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I'm applying for a tech support job and I got a test that I have a week to complete, so I assume they expect me to do some research for it, so I was wondering if anyone here might be willing to lend a hand.

I'm supposed to give my response to a support ticket. The scenario is that a client is not receiving email alerts we send out and the mail delivery report says "smpt;550 5.6.0. Sorry, looks like SPAM to me"

Now, I've done a bit of googling and asking around, but my understanding of all this is still very shaky.

My response to this would be that we should tell the client to tell their IT dept to whitelist our domain or our IP, because it appears their mail server has blacklisted us.

Now, my questions are:

1) Does that sound right to you? Is that what should be done here?

2) From what I gather, there are other possible concerns here:

a) blacklisting on a broader level

Maybe our domain or our IP has been added to some blacklist and now mail servers across the internet will be rejecting our email.

b) SPF issues

Elsewhere, I've been advised that this may be due to SPF issues. I barely understand what SPF is, but with some googling, I've gotten a vague image.

Are those two legitimate concerns in the sense that besides telling the client to whitelist us we would need to look into whether there's a problem with either of these two because others may be not getting our mail.

Is there anything else besides these two possibilities I should check?

Dimitri001
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  • This looks like content-analysing spam filter. Maybe you used some word or phrase that triggered high spam status in the client software. It is possible that some kind of statistical ("bayessian") classifier identified it as highly probable to be spam, highly enough to reject without queuing. The exact features which led to such classification could be omission or incorrectness of DMARC (SPF & DKIM); message size; too loose message headers and so on. Even your client could be unable to say which exactly triggered that. – Nikita Kipriyanov Oct 11 '19 at 19:04
  • I'm not sure I'm understanding you right. You're saying that something in the content of the email might have triggered a spam filter. Do you mean by content the text that is actually written in the email by the person who is writing and sending it (not including the technical stuff that the mail server/mail client add to it). I ask because you mention as possible causes omission or incorrectness of DMARC (SPF & DKIM); message size; too loose message headers, these seem to me not to be part of the content of the message. Sorry, I don't have the best understanding of this stuff. – Dimitri001 Oct 11 '19 at 19:56
  • I should add (and maybe I should have included this in my original post), that in this test scenario the client has complained of not getting these email alerts before, so, based on that, it seems unlikely that it would have been the content of the email that would have triggered the spam filter, unless it's some content that is part of every alert that gets sent. – Dimitri001 Oct 11 '19 at 19:56
  • There were cases in my experience customer marked messages as spam thereby training their spam filter to reject them, because they didn't understand these messages are exactly what they requested. In all cases, the only direct way to understand why message was rejected is to ask administrator of the system which rejected them. If they then would kind enough to investigate your case and able to say more, you're lucky. – Nikita Kipriyanov Oct 12 '19 at 04:53

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