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The Hostile Email Landscape

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There was an interesting post on slashdot today about how we've entered an age where only the big players in email domain hosting can reliably expect their emails to be received and not discarded as untrustworthy.

While it's not *yet* impossible to just run a mail server from your local domain, it is becoming increasingly likely that if you do, some recipients will have your mail automatically filed in their spam folders or outright rejected.

To me this is just another consequence of the big players slowly exerting their dominance over the rest of us.. there is just no incentive for them not to do this, and every incentive for them to make it harder and harder for small players to coexist with them.

As we consolidate on just a few major email services, it becomes more and more difficult to launch your own mail server. From the article: "Email perfectly embodies the spirit of the internet: independent mail hosts exchanging messages, no host more or less important than any other. Joining the network is as easy as installing Sendmail and slapping on an MX record. At least, that used to be the case. If you were to launch a new mail server right now, many networks would simply refuse to speak to you. The problem: reputation. ... Earlier this year I moved my personal email from Google Apps to a self-hosted server, with hopes of launching a paid mail service à la Fastmail on the same infrastructure. ... I had no issues sending to other servers running Postfix or Exim; SpamAssassin happily gave me a 0.0 score, but most big services and corporate mail servers were rejecting my mail, or flagging it as spam: accepted my email, but discarded it. GMail flagged me as spam. MimeCast put my mail into a perpetual greylist. Corporate networks using Microsoft's Online Exchange Protection bounced my mail."

--- End quote ---

My main email address is hosted on a shared server at Bluehost. Not only is my  email occasionally marked as spam but the shared IP address is often blacklisted. It's very frustrating when you send a cold email and no reply is received... you don't know if the person just didn't respond or if your email just never got through.

Stoic Joker:
MimeCast put my mail into a perpetual greylist.-mouser (October 19, 2015, 01:02 PM)
--- End quote ---

Perpetual Greylist?? Greylisting just means to refuse everything on first contact to see if the try resending, because supposedly many(/most?) of the naughty mail servers don't do speed up Directory Harvesting I suppose..

Honestly it sounds like they got a semi blacklisted IP address from their ISP. I had that happen here when we switched ISP. Our mail servers previously pristine reputation (by IP) went out the window the instant I put it behind the new guilted by association because it was in an ISP customer address block IP address. MX-Toolbox said the address was "clean" but we were still getting rejections from (see above... :D) other mail systems. After much - panicked 3am class digging - I found the system that had us listed as guilty by association and forwarded that info to the ISP who swore (front line support) that the address wasn't blacklisted. This resulted in me swearing, mild hostility (3am...), the finding of a supervisor...who dug up an engineer to "prove me wrong".

Thankfully the engineer was not nearly as retarded as the rest of the staff...and therefore was able to grasp the gravity of the situation, actually read the information I'd sent, and then contacted the listing company to have the address (actually a CIDR block of 16 addresses) removed from the naughty.

And the mail began to flow...

I've run my own mail server from home for about fifteen years now and came across this type of issue a couple years ago.  What I had to do was ask my ISP to create a reverse PTR record so that the reverse lookup of my IP address pointed at my mail domain instead of their pool name.  This solved the majority of the issues I was experiencing and I also thanked my lucky stars that my ISP was cool enough to allow that on a home connection.

I have hmailserver installed and it works VERY well for a full-fledged mail server.  But I discovered that my messages were being bounced by the other recipient domains because I did not have reverse DNS configured for my domain.  That was an issued to be solved with my ISP.  We ended up using a Google Apps domain anyway so the problem became moot.

Oh, I just noticed that Skwire said the same thing...  hahahhaa


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