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reportbug and GMail SMTP servers

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  reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-05 15:50 +0100
    Re: reportbug and GMail SMTP servers Henning Follmann <hfollmann@itcfollmann.com> - 2016-11-05 16:50 +0100
      Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-05 17:30 +0100
        Re: reportbug and GMail SMTP servers Henning Follmann <hfollmann@itcfollmann.com> - 2016-11-06 13:10 +0100
          Re: reportbug and GMail SMTP servers Brad Rogers <brad@fineby.me.uk> - 2016-11-06 13:30 +0100
            Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-06 16:00 +0100
              Re: reportbug and GMail SMTP servers Brad Rogers <brad@fineby.me.uk> - 2016-11-06 16:10 +0100
                Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-07 14:00 +0100
              Re: reportbug and GMail SMTP servers Henning Follmann <hfollmann@itcfollmann.com> - 2016-11-06 16:30 +0100
                Re: reportbug and GMail SMTP servers Brian <ad44@cityscape.co.uk> - 2016-11-06 16:50 +0100
                  Re: reportbug and GMail SMTP servers Mark Fletcher <mark27q1@gmail.com> - 2016-11-07 00:00 +0100
                    Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-07 13:50 +0100
                      Re: reportbug and GMail SMTP servers David Wright <deblis@lionunicorn.co.uk> - 2016-11-07 15:00 +0100
                        Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-07 15:40 +0100
                          Re: reportbug and GMail SMTP servers Brian <ad44@cityscape.co.uk> - 2016-11-07 18:40 +0100
                            Re: reportbug and GMail SMTP servers Henning Follmann <hfollmann@itcfollmann.com> - 2016-11-07 18:50 +0100
                              Re: reportbug and GMail SMTP servers Lisi Reisz <lisi.reisz@gmail.com> - 2016-11-09 16:00 +0100
                              Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-09 16:00 +0100
    Re: reportbug and GMail SMTP servers emetib <chadbrabec@gmail.com> - 2016-11-05 18:00 +0100
      Re: reportbug and GMail SMTP servers Michael Milliman <michael.e.milliman@gmail.com> - 2016-11-05 20:30 +0100
        Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-05 22:10 +0100
          Re: reportbug and GMail SMTP servers Lisi Reisz <lisi.reisz@gmail.com> - 2016-11-06 13:00 +0100
            Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-06 16:00 +0100
              Re: reportbug and GMail SMTP servers Henning Follmann <hfollmann@itcfollmann.com> - 2016-11-06 16:50 +0100
                Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-07 14:00 +0100
                  Re: reportbug and GMail SMTP servers Lisi Reisz <lisi.reisz@gmail.com> - 2016-11-07 17:10 +0100
      Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-05 22:00 +0100
        Re: reportbug and GMail SMTP servers emetib <chadbrabec@gmail.com> - 2016-11-05 23:20 +0100
          Re: reportbug and GMail SMTP servers Sophoklis Goumas <olspookishmagus@gmail.com> - 2016-11-06 16:00 +0100
            Re: reportbug and GMail SMTP servers emetib <chadbrabec@gmail.com> - 2016-11-06 17:00 +0100

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#174213

On 5 November 2016 at 21:27, Michael Milliman
<michael.e.milliman@gmail.com> wrote:
> On Sat, 2016-11-05 at 09:30 -0700, emetib wrote:
> 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

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#174235

On Saturday 05 November 2016 21:05:06 Sophoklis Goumas wrote:
> I have supplied more information in my initial message:
> 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

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#174244

On 6 November 2016 at 13:54, Lisi Reisz <lisi.reisz@gmail.com> wrote:
> ...
>
> 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

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

I am inputting my Google Account password (correctly and checked).

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

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

Sophoklis

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#174250

On Sun, Nov 06, 2016 at 04:53:39PM +0200, Sophoklis Goumas wrote:
> On 6 November 2016 at 13:54, Lisi Reisz <lisi.reisz@gmail.com> wrote:
> > ...
> >
> > 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
> 

It is not configured at all.


> >
> > 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)
 
> >
> > What have you got in /home/$USER/.reportbugrc?
> >
> 
> Here is my ~/.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           | hfollmann@itcfollmann.com

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#174285

On 6 November 2016 at 17:48, Henning Follmann <hfollmann@itcfollmann.com> wrote:
>
> 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

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#174314

On Monday 07 November 2016 12:52:30 Sophoklis Goumas wrote:
> - 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

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#174212

On 5 November 2016 at 18:30, emetib <chadbrabec@gmail.com> wrote:
> On Saturday, November 5, 2016 at 9:50:04 AM UTC-5, Sophoklis Goumas wrote:
> ...
>
>>
>> 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

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#174217

On Saturday, November 5, 2016 at 4:00:03 PM UTC-5, Sophoklis Goumas wrote:
> 
> > On Saturday, November 5, 2016 at 9:50:04 AM UTC-5, Sophoklis Goumas wrote:
> > ...
> >
> >>
> >> 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

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?

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#174243

On 5 November 2016 at 23:56, emetib <chadbrabec@gmail.com> wrote:
> On Saturday, November 5, 2016 at 4:00:03 PM UTC-5, Sophoklis Goumas wrote:
>
> i'm not a sysadmin, yet from what people are saying in there reports, no.
>

Ok.

>
> when is the last time that you used this before this rejection?
>

20160413
https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=820830

>
> have you changed your gmail passwd lately?
>

No.

>
> gmail only supports up to 500 relays a day, are these failed attempts counting?
>

I don't know.

>
> 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?

>
> 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

>
> 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

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#174252

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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