Thanks for the insights Brandon (everyone else in the group as well).
Appreciate your time. should be simple enough for us to make a a change and
stop allowing for underscores.

On Wed, Nov 18, 2015 at 5:37 PM, Brandon Long <bl...@google.com> wrote:

> I1118 16:23:16.785929 spf_checker.cc:520] Invalid helo domain:
> o1.mail_sg1.thehubpeople.com
>
> underscores in domain names are not valid for smtp... and the ABNF in rfc
> 5321 doesn't allow it for HELO arguments either.
>
> Now, whether we should be that anal, yeah, doesn't quite seem worth it,
> especially since we don't need to fall back to using the HELO domain for
> this, we're just validating all of the arguments to our spfchecker up front.
>
> We just got tripped up ourselves about this because we were using
> underscore in DKIM key names, and Ironports were refusing them, so even if
> we fixed it, we might not be the only folks you have issues with.
>
> The best guess stuff in the comment seems all bizarre, a poor interface
> from the spf check code back to smtp, doesn't have a concept of "invalid
> spf check request" which is what we're basically saying here.  Our spf
> check code predates me, which is saying something.
>
> The number of messages we accept from transactions with an underscore in
> the HELO argument is pretty vanishingly small.
>
> Brandon
>
>
> On Wed, Nov 18, 2015 at 4:11 PM, Luke Martinez <luke.marti...@sendgrid.com
> > wrote:
>
>> I actually didn't mean to obfuscate the domain...Mistakenly copy and
>> pasted from a conversation with a different group. Obviously didn't take
>> much to figure out the domain in question...
>>
>> Its interesting that the issue persists..Here is a header from a test
>> message I sent just minutes ago...same issue.
>>
>> Seems like gmail is having trouble fetching the records for some reason.
>>
>> Delivered-To: luke.marti...@sendgrid.com
>> Received: by 10.37.10.5 with SMTP id 5csp1454076ybk;
>>         Wed, 18 Nov 2015 16:06:53 -0800 (PST)
>> X-Received: by 10.107.47.28 with SMTP id j28mr5555944ioo.168.1447891594041;
>>         Wed, 18 Nov 2015 16:06:34 -0800 (PST)
>> Return-Path: 
>> <bounces+2035510-7255-luke.martinez=sendgrid....@email.thehubpeople.com>
>> Received: from o1.mail_sg1.thehubpeople.com (o1.mail_sg1.thehubpeople.com. 
>> [167.89.67.186])
>>         by mx.google.com with ESMTPS id 
>> l102si8090776iod.142.2015.11.18.16.06.33
>>         for <luke.marti...@sendgrid.com>
>>         (version=TLSv1.2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
>>         Wed, 18 Nov 2015 16:06:33 -0800 (PST)
>> Received-SPF: softfail (google.com: best guess record for domain of 
>> transitioning 
>> bounces+2035510-7255-luke.martinez=sendgrid....@email.thehubpeople.com does 
>> not designate 167.89.67.186 as permitted sender) client-ip=167.89.67.186;
>> Authentication-Results: mx.google.com;
>>        spf=softfail (google.com: best guess record for domain of 
>> transitioning 
>> bounces+2035510-7255-luke.martinez=sendgrid....@email.thehubpeople.com does 
>> not designate 167.89.67.186 as permitted sender) 
>> smtp.mailfrom=bounces+2035510-7255-luke.martinez=sendgrid....@email.thehubpeople.com;
>>        dkim=pass header.i=@thehubpeople.com;
>>        dmarc=pass (p=NONE dis=NONE) header.from=thehubpeople.com
>> DKIM-Signature: v=1; a=rsa-sha1; c=relaxed; d=thehubpeople.com;
>>      h=content-type:from:mime-version:subject:to; s=m1;
>>      bh=G2iZV5vFKTfsKWLw4qSi713I8u0=; b=JHzqGRs5nxiMeg5ehVfoE7EaEHNB/
>>      exBjskedL7iQDWElEr1smQujnbapPXorReWUR2fCzEKMsOUCgO6OpXuZPCYiaVTL
>>      iiWC5mv5o/jc0z8NMoXt0PIu4367BP1mlei23nSDHh1GuMoQylt0dC9JsdjKjvBO
>>      BxfG5nsjUOodaM=
>> Received: by filter0486p1mdw1.sendgrid.net with SMTP id 
>> filter0486p1mdw1.17942.564D128461
>>         2015-11-19 00:06:28.743096475 +0000 UTC
>> Received: from MjAzNTUxMA (o16789125x234.outbound-mail.sendgrid.net 
>> [167.89.125.234])
>>      by ismtpd0003p1iad1.sendgrid.net (SG) with HTTP id 
>> nueVgwhYQ16eFpprFkAAZA
>>      for <luke.marti...@sendgrid.com>; Thu, 19 Nov 2015 00:06:28.987 +0000 
>> (UTC)
>> Content-Type: multipart/alternative; 
>> boundary=f88976723345e813177149e6bfa1985024fe12bf494ae2852e2ba0395276
>> Date: Thu, 19 Nov 2015 00:06:28 +0000
>> From: managem...@thehubpeople.com
>> Mime-Version: 1.0
>> Subject: A Test From SendGrid
>> To: luke.marti...@sendgrid.com
>> Message-ID: <nuevgwhyq16efpprfka...@ismtpd0003p1iad1.sendgrid.net>
>> X-SG-EID: 
>> bmBsS0SGvj5DV4MzWktq1SFvXko3/0Ze1iVVFHnU9JhhIV+69vl2/ow+yjVFsFlRN7LD+HYXWm3J3m
>>  
>> 3xFRZWCKLz7+3aGdiDkJu2/jRf6tFH/QQ8gqixM5mBceuCrtGYZx5IH0LooZiotfZ3p7SrydYYE9bz
>>  D6ZNepacL8eFB1dFAQ6ka3YxJQ++VjVnkNWb
>>
>>
>>
>> On Wed, Nov 18, 2015 at 4:01 PM, Derek Diget <
>> derek.diget+mai...@wmich.edu> wrote:
>>
>>>
>>> On Wed, 18 Nov 2015 at 15:33 -0700, Luke Martinez wrote:
>>> =>Hey team,
>>> =>
>>> =>I've got an interesting SPF softfail occurring for one of our senders.
>>> =>
>>> =>This softfail is readily repeatable and seems to be isolated to this
>>> single
>>> =>sender.
>>> =>
>>> =>All necessary records are in place, and their mail passes SPF at all
>>> major
>>> =>inbox providers other than gmail.
>>> =>
>>> =>Last resort seems to be a DNS lookup failure on Gmail's side. Can
>>> anyone
>>> =>see if I'm missing something silly?
>>>
>>> With SPF records there is no need to obfuscate the sending domain
>>> since it makes troubleshooting harder to impossible.  (See many posts on
>>> SPF-Help.)
>>>
>>> Here is what I see right now[1].
>>>
>>> Running SPF query with:
>>>    IP address: 167.89.67.186
>>>        Domain: email.thehubpeople.com
>>>        Sender: bounces+2035510-7255-luke.martinez=
>>> sendgrid....@email.thehubpeople.com (local-part:
>>> bounces+2035510-7255-luke.martinez=sendgrid.com)
>>>   HELO Domain: o1.mail_sg1.thehubpeople.com
>>>
>>> 17:50:16.94:
>>> ----------------------------------------------------------------
>>> 17:50:16.94: SPFcheck_host called:
>>> 17:50:16.94:       source ip = 167.89.67.186
>>> 17:50:16.94:          domain = email.thehubpeople.com
>>> 17:50:16.94:          sender = bounces+2035510-7255-luke.martinez=
>>> sendgrid....@email.thehubpeople.com
>>> 17:50:16.94:      local_part = bounces+2035510-7255-luke.martinez=
>>> sendgrid.com
>>> 17:50:16.94:     helo_domain = o1.mail_sg1.thehubpeople.com
>>> 17:50:16.94:
>>> 17:50:16.94:   Looking up "v=spf1" records for email.thehubpeople.com
>>> 17:50:16.94:     DNS query status: Pass
>>> 17:50:16.94:       "v=spf1 ip4:167.89.67.186 include:sendgrid.net ~all"
>>> 17:50:16.94:
>>> 17:50:16.94:   Parsing mechanism: "  ip4 : 167.89.67.186"
>>> 17:50:16.94:     Assuming a Pass prefix
>>> 17:50:16.94:     Comparing against 167.89.67.186
>>> 17:50:16.94:       Matched; returning Pass
>>> 17:50:16.95:   Mechanism matched; returning Pass
>>> 17:50:16.95:
>>> 17:50:16.95:   Parsing mechanism: "  include : sendgrid.net" (not
>>> evaluated)
>>> 17:50:16.95:
>>> 17:50:16.95:   Parsing mechanism: "~ all : " (not evaluated)
>>> 17:50:16.95:
>>> 17:50:16.95: SPFcheck_host is returning Pass
>>> 17:50:16.95:
>>> ----------------------------------------------------------------
>>>
>>> So, a SPF MailFrom check would pass.
>>>
>>>
>>> 1: Who knows what DNS looked like earlier (and what Google might have
>>> cached.)  If I am reading the SOA record the serial number is "23" which
>>> doesn't leak any info on when a change was made. :(
>>>
>>> --
>>> ***********************************************************************
>>> Derek Diget                            Office of Information Technology
>>> Western Michigan University - Kalamazoo  Michigan  USA - www.wmich.edu/
>>> ***********************************************************************
>>>
>>>
>>>
>>>
>>> =>Below is a full header:
>>> =>
>>> =>> Delivered-To: luke.marti...@sendgrid.com
>>> =>> Received: by 10.37.10.5 with SMTP id 5csp545399ybk;
>>> =>>         Tue, 17 Nov 2015 06:47:00 -0800 (PST)
>>> =>> X-Received: by 10.107.10.233 with SMTP id
>>> =>> 102mr38147900iok.31.1447771620037;
>>> =>>         Tue, 17 Nov 2015 06:47:00 -0800 (PST)
>>> =>> Return-Path: <bounces+2035510-7255-luke.martinez=
>>> =>> sendgrid....@email.domain.com>
>>> =>> Received: from o1.mail_sg1.DOMAIN.com (o1.mail_sg1.DOMAIN.com.
>>> =>> [167.89.67.186])
>>> =>>         by mx.google.com with ESMTPS id
>>> =>> f11si24972237ioj.131.2015.11.17.06.46.59
>>> =>>         for <luke.marti...@sendgrid.com>
>>> =>>         (version=TLSv1.2 cipher=ECDHE-RSA-AES128-GCM-SHA256
>>> bits=128/128);
>>> =>>         Tue, 17 Nov 2015 06:46:59 -0800 (PST)
>>> =>> Received-SPF: softfail (google.com: best guess record for domain of
>>> =>> transitioning bounces+2035510-7255-luke.martinez=
>>> =>> sendgrid....@email.domain.com does not designate 167.89.67.186 as
>>> =>> permitted sender) client-ip=167.89.67.186;
>>> =>> Authentication-Results: mx.google.com;
>>> =>>        spf=softfail (google.com: best guess record for domain of
>>> =>> transitioning bounces+2035510-7255-luke.martinez=
>>> =>> sendgrid....@email.domain.com does not designate 167.89.67.186 as
>>> =>> permitted sender) smtp.mailfrom=bounces+2035510-7255-luke.martinez=
>>> =>> sendgrid....@email.domain.com;
>>> =>>        dkim=pass header.i=@DOMAIN.com;
>>> =>>        dmarc=pass (p=NONE dis=NONE) header.from=DOMAIN.com
>>> =>> DKIM-Signature: v=1; a=rsa-sha1; c=relaxed; d=DOMAIN.com;
>>> =>>   h=content-type:from:mime-version:subject:to; s=m1;
>>> =>>   bh=9pEwAB7wqoG5R88T7P/hW0cn0vg=; b=nU5wIVQOhrCw9obvdFNePBXYVtVRZ
>>> =>>   w4ZRkebUzg+gPmeOPPPVY97NnYUJvg0wSX4nxgoBZCeORxpfQgPGlurZbL4cbNDH
>>> =>>   kVZJ85hrHCCNxe2mgqSj6WPES1BppblBwLeeCi3I4/YVMrZInckQ+EoBX/JtV+H8
>>> =>>   f1E8xty32c/sSQ=
>>> =>> Received: by filter0494p1mdw1.sendgrid.net with SMTP id
>>> =>> filter0494p1mdw1.32759.564B3DCA2A
>>> =>>         2015-11-17 14:46:34.302768619 +0000 UTC
>>> =>> Received: from MjAzNTUxMA (o16789125x222.outbound-mail.sendgrid.net
>>> =>> [167.89.125.222])
>>> =>>   by ismtpd0006p1iad1.sendgrid.net (SG) with HTTP id
>>> =>> Qc2SQ2SmT1GH_bTla6DiMg
>>> =>>   for <luke.marti...@sendgrid.com>; Tue, 17 Nov 2015 14:46:34.248
>>> +0000
>>> =>> (UTC)
>>> =>> Content-Type: multipart/alternative;
>>> =>> boundary=3a3da2a7878431dd1b945889881ae3216018141f8c0222fd3cf0d5daa3b3
>>>
>>> _______________________________________________
>>> mailop mailing list
>>> mailop@mailop.org
>>> http://chilli.nosignal.org/mailman/listinfo/mailop
>>>
>>
>>
>>
>> --
>>
>> Luke Martinez
>> SendGrid Deliverability Consultant
>> 520.400.5693
>>
>> _______________________________________________
>> mailop mailing list
>> mailop@mailop.org
>> http://chilli.nosignal.org/mailman/listinfo/mailop
>>
>>
>


-- 

Luke Martinez
SendGrid Deliverability Consultant
520.400.5693
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