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I was having problems with emails sent from my server being blocked completely by Hotmail, but I found out Hotmail had blocked my IP and by contacting Hotmail I had the block removed. See this question for more info: Email sent from server with rDNS & SPF being blocked by Hotmail

But now all emails from my server are going directly to recipients "Junk" folder on hotmail and I can't figure out why. Hotmail says "Microsoft SmartScreen marked this message as junk and we'll delete it after ten days."

I tried contacting the same people at Hotmail who had my IP block removed, but I haven't received any reply and its been almost a week.

Here are some details:

  1. I have a valid SPF record for my domain "v=spf1 a include:_spf.google.com ~all"
  2. I have reverse DNS setup
  3. I have a Sender Score of 100 https://www.senderscore.org/lookup.php?lookup=66.199.162.177&ipLookup.x=55&ipLookup.y=14
  4. I have signed up for Microsoft's SNDS and was approved. My ip says "All of the specified IPs have normal status."
  5. Microsoft added my IP to the JMRP Database
  6. My IP is not on any credible spam lists http://www.anti-abuse.org/multi-rbl-check-results/?host=66.199.162.177
  7. my FROM header is being sent in proper format "From: CKA <xxxx@canadaka.net>"
  8. By IP's Senderbase score is "Good": http://www.senderbase.org/senderbase_queries/detailip?search_string=66.199.162.177

Here is a test email source: example email that was sent directly to junk folder

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Could it be that Microsoft's email filter thinks that messages with few words that contain the words "test" and "message" are flagged as junk? I'm grasping at straws here, but sometimes the problem isn't your problem/fault, but is entirely on the destination side. –  JeffG Mar 4 '11 at 22:24
    
@Canadaka - how is this question different from your question here: serverfault.com/questions/240980/… –  Mark Henderson Mar 4 '11 at 22:33
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See also: serverfault.com/questions/241189/… Honestly, I tell me users if hotmail blocks you, don't be surprised, and there's basically nothing I or and small business can do to really fix it. –  Chris S Mar 4 '11 at 22:35
    
@MarkHenderson that question is about Hotmail blocking me entirely, this one is about being filtered as junk mail. –  Canadaka Mar 4 '11 at 22:44
    
@JeffG I have tried sending proper emails, for example a new user registration email with an activation link, which has a full subject and body, the results are the same. –  Canadaka Mar 4 '11 at 22:45
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2 Answers

Change your reverse pointers to reflect only the mailname stated in the SMTP-connection (canadaka.net).

Your SPF-records show v=spf1 a include:_spf.google.com ~all
Make sure to update them to reflect your current situation.

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hmm I asked my data-center to change my IP's reverse DNS to "canadaka.net" but it seems they left the old PTR rather than replacing. mxtoolbox.com/SuperTool.aspx?action=ptr%3a66.199.162.177 I will have them correct this, thanks. –  Canadaka Mar 6 '11 at 4:25
    
Once "canadaka.net" is the only PTR, the current SPF is valid right? –  Canadaka Mar 6 '11 at 4:25
    
At 2am last night I actually missed the a. However, you could add your IP, assuming its static. "v=spf1 a ip4:66.199.162.177/32 include:_spf.google.com ~all" –  Mark Mar 6 '11 at 7:01
    
canadaka.net is now the only PTR showing up, but my emails are still being marked as spam. Do I need to add my IP to the SPF, since it should be covered by the "a"? It is a static ip. –  Canadaka Mar 8 '11 at 9:12
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Hotmail uses senderId, which pretty much is spf but with different syntax.

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