104.47.37.131 is not covered under spf.protection.outlook.com 
<http://spf.protection.outlook.com/>:

dig spf.protection.outlook.com TXT

> ;; QUESTION SECTION:
> ;spf.protection.outlook.com.  IN      TXT
> 
> ;; ANSWER SECTION:
> spf.protection.outlook.com. 500       IN      TXT     "v=spf1 
> ip4:207.46.101.128/26 ip4:207.46.100.0/24 ip4:207.46.163.0/24 
> ip4:65.55.169.0/24 ip4:157.56.110.0/23 ip4:157.55.234.0/24 
> ip4:213.199.154.0/24 ip4:213.199.180.0/24 include:spfa.protection.outlook.com 
> -all”


Essentially, Ned’s SPF TXT record is saying that emails are valid only if they 
come from 107.22.254.64, or any of the addresses/records specified in the SPF 
TXT record for spf.protection.outlook.com <http://spf.protection.outlook.com/>, 
which as you can see above, doesn’t include the 104.

Whois’ing that 104 address shows the entire Class A (for the pedants: yes its 
classless and I called it a class A anyway; really, i promise, nobody cares) 
belongs to Microsoft, so if you are sending those messages through Outlook.com 
<http://outlook.com/> or through an outlook.com <http://outlook.com/> relay,  
they seemingly haven’t updated their SPF protection ranges to include a new 
range of servers.

-nick

—
Nick Peelman
n...@peelman.us




> On Dec 7, 2016, at 11:29 AM, cpol...@surewest.net wrote:
> 
> Edward Ned Harvey (lopser) wrote:
>>> From: tech-boun...@lists.lopsa.org [mailto:tech-boun...@lists.lopsa.org]
>>> On Behalf Of Edward Ned Harvey (lopser)
>>> 
>>> This sender failed our fraud detection checks and may not be who they appe
>>> ar to be. Learn about http://aka.ms/LearnAboutSpoofing
>> 
>> I pasted the headers of this message into the o365 Message Analyzer at 
>> https://testconnectivity.microsoft.com/
>> It confirms that the message is flagged as spam, but nothing jumps out at me 
>> to explain *why*.
> 
> I looked up your SPF record:
> 
>    $ dig TXT +short nedharvey.com 
>    "v=spf1 ip4:107.22.254.64 include:spf.protection.outlook.com -all"
>                ^^^^^^^^^^^^^
> 
> From your headers as I received them it seems your email emits from 
> a different IP address (104.47.37.131). Not that familiar with SPF,
> but could that be an issue?
> 
> *   received-spf: None (protection.outlook.com: nedharvey.com
>                                                ^^^^^^^^^^^^^
> *           does not designate permitted sender hosts)
>            ^^^^ ^^^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^ ^^^^^                          
>  
>    <snip />
>    X-Original-Sender: lop...@nedharvey.com
> *                            ^^^^^^^^^^^^^^
>    X-Original-Authentication-Results: mx.google.com;       dkim=pass
>            header.i=@nedharvey.onmicrosoft.com; spf=pass (google.com: domain 
> of
> *                                                ^^^^^^^^
>            lop...@nedharvey.com designates 104.47.37.131 as permitted sender)
> *                 ^^^^^^^^^^^^^^            ^^^^^^^^^^^^^    ^^^^^^^^^ ^^^^^^ 
>            smtp.mailfrom=lop...@nedharvey.com
> *                               ^^^^^^^^^^^^^^
> 
> 
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