Re: Email direct from IBM i without relay (was: New lower cost IBM i announced)

Arco,

When I say authentication I of course mean you need to pass along your user
id and password that is associated with the account (or from address) that
is sending the email.

Otherwise you could spoof emails and the from address using the GMail
servers, which I don't think they would allow. I just ran a quick test,
and here's what GMail says over port 25 without TLS or authentication:

Here's what GMail says when you don't authenticate:
02/16/2017 18:26:54 Attempting to connect to server SMTP.GMAIL.COM on port
25...
02/16/2017 18:26:54 Connection to server SMTP.GMAIL.COM on port 25
succeeded!

..snip..
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8

02/16/2017 18:26:54 <MAILTOOL says:> MAIL FROM: <bvstone@xxxxxxxxx>
02/16/2017 18:26:54 <SMTP.GMAIL.COM says:> 530 5.7.0 Must issue a STARTTLS
command first. n67sm3927291ith.0 - gsmtp
02/16/2017 18:26:54 MAIL FROM: not accepted. Quitting...

Interestingly it says 25 requires TLS. Hmmm.. so what happens if we use
TLS and no authentication?

02/16/2017 18:28:17 Attempting to connect to server SMTP.GMAIL.COM on port
25...
02/16/2017 18:28:17 Connection to server SMTP.GMAIL.COM on port 25
succeeded!
..snip..
02/16/2017 18:28:17 <SMTP.GMAIL.COM says:> 220 2.0.0 Ready to start TLS
02/16/2017 18:28:17 Attempting SSL connection...
..snip..
02/16/2017 18:28:18 SSL handshake succeeded!
..snip..
02/16/2017 18:28:18 <SMTP.GMAIL.COM says:> 250-smtp.gmail.com at your
service, [69.24.164.121]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-CHUNKING
250 SMTPUTF8
02/16/2017 18:28:18 <MAILTOOL says:> MAIL FROM: <bvstone@xxxxxxxxx>
02/16/2017 18:28:18 <SMTP.GMAIL.COM says:> 530-5.5.1 Authentication
Required. Learn more at
530 5.5.1 https://support.google.com/mail/?p=WantAuthError
m198sm4863861itg.1 - gsmtp

Now, we connected on port 25, turned on TLS but it's now erroring out
saying that authentication is required.

Now, you CAN send email with a from address of something@xxxxxxxxx and
bypass the GMail server (ie, deliver directly to the recipients email
server). And if it does go through it will be a spoofed email, but that's
not using GSuite/GMail for the SMTP server as it should be.


Bradley V. Stone
www.bvstools.com
Native IBM i e-Mail solutions for Microsoft Office 365, Gmail, or any Cloud
Provider!

On Thu, Feb 16, 2017 at 5:22 PM, Arco Simonse <arco400@xxxxxxxxx> wrote:

You probably speak from experience and I respect that. But the
documentation at the given link states otherwise.

Regards,
-Arco

Op donderdag 16 februari 2017 heeft Bradley Stone <bvstone@xxxxxxxxx> het
volgende geschreven:

Yes, Gmail does allow non SSL/TLS over port 25, but they still require
authentication.

Bradley V. Stone
www.bvstools.com
Native IBM i e-Mail solutions for Microsoft Office 365, Gmail, or any

Cloud

Provider!

On Thu, Feb 16, 2017 at 4:51 PM, Arco Simonse <arco400@xxxxxxxxx
<javascript:;>> wrote:

No. If you are allowed to use G Suite SMTP relay service with your

account

then TLS is optional.

Don't get me wrong. It would be better to use SSL/TLS between all
mailservers, but in this configuration there is a kind of trust because

of

the registered ipaddress.

Regards,
-Arco

Op donderdag 16 februari 2017 heeft Bradley Stone <bvstone@xxxxxxxxx

<javascript:;>> het

volgende geschreven:

Google's SMTP relay requires authentication at the account level as

well

as

either SSL or TLS.

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