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I'm dealing with this for almos a month. Tried several changes but no luck.

Some users manage their e-mail addresses through standard Gmail. NOT Google Apps. Their accounts were configured as aliases.

Some users manage their e-mail addresses using MSOutlook software.

When USER1 (from outlook client software) sends a message to USER2 (alias on gmail), I get softfail and that message get marked as junk.

Both users have same domain addresses and sending to another domains works ok (not identified as spam by other domains).

On hosting settings I had this TXT

v=spf1 include:spf.hostmar.com -all

and changed to this:

v=spf1 ip4:200.58.114.60 include:spf.hostmar.com -all

where 200.58.114.60 is my MX server IP. Not included "mx" into spf as for this.

I checked spf with kitterman's tool and it's ok).

Resuming: How can I eliminate softfail error when sending from outlook to other e-mail addresses on same domain? If anyone can point me on the right direction I will appreciate.

PS: Sorry if lacks of information, I tried several times to send this but always got a "This looks like SPAM" message and can't send it.

Delivered-To: xxxxx@gmail.com
Received: by 10.112.91.4 with SMTP id ca4csp2030121lbb;
        Tue, 26 May 2015 11:32:53 -0700 (PDT)
X-Received: by 10.112.63.201 with SMTP id i9mr23815978lbs.93.1432665172679;
        Tue, 26 May 2015 11:32:52 -0700 (PDT)
Authentication-Results: mx.google.com;
       spf=softfail (google.com: best guess record for domain of transitioning yyyyy@dominguezlab.com.ar does not designate <unknown> as permitted sender) smtp.mail=yyyyy@dominguezlab.com.ar
Received-SPF: softfail (google.com: best guess record for domain of transitioning yyyyy@dominguezlab.com.ar does not designate <unknown> as permitted sender)
Received: by 10.112.34.13 with POP3 id v13mf5100257lbi.12;
        Tue, 26 May 2015 11:32:51 -0700 (PDT)
X-Gmail-Fetch-Info: xxxxx@dominguezlab.com.ar 1 mail.dominguezlab.com.ar 110 xxxxx@dominguezlab.com.ar
Return-path: <yyyyy@dominguezlab.com.ar>
Envelope-to: xxxxx@dominguezlab.com.ar
Delivery-date: Tue, 26 May 2015 15:06:59 -0300
Received: from [123.123.123.123] (helo=PC)
    by fiorenza.dattaweb.com with esmtpsa (TLSv1:AES256-SHA:256)
    (Exim 4.77)
    (envelope-from <yyyyy@dominguezlab.com.ar>)
    id 1YxJFi-0007Cr-NO; Tue, 26 May 2015 15:06:59 -0300
From: "YYYYY" <yyyyy@dominguezlab.com.ar>
To: "'XXXXX'" <xxxxx@dominguezlab.com.ar>,
    "'HHHHH'" <hhhhh@dominguezlab.com.ar>,
    <zzzzz@dominguezlab.com.ar>,
    "'MMMMM'" <mmmmm@dominguezlab.com.ar>
Subject: RV: XYZ
Date: Tue, 26 May 2015 15:06:54 -0300
Organization: XYZ
Message-ID: <011901d097de$c0faf330$42f0d990$@com.ar>
MIME-Version: 1.0
Content-Type: multipart/related;
    boundary="----=_NextPart_000_011A_01D097C5.9BADBB30"
X-Priority: 1 (Highest)
X-MSMail-Priority: High
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: AdCX13bKq0tzzNdFRNeXqALiO+XCOgABxTAQ
Content-Language: es-ar
Importance: High
X-Antivirus: avast! (VPS 150526-0, 26/05/2015), Outbound message
X-Antivirus-Status: Clean

This is a multi-part message in MIME format.

------=_NextPart_000_011A_01D097C5.9BADBB30
Content-Type: multipart/alternative;
    boundary="----=_NextPart_001_011B_01D097C5.9BADBB30"


------=_NextPart_001_011B_01D097C5.9BADBB30
Content-Type: text/plain;
    charset="iso-8859-1"
Content-Transfer-Encoding: quoted-printable
dragonauta
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1 Answers1

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Ok, this is it.

Microsoft Outlook is NOT RFC2821 compliant.

Gmail expects a valid domain but all that gets it's machine NetBios name.

That's why all e-mail sent using an Outlook client get caught as junk and ends into spam folder.

Solution, use a RFC2821 compliant mail client software.

Thanks to all

dragonauta
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