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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

Page 1 of 2  [1] 2  Next page →

#174193 — reportbug and GMail SMTP servers

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 "olspookishmagus@gmail.com"
smtptls

Error messages received:
Enter SMTP password for olspookishmagus@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed.  Try again.
Connecting to smtp.gmail.com:587 via SMTP...
Enter SMTP password for olspookishmagus@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed.  Try again.
Connecting to smtp.gmail.com:587 via SMTP...
Enter SMTP password for olspookishmagus@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

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#174195

On Sat, Nov 05, 2016 at 04:42:55PM +0200, Sophoklis Goumas wrote:
> 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 "olspookishmagus@gmail.com"
> smtptls
> 
> Error messages received:
> Enter SMTP password for olspookishmagus@gmail.com@smtp.gmail.com:587:
> SMTP error: authentication failed.  Try again.
> Connecting to smtp.gmail.com:587 via SMTP...
> Enter SMTP password for olspookishmagus@gmail.com@smtp.gmail.com:587:
> SMTP error: authentication failed.  Try again.
> Connecting to smtp.gmail.com:587 via SMTP...
> Enter SMTP password for olspookishmagus@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
> 


What's not to understand. You do not authenticate properly.
Why is that a debian issue? (It is not)

-H


-- 
Henning Follmann           | hfollmann@itcfollmann.com

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#174196

On 5 November 2016 at 17:47, Henning Follmann <hfollmann@itcfollmann.com> wrote:
> On Sat, Nov 05, 2016 at 04:42:55PM +0200, Sophoklis Goumas wrote:
> 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.

>
> 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

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#174236

On Sat, Nov 05, 2016 at 06:22:56PM +0200, Sophoklis Goumas wrote:
> On 5 November 2016 at 17:47, Henning Follmann <hfollmann@itcfollmann.com> wrote:
> > On Sat, Nov 05, 2016 at 04:42:55PM +0200, Sophoklis Goumas wrote:
> > 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.
> 
> >
> > 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
> 
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           | hfollmann@itcfollmann.com

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#174239

[Multipart message — attachments visible in raw view] — view raw

On Sun, 6 Nov 2016 07:16:29 -0500
Henning Follmann <hfollmann@itcfollmann.com> wrote:

Hello Henning,

This is really for the benefit of the OP, rather than yourself....

>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

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#174245

On 6 November 2016 at 14:20, Brad Rogers <brad@fineby.me.uk> wrote:
>
> 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

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#174246

[Multipart message — attachments visible in raw view] — view raw

On Sun, 6 Nov 2016 16:57:02 +0200
Sophoklis Goumas <olspookishmagus@gmail.com> wrote:

Hello Sophoklis,

>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

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#174284

On 6 November 2016 at 17:07, Brad Rogers <brad@fineby.me.uk> wrote:
> ...
>
> 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

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#174248

On Sun, Nov 06, 2016 at 04:57:02PM +0200, Sophoklis Goumas wrote:
> On 6 November 2016 at 14:20, Brad Rogers <brad@fineby.me.uk> wrote:
> >
> > 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           | hfollmann@itcfollmann.com

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#174251

On Sun 06 Nov 2016 at 10:28:38 -0500, Henning Follmann wrote:

> On Sun, Nov 06, 2016 at 04:57:02PM +0200, Sophoklis Goumas wrote:
> > On 6 November 2016 at 14:20, Brad Rogers <brad@fineby.me.uk> wrote:
> > >
> > > 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 "olspookishmagus@gmail.com"
 #smtppasswd "my password here"

The third line is commented out.

> 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.

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#174259

On Sun, Nov 06, 2016 at 03:44:49PM +0000, Brian wrote:
> On Sun 06 Nov 2016 at 10:28:38 -0500, Henning Follmann wrote:
> 
> > On Sun, Nov 06, 2016 at 04:57:02PM +0200, Sophoklis Goumas wrote:
> > > On 6 November 2016 at 14:20, Brad Rogers <brad@fineby.me.uk> wrote:
> > > >
> > > > 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 "olspookishmagus@gmail.com"
>  #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

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#174281

On 7 November 2016 at 00:51, Mark Fletcher <mark27q1@gmail.com> wrote:
> On Sun, Nov 06, 2016 at 03:44:49PM +0000, Brian wrote:
>>
>> 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 "olspookishmagus@gmail.com"
>>  #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 olspookishmagus@gmail.com@smtp.gmail.com:587:
SMTP error: authentication failed.  Try again.

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

Sophoklis

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#174294

On Mon 07 Nov 2016 at 14:46:01 (+0200), Sophoklis Goumas wrote:
> On 7 November 2016 at 00:51, Mark Fletcher <mark27q1@gmail.com> wrote:
> > On Sun, Nov 06, 2016 at 03:44:49PM +0000, Brian wrote:
> >>
> >> 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 "olspookishmagus@gmail.com"
> >>  #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 olspookishmagus@gmail.com@smtp.gmail.com:587:
> 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.

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#174302

On 7 November 2016 at 15:52, David Wright <deblis@lionunicorn.co.uk> wrote:
>
> 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

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#174319

On Mon 07 Nov 2016 at 16:32:24 +0200, Sophoklis Goumas wrote:

> On 7 November 2016 at 15:52, David Wright <deblis@lionunicorn.co.uk> wrote:
> >
> > 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.

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#174321

On Mon, Nov 07, 2016 at 05:32:24PM +0000, Brian wrote:
> On Mon 07 Nov 2016 at 16:32:24 +0200, Sophoklis Goumas wrote:
> 
> > On 7 November 2016 at 15:52, David Wright <deblis@lionunicorn.co.uk> wrote:
> > >
> > > 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           | hfollmann@itcfollmann.com

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#174423

On Wednesday 09 November 2016 14:50:03 Sophoklis Goumas wrote:
> 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.

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

Lisi

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#174424

On 7 November 2016 at 19:56, Henning Follmann <hfollmann@itcfollmann.com> wrote:
>
> 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

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#174199

On Saturday, November 5, 2016 at 9:50:04 AM UTC-5, Sophoklis Goumas wrote:
> Hello.
> 
> Anybody else having troubles when using GMails' SMTP servers?
>
no
 
> 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/

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#174206

On Sat, 2016-11-05 at 09:30 -0700, emetib wrote:
> On Saturday, November 5, 2016 at 9:50:04 AM UTC-5, Sophoklis Goumas wrote:
> > 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.

>  
> > 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

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