Lot of messages, try to recap:

There are 2 messages that are not the message I'm "curious" about

1) "Hard" Spoofing:
*"Be careful with this message. Our systems couldn't verify that this
message was really sent by gmail.com <http://gmail.com/>. You might want to
avoid clicking links or replying with personal information."*

This result in spam folder and it happens when you replace a char in the
from email (e.g: an "o" letter with a "0" zero). The help describe this
clearly and tests confirm..

2) Sender authentication:
*"This message may not have been sent by: sender@address"*
This seems to happen on SPF failure (even SOFTFAIL) and result in spam
folder.

Now, the "new" message I'm seeing is instead:

3) "Self-send" Spoofing:
*"This may be a spoofed message. Gmail couldn't verify that it was actually
sent from your account."*

In my tests this *didn't result in spam folder* and it only happened when:
  5321/smtp.from: NON-Gmail
  5321/smtp.to: Target-Gmail-account
  5322/mime.from: Target-Gmail-account
  5322/mime.to: Target-Gmail-account (with no dots in local part)
  SPF: PASS, otherwise you get the error #2 above.
  DMARC: FAIL (or in other words, a "non-gmail" smtp.from as they correlate)

If I send an email from another Gmail account then:
  5321/smtp.from: Sender-Gmail-Account (different from the target)
  5321/smtp.to: Target-Gmail-account
  5322/mime.from: Target-Gmail-account
  5322/mime.to: Target-Gmail-account (with no dots in local part)
  SPF: PASS (I'm sending from gmail)
  DMARC: PASS (smtp.from is a gmail.com email)

Then I get no warnings.

I don't understand the reason why this case doesn't show the warning (isn't
this a message pretending to be me but not being sent by me like the
previous one?).

Trying the #3 combination against a GSuite account doesn't show that
warning (I get an "?" icon as gravatar and a *tooltip* saying *"My Gsuite
name couldn't verify that mygsuitedomain actually sent this message (and
not a spammer)"*. This tooltip is there since maybe 1 year, so it is not a
"new thing" and also "OT" as I'm focused on the yellow warnings (as almost
no one looks at the tooltip of the gravatar).

The only explanation I found for introducing a similar message with such a
narrow scope is a very conservative path to a larger scope that we'll see
in the next weeks/months.

Stefano

PS: note that if your gmail account is name.surn...@gmail.com then the
warning will not appear if you do the "self test" above unless you remove
the dot from the localpart of the "rfc5322/mime.to" header (so, you'll see
the watning only if To is namesurn...@gmail.com ). But this simply sounds
like a bug, not a feature.

On 15 June 2017 at 08:08, Stefano Bagnara <mai...@bago.org> wrote:

> On 15 June 2017 at 00:37, Laura Atkins <la...@wordtothewise.com> wrote:
>
>>
>> On Jun 14, 2017, at 1:55 PM, Stefano Bagnara <mai...@bago.org> wrote:
>>
>> Not what I saw here: if I send a message with the same rfc5322.from/to (
>> ema...@gmail.com) to ema...@gmail.com I don't see warnings.
>>
>>
>> I think this is where you’re misunderstanding me. Those are not the same
>> email address, therefore, you do not get the warning. ema...@gmail.com and
>> ema...@gmail.com are not the same address. So they’re not triggering the
>> warning message.
>>
>
> rfc5321.from: mydomain
> rfc5321.to: ema...@gmail.com
> rfc5322.from: ema...@gmail.com
> rfc5322.to: ema...@gmail.com
>
> This doesn't show the alert when I read it on ema...@gmail.com inbox. So
> the message is not only for rfc5322.from + rfc5322.to to be the same, but
> ALSO to match your receiving account.
>
> At this time the only way I see the message is if all of this are the
> same, AND DMARC fails:
> rfc5321.to: ema...@gmail.com
> rfc5322.from: ema...@gmail.com
> rfc5322.to: ema...@gmail.com
>
> Unfortunately (of course) I can't DKIM sign using gmail.com signature, so
> we'll never know if they really check DMARC or if they check the received
> headers or what technical mean they use to detect the message did not
> originate from my account.
>
> Maybe Brandon will tell us, but it is not really a big point here.
>
> Let me ask you this, does the warning box have a “learn more” button on
>> it? What happens when you click that? Does it take you to a page like:
>> https://support.google.com/mail/answer/185812?visit_id
>> =1-636330759213411049-1547491413&p=sent_warning&hl=en&rd=2 (that’s the
>> page I get from “not sent from your account”)
>>
>> Note, that support.google.com link provides instructions on how to
>> remove the warning.
>>
>
> Brings me here:
> https://support.google.com/mail/answer/1366858?hl=en&expand=5
>
> Note that "expand=5" seems to not expand anything.
> The "Spoofed email address" topic in that page describe a different
> behavior (the one that will show the other message I talked about in my
> first post, but this is unrelated and IMHO is clearly understandable).
>
>
>> In my sample there are more false positives than spam email matching the
>> criteria. But I admit I have a very limited sample. So I trust you when you
>> say it is a very common spam technique.. Maybe I already filter those spam
>> at SMTP level using spamhaus or that I'm just "lucky" ;-)
>>
>>
>> It’s not a false positive! It’s an accurate statement: this message sent
>> to you, from you was not sent through gmail’s servers. It’s simply a
>> descriptive message. It’s making sure you notice something about this
>> message. Yes, DMARC is showing failed, but DMARC fails when you send from
>> addre...@gmail.com to addre...@gmail.com. Those messages don’t get the
>> warning. Therefore: the warning is not about a DMARC failure.
>>
>
> Yes, it is accurate. But "This may be a spoofed message." is accurate for
> every DMARC failing message.
> I meaan "False positive" because in my case the message in fact where NOT
> spoofing messages.
>
> Yeah, they say "MAY BE" so it is accurate. But False positive in spam is
> the same.. they put it in spam because it "MAY BE" spam,... so if it is not
> spam it is a false positive.
>
> Particularly in the case of Google, not everything they do is about spam.
>> Sometimes they’re just telling subscribers more about the mail. A prime
>> example of this - like the TLS indicators. TLS has zero to do with spam.
>> Yet, they show the TLS status of every message coming into google. It’s a
>> security piece. This, too.
>>
>
> Agree. In my opinion the TLS issue is about much more emails than this
> "spoofing" issue. AND the TLS issue is 100% correct, because the message
> did some transit in plain text.
>
> If we want to be "accurate" then EVERY message that fails DMARC PLUS every
> message that didn't transit in TLS "may be spoofed" (ignoring what the "To"
> header say).
>
> "rfc5321.to/rfc5322.from/rfc5322.to matching and dmarc failing" (Yes,, I
> got thay you think  that google detect the origin of the message not
> looking DMARC result, but DMARC failing is a correct description in that
> case unless you have an use case where the 3 address are the same, DMARC
> pass, and the warning is shown anyway). There are many ways to do that
> check.
>
> Stefano
>
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