Cisco :: Why ESMTP Corrupts Emails So Badly From Exchange Server

Mar 18, 2011

since upgrading to 8.4(1) on our ASA 5520 I've had nothing but issues with our email server not being able to send out emails (timeouts,corruption, etc) and tried everything and then it dawned on me to turn off ESMTP inspection on the ASA's.Since I've down that our Exchange server SMTP works perfectly again.Why is it that ESMTP corrupts emails so badly from exchange server? (ours is a 2010 sp1)does anyone actually use ESMTP inspection at all?

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Our ASA 5510 has been in place for nearly two years, we never have any issue what so ever with it. All along the ASA has been using the default policy. Lately, we beeen getting email deferred in our Barracuda Spam firewall. Google quickly reveals that ESMTP does not play nice with Barracuda witch i disabled eventhough we haven't had any issue with it before. However, the issue remains, we still getting email deferred in the barracuda.
 
While doing more troubleshooting on the ASA, I constated when issue the command show local-host + IP of the Barracuda, there is an IP address in outside of the interface that can get up to 96 UDP port 53 connections with the Barracuda, this connection never get lower than 20! However, when checking the default setup for the Barracuda, i have the values below:
 
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[URL] 
 
I'm looking to do this with smtp so I added these lines to the config:
 
static (inside,DMZ) 10.2.2.30 10.1.1.11 netmask 255.255.255.255
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!
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I just recently replaced an older linksys pre-N router with a RV 120W.  I thought this would be a good choice as a more professional router.  I installed this router last week and things seemed to be working normally for web browsing, though I was receiving more incomplete pages and broken graphics.  Yesterday, I tried to watch a youtube video a friend had sent me and it would not play.  I tried several other videos from youtube and other sources with the same result: stalled videos, partial played videos followed by a spinning wheel. It was late, so I figured something was going on with Comcast and went to sleep.  This morning, I was trying to download Anti-virus updates.  The updates failed multiple times.  I then tried some videos again with the same results.  I tried downloading .ZIP files from several sources, and while the file completely downloaded, each and every file was corrupted and unusable.  Before I called Comcast to complain about my Internet being flaky, I unplugged the Comcast Arris TM502G device from the Cisco router and plugged it directly into my computer fully expecting the problem to persist, but the problem immediately dissapeared.  The immediate evidence is that the problem lays with the Cisco Router.  It appears that I can't make any changes on the Comcast device as it has a comcast public IP address and does not seem to have any web or telnet interface to change the settings. 
 
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- I power cycled the comcast device
 
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We have several customers running ASA 8.4x code and all seem to be plagued with the ESMTP inspection bug CSCtr92976.I have tested this in the lab with an ASA 5505 running 8.4(1), 8.4(2) and 8.4(4)1 & 8.4(4)3 and the behaviour is always the same.  I have an Exchange 2007 server and I can see in the logs the following messages:

2012-08-10T13:04:37.331Z,EXCHANGEDefault EXCHANGE,08CF3610468A42D7,3,192.168.102.28:25,192.168.250.26:52756,<,XXXX XXXXXXXXXXXXXXX,
2012-08-10T13:04:42.345Z,EXCHANGEDefault EXCHANGE,08CF3610468A42D7,4,192.168.102.28:25,192.168.250.26:52756,>,500 5.3.3 Unrecognizedcommand, 2012-08-10T13:05:20.506Z,EXCHANGEDefault EXCHANGE,08CF3610468A42D7,5,192.168.102.28:25,192.168.250.26:52756,<,XXX,

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We are working with an ASA 5520 and it seems there is an issue with some email messages sent throught it. When there are many recipients in the emails the email messages are not sent, and I have revised the server an the only thing I see is connecting dropped. When I went to see ASA log and see this log report: ESMTP Classification: Dropped connection for ESMTP Request from 'interface': servername/portnumber to outside: IP address/25; matched Class 2: cmd RCPT count gt 100 tcp flow from interface:servername/portnumber to outside: IP address/25 terminated by inspection engine, reason - inspector disconnected, dropped packet. So I think there should be an inspection of ESMTP packets and if they detect an email message sent to over 100 addresses, then the packet is dropped, am I right? if so, what should I do to let those email messages be sent?

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I am having an issue with an ASA 5510, running 8.4(1) code, causing outbound mail to remain in the SMTP server queue (Exchange 2007). This only happens with some remote mail servers. The connection usually ends with the remote server eventually sending a TCP reset.
 
I've taken multiple inside and outside packet traces.Other trace's contain either X's preceding various sections of the stream content or all X's in the content. The X's only appear when inspection is enabled.
 
Disabling inspection is the only thing that seems to allow mail to flow. I find this curious because I'm running this same ESMTP policy on other ASA's. However, they are on 8.3 code.
 
Most everything I find when searching on this subject says to disable ESMTP inspection. [code]

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Jan 26, 2011

We updated our business website in December and moved the hosting to our web designer's servers.Very shortly afterwards, we discovered that we could not view our own website, nor access our emails, which are hosted through our web domain name via cPanel.We run two Apple Macs through a Linksys router connected by two ethernet cables. We also have a Vonage internet phone connected to the network, which works either connected directly to the modem, or routed through the Linksys.We had this set up since March and had never had any problems until we had the new website. We don't know if its related, or just a coincidence.

We first went through a process of elimination:

First we connected the computers directly to the modem (one at a time, as obviously both can't connect directly) and we could access our emails and website absolutely fine. Not a solution though, as we need access on two machines.This led us to believe the problem was with the router. Both the Linksys and the Vonage device (box that the phone is plugged into, which is in turn connected to the internet) work as routers and we could view both router's home pages through their ip addresses.

We first called Vonage customer support, and no matter what they suggested in the nearly 2 hour call, nothing worked.We found a solution that suggested changing the MAC address of our router. After looking at the settings of the Vonage box, we couldn't work out how to change the MAC on this, so we changed the MAC of the Linksys instead - and it worked. We could view our emails and website again.However, plugging the Vonage box back in resulted in us losing access to our emails and website again. The set up solution worked for about a day before the same problems came back.

So we again unplugged the Vonage phone device and just ran our two Macs from the Linksys router - all fine, for a bit.A couple of days later the emails and website became inaccesible again. In desperation I changed the Mac address of the Linksys router and we were up and running again.

This solution worked for another day or so, until the old problems arose again.Now, whenever we reset the Mac address of the Linksys, it works, but emails and the website become inaccesible sometimes as soon as half an hour afterwards, sometimes longer, but however long we can gain access to the emails for, we constantly have to stop to reset the router, then restart everything.We now know that its nothing to do with the Vonage phone, so I'm discounting that from the equation now. Also, we've just tried running each of our computers in turn when plugged directly into the modem via an ethernet cable. Interestingly, one machine works fine, and can access the emails and our website, but the other machine now can't access the email or the website, but loads all other sites fine. Is this significant?

We've been reading up on our problems again, and it has been suggested that the issues are being caused by the website/email server blocking our ip address and that we can solve this issue by having a static ip address instead of the dynamic one that Virgin Media assigns. As we are on a home broadband service, we understand that this isn't possible though. Surely, if Virgin reassigns ip addresses every session, our ip would be constantly changing, therefore if we were blocked by the website server, wouldn't it be more likely to be blocking a static one, not one that is constantly changing? And also, how come one of our machines can access the emails etc when directly connected to the modem, but the other can't?

Other solutions proposed have been:
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-Move our website to a new server
-Move our emails to a new server and access our own website through a proxy.

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