumas
Hello.
Anybody else having troubles when using GMails' SMTP servers?
Does one need to to enable adjust appropriately the "Allow less secure
apps" setting [1] ?
smtphost "smtp.gmail.com:587"
smtptls
SMTP error: authentication failed. Try again.
Connecting to smtp.gmail.com:587 via SMTP...
SMTP error: authentication failed. Try again.
Connecting to smtp.gmail.com:587 via SMTP...
SMTP error: authentication failed. Try again.
SMTP send failure: (534, '5.7.14
<https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbs-\n5.7.14
4KseUxkpnd4ZLZDr-do4jBwza3dZKvET3qBcCazVkiD2TVwsWeD1KwWbj4Cz_b8m7O7HE-\n5.7.14
-7ZjAjS6oxY5WVTKtlcKpofyX3HkQPsSkhhTsCnAiYgKPFD_fjiLUMCZnMe18bezc237Xq\n5.7.14
gUUazTO6tHljaGpzmXMhJdm8qLK_W5mm2cTE0gfSNKu6MrYwWAoTwT-3GzQBOl7XWRgDji\n5.7.14
s1KvnQqzHAr9ArBlw7aDzhVoSAQX0> Please log in via your web browser
and\n5.7.14
then try again.\n5.7.14 Learn more at\n5.7.14
https://support.google.com/mail/answer/78754 k2sm8729843wjv.11 -
gsmtp'). Do you want to retry (or else save the report and exit)?
[Y|n|q|?]? q
What's not to understand. You do not authenticate properly.
Why is that a debian issue? (It is not)

-H
--
Henning Follmann | ***@itcfollmann.com
Sophoklis Goumas
2016-11-05 16:22:56 UTC
Permalink
Post by Henning Follmann
What's not to understand. You do not authenticate properly.
Well, some useful feedback to it would be if someone just using those
configurations options I've showcased (or others) can authenticate succesfuly.
Post by Henning Follmann
Why is that a debian issue? (It is not)
Did I claim this is a debian issue?
I was asking for some help on resolving this as I'm inputting my
password correctly
hoping to fix my issue and correct/update the relevant information on
debian's wiki:
https://wiki.debian.org/reportbug#Using_GMail.27s_SMTP_Server

Sophoklis
Henning Follmann
2016-11-06 12:16:29 UTC
Permalink
Post by Sophoklis Goumas
Post by Henning Follmann
What's not to understand. You do not authenticate properly.
Well, some useful feedback to it would be if someone just using those
configurations options I've showcased (or others) can authenticate succesfuly.
Post by Henning Follmann
Why is that a debian issue? (It is not)
Did I claim this is a debian issue?
I was asking for some help on resolving this as I'm inputting my
password correctly
hoping to fix my issue and correct/update the relevant information on
https://wiki.debian.org/reportbug#Using_GMail.27s_SMTP_Server
Hello,

well this is an Debian mailing list, and in general debian related issues
are discussed here.

However...
So you said that you were able to relay mails axacly this way and now it's
not working anymore?
Because it looks like you did not send this e-mail this way. So I suspect
that your mail system is not properly configured.

So anyone can help you it would help if you provide a little more useful
information.
What MTA are you using? (Exim, Postfix...)
Have you ever sent a mail via this successfully?

BTW. I still think that setting up mail is one of the most problematic
issues when it comes to system administration. 100 ways to do it 1000 ways
to get it wrong.


-H
--
Henning Follmann | ***@itcfollmann.com
Brad Rogers
2016-11-06 12:20:44 UTC
Permalink
On Sun, 6 Nov 2016 07:16:29 -0500
Henning Follmann <***@itcfollmann.com> wrote:

Hello Henning,

This is really for the benefit of the OP, rather than yourself....
Post by Henning Follmann
So you said that you were able to relay mails axacly this way and now
it's not working anymore?
Because google consider anything not written by them to be "insecure".
For some time now google has disallowed (by default) what they deem to be
insecure connections. As a result, one has to alter settings to "allow
unsafe connections", or whatever they call it.

No idea where to look in google's setting pages, since I don't use
google.
--
Regards _
/ ) "The blindingly obvious is
/ _)rad never immediately apparent"
They said we'd be artistically free, but that was on a bit of paper
Complete Control - The Clash
Sophoklis Goumas
2016-11-06 14:57:02 UTC
Permalink
Post by Brad Rogers
Because google consider anything not written by them to be "insecure".
For some time now google has disallowed (by default) what they deem to be
insecure connections. As a result, one has to alter settings to "allow
unsafe connections", or whatever they call it.
Is that really the case?

Is Google just being stubborn or are they just actually trying to
enforce, in their way, some more secure way which reportbug is not
compatible to comply with yet?

Sophoklis
Brad Rogers
2016-11-06 15:07:05 UTC
Permalink
On Sun, 6 Nov 2016 16:57:02 +0200
Sophoklis Goumas <***@gmail.com> wrote:

Hello Sophoklis,
Post by Sophoklis Goumas
Is Google just being stubborn or are they just actually trying to
enforce, in their way, some more secure way which reportbug is not
compatible to comply with yet?
It's google being google. It's their servers, their rules. Like I said,
it is possible to configure a google account to allow connections to
non-google software, but where to find the right box to (un)tick, I have
no idea.
--
Regards _
/ ) "The blindingly obvious is
/ _)rad never immediately apparent"
Bet you thought you knew what I was about
Problem - Sex Pistols
Sophoklis Goumas
2016-11-07 12:49:42 UTC
Permalink
Post by Brad Rogers
...
It's google being google. It's their servers, their rules. Like I said,
it is possible to configure a google account to allow connections to
non-google software, but where to find the right box to (un)tick, I have
no idea.
http://www.google.com/settings/security/lesssecureapps

Sophoklis
Henning Follmann
2016-11-06 15:28:38 UTC
Permalink
Post by Sophoklis Goumas
Post by Brad Rogers
Because google consider anything not written by them to be "insecure".
For some time now google has disallowed (by default) what they deem to be
insecure connections. As a result, one has to alter settings to "allow
unsafe connections", or whatever they call it.
Is that really the case?
Is Google just being stubborn or are they just actually trying to
enforce, in their way, some more secure way which reportbug is not
compatible to comply with yet?
It has nothing to do with reportbug. Forget about reportbug here.
Configure you mail setup properly and then reportbug will work too.

-H
--
Henning Follmann | ***@itcfollmann.com
Brian
2016-11-06 15:44:49 UTC
Permalink
Post by Henning Follmann
Post by Sophoklis Goumas
Post by Brad Rogers
Because google consider anything not written by them to be "insecure".
For some time now google has disallowed (by default) what they deem to be
insecure connections. As a result, one has to alter settings to "allow
unsafe connections", or whatever they call it.
Is that really the case?
Is Google just being stubborn or are they just actually trying to
enforce, in their way, some more secure way which reportbug is not
compatible to comply with yet?
It has nothing to do with reportbug. Forget about reportbug here.
I'd agree with that (it can be tested if needs be). In his reportbug
preferences file Sophoklis Goumas has

smtphost "smtp.gmail.com:587"
smtpuser "***@gmail.com"
#smtppasswd "my password here"

The third line is commented out.
Post by Henning Follmann
Configure you mail setup properly and then reportbug will work too.
Postfix has nothing to do with it either because it is not being used.
The mail is going directly to gmail.

Google accepts mail for relaying on port 25;

sendemail -vv -t <A> -f <B> -m TEST -u test -s smtp.gmail.com:25 -xu <C> -xp <D>

STARTTLS is used.

The sendemail package is useful for this sort of test.
--
Brian.
Mark Fletcher
2016-11-06 22:51:39 UTC
Permalink
Post by Brian
Post by Henning Follmann
Post by Sophoklis Goumas
Post by Brad Rogers
Because google consider anything not written by them to be "insecure".
For some time now google has disallowed (by default) what they deem to be
insecure connections. As a result, one has to alter settings to "allow
unsafe connections", or whatever they call it.
Is that really the case?
Is Google just being stubborn or are they just actually trying to
enforce, in their way, some more secure way which reportbug is not
compatible to comply with yet?
It has nothing to do with reportbug. Forget about reportbug here.
I'd agree with that (it can be tested if needs be). In his reportbug
preferences file Sophoklis Goumas has
smtphost "smtp.gmail.com:587"
#smtppasswd "my password here"
The third line is commented out.
This. This is the answer. As usual Brian has nailed it. The OP is not
supplying a password when logging in. Google are not going to be happy
about that.

Mark
Sophoklis Goumas
2016-11-07 12:46:01 UTC
Permalink
Post by Mark Fletcher
Post by Brian
I'd agree with that (it can be tested if needs be). In his reportbug
preferences file Sophoklis Goumas has
smtphost "smtp.gmail.com:587"
#smtppasswd "my password here"
The third line is commented out.
This. This is the answer. As usual Brian has nailed it. The OP is not
supplying a password when logging in. Google are not going to be happy
about that.
Instead of having my password in cleartext in a text file, I've
prefere to have it
commented out, so whenever reportbugs will need it, it will ask me for it.

As I've displayed in my initial post, namely:

Enter SMTP password for ***@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed. Try again.

Between these lines I input my password and then hit Enter.

Sophoklis
David Wright
2016-11-07 13:52:08 UTC
Permalink
Post by Sophoklis Goumas
Post by Mark Fletcher
Post by Brian
I'd agree with that (it can be tested if needs be). In his reportbug
preferences file Sophoklis Goumas has
smtphost "smtp.gmail.com:587"
#smtppasswd "my password here"
The third line is commented out.
This. This is the answer. As usual Brian has nailed it. The OP is not
supplying a password when logging in. Google are not going to be happy
about that.
Instead of having my password in cleartext in a text file, I've
prefere to have it
commented out, so whenever reportbugs will need it, it will ask me for it.
SMTP error: authentication failed. Try again.
Between these lines I input my password and then hit Enter.
Did you encode it in Base64, or is what you type it into
doing this on your behalf?

Cheers,
David.
Sophoklis Goumas
2016-11-07 14:32:24 UTC
Permalink
Post by David Wright
Did you encode it in Base64, or is what you type it into
doing this on your behalf?
Just typed the password, as always. Meaning unencoded.
This is another part that maybe I haven't cleared out.

I never had an MTA setup, I always had the postfix packages
and their documentation for educational purposes, but this
was never actually setup to send and receive email.

Regardless, reportbug WAS working.

Once more, what I'm trying to figure out is why should reportbug
be labeled as a less secure app and what needs to be done
in order to be able to send reports through it without having to
"lower" down your Google security profile.

Sophoklis
Brian
2016-11-07 17:32:24 UTC
Permalink
Post by Sophoklis Goumas
Post by David Wright
Did you encode it in Base64, or is what you type it into
doing this on your behalf?
Just typed the password, as always. Meaning unencoded.
This is another part that maybe I haven't cleared out.
I never had an MTA setup, I always had the postfix packages
and their documentation for educational purposes, but this
was never actually setup to send and receive email.
Regardless, reportbug WAS working.
Once more, what I'm trying to figure out is why should reportbug
be labeled as a less secure app and what needs to be done
in order to be able to send reports through it without having to
"lower" down your Google security profile.
I do not know what a Google security profile is and have no intention
of finding out. I do not want one but presumably you do. How do you
know reportbug is being labelled as anything by Google? If your mail
is not being relayed by Google it is between you and them and nothing
to do with reportbug. A command to use for testing has been given.

Anyway, I followed the "Using GMail's SMTP Server" section on the wiki
to the letter and had no problem sending a report to the BTS. It was
done with complete security.

That is the second test of the Google mail system I have done. Your
setup at Google may be different from mine. That is where you want to
look. It is you that have to change; don't expect Google to.
--
Brian.
Henning Follmann
2016-11-07 17:56:12 UTC
Permalink
Post by Brian
Post by Sophoklis Goumas
Post by David Wright
Did you encode it in Base64, or is what you type it into
doing this on your behalf?
Just typed the password, as always. Meaning unencoded.
This is another part that maybe I haven't cleared out.
I never had an MTA setup, I always had the postfix packages
and their documentation for educational purposes, but this
was never actually setup to send and receive email.
Regardless, reportbug WAS working.
Once more, what I'm trying to figure out is why should reportbug
be labeled as a less secure app and what needs to be done
in order to be able to send reports through it without having to
"lower" down your Google security profile.
I do not know what a Google security profile is and have no intention
of finding out. I do not want one but presumably you do. How do you
know reportbug is being labelled as anything by Google? If your mail
is not being relayed by Google it is between you and them and nothing
to do with reportbug. A command to use for testing has been given.
Anyway, I followed the "Using GMail's SMTP Server" section on the wiki
to the letter and had no problem sending a report to the BTS. It was
done with complete security.
That is the second test of the Google mail system I have done. Your
setup at Google may be different from mine. That is where you want to
look. It is you that have to change; don't expect Google to.
Amen!
This should now be official gospel for the rest of this thread.

Class dismissed.

-H
--
Henning Follmann | ***@itcfollmann.com
Sophoklis Goumas
2016-11-09 14:50:03 UTC
Permalink
Post by Henning Follmann
Amen!
This should now be official gospel for the rest of this thread.
Class dismissed.
Agreed.

But let's just clarify that these authentication failures are not
because of MTA configuration only but also a matter of
Google's "email relay hardening".

One should allow "less secure apps" [1] in order to be able to send
out bug reports via his GMail account.

Thanks everyone for your valuable contribution,
Sophoklis

[1] https://support.google.com/accounts/answer/6010255
https://www.google.com/settings/security/lesssecureapps
Lisi Reisz
2016-11-09 14:58:15 UTC
Permalink
Post by Sophoklis Goumas
But let's just clarify that these authentication failures are not
because of MTA configuration only but also a matter of
Google's "email relay hardening".
That is why it is a matter for _Google_ and your relationship with Google, and
nothing to do with this list.
Post by Sophoklis Goumas
One should allow "less secure apps" [1] in order to be able to send
out bug reports via his GMail account.
Lisi

emetib
2016-11-05 16:30:31 UTC
Permalink
Post by Sophoklis Goumas
Hello.
Anybody else having troubles when using GMails' SMTP servers?
no
Post by Sophoklis Goumas
Does one need to to enable adjust appropriately the "Allow less secure
apps" setting [1] ?
yes

https://www.howtoforge.com/tutorial/configure-postfix-to-use-gmail-as-a-mail-relay/
Michael Milliman
2016-11-05 19:27:38 UTC
Permalink
Post by emetib
Post by Sophoklis Goumas
Hello.
Anybody else having troubles when using GMails' SMTP servers?
no
It would help to know exactly what the problem is that you are having.
What email client are you using? What is happenning? It is impossible to give you any real information without knowing what the problem is with what software.
Post by emetib
Post by Sophoklis Goumas
Does one need to to enable adjust appropriately the "Allow less secure
apps" setting [1] ?
yes
https://www.howtoforge.com/tutorial/configure-postfix-to-use-gmail-as-a-mail-relay/
--
73s de WB5VQX
--
73s de WB5VQX
Sophoklis Goumas
2016-11-05 21:05:06 UTC
Permalink
On 5 November 2016 at 21:27, Michael Milliman
Post by Michael Milliman
It would help to know exactly what the problem is that you are having.
What email client are you using? What is happenning? It is impossible to give you any real information without knowing what the problem is with what software.
I used to have reportbug relay bugs reports from my GMail account
to debian's bug repository and I have begun receiving authentication
errors.

Seems like, that you need to "lower" your security capabilities
in order to have it working and I'm currently working on poking about
whether that is the only way for things to be anymore or one would
expect things to improve.

I have supplied more information in my initial message:
https://lists.debian.org/debian-user/2016/11/msg00087.html

Sophoklis
Lisi Reisz
2016-11-06 11:54:16 UTC
Permalink
Post by Sophoklis Goumas
https://lists.debian.org/debian-user/2016/11/msg00087.html
That is a matter of opinion.

You haven't said what email client you are using, for a start. Some people
have assumed that you are using your own mail server. Are you? Are you
perhaps just using Gmail's own mail interface??

What exactly are you doing immediately before you fail to send?

What have you got in /home/$USER/.reportbugrc?

Etc.

It is difficult to impossible to help you without some basic information.

Lisi
Sophoklis Goumas
2016-11-06 14:53:39 UTC
Permalink
Post by Lisi Reisz
...
You haven't said what email client you are using, for a start. Some people
have assumed that you are using your own mail server. Are you? Are you
perhaps just using Gmail's own mail interface??
Postfix.
Here is my /etc/postfix/main.cf :
http://paste.debian.net/plain/892989
Post by Lisi Reisz
What exactly are you doing immediately before you fail to send?
I am inputting my Google Account password (correctly and checked).
Post by Lisi Reisz
What have you got in /home/$USER/.reportbugrc?
Here is my ~/.reportbugrc :
http://paste.debian.net/plain/892990

Sophoklis
Henning Follmann
2016-11-06 15:48:18 UTC
Permalink
Post by Henning Follmann
Post by Lisi Reisz
...
You haven't said what email client you are using, for a start. Some people
have assumed that you are using your own mail server. Are you? Are you
perhaps just using Gmail's own mail interface??
Postfix.
http://paste.debian.net/plain/892989
It is not configured at all.
Post by Henning Follmann
Post by Lisi Reisz
What exactly are you doing immediately before you fail to send?
I am inputting my Google Account password (correctly and checked).
how?
In your postfix config you have not provided a relay host or a smtp
authentication map.
You have not configure TLS, I assume google allows only authentication over
TLS. (I would)
Post by Henning Follmann
Post by Lisi Reisz
What have you got in /home/$USER/.reportbugrc?
http://paste.debian.net/plain/892990
Yes,
you are not using your local setup.

You are submitting directly to googles MTA.
You have to figure out, how google expects you to authenticate.


May I suggest you configure your local mail setup properly, and then use
that setup for everything? It is much easier that way.

-H
--
Henning Follmann | ***@itcfollmann.com
Sophoklis Goumas
2016-11-07 12:52:30 UTC
Permalink
Post by Henning Follmann
You are submitting directly to googles MTA.
You have to figure out, how google expects you to authenticate.
This is exactly the purpose of this thread, let's investigate of a way that one:
- could sent directly to Google's MTA but
- without having to "lower" his security (why would "reportbug" need
to be less secure, after all?)
- update the corresponding debian's wiki page on reportbug

Sophoklis
Lisi Reisz
2016-11-07 16:04:17 UTC
Permalink
Post by Sophoklis Goumas
- update the corresponding debian's wiki page on reportbug
Since you obviously don't want to use any of what has been suggested, and
since reportbug seems to be the only/main(?) bugbear, why not:

Purge reportbug
Make sure you have removed/deleted all reportbug config files and all
reportbug packages from your database (locate is your friend).
(Re)install reportbug, but when answering the setup questions say that you
want reportbug to use Debian's SMTP, as offered.

Presenting problem solved, without in any way compromising your security. You
just bypass Gmail.

Lisi
Sophoklis Goumas
2016-11-05 20:58:03 UTC
Permalink
Post by emetib
...
Post by Sophoklis Goumas
Does one need to to enable adjust appropriately the "Allow less secure
apps" setting [1] ?
yes
https://www.howtoforge.com/tutorial/configure-postfix-to-use-gmail-as-a-mail-relay/
Exactly what type of "tighter security" Google is compatible with
with which reportbug cannot comply?

Are reportbug bug reports:
#810933 [1], #412914 [2], #539157 [3], #825408 [4] anyhow related?

Sophoklis

[1] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=810933
[2] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=412914
[3] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=539157
[4] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=825408
emetib
2016-11-05 21:56:47 UTC
Permalink
Post by Sophoklis Goumas
Post by emetib
...
Post by Sophoklis Goumas
Does one need to to enable adjust appropriately the "Allow less secure
apps" setting [1] ?
yes
https://www.howtoforge.com/tutorial/configure-postfix-to-use-gmail-as-a-mail-relay/
Exactly what type of "tighter security" Google is compatible with
with which reportbug cannot comply?
#810933 [1], #412914 [2], #539157 [3], #825408 [4] anyhow related?
Sophoklis
[1] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=810933
[2] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=412914
[3] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=539157
[4] https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=825408
i'm not a sysadmin, yet from what people are saying in there reports, no.

when is the last time that you used this before this rejection?
are you using postfix, exim, ....? what are you using for your localhost mailing system?
have you updated your localhost mail system lately?
have you changed your gmail passwd lately?
gmail only supports up to 500 relays a day, are these failed attempts counting?
have you looked at these to make sure that things are ok?
https://support.google.com/mail/answer/7126229?p=BadCredentials&rd=2#cantsignin
https://support.google.com/accounts/answer/6010255

as henning wrote, you're having an authentication issue. what have you changed lately?
Sophoklis Goumas
2016-11-06 14:51:17 UTC
Permalink
Post by emetib
i'm not a sysadmin, yet from what people are saying in there reports, no.
Ok.
Post by emetib
when is the last time that you used this before this rejection?
20160413
https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=820830
Post by emetib
have you changed your gmail passwd lately?
No.
Post by emetib
gmail only supports up to 500 relays a day, are these failed attempts counting?
I don't know.
Post by emetib
have you looked at these to make sure that things are ok?
https://support.google.com/mail/answer/7126229?p=BadCredentials&rd=2#cantsignin
https://support.google.com/accounts/answer/6010255
Yes. I have looked at those and what I'm looking into is:
"why" does "reportbug" need to be characterized a "less secure app"?
To what of Google's requirement it cannot comply?
Post by emetib
are you using postfix, exim, ....? what are you using for your localhost mailing system?
have you updated your localhost mail system lately?
Postfix.
Here is my /etc/postfix/main.cf :
http://paste.debian.net/plain/892989
Post by emetib
as henning wrote, you're having an authentication issue. what have you changed lately?
No, I waven't fiddled with it's configuration since then.
But I did a dist-upgrade.

Here is my ~/.reportbugrc :
http://paste.debian.net/plain/892990

Sophoklis
emetib
2016-11-06 15:39:19 UTC
Permalink
from the link that i posted earlier-
https://www.howtoforge.com/tutorial/configure-postfix-to-use-gmail-as-a-mail-relay/

you are supposed to have these in your main.cf-
relayhost = [smtp.gmail.com]:587
smtp_use_tls = yes
smtp_sasl_auth_enable = yes
smtp_sasl_security_options =
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_tls_CAfile = /etc/ssl/certs/ca-certificates.crt

which i don't see in your paste.debian.net...

from me configuring a couple of different virtual machines to use googles smtp you are going to have to change the line-
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
in debian to-
smtp_sasl_password_maps = hash:/etc/postfix/sasl/sasl_passwd

for some reason, that i don't know, in my two debian virts-
cat /etc/os-release
PRETTY_NAME="Debian GNU/Linux 8 (jessie)"
dpkg -l | grep postfix
ii postfix 2.11.3-1

cat /etc/os-release
PRETTY_NAME="Debian GNU/Linux stretch/sid"
dpkg -l | grep postfix
ii postfix 3.1.3-1

the extra dir-
/etc/postfix/sasl
is created

and then you have to run-
postmap /etc/postfix/sasl/sasl_passwd
to make things work properly.

for your actual google settings you are going to have to go to-
https://support.google.com/accounts/answer/6010255?hl=en
and work your way through that.

test your system by sending an email to another one of your email addresses from the machine that you are trying to send from (the one you're having problems with)
mail -s test.hostmachine email.address

once that is done then you can go back and flip the switch back to shut off the 'less secure' in your google account (worked for mine anyway)

i have 6 virtuals of different distros that i have set up to relay through google.smtp for testing purposes by using that howtoforge link.

check the change logs on what might have changed in postfix when you did your dist-upgrade (if postfix upgraded) and then trouble shoot it from there.

google is your friend
please remove my email address from your replies and only reply to this group instead of all

thank you
em
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