Question

Outbound emails blocked by ASA

Asked by: Cogit140

Inbound email works along with all internet traffic, but all internal users are unable to send out emails and the queue on my exchange is up over 1,000. Here is my ASA config

name 204.8.9.42 OWA-External description External IP address of frontmail.greenfieldin.org
name 204.8.9.37 Mail-External description External IP address of antispam.greenfieldin.org
name 10.16.2.3 Mail-Internal description Internal IP address of antispam.greenfieldin.org
name 10.16.2.5 OWA-Internal description Internal IP address of frontmail.greenfieldin.org
!
interface Ethernet0/0
nameif outside
security-level 0
ip address 204.8.9.62 255.255.255.224 standby 204.8.9.61
!
interface Ethernet0/1
nameif inside
security-level 100
ip address 10.16.7.250 255.255.255.0 standby 10.16.7.251
!
interface Ethernet0/2
nameif DMZ
security-level 50
ip address 192.168.51.254 255.255.255.0 standby 192.168.51.253
!
interface Ethernet0/3
description LAN/STATE Failover Interface
!
interface Management0/0
shutdown
nameif management
security-level 100
ip address 192.168.1.1 255.255.255.0 standby 192.168.1.2
!
banner login #############################################################
banner login # This device is the property of #
banner login # City of Greenfield #
banner login # Only authorized users are permited access to this device! #
banner login # All activity on this system is monitored and LOGGED. #
banner login # Unauthorized access or activity is PROHIBITED. #
banner login # All violators will be PROSECUTED! #
banner login #############################################################
ftp mode passive
clock timezone EST -5
clock summer-time EDT recurring
dns domain-lookup outside
dns domain-lookup inside
dns domain-lookup DMZ
dns server-group DefaultDNS
domain-name greenfieldin.org
access-list inside_nat0_outbound extended permit ip any 10.16.253.0 255.255.255.248
access-list inside_nat0_outbound extended permit ip any 10.16.253.8 255.255.255.248
access-list Email-Out extended permit tcp any host Mail-Internal eq smtp
access-list Email-Out extended permit tcp any host OWA-Internal eq https
access-list Email-In extended permit tcp any host Mail-External eq smtp
access-list Email-In extended permit tcp any host OWA-External eq https
pager lines 24
logging enable
logging asdm informational
mtu outside 1500
mtu inside 1500
mtu DMZ 1500
mtu management 1500
ip local pool dhcpCOREvpn 10.16.253.1-10.16.253.6 mask 255.255.255.248
ip local pool dhcpUSERSvpn 10.16.253.9-10.16.253.15 mask 255.255.255.248
failover
failover lan unit primary
failover lan interface HeartBeat Ethernet0/3
failover key *****
failover link HeartBeat Ethernet0/3
failover interface ip HeartBeat 10.16.255.1 255.255.255.252 standby 10.16.255.2
no monitor-interface management
icmp unreachable rate-limit 1 burst-size 1
asdm image disk0:/asdm-613.bin
no asdm history enable
arp timeout 14400
global (outside) 1 interface
global (outside) 3 OWA-External netmask 255.255.255.255
global (outside) 2 Mail-External netmask 255.255.255.255
nat (inside) 0 access-list inside_nat0_outbound
nat (inside) 2 Mail-Internal 255.255.255.255
nat (inside) 3 OWA-Internal 255.255.255.255
nat (inside) 1 0.0.0.0 0.0.0.0
static (inside,outside) Mail-External Mail-Internal netmask 255.255.255.255
static (inside,outside) OWA-External OWA-Internal netmask 255.255.255.255
access-group Email-In in interface outside
route outside 0.0.0.0 0.0.0.0 204.8.9.35 1
route inside 10.0.0.0 255.0.0.0 10.16.7.254 1

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Asked On: 2009-02-26 at 11:35:58ID24181357
Topic: Cisco PIX Firewall
Participating Experts: 2
Points: 500
Comments: 32

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Answers

by: x-samPosted on 2009-02-26 at 12:02:00ID: 23748977

On the CISCO ASA.. You need to disable ESMTP PACKET INSPECTION..
This is not recomended to be enabled on it.
I am sure this will fix the issue

-x

by: Cogit140Posted on 2009-02-26 at 12:08:47ID: 23749045

tried that issuing the following commands:

(config)#policy-map global_policy
(config-pmap)#class inspection_default
(config-pmap-c)#no inspect esmtp
(config-pmap-c)#exit
(config-pmap)#exit

Still no luck? The packet inspection came enabled by default from Cisco.

by: fgrushevskyPosted on 2009-02-26 at 12:12:12ID: 23749091

You need to make sure that smtp fixup is disabled. Take a look here

http://www.experts-exchange.com/Security/Software_Firewalls/Enterprise_Firewalls/Cisco_PIX_Firewall/Q_22967873.html

by: x-samPosted on 2009-02-26 at 12:13:13ID: 23749104

My dear friend.. i dont know abt cisco.. much.. but i am an Expert in exchange server .. so Just i know what need to be done..

if you do telnet to a remote domain's MX from your exchange server on port 25 what do you get...
do you get something like

************************* banner?

by: x-samPosted on 2009-02-26 at 12:16:27ID: 23749138

this is for Cisco Pix.. hope this can give you some idea..
Just trying to help

http://support.microsoft.com/kb/295725

by: fgrushevskyPosted on 2009-02-26 at 12:18:52ID: 23749178

This issue is caused by SMTP FIXUP problem
Please read http://www.experts-exchange.com/Security/Software_Firewalls/Enterprise_Firewalls/Cisco_PIX_Firewall/Q_22967873.html

it tells how to fix it

by: Cogit140Posted on 2009-02-26 at 12:20:29ID: 23749196

Tried the no fixup protocol...no luck. Tried to telnet from exchange server via cmd : telnet mail.yahoo.com 25 ...could not connect. I can telnet from an internal workstation to our exchange server and front end server and get respones on ehlo from both.

by: x-samPosted on 2009-02-26 at 12:22:34ID: 23749229

try with the IP address

from your exchange server to yahoo...

telnet 67.18.199.2 25
ehlo yourdomain.com

--does it connect ?

by: Cogit140Posted on 2009-02-26 at 12:26:00ID: 23749272

From my exchange server, I opened the command prompt, telneted to 67.18.199.2 25 and got a response, elho domain and got response. Tried emailing from inside to outside gmail account...no go.

by: Cogit140Posted on 2009-02-26 at 12:28:48ID: 23749319

Ok..I just noticed that the hello I recieved back from the ehlo was to the address 204.8.9.62 That is our main external address on the outside interface of the ASA. Our external exchange address however is 204.8.9.42 Does that make a difference? Or does it just reply back to the main ip that was nated from my firewall?

by: x-samPosted on 2009-02-26 at 12:29:08ID: 23749320

ok coolll.. so you were able to connect to gmail .. Hope you got the gmail banner too...
then you dropped a mail through telnet.. and it didnt reach gmail .. (check gmail Junk folder too.. coz sometime it goes there)

so i guess the email should be stuck in the queue right... so in the queue... if u check cleary.. it gives a Last error.. whats the last error showing up ???

-x-sam

by: x-samPosted on 2009-02-26 at 12:29:45ID: 23749326

any errors on the event viewer ? or do you get any NDR ?
what is your server ? exch 2003 or 2007?

by: x-samPosted on 2009-02-26 at 12:31:23ID: 23749345

204.8.9.62 is your connecting Ip address which you use to send mails Out... the other one is your Public IP address which you use for inbound...
what is your domain name ?

by: Cogit140Posted on 2009-02-26 at 12:33:17ID: 23749362

I didn't see any errors in the event log on the exchange server which is 2003 and our domain is greenfieldin.org. Also, nothing in the junk folders.

by: x-samPosted on 2009-02-26 at 12:38:06ID: 23749424

what is your server ... exch 2003 or 2007?

do message tracking for a new email... do u see any emails in the Queue ?

by: Cogit140Posted on 2009-02-26 at 12:38:21ID: 23749431

I apologize, I our external email address is 204.8.9.37. the x.x.x.42 is our owa

by: Cogit140Posted on 2009-02-26 at 12:39:38ID: 23749452

Exchange 2003 with about 900 messages in the queue. I believe this to be a firewall issue since we recently changed from a linux box to the ASA. Prior to the change it worked fine.

by: x-samPosted on 2009-02-26 at 12:40:12ID: 23749460

Yea .. i had figured it out..
MX :

mail.greenfieldin.org internet address = 204.8.9.37

by: Cogit140Posted on 2009-02-26 at 12:43:54ID: 23749509

i did the message tracking and recieved the following messages
SMTP Store Driver: Message Submitted from Store
SMTP: Message Submitted to Advanced queuing
SMTP: Started message submission to advanced queue
SMTP: message submitted to categorizer
SMTP: message categorized and queued for routing
SMTP: message routed and queued for remote delivery

by: x-samPosted on 2009-02-26 at 12:45:13ID: 23749530

Ok.. let me know when you are done with troubleshooting firewall... Exchange point of view.. i can help...lets verify that...
lets do one thing...
go to properties of your default smtp virtual server general tab-- check on enable logging.. and select NCSA Log format...
restart the smtp service.. try to do the telnet again and also send a new email..
this wil be captured in that log
you can find the log at ---> start--> run--> type logfiles--> smtpsvc folder --> there you will find the ncsa log..

just attach that file here in this .. let me see who is droping the connection...

by: x-samPosted on 2009-02-26 at 12:46:29ID: 23749545

Ok.. so u did message tracking for which email... is it for the one stuck in the queue? fine...
disable all the third party application on the server and try..

by: Cogit140Posted on 2009-02-26 at 12:49:08ID: 23749583

This is the log:

10.16.11.45 - - [26/Feb/2009:15:48:25 -0500] "QUIT - SMTP" 240 71

by: x-samPosted on 2009-02-26 at 12:50:13ID: 23749597

this is not enough buddy.. please send me atleast few content.. to see who sends what .. when.. and then this Quit.. etc...

thanks

by: Cogit140Posted on 2009-02-26 at 12:51:07ID: 23749607

This may be more useful

10.16.11.45 - - [26/Feb/2009:15:48:25 -0500] "QUIT - SMTP" 240 71
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:49:35 -0500] "EHLO -? antispam.greenfieldin.org SMTP" 250 311
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:49:35 -0500] "MAIL -? FROM:<rlivengood@greenfieldcc.org> SMTP" 250 52
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:49:35 -0500] "RCPT -? TO:<bdereamer@greenfieldin.org> SMTP" 250 39
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:49:35 -0500] "RCPT -? TO:<lmcguire@greenfieldin.org> SMTP" 250 38
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:49:35 -0500] "DATA -? <20090226204929.27A303F8420@hoist.hrtc.net> SMTP" 250 127
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:49:35 -0500] "QUIT -?antispam.greenfieldin.org SMTP" 240 71
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:50:15 -0500] "EHLO -? antispam.greenfieldin.org SMTP" 250 311
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:50:15 -0500] "MAIL -? FROM:<noreply@experts-exchange.com> SMTP" 250 53
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:50:15 -0500] "RCPT -? TO:<nriedman@greenfieldin.org> SMTP" 250 38
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:50:15 -0500] "DATA -? <1732684611.1235681414515.JavaMail.ee@www22.experts-exchange.com> SMTP" 250 149
10.16.2.3 - antispam.greenfieldin.org [26/Feb/2009:15:50:15 -0500] "QUIT -?antispam.greenfieldin.org SMTP" 240 71

by: x-samPosted on 2009-02-26 at 12:53:36ID: 23749638

Now what is -?antispam.greenfieldin.org ??? i mean why antispam?? do you have any antispam filter after your exchange server who sends your mail Out to internet..?

exch--> antispam--> cisco--> internet?

by: Cogit140Posted on 2009-02-26 at 12:55:52ID: 23749667

Yes, it does both inbound and outbound filtering. I noticed that too so for the time being i have disabled outbound filtering.

by: x-samPosted on 2009-02-26 at 12:56:04ID: 23749669

On your CISCO asa I guess you guys have some kind of logging there too...
see if you are gettng any emails from the exchange server itself... in the log

by: x-samPosted on 2009-02-26 at 12:56:47ID: 23749676

is that filter on the server or is it a separate Box?

by: x-samPosted on 2009-02-26 at 12:57:41ID: 23749689

if on the server.. you need to disable it in the services console and reboot the server
if its not on the server... can we Bypass that ?

by: Cogit140Posted on 2009-02-26 at 13:03:07ID: 23749737

It is on a separte virtual server. I could see a few deny's in the cisco log, but nothing that tied directly to the exchange server. They looked like external connections. I turned off the outbound filtering, I will see what else I can do to bypass the antispam box.

by: x-samPosted on 2009-02-26 at 13:24:53ID: 23750000

adter turning off.. restrt the smtp service and routing engine service... on the sever

by: Cogit140Posted on 2009-02-27 at 06:29:45ID: 23755886

I was able to telnet outside to another mail provider (i.e. hotmail) from our exchange box so then I knew it had to be an issue with our exchange box and not the antispam or firewall. It turned out that our smtp connector was stuck on an old address, so I changed it to the appropriate address and restart the smtp service and outbound mail was working again. I am awarding x-sam most of the points because even though we didn't solve the issue, he was very helpful in diagnosing several different options. Thanks all for your responses.

20120131-EE-VQP-002

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Outbound emails blocked by ASA

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