The problem is that the large email purveyors like
AOL, Yahoo, Microsoft, etc,
use large server farms that balance the load between multiple hosts, so
when the mail retries it comes from different IP addresses on every retry.
Microsoft, for example, lists thousands of IP addresses as part of their
email service.
Greylisting by IP address hasn't got a chance of
working in that
environment.
When I ran my own mailserver I had greylisting that only worked by sender mail address.
Additionally, it did the usual SPF checking etc.
This did not cause the abovementioned problem, but I'm not sure it added much spam
prevention.
I had other methods to detect trojaned PCs with bad SMTP senders (e.g. doing PIPELINING
without
having negotiated it) and that was much more effective.
Rob