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Why does Gmail think my server sends spam email?
Small Website Guy




msg:3728541
 2:50 am on Aug 22, 2008 (gmt 0)

I recently purchased a Windows Server 2003 VPS hosting plan. This is my first time managing a web server. Previously, I had shared hosting.

So I set up the SMTP Server and sent emails to my Gmail account, and th SMTP part seems to work, but Gmail puts the emails into the spam folder!

Why is Gmail doing that? What factors makes Gmail think my test emails are spam?

 

stapel




msg:3728809
 1:28 pm on Aug 22, 2008 (gmt 0)

Since we have no idea what you are sending, to whom, why, or under what circumstances; and since we have no idea who, if anyone, shares (or, in the past, used) your current IP address; it is difficult to say why whatever you're doing is being regarded as spam. Sorry.

Eliz.

MatthewHSE




msg:3728814
 1:42 pm on Aug 22, 2008 (gmt 0)

Gmail incorrectly flags quite a lot of email as spam. Many of the perfectly legitimate (and well-known) newsletters I receive get put into the spam folder automatically.

Of course, there's a possibility that your server has been compromised and is being used to send spam, but if Gmail is the only provider you're having trouble with, I'd chalk it up to their bad spam filtering.

nixwebo




msg:3728817
 1:47 pm on Aug 22, 2008 (gmt 0)

If your server has an ip address that has been used by a spam sender in the past it may already be blacklisted due to this. If you are sending more than one message with the same title and little content in the message, this may be flagged as well.

I found that if you tell gmail what is spam and what is not it is rather accurate with its filtering and spam features.

Is this a new gmail account or one you have used for some time?

Jack_Hughes




msg:3728898
 3:12 pm on Aug 22, 2008 (gmt 0)

Have you set up reverse DNS for your email server and SPF for your domain?

Small Website Guy




msg:3728913
 3:44 pm on Aug 22, 2008 (gmt 0)

Well, I have a static IP address. I have no idea who, if anyone, was using the IP address before me. There are two other static IP addresses on my server I could use instead.

Here are some things I was doing that might trigger some sort of spam filter:

(1) one line email
(2) return address did not match the domain name of the IP address, in fact, i made up some totally bogus reply address. the full header shows that the email is coming from MyName.HosingCompanyDomainName.com. (I had no idea that, when I set up the account and chose MyName as a subdomain, I was permanently placing my name on all outbound emails!)

Now that I think about it, it seems that anyone with an SMPT server on their computer can send out unlimited emails, so there needs to be some way to filter out fly-by-nighters.

My goal is to send out emails to people who register with my website, and I'd like the emails to not get filtered out, so I'd like to know what I'm doing wrong, if anything. Are there any resources on the web that explain these issues?

Small Website Guy




msg:3728940
 4:26 pm on Aug 22, 2008 (gmt 0)

Here's some more info:

Here is what the Gmail header says (in which I replaced the real numbers and domain name with bogus values):

Received-SPF: neutral (google.com: 100.100.100.100 is neither permitted nor denied by best guess record for domain of auto@mydomain.com) client-ip=100.100.100.100;
Authentication-Results: mx.google.com; spf=neutral (google.com: 100.100.100.100 is neither permitted nor denied by best guess record for domain of auto@mydomain.com) smtp.mail=auto@mydomain.com

So the question is, how do I get MyDomain.com to permit 100.100.100.100? Do I have to change something at my hosting records at Register.com? Or do I have to change something on my SMTP server setup?

rocknbil




msg:3729075
 7:25 pm on Aug 22, 2008 (gmt 0)

it is difficult to say why whatever you're doing is being regarded as spam.

Let's assume an email is an "ordinary email" for the sake of argument. This is a highly frustrating issue for me too, nearly every mail I send to gmail goes "poof" . . straight to spam.

My DNS report is clean.

My dedi and all of it's IP's are not on any RBL's, they too appear to be clean.

It's a simple plain text mail, like "Hello Bill, this is Bill, testing your gmail account" with a valid subject line.

Most of G's docs in relation to this tell you to mark it as "not spam" and G will "learn" to accept email from these actions.

This is not acceptable. I don't do bulk mail, and have emailed several clients with gmail accounts, all with the same result. "Oh here it is, in spam." ARGH . . . .

pageoneresults helped me work through some of the DNS issues, but even once those were resolved I still have this problem. And I still get this, like S.W.G. does:

"Received-SPF: neutral (google.com: 100.100.100.100 is neither permitted nor denied by best guess record for domain of auto@mydomain.com) client-ip=100.100.100.100;"

I **believe** this is because our dedicated server actually sends mail using the ISP's internal relay server. So although it comes from mydomain.com, the official sender is myisp.com. Does that make any sense?

If it's just this reason G is spam boxing my mail, I'm screwed. :-( This is not something we can reconfigure for our dedi.

Small Website Guy




msg:3729261
 12:38 am on Aug 23, 2008 (gmt 0)

PROBLEM SOLVED!

I went to Register.com (which btw has a much nicer management website than GoDaddy, although I don't know if that's worth an extra $25/year), added the following TXT record (and note that at Register.com, you have to use the at-symbol, @, as your host subdomain):

v=spf1 ip4:100.100.100.100 -all

This tells Gmail and other mail hosts using this system that the IP address is authorized for the domain, and all other IP addresses are not authorized (you don't want spammers using your domain name in their emails). There are other settings you could use, but using the IP address of my server seemed like the simplest way to fix the problem.

Now this is what showed up when I sent myself a test email(wow, that's fast propagation!):

Received-SPF: pass (google.com: domain of contact@mydomain.com designates 100.100.100.100 as permitted sender) client-ip=100.100.100.100;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of contact@mydomain.com designates 100.100.100.100 as permitted sender) smtp.mail=contact@mydomain.com

Yay! Gmail likes me now!

To read more about SPF, you can go to this web page:

[openspf.org...]

Quadrille




msg:3729283
 1:46 am on Aug 23, 2008 (gmt 0)

Google actualkly has just about the best spam filters of any webmail - the few 'legit' mails that get marked as spam are probably because a few recipients label them as spam because they are too lazy to unsubsubscribe; a fate that can befall any newsletter sender!

I don't think I've had more than half a dozen false spamatives in the couple of years I've used gmail for 100% of my mail. They miss a few - but learn fast once you label any 'new style' spam.

As with most webmail, the best way to 'whitelist' an email address, is to add it to your contacts list.

Small Website Guy




msg:3729289
 2:40 am on Aug 23, 2008 (gmt 0)

Google actualkly has just about the best spam filters of any webmail

Yep, that's why I've given up on actually trying to host my own email, Gmail does a way better job of getting rid of spam.

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