Greylisting

So I tried a spam deterring technique known as "greylisting". Basically, you tell your mailserver that any messages from an unknown source should be met with a temporary error under the expectation that very few spam agents will resend the message later whereas legitimate mail servers will.

Ok, interesting. This can be a highly effective technique and likely to deter 99% of spam. However, this involving making your mailserver respond with an error by default.

What happens is that each incoming message is first checked by the greylisting service (I tried Postgrey). The greylist service checks "has this mail server tried to send a message from Alexa to Bree before?" and if not, then an error 450, "mailbox unavailable" error is sent. The sending server will then queue Alexa's message for later transmission. When it is retransmitted, the greylist service says "ah, I recognize this so therefore it is probably not spam" and allows the message from Alexa to Bree to pass through and subsequent messages from that source to go through.

The playout is that it is a highly effective method of detecting spam, however when messages are being queued for delivery "later", that turns out to be anywhere from one to four hours later. For people that are sending lots of messages back and forth, this is not a big problem since the greylist tracks who has successfully sent messages in the past but for any arbitrary exchanges, like say a customer sending a message to sales or tech support for example, greylisting really slows down mail delivery.

All-in-all, it's a pretty drastic anti-spam measure. I ended up disabling it once I realized just how long mailservers will arbitrarily queue mail.