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Routing emails to Exchange server - Routing tables

Posted on 2009-04-07
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Last Modified: 2012-05-06
We use Kaseya on our domain server (int. ip = 192.168.1.10, ext. ip = X.X.235.173, MS Server 2003) to manage Service Tickets which has the capability to send an email to the requestor when we add notes about their issue.  This week our Barracuda spam filter was updated and started denying these emails because they have our domain in the From field and come from the outside ip of the domain server into our Email server (int. ip = 192.168.1.20, ext. ip = X.X.235.171, MS Server 2003 R2).

I understand I have to use the Routing Tables to route these emails from the domain server to the email server, yet I have no idea how to do that and research has not shed a lot of light on what I must do. Any help would be appreciated.
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Question by:CLC_IT
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by:abhaigh
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Does this mean you are running with your DC exposed to the internet? And multi-homed? Neither of which are good ideas.

Anyway - what you want to do is on the command line

Route -p Add 192.168.1.0 MASK 255.255.255.0 %INTERNAL_GATEWAY_IP% METRIC 1 IF 2

This will add a persistent static route to your internal network via the second NIC card (modify that to suit)

Though you do want to do a ROUTE PRINT first to see if the route already exists
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by:CLC_IT
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I have one port forwarded through an outside ip to the DC to allow for pc's outside our domain (about 8 of em) to connect to Kaseya through the internet.

Back to the issue...
The command you gave me "Route -p Add 192.168.1.0 MASK 255.255.255.0 %INTERNAL_GATEWAY_IP% METRIC 1 IF 2", is the 192.168.1.0 supposed to be 1.10, or is that correct? Also, I assume the %Inter...IP% is to be the ip of my gateway not this actual text? There is one active route similar but has the DC as the gateway.
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by:abhaigh
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the 1.0 defines the entire subnet

the %....% does need to be replaced with your internal default gateway

the active route with the dc as its' gateway is probably 127.0.0.1 correct? That's the local route to locahost
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by:CLC_IT
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Thanks for the clarification. I had the idea but thought it wouldn't hurt to ask.

The Active route I mentioned is
Destination              Mask               Gateway          Interface       Metric
192.168.1.0     255.255.255.0     192.168.1.10   192.168.1.10     10

I will try the command here in about 10 mins.
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by:abhaigh
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the gateway should be your router address - not the machine itself

you should change the tcp/ip properties of the connection instead of using ROUTE ADD
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by:CLC_IT
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The gateway in the tcp\ip properties of my NIC is 192.168.1.1 So that is correct.

I tried the command and it failed.  Said "Either the interface index is wrong or the gateway does not lie on the same network as the interface. Check the Ip Address table for the machine."

Is there supposed to be more to this command? To define the interface maybe?
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by:abhaigh
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you need to pick the interface number - not the ip address
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by:CLC_IT
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I tried this command:
Route -p Add 192.168.1.0 MASK 255.255.255.0 192.168.1.1 METRIC 1 IF 2
And receieved the error.

I took off the "IF 2" because I understand that it will choose the best interface if not specified. It did then add a persistent route but this still didn't correct my problem.

I'm thinking I need to up the point value on this one if you can get it!! haha
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by:abhaigh
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can you paste the dump from an "ipconfig /all" and "ROUTE PRINT" please?

Then i can better understand your config better and see what it is you need to tweak

and why on earth do you have your DC multi-homed and exposed to the net?
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by:abhaigh
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actually - can you add a rule to your barracuda box to add the external ip of your dc to its white list and permit relaying for the that machine?

that would be easier than mucking about with the routing tables
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by:CLC_IT
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This DC has been setup this way since I started.  Our Barracuda box is hosted from Tangent services so I am waiting to hear back from them if they can whitelist the DC.

This is all default setup. We have edited the routing tables before.  I deleted the persistent route I added earlier so it is back to the way it was before I started looking at it. Here is the Route Print and IP config:



C:\Documents and Settings\Administrator.CLCCAMPUS>route print

IPv4 Route Table
===========================================================================
Interface List
0x1 ........................... MS TCP Loopback interface
0x10003 ...00 15 17 10 08 9c ...... Intel(R) PRO/1000 EB Network Connection with
 I/O Acceleration
===========================================================================
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface        Metric
          0.0.0.0          0.0.0.0                 192.168.1.1       192.168.1.10     10
        127.0.0.0        255.0.0.0              127.0.0.1        127.0.0.1      1
      192.168.1.0    255.255.255.0        192.168.1.10     192.168.1.10     10
     192.168.1.10  255.255.255.255        127.0.0.1        127.0.0.1     10
     192.168.1.15  255.255.255.255      192.168.1.1     192.168.1.10      1
     192.168.1.20  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.102  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.112  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.115  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.117  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.118  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.121  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.124  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.125  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.126  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.127  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.128  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.129  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.137  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.139  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.140  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.141  255.255.255.255      192.168.1.1     192.168.1.10      1
    192.168.1.255  255.255.255.255     192.168.1.10     192.168.1.10     10
     192.168.2.10  255.255.255.255      192.168.1.2     192.168.1.10      1
     192.168.2.55  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.100  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.101  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.102  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.103  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.104  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.105  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.106  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.107  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.108  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.111  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.113  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.116  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.117  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.118  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.119  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.120  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.121  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.122  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.123  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.124  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.125  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.126  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.127  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.128  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.129  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.130  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.131  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.132  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.133  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.134  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.135  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.138  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.139  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.140  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.141  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.142  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.143  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.144  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.146  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.147  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.148  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.2.150  255.255.255.255      192.168.1.2     192.168.1.10      1
     192.168.3.10  255.255.255.255      192.168.1.3     192.168.1.10      1
     192.168.3.40  255.255.255.255      192.168.1.3     192.168.1.10      1
     192.168.3.41  255.255.255.255      192.168.1.3     192.168.1.10      1
     192.168.3.55  255.255.255.255      192.168.1.3     192.168.1.10      1
     192.168.3.58  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.100  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.101  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.102  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.103  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.104  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.105  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.106  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.107  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.108  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.109  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.110  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.111  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.112  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.113  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.114  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.115  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.116  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.117  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.118  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.120  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.121  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.122  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.123  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.125  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.126  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.127  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.128  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.129  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.130  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.131  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.132  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.133  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.134  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.135  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.136  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.137  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.139  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.140  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.141  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.142  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.146  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.147  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.148  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.149  255.255.255.255      192.168.1.3     192.168.1.10      1
    192.168.3.150  255.255.255.255      192.168.1.3     192.168.1.10      1
     192.168.4.10  255.255.255.255      192.168.1.2     192.168.1.10      1
     192.168.4.41  255.255.255.255      192.168.1.2     192.168.1.10      1
     192.168.4.43  255.255.255.255      192.168.1.2     192.168.1.10      1
     192.168.4.60  255.255.255.255      192.168.1.2     192.168.1.10      1
     192.168.4.99  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.100  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.101  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.103  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.104  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.105  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.107  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.109  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.110  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.111  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.112  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.113  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.114  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.115  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.116  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.117  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.118  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.119  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.121  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.122  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.123  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.124  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.126  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.128  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.130  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.131  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.133  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.134  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.135  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.137  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.138  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.139  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.140  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.141  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.142  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.143  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.145  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.147  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.148  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.150  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.151  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.152  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.153  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.157  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.158  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.165  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.166  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.168  255.255.255.255      192.168.1.2     192.168.1.10      1
    192.168.4.169  255.255.255.255      192.168.1.2     192.168.1.10      1
        224.0.0.0        240.0.0.0     192.168.1.10     192.168.1.10     10
  255.255.255.255  255.255.255.255     192.168.1.10     192.168.1.10      1
Default Gateway:       192.168.1.1
===========================================================================
Persistent Routes:
  None

C:\Documents and Settings\Administrator.CLCCAMPUS>ipconfig /all

Windows IP Configuration

   Host Name . . . . . . . . . . . . : 2kserver
   Primary Dns Suffix  . . . . . . . : clccampus.christianlivingcampus.org
   Node Type . . . . . . . . . . . . : Hybrid
   IP Routing Enabled. . . . . . . . : Yes
   WINS Proxy Enabled. . . . . . . . : No
   DNS Suffix Search List. . . . . . : clccampus.christianlivingcampus.org
                                       christianlivingcampus.org

Ethernet adapter Local Area Connection 5:

   Connection-specific DNS Suffix  . :
   Description . . . . . . . . . . . : Intel(R) PRO/1000 EB Network Connection w
ith I/O Acceleration
   Physical Address. . . . . . . . . : 00-15-17-10-08-9C
   DHCP Enabled. . . . . . . . . . . : No
   IP Address. . . . . . . . . . . . : 192.168.1.10
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . : 192.168.1.1
   DNS Servers . . . . . . . . . . . : 192.168.1.10
0
 
LVL 15

Expert Comment

by:abhaigh
Comment Utility
This

 192.168.1.20  255.255.255.255      192.168.1.1     192.168.1.10      1

looks fine.


I can't see any external IP addresses in your routing table or the ipconfig dump

If this is all internal, why not just configure your Kaseya system to send straight to your exchange box and bypass the barracuda filter altogether?

0
 

Author Comment

by:CLC_IT
Comment Utility
Yeah I know.

I have been talking with Kaseya as well as Tangent services that hosts our Spam filtering.  I hope one of the 2 will be able to adjust the boxes. Otherwise it is left to me to figure out these routing tables.
0
 
LVL 15

Accepted Solution

by:
abhaigh earned 125 total points
Comment Utility
modifying the routing tables won't work if Kaseya is sendingsmtp mail out via dns and smtp

as it is, the route to the exchange box is already there [192.168.1.20  255.255.255.255      192.168.1.1     192.168.1.10      1]

you need to modify your Kaseya mail config

checking this http://portal.knowledgebase.net/display/2/kb/article.asp?aid=296524&n=2&s= it looks like it uses the smtp service used by IIS - change the configuration on the smtp virtual server to send to a smarthost at 192.168.1.20 instead of using DNS and your problem should go away

if it doesn't - then you need to configure the virtual smtp server on Exchange to allow connectionf from 192.168.1.10
0
 
LVL 15

Expert Comment

by:abhaigh
Comment Utility
and yeah - 500 points and an A would be nice
0
 

Author Closing Comment

by:CLC_IT
Comment Utility
Thanks for all your help.  We are going to go through either Kaseya to edit the mail configuartion or through our Spam filter host to add our servers IP to a global whitelist.  You provided a lot of direction for this issue so I appreciate it.
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