It can take some time while GMail pushes a mail through your GrayList. The reason is that Google has several SMTP outgoing mail servers. The problem is that Google is rotating these mail servers to send even a single mail. Another complication is that Google SMTP mail servers does not have a single IP but they rotate several IPs for a single mail server. All these together does not make a good friend with graylisting systems.
Google can sometimes cause headache if you have a GrayList system implemented on your mail server.
What Graylisting does is that it records tripples: IP + sender + receiver.
When an email is sent from GMail, it is temporarily refused by our mail server (code 450 or 451)
Aug 13 16:29:14 ns2 policyd: rcpt=170846, greylist=new, host=64.233.178.241 (hs-out-0708.google.com), from=somegoogleuser@gmail.com, to=somebody@yourdomain.com, size=0 Aug 13 16:36:21 ns2 policyd: rcpt=170872, greylist=new, host=64.233.184.235 (wr-out-0506.google.com), from=somegoogleuser@gmail.com, to=somebody@yourdomain.com, size=0 Aug 13 16:56:04 ns2 policyd: rcpt=170914, greylist=new, host=66.249.82.234 (wx-out-0506.google.com), from=somegoogleuser@gmail.com, to=somebody@yourdomain.com, size=0 Aug 13 17:29:50 ns2 policyd: rcpt=170982, greylist=update, host=64.233.184.231 (wr-out-0506.google.com), from=somegoogleuser@gmail.com, to=somebody@yourdomain.com, size=0 # host hs-out-0708.google.com hs-out-0708.google.com has address 64.233.178.251 hs-out-0708.google.com has address 64.233.178.240 hs-out-0708.google.com has address 64.233.178.241 hs-out-0708.google.com has address 64.233.178.242 hs-out-0708.google.com has address 64.233.178.243 hs-out-0708.google.com has address 64.233.178.244 hs-out-0708.google.com has address 64.233.178.245 hs-out-0708.google.com has address 64.233.178.246 hs-out-0708.google.com has address 64.233.178.247 hs-out-0708.google.com has address 64.233.178.248 hs-out-0708.google.com has address 64.233.178.249 hs-out-0708.google.com has address 64.233.178.250 # host wr-out-0506.google.com wr-out-0506.google.com has address 64.233.184.235 wr-out-0506.google.com has address 64.233.184.236 wr-out-0506.google.com has address 64.233.184.237 wr-out-0506.google.com has address 64.233.184.238 wr-out-0506.google.com has address 64.233.184.239 wr-out-0506.google.com has address 64.233.184.224 wr-out-0506.google.com has address 64.233.184.225 wr-out-0506.google.com has address 64.233.184.226 wr-out-0506.google.com has address 64.233.184.227 wr-out-0506.google.com has address 64.233.184.228 wr-out-0506.google.com has address 64.233.184.229 wr-out-0506.google.com has address 64.233.184.230 wr-out-0506.google.com has address 64.233.184.231 wr-out-0506.google.com has address 64.233.184.232 wr-out-0506.google.com has address 64.233.184.233 wr-out-0506.google.com has address 64.233.184.234 # host wx-out-0506.google.com wx-out-0506.google.com has address 66.249.82.236 wx-out-0506.google.com has address 66.249.82.237 wx-out-0506.google.com has address 66.249.82.238 wx-out-0506.google.com has address 66.249.82.239 wx-out-0506.google.com has address 66.249.82.224 wx-out-0506.google.com has address 66.249.82.225 wx-out-0506.google.com has address 66.249.82.226 wx-out-0506.google.com has address 66.249.82.227 wx-out-0506.google.com has address 66.249.82.228 wx-out-0506.google.com has address 66.249.82.229 wx-out-0506.google.com has address 66.249.82.230 wx-out-0506.google.com has address 66.249.82.231 wx-out-0506.google.com has address 66.249.82.232 wx-out-0506.google.com has address 66.249.82.233 wx-out-0506.google.com has address 66.249.82.234 wx-out-0506.google.com has address 66.249.82.235
Graylisting and email comming from GMail