How To: Setup Cisco EtherChannel with ESX Server

In this blog, I will go through on how to setup a Port-Channel in a Cisco Catalyst 3750G switch, and setup that port-channel (etherchannel) to work properly with ESXi Server version 5.5. In my environment, it took, much, much longer to get this running because I had to completely re-architect my network to function this way. But if you’re building an environment from scratch, then this should be pretty easy to do.

I’ve verified that this config will also work with other Catalyst switches (2960’s, 3500’s, 3700’s, 4500’s, and 6500 series switches). This configuration will NOT work with Cisco Nexus switches, because the Cisco Nexus switches have different command line parameters than their Catalyst cousins.

So, let’s get going here.

I’m going to start by configuring a Port-Channel on my Catalyst switch.

interface Port-channel2
description Port Channel interface to DL380 Server
switchport trunk encapsulation dot1q
switchport mode trunk

After you create your port channel, you need to add switch ports to that port-channel. See below, as I add 8 ports to this port-channel.

interface GigabitEthernet4/0/11
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/12
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/14
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/15
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/21
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/22
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/23
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

interface GigabitEthernet4/0/24
description Port-Channel group to DL-380 ESXi Server
switchport trunk encapsulation dot1q
switchport mode trunk
channel-group 2 mode on

From here I need to mirror the same VLANs that the ESXi server will have on it. So, lets create 5 VLANs to start. We can add more at any time.

interface Vlan1
no ip address
interface Vlan10
description Outside zone between pfSense and ASA
no ip address
interface Vlan20
description Inside network
ip address

interface Vlan30
description Front DMZ for direct connections from the Internet
no ip address

interface Vlan40
description Back DMZ -- Teired DMZ for server systems
no ip address

interface Vlan50
description Wireless network
no ip address

Now that the Cisco Catalyst switch is configured, let’s log into ESXi vSphere Client and configure the server to communicate with our switch.

I actually just bought a new quad port network adapter off of eBay just for this project. So after I installed it in my HP DL 380 G6 Server, I went in to verify that the card worked. And from this screenshot, it looks like it is working just fine.


Now go over to the “Networking” section. You can see I already have multiple vSwitches defined for my other 4 port network card that was already installed in the server. What my plan is going to be, is that I want all eight of my network adapters to be part of one port-channel. This will maximize the throughput and bandwidth to and from the server, as well as provide a reliable 8 way path to my core switch. The only downside to this is that my core switch is now my single point of failure on the network. I recommend that if you’re going to do this in your environment, you should have an identical switch and a full backup of the configuration on your primary switch so that you can swap out if the primary fails.


From here, click on “Add Networking…”


You need to select “VMkernel” here. You’ll be using “Virtual Machine” network type later. For now, VMkernel, then click “Next”:


Select the network adapters you want to participate in the port channel, then click “Next”:


Since this is a Port-Channel, or Etherchannel, you want this to trunk all of your VLANs from the Cisco Catalyst switch to your ESXi server. Make it easy and name this “Port-Channel” and allow all VLANs to traverse the link, then click “Next”:


You’ll want to enable management on this, so give it an IP address on your Internal network. Please, for the love of all that is right and just, do NOT open up management access to the Internet or any of your DMZs!


Verify your settings on the “Summary” screen, then click “Finish” to continue.


After you create your switch, you’ll see it appear in the “Networking” screen of your vSphere client. You’ll see that I haven’t attached network cables yet, which is why all my adapters are showing as “Down” with the red “X” next to each physical adapter.

Go ahead and click on “Properties…” to continue.


Make sure your vSwitch is highlighted in the left column, then click, “Edit…”


In the vSwitch Properties window, make sure that you have ESXi “Route based on IP Hash”, then click okay.


Now you can add in all your VLANs that will live on this vSwitch. So click on “Add Networking…” to continue:


Here is where you’re going to use the “Virtual Machine” connection type. Click Next to continue.


We’re going to bind this VLAN to the new switch we created. So select the vSwitch you created earlier in this process, then click “Next” to continue.


Here, I will create a Business-to-Business VLAN, and I’ll tag all traffic in this VLAN to #75. Then click “Next” to continue.


Verify your changes in the “Summary” screen, then click “Finish” to continue.


After you create all of your VLANs and add your virtual machines to each network you desire, your end result will look like this:

If you have any questions, please feel free to contact me at any time!

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AT&T u-Verse Static IP work around with pfSense

First off, I’d like to give AT&T an honorable mention (sarcasm) for using the fucking worst, P.O.S. garbage, DSL Modems on the planet: 2WIRE. These things are ridiculous. You’d think that if a provider was able to route a /28 subnet to your home/business, that they’d be able to properly manage that subnet through their “firewall” or whatever you want to call it. The way this normally works is through routing a network range to your device. But AT&T and 2WIRE ensure that for every public static IP address you have, it has to have a unique MAC address and it must look like a different device all together. This is asinine.

So, with the help of my business partner, we’ve come up with a solution on how to get a set of static IP addresses to work so that you can host services on AT&T u-Verse. The way we accomplished this was through the use of an open source and free operating system named, “pfSense”. I’m sure there are other systems out there that we could have used, or just done it in Linux, but pfSense is really robust and has a nice interface. So that’s what we went with.

Additionally, I’m sure not everyone and their mother have an HP DL380 running in their basement, but… welcome to the Erdmanor. I have a DL380 in my basement. So what we’ve done is virtualized a firewall. We’re running pfSense in a virtual machine on the DL 380, which is running ESXi 5.5. I know ESXi 6.0 has been out for a few months now, but to be honest, I’m just too damn lazy to upgrade my box.

Anyways, here’s how we configured the virtual firewall. In ESX, we provisioned the system to have 8 network adapters, a 10GB HDD, 2GB RAM, and 1 virtual CPU. From there we added the VM to access the three different network segments (DMZ, Internal, Outside), and created the interfaces within pfSense. Then we programmed the AT&T gateway to use the external addresses that were provided by them, making sure that the proper interfaces and MAC addresses lined up between the ESX server, the AT&T gateway and the pfSense console. Also, in the AT&T gateway, we setup the system to be in DMZplus Mode, which you can read about in the screenshot below.








Now that our AT&T gateway is properly forwarding External IP traffic to the proper interfaces on our pfSense firewall, we can go through and create all the inbound NATs, firewall rules and network security that we wish to have.

If you have any further questions on how to set this up, just ask!


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Creating a Reverse Proxy with Apache2

Sometimes there is a need for hosting multiple websites from one server, or from one external IP address. For whatever your reason or need is, in this tutorial, I’ll just go through what I did to setup Apache server to forward requests.

In my setup here, I have a Debian Wheezy server in my DMZ, and in my tier 2 DMZ I have 5 Web servers. My objective is to host all these server from 1 IP address, and introduce some security.

I found a ton of info out there on setting up Apache as a reverse proxy, but none of them really spelled out exactly what to do, and what the results would be. Some of them did, but it wasn’t what I was looking for. So I took a bunch of stuff I see others doing, modify it to fit my needs and report back to you. I hope this helps.

Lets get started.

You’ll want a base install of Debian Wheezy which you can find at After you download that, just follow my guide for install if you need: Debian Minimal Install: The base for all operations

As I stated before, I have a bunch of web servers in my tier 2 DMZ, and a Debian box in my Internet facing DMZ. It is my intention that the web servers never actually communicate with the end users. I want my end users to talk to my Debian box, the Debian box to sanitize and optimize the web request, and then forward that request on to the web server. The web server will receive the request from the Debian box, process it, and send back all the necessary data to the Debian server, which will in turn reply to the end user who originally made the request.

It sounds complicated to some people, but in reality it’s pretty simple, and the reverse proxy is transparent to the end user. Most people out there don’t even realize that many sites out there utilize this type of technology.

My Debian server needs some software, so I installed these packages:

sudo apt-get install apache2 libapache2-mod-evasive libapache2-mod-auth-openid libapache2-mod-geoip
libapache2-mod-proxy-html libapache2-mod-spamhaus libapache2-mod-vhost-hash-alias libapache2-modsecurity

From here you’ll want to get into the Apache directory.

cd /etc/apache2

Let’s get going with editing the main Apache config file. These are just recommendations, so you’ll want to tweak these for what ever is best for your environment.

sudo vim apache2.conf

I modified my connections for performance reasons. The default is 100.

# MaxKeepAliveRequests: The maximum number of requests to allow
# during a persistent connection. Set to 0 to allow an unlimited amount.
# We recommend you leave this number high, for maximum performance.
MaxKeepAliveRequests 500

Also, what security engineer out there doesn’t know that without logs you have no proof that anything is happening. We’ll cover log rotation and retention in another blog, but for now, I set my logging to “notice”. Default was “warn”.

# LogLevel: Control the number of messages logged to the error_log.
# Possible values include: debug, info, notice, warn, error, crit,
# alert, emerg.
LogLevel notice

Perfect. Now, you may want to tweak your server a little differently, but for now this is all we need for here.

Now let’s get into some security hardening of the server.

sudo vim /etc/apache2/conf.d/security

We do have security in mind, so let’s not divulge any information that we don’t need to. Set “ServerTokens Prod”

# ServerTokens
# This directive configures what you return as the Server HTTP response
# Header. The default is 'Full' which sends information about the OS-Type
# and compiled in modules.
# Set to one of:  Full | OS | Minimal | Minor | Major | Prod
# where Full conveys the most information, and Prod the least.
#ServerTokens Minimal
#ServerTokens OS
#ServerTokens Full
ServerTokens Prod

Now let’s set “ServerSignature Off”

# Optionally add a line containing the server version and virtual host
# name to server-generated pages (internal error documents, FTP directory
# listings, mod_status and mod_info output etc., but not CGI generated
# documents or custom error documents).
# Set to "EMail" to also include a mailto: link to the ServerAdmin.
# Set to one of:  On | Off | EMail
#ServerSignature Off
ServerSignature On

And lastly, go ahead and uncomment these three lines in your config. We’ll configure “mod_headers” later.

Header set X-Content-Type-Options: "nosniff"

Header set X-XSS-Protection: "1; mode=block"

Header set X-Frame-Options: "sameorigin"

Sweet, looking good. Go ahead and save that, and we can get “mod_headers” activated. First, I’d like to point out that you can view what modules you have installed by using the “a2dismod” program. Simply enter the command, and it will ask you what modules you’d like to disable. Obviously, if you see it in the list, it’s already enabled. just hit “Ctrl+C” to stop the program.

To enable a module in Apache, you need to first made sure it’s installed, then you can just use the program “a2enmod”… like this:

sudo a2enmod headers

Now that we’ve enabled “mod_header”, lets verify we have the other necessary modules enabled as well.

steve @ reverseproxy ~ :) ᛤ>   a2enmod
Which module(s) do you want to enable (wildcards ok)?
Enabling module cache.
Could not create /etc/apache2/mods-enabled/cache.load: Permission denied
steve @ reverseproxy ~ :( ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Enabling module cache.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Considering dependency proxy for proxy_ajp:
Module proxy already enabled
Enabling module proxy_ajp.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Considering dependency proxy for proxy_balancer:
Module proxy already enabled
Enabling module proxy_balancer.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Considering dependency proxy for proxy_connect:
Module proxy already enabled
Enabling module proxy_connect.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Considering dependency proxy for proxy_ftp:
Module proxy already enabled
Enabling module proxy_ftp.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Considering dependency proxy for proxy_http:
Module proxy already enabled
Enabling module proxy_http.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Enabling module rewrite.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Enabling module vhost_alias.
To activate the new configuration, you need to run:
  service apache2 restart
steve @ reverseproxy ~ :) ᛤ>   sudo a2enmod
Which module(s) do you want to enable (wildcards ok)?
Enabling module vhost_hash_alias.
To activate the new configuration, you need to run:
  service apache2 restart

Here is a list of the Modules I just enabled:
cache proxy_ajp proxy_balancer proxy_connect proxy_ftp proxy_http rewrite vhost_alias vhost_hash_alias

Now let’s just restart Apache, and keep going.

steve @ reverseproxy ~ :) ᛤ>   sudo service apache2 restart
[ ok ] Restarting web server: apache2 ... waiting .

Perfect, moving right along… Now what we need to do is setup a new file in the “/etc/apache2/conf.d/sites-available” directory. I named mine, “reverseproxy”, as it’s easy to figure out what it is.

Now, to correctly setup your reverse proxy, this server should not be hosting ANY websites. This is a proxy server, not a web host. So go ahead and delete the config sym link for the default website. We don’t want to host that.

sudo rm /etc/apache2/sites-enabled/000-default

Now we can edit our “reverseproxy” file.

sudo vim /etc/apache2/sites-available/reverseproxy

#enter this code into your file

<VirtualHost *:80>
  ProxyPreserveHost On
  ProxyPass /
  ProxyPassReverse /
  <Proxy *>
        Order allow,deny
        Allow from all
  ErrorLog /var/log/apache2/
  CustomLog /var/log/apache2/ combined

<VirtualHost *:80>
  ProxyPreserveHost On
  ProxyPass /
  ProxyPassReverse /
  <Proxy *>
        Order allow,deny
        Allow from all
  ErrorLog /var/log/apache2/
  CustomLog /var/log/apache2/ combined

<VirtualHost *:80>
  ProxyPreserveHost On
  ProxyPass /
  ProxyPassReverse /
  <Proxy *>
        Order allow,deny
        Allow from all
  ErrorLog /var/log/apache2/
  CustomLog /var/log/apache2/ combined

Awesome, now save that file and we can get it enabled. Just like setting up new modules, we’re going to sym-link our new file to the “sites-enabled” folder.

sudo ln -s /etc/apache2/sites-available/reverseproxy /etc/apache2/sites-enabled

Now we can just reload the Apache server (no restart required) the server so that it picks up the new settings.

sudo service apache2 reload

Now we need to edit the /etc/hosts file so that our reverse proxy server knows where to push site traffic to on our DMZ. So lets do that:       localhost       reverseproxy.internal.dmz  reverseproxy

# The following lines are desirable for IPv6 capable hosts
::1     localhost ip6-localhost ip6-loopback
ff02::1 ip6-allnodes
ff02::2 ip6-allrouters

Sweet, all done!
Now you can test from a computer that all your sites are working. They *should* be! 🙂

I’ll work on a blog eventually to show how to enable mod_security with this setup so that we can sanitize user interaction with our site. Our visitors are probably good people, but attackers and skiddies are always out there trying to damage stuff.

Thanks for reading!!


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Microsoft Exchange: Fortify and secure your mail server!

So, I just (mostly) finished with writing a blog on how to setup a Postfix Reverse Mail Proxy that works as a SPAM filter for your Exchange Server. A blog I wrote before that was about network architecture that I feel any organization should be able to do, regardless of the size of the company. Those two blogs really had a lot to do with security at the perimeter of the network. I would like to continue working on securing email and increasing the security and reliability of your MS Exchange environment, while at the same time not impeding on usability or scalability.

In this blog we’ll look at securing and fortifying your Exchange Server. If you look at Microsoft’s website, and the people talking out on the “” site, you’ll hear people say asinine things like, “upon installation it’s already secure,” or, “Exchange server comes secure by default,” or something like that. I’m sorry, but any product that you purchase can be made more secure. If that weren’t the case, then why run “Windows Updates”, install patches, configure firewalls or setup SPAM filtering? I don’t care what product you’re talking about, there is ALWAYS something you can do in order to make things more secure.

There are many reasons for wanting to secure your Exchange infrastructure, but the main reason why is for availability. Many organizations rely on email as a backbone to their communications; especially small businesses. If your company lost email communications for even a day, how much productivity would be lost? How much credibility would be lost if outside senders couldn’t get their mail to your organization? But most of all, what if your Exchange server was used as a mass SPAM gateway that caused many other companies, partners or customers to be infected? The cost of cleaning up SPAM, junk, viruses, Malware, or in worst case scenario, a breach, could be in the tens or hundreds of thousands of dollars.

In this economy, no one can afford to go through something like that. It’s not even an option. So in this blog, it is my intention to show you how to effectively secure your Exchange Server(s), increase SPAM fighting ability, lock down users mailboxes, and I’ll do my best at providing some Power Shell Scripts to help out scripting a lot of these tasks. Most of all, I’m going to tell you that over time, this blog will grow to be pretty long. I don’t expect that this blog will just be a “set it and forget it” deal. Exchange administration is an ongoing effort, much like the hacking community. It’s constantly evolving with trying to minimize SPAM, decrease the frontage of your environment, while at the same time, allowing users to Sync with their phones, check web mail on the road, connect with MS Outlook and still receive the same level of service that they would expect from any other company. The last thing I want to hear is that something detailed and outlined on this blog caused an IT guy his job, or got him in trouble, because he implemented something that broke Exchange or caused an outage.

As for this blog, I want to set some barriers on what this blog IS, and IS NOT. If you’re looking for a Windows Server Hardening guide, you’re in the wrong spot. I’m currently working on a Windows Server hardening guide that will take existing MSBs, take the best of breed, and get them into GPOs and scripts that you can use on your Windows Server infrastructure. That blog can be found #here# when it is complete. Until then, what this blog is going to focus on will not be the OS layer. We’re looking at hardening Exchange, and Exchange only!


First thing we’re going to do is provide a brief overview of what’s going on with Exchange from a AD permissions standpoint. Most everything that Exchange does is based on Kerberos tickets, so my biggest suggestion is that you keep time on your domain extremely tightly. A hardware clock on a server can get out of sync pretty quickly, especially if the CMOS battery is going bad, so it’s best to make sure that your Exchange server and your domain controllers are all synced together by an external time source. Another good practice is to designate two (2) or more computers, preferably servers, to host an NTP service that is able to sync with the outside world at a reputable time source like NIST, Microsoft, or NASA. That server should be the only one that can communicate over port udp/123 to the outside world. Then you can allow all your servers, regardless of what network segment you put them in, to talk to your NTP server(s). Refer to my Network Architecture blog for what your forward facing DMZ should look like.

I’m going to skip going through setting up Exchange Roles. Reason being is that in smaller environments it’s really not feasible to delegate administrative access and give certain Admins a read only view, or that group of Admins Exchange Recipient Admins access, and so on. Even in larger companies, you may only have a small handful of Exchange Admins who all have full administration rights. So we wont get into those roles and permissions. It is possible to do that stuff, but at the end of the day, most companies these days do a pretty good job at vetting out who they give administrator rights to, there are signed agreements with those employees, and other mitigating controls. You’re going to have to trust your Exchange Admins. And if you don’t, you better trust your Backup Administrators.

You’ve probably noticed that Exchange 2010 permissions have even changed since prior editions. No longer are you setting up Exchange permissions inside the Exchange Management Console. You’ll be taking care of this stuff in Active Directory from now on due to Microsoft’s new security model. They’ve taken the approach of a true Role Based Access Control (RBAC) and they outline all of this information here at their site. The main permission that you’ll be concerned with is the Organization Management role. You can see that all the roles are in the “Microsoft Exchange Security Groups” OU in AD. See below:


Next thing to talk about is your Exchange Server, or at least the Physical- or VM-Server that you have Exchange running on. The underlying setup of this machine is very important to how Exchange will operate. If there are issues with the server getting DNS update mail will stop flowing, if the time is off your admins wont be able to administer the box, if there are errors or warnings in the event logs those need to be fixed, etc… It’s very important to monitor the event logs of your Server(s). While I am not blind to the fact that in the real world there are constantly issues arising on the network, but many issues can be minor issues if they aren’t let go to become large issues. The underlying theme here is to Harden Server 2008. Please go through that blog first, before venturing forward here.


Please go harden you Server 2008 Box before going forward


So now that your Server 2008 box is hardened, we can move on. To be honest, there really isn’t much to do on the Exchange side of the house. If you’ve gotten a SPAM filter sitting in front of your Exchange Servers, as I’ve outlined in my previous Postfix Mail Relay SPAM Filter blog, you’re already doing pretty well. There are many things that a front-end SPAM filter should be doing that Exchange shouldn’t. Exchange is a messaging platform. It’s really good at doing things like delivering email, working with Calendars, scheduling appointments, and keeping lines of communication open. From here on out it’s pretty much just controlling permissions to Exchange, between mailboxes and calendars, etc… There are other tasks such as Microsoft’s Security Configuration Wizard (SCW), granting users access to other mailboxes, creating conference rooms, Federation Services with other domains, ActiveSync controls, remote device wipe, internal and external receive connectors, and Exchange Certificates, that I’ll attempt to cover here.


One of the biggest things I hate to see is when you look at the message headers on an email from outside your organization. Hardly anyone updates the info on those things. I know it’s not really that much information, but you can easily divulge a few pretty important pieces of information from email message headers. The main two are your Internal Domain Name and your Internal IP Address space where your Exchange server lives. Especially in small companies, it’s extremely common to see that the server farm sits at either the top or the bottom of a /24 (like What I mean is, these small companies have less than 10 servers most of the time, so you know all of their internal systems are on the same subnet. We want to take those pieces of information out of the header. To do that is very easy, just two or three Exchange PowerShell commands.

The following command, according to Microsoft’s Social pages, “When you remotely connect to PoSh (enter-pssession, invoke-command), unless you specify otherwise, it loads the default PowerShell shell with no added modules. When you run the command from your Exchange 2010 server, you’re probably running the commands from the Exchange Management Shell (EMS) that preloads a bunch of cmdlets in the background — that’s how you get the tip-of-the-day and such.

Add-PSSnapin Microsoft.Exchange.Management.PowerShell.E2010 -ea SilentlyContinue


This command will disable ms-Exch-Send-Headers-Routing extended right, which in turn enabled the header firewall. Make sure to change “InternetConnectorName” to whatever your send connector is named.

Get-SendConnector –InternetConnectorName | Remove-ADPermission –User “NT AUTHORITY\ANONYMOUS LOGON”
–ExtendedRights ms-Exch-Send-Headers-Routing


Then to make sure that your settings are taken care of, push a synchronization to your edge servers like this:



After running your commands you can log into a Domain Controller (given that you have the available rights) and check this in the ASDI Editor. You can see that the send connector security has changed. To do this, run ADSI Edit from the Start Menu, then Administrative Tools, ASDI Editor. When that starts up, click on File, then “Connect to” and connect to the configuration naming context (the drop down menu in the center of the screen), as you can see below:

After you get to this point, Expand “Domain Root \ your domain\ Services \ Microsoft Exchange \ {your Exchange organization} \ Administrative Groups \ Exchange Administrative Group (FYDIBOHF23SPDLT) \ Routing Groups \ Exchange Routing Group (DWBGZMFD01QNBJR) \ Connections”. As seen below:

As you see here, you will find the send connectors in the center panel. To verify the security changes have taken effect, double-click on the connector that you are working on and then click the “Security” tab. verify that the “ANONYMOUS LOGON” user has no check boxes enabled except for “Special Permissions” as you can see below:


I don’t know why I am saying this, but I feel that it should be stated that Exchange shouldn’t be running on a Domain Controller. I know Microsoft ships Windows Small Business Server with Exchange and SQL and other technologies built into it, but that is the only exception I’ll be making here. There are many reasons for wanting to separate Exchange services from a domain controller, but I would say the main reasons are, separation of duties and that if your Exchange box gets popped, the attackers already own your DC. Separation of duties is simple; each server in your organization should only be hosting 1 service. We do that for a number of reasons, such as making troubleshooting easier. Also, don’t forget, your Exchange box hosts web mail for your organization. Do you want a website hosted off your DC that is publicly available to everyone on the Internet? I think not.


Another good tool to use is the Exchange Best Practices Analyzer. Pending how large your organization is, this can take a significant amount of time to complete, but the information you’ll get out of it is pretty useful. There are a few different areas you can test in there including, Performance, Permissions, Baseline and a Connectivity Test. I would suggest finding the time to run all of the scans.


Don’t forget to be constantly updating settings in your Exchange Spam Filtering, too. I know what you’re thinking. You’re probably thinking, “This dude just told me that we shouldn’t use the Exchange SPAM filter, that we should be using his Postfix Mail Relay instead.” And you would be right. You should use that. BUT! Everything in moderation, and security in layers. If you put all your faith in any one piece of technology, that’s bad. Like I said before, the day that you can buy one product that will secure everything, is the day that I’m out of a job.

First, if you haven’t already, you’ll have to enable some stuff. Let’s get the SPAM filter enabled.

 cd 'C:\Program Files\Microsoft\Exchange Server\V14\Scripts'
Restart-Service MSExchangeTransport


Once that’s completed, we can tune the SPAM filter that is part of Exchange. You’ll find that in the Hub Transport area of the Organization Configuration in the EMC (seen below):


Make sure to go through all of those Features and set them up the way you want them to work. Some of this stuff overlaps the stuff in the Postfix Mail Relay, but if you aren’t using that go ahead and set them up here. The nice thing about setting up these options in the Exchange Server is that it’s scriptable. I mean, for all intensive purposes, it is scriptable in the Postfix Mail Relay too, but you have the ability to do that here too. Get a couple PowerShell cmdlets together and you can add stuff on the fly to this SPAM filter.

One nice thing here is that if you don’t want to tie your Postfix Mail Relay into Active Directory, you can block the messages here as well. What I mean by that is, Exchange will receive an email, check to see if the person exists in AD, and if they don’t it will block the message. The Postfix Mail Relay has the same capability, but with much more setup work to be done. This is just a simple checkbox, as seen below.


You’ll want to go through the settings in both the Exchange ActiveSync Mailbox Policies, as well as the Outlook Web App Mailbox Policies. There are many settings in there that


Another thing that should be obvious, but I’ll mention anyways, is that POP3 and IMAP should be disabled, and left disabled. There’s no need for that stuff. In Linux you can run DavMail for your local mail proxy, and in Windows and Mac you should be just running MS Office (with some version of Outlook). If you’re running an AD and Exchange environment, most of your users are probably using Outlook anyways, and they should be using Outlook 2007 or 2010 in order to get the most functionality out of Exchange. In all actuality, Even your Linux people really should have a Windows 7 VM running for Outlook, Visio and Office.


I’ll be going through and updating this as I have time… I’m burnt out on all this stuff, so check back periodically for updates!













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Cisco ASAs: Baseline Configurations

So, I’ve been dabbling around in the Cisco field for many years now. I started taking Cisco Academy courses at a local college in the Fall of 2002 and since then I’ve completed all the CCNA, CCNP and most recently the CCNA Security courses. By no means am I calling myself an expert, the best Cisco Engineer on the planet, or even on par with a Cisco engineer that’s been in the field for at least a year or so. But what I am saying is that, I feel that I’ve got a decent background.

I bought a Cisco ASA 5505 a few years ago, played with it for a while and then got side tracked with other work. I even forgot I even owned the device for a while, until I took my CCNA Security course in the Fall of 2012.

Again, my purpose of this blog site is to help give back to the community. So I just want to throw down a little ASA knowledge for anyone interested in buying an ASA for home use. This stuff is even transferable to the high class 5510’s up to the 5585’s.

Now, I host my own services for many reasons; mail, web, remote access, etc… Mainly the reason I do this is because for every service I run out of my house, the more knowledge I gain in IT management, Securing networks, and knowing what it takes to run both sides of the house (IT and Security). What I want to do here is go over how to create a baseline configuration for a Cisco ASA unit. It really is easier than you think.


So lets get going here!


If you’ve got a brand new Cisco ASA, right out of the box and you’re about to plug it in, you’re in a perfect spot. If you bought one off eBay or something like that, you’ll want to wipe the configuration on the device.

In order to wipe an ASA you need to know the enable password to the device, or you need to boot it into recovery mode. If you’re having issues with the password, I recommend you just reset it with the information on Cisco’s website.

I’m doing this work from a Debian box, but you can do this from virtually any OS. You’ll need a Cisco serial cable, which you should’ve gotten with your purchase of an ASA. For those of you who haven’t seen one, they look like this:
Cisco Serial Cable

And if you’re connecting with a laptop made in the last few years you’ll need a USB to serial adapter. Many computers don’t even have Serial ports anymore, so this adapter is essential.
USB to Serial (RS-232)

To connect to the Cisco ASA, connect your USB connector to your computer, and the Cisco serial cable to your ASA device. Then the easiest thing to use is Putty, which you can get from the Putty Website. There is the installer for pretty much every Windows OS as well as the source code that you can compile on just about every Unix/Linux platform out there.

After you get Putty installed and running, you can modify the settings to your liking. I like being able to see all the scroll-back of my sessions, so I normally set that to “999999” or something like that, and I also save all session output to putty.log on the Desktop of whatever OS I’m on at the time.

To connect to your Cisco ASA, on the main screen, click on “Serial” verify that your serial port is properly setup and click “Connect”. For Windows based machines, your USB to Serial connector usually will create a COM port that you’ll have to verify in the “Device Manager”. In Linux, the USB to Serial Adapter creates a device in your “/dev” directory, usually named “/dev/ttyUSB0”, but again, you’ll want to verify that. Also, most Linux distro’s require that you access that device as Root. You may have to start Putty from the Command line like this:

sudo putty


You should see this window appear after a few seconds:

Putty Screen in Linux


Alright enough messing around. Connect to your ASA and then power it on. You’ll see a bunch of scroll back as your device is starting. Like this:

Embedded BIOS Version 1.0(12)6 08/21/06 17:26:53.43

Low Memory: 632 KB
High Memory: 251 MB
PCI Device Table.
Bus Dev Func VendID DevID Class              Irq
 00  01  00   1022   2080  Host Bridge        
 00  01  02   1022   2082  Chipset En/Decrypt 11
 00  0C  00   1148   4320  Ethernet           11
 00  0D  00   177D   0003  Network En/Decrypt 10
 00  0F  00   1022   2090  ISA Bridge        
 00  0F  02   1022   2092  IDE Controller    
 00  0F  03   1022   2093  Audio              10
 00  0F  04   1022   2094  Serial Bus         9
 00  0F  05   1022   2095  Serial Bus         9

Evaluating BIOS Options ...
Launch BIOS Extension to setup ROMMON

Cisco Systems ROMMON Version (1.0(12)6) #0: Mon Aug 21 19:34:06 PDT 2006

Platform ASA5505

Use BREAK or ESC to interrupt boot.
Use SPACE to begin boot immediately.
Launching BootLoader...
Default configuration file contains 1 entry.

Searching / for images to boot.

Loading /asa845-k8.bin... Booting...
Platform ASA5505

IO memory blocks requested from bigphys 32bit: 9672
�dosfsck 2.11, 12 Mar 2005, FAT32, LFN
Starting check/repair pass.
Starting verification pass.
/dev/hda1: 96 files, 10581/31033 clusters
dosfsck(/dev/hda1) returned 0
Processor memory 109051904, Reserved memory: 41943040

Total SSMs found: 0

Total NICs found: 10
88E6095 rev 2 Gigabit Ethernet @ index 09 MAC: 0000.0003.0002
88E6095 rev 2 Ethernet @ index 08 MAC: 0019.0724.43f6
88E6095 rev 2 Ethernet @ index 07 MAC: 0019.0724.43f5
88E6095 rev 2 Ethernet @ index 06 MAC: 0019.0724.43f4
88E6095 rev 2 Ethernet @ index 05 MAC: 0019.0724.43f3
88E6095 rev 2 Ethernet @ index 04 MAC: 0019.0724.43f2
88E6095 rev 2 Ethernet @ index 03 MAC: 0019.0724.43f1
88E6095 rev 2 Ethernet @ index 02 MAC: 0019.0724.43f0
88E6095 rev 2 Ethernet @ index 01 MAC: 0019.0724.43ef
y88acs06 rev16 Gigabit Ethernet @ index 00 MAC: 0019.0724.43f7
Encryption hardware device : Cisco ASA-5505 on-board accelerator (revision 0x0)
                             Boot microcode   : CN1000-MC-BOOT-2.00
                             SSL/IKE microcode: CNLite-MC-SSLm-PLUS-2.03
                             IPSec microcode  : CNlite-MC-IPSECm-MAIN-2.06
Verify the activation-key, it might take a while...
Running Permanent Activation Key:  

Licensed features for this platform:
Maximum Physical Interfaces       : 8              perpetual
VLANs                             : 3              DMZ Restricted
Dual ISPs                         : Disabled       perpetual
VLAN Trunk Ports                  : 0              perpetual
Inside Hosts                      : 50             perpetual
Failover                          : Disabled       perpetual
VPN-DES                           : Enabled        perpetual
VPN-3DES-AES                      : Enabled        perpetual
AnyConnect Premium Peers          : 2              perpetual
AnyConnect Essentials             : Disabled       perpetual
Other VPN Peers                   : 10             perpetual
Total VPN Peers                   : 12             perpetual
Shared License                    : Disabled       perpetual
AnyConnect for Mobile             : Disabled       perpetual
AnyConnect for Cisco VPN Phone    : Disabled       perpetual
Advanced Endpoint Assessment      : Disabled       perpetual
UC Phone Proxy Sessions           : 2              perpetual
Total UC Proxy Sessions           : 2              perpetual
Botnet Traffic Filter             : Disabled       perpetual
Intercompany Media Engine         : Disabled       perpetual

This platform has a Base license.

Cisco Adaptive Security Appliance Software Version 8.4(5)

  ****************************** Warning *******************************
  This product contains cryptographic features and is
  subject to United States and local country laws
  governing, import, export, transfer, and use.
  Delivery of Cisco cryptographic products does not
  imply third-party authority to import, export,
  distribute, or use encryption. Importers, exporters,
  distributors and users are responsible for compliance
  with U.S. and local country laws. By using this
  product you agree to comply with applicable laws and
  regulations. If you are unable to comply with U.S.
  and local laws, return the enclosed items immediately.

  A summary of U.S. laws governing Cisco cryptographic
  products may be found at:

  If you require further assistance please contact us by
  sending email to
  ******************************* Warning *******************************

Copyright (c) 1996-2012 by Cisco Systems, Inc.

                Restricted Rights Legend

Use, duplication, or disclosure by the Government is
subject to restrictions as set forth in subparagraph
(c) of the Commercial Computer Software - Restricted
Rights clause at FAR sec. 52.227-19 and subparagraph
(c) (1) (ii) of the Rights in Technical Data and Computer
Software clause at DFARS sec. 252.227-7013.

                Cisco Systems, Inc.
                170 West Tasman Drive
                San Jose, California 95134-1706

Reading from flash...
Flash read failed

Cryptochecksum (changed):  

Pre-configure Firewall now through interactive prompts [yes]?


From here the ASA is going to ask a series of questions in order to get a very minimal configuration setup. You can go through them or not. Either way will be fine. I’m going to go through the prompts just to show what questions are asked:

Pre-configure Firewall now through interactive prompts [yes]?
Firewall Mode [Routed]: Routed
Enable password [<use current password>]: {strong-password-here}
Allow password recovery [yes]?
Clock (UTC):
  Year [2012]:
  Month [Dec]:
  Day [21]:
  Time [22:57:31]: 18:00:35
Management IP address:
Management network mask:
Host name: Erdmanor-ASA
Domain name:
IP address of host running Device Manager:

The following configuration will be used:
Enable password:
Allow password recovery: yes
Clock (UTC): 18:00:35 Dec 21 2012
Firewall Mode: Routed
Management IP address:
Management network mask:
Host name: Erdmanor-ASA
Domain name:

Use this configuration and write to flash? yes
INFO: Security level for "management" set to 0 by default.
Cryptochecksum: e661f916 9e00a961 ba015bae 20f4d894

2081 bytes copied in 1.50 secs (2081 bytes/sec)


It’s very import here that you setup your ASA with Routed mode. The reason why is that the only way to have an Internal, External and DMZ interface on your network with a base licensed ASA is to have it in Routed mode. According to Cisco, “For the Base license, allow this interface to be the third VLAN by limiting it from initiating contact to one other VLAN using the following command:

hostname(config-if)# no forward interface vlan number

Where number specifies the VLAN ID to which this VLAN interface cannot initiate traffic.

With the Base license, you can only configure a third VLAN if you use this command to limit it.

For example, you have one VLAN assigned to the outside for Internet access, one VLAN assigned to an inside business network, and a third VLAN assigned to your home network. The home network does not need to access the business network, so you can use the no forward interface command on the home VLAN; the business network can access the home network, but the home network cannot access the business network.

If you already have two VLAN interfaces configured with a nameif command, be sure to enter the no forward interface command before the nameif command on the third interface; the adaptive security appliance does not allow three fully functioning VLAN interfaces with the Base license on the ASA 5505 adaptive security appliance.”


My suggestion here is that our Outside interface should never initiate traffic to the Internal network. The purpose of the Internal network is to communicate with Internet Hosts and the DMZ. It is the most secure network we have, therefore we should never accept incoming traffic. The DMZ will accept all incoming traffic and if there are any reverse proxies, then the DMZ will hold all of those systems and communicate to the internal for any Internet host. A few examples of this would be a Reverse SMTP Proxy or a HTTP or HTTPS Reverse Proxy. There is NEVER a reason for the Internal network to accept Internet traffic…… unless you have a lazy admin, or your company doesn’t know shit about security.


By default, interfaces on the same security level cannot communicate with each other. Allowing communication between same security interfaces lets traffic flow freely between all same security interfaces without access lists. If you enable NAT control, you do not need to configure NAT between same security level interfaces. If you enable same security interface communication, you can still configure interfaces at different security levels as usual. While I highly discourage this!, if you want to enable interfaces on the same security level so that they can communicate with each other, enter the following command:

hostname(config)# same-security-traffic permit inter-interface


So let’s see. What should we start with? Well, if you saw my blog on network architecture you’ll know that we should start things off securely. Let’s get a DMZ up and running as well as our internal and external interfaces.

conf t
(config)# interface vlan 1
(config-if)# ip address ( ### Change this to match your internal network
(config-if)# nameif Inside
(config-if)# security-level 100
(config-if)# no shut
(config-if)# exit
(config)# interface vlan 100
(config-if)# ip address (outside IP) ### Change this to match your ISP Static IP Address
(config-if)# nameif Outside
(config-if)# security-level 0
(config-if)# no shut
(config-if)# exit
(config)# interface vlan 200
(config-if)# ip address ( ### Change this to match your DMZ network
(config-if)# nameif DMZ
(config-if)# security-level 50
(config-if)# no forward interface vlan 100
(config-if)# end
write mem

What we’ve done here is setup the three VLANs that we’ll be using in our network. Once you setup these VLANs, issue the “end” command followed by the “write mem” command to save your current running config. Then issue the “show run” command to view your config.


Now, let’s get rid of some junk configurations that Cisco throws in there.

conf t
(config)# no service-policy global_policy global
(config)# clear config call-home
(config)# no ftp mode passive
(config)# no snmp-server enable
(config)# no telnet timeout 5
(config)# end
wr mem


Now you can go back and check your config again by issuing the “show run” command.

So, let’s get off this console connection and get our SSH running. Once SSH is running we can not only access our Cisco ASA from the Linux command line where most of us are more comfortable, but we can also build up some pretty sweet Python scripts that we can use to manage our ASA much easier. My coworker Adrian, (AKA, IronGeek), wrote up some pretty bad ass Python scripts to do some various management tasks on some higher end 5500 Series ASA’s (fully tested on 5510, 5520 and 5540’s).

(config)# crypto key generate rsa modulus 2048
WARNING: You have a RSA keypair already defined named <Default-RSA-Key>.

Do you really want to replace them? [yes/no]: yes
Keypair generation process begin. Please wait...
(config)# ssh inside
(config)# ssh timeout 45
(config)# ssh version 2
(config)# aaa aut
(config)# aaa authen
(config)# aaa authentication ssh console LOCAL
WARNING: local database is empty! Use 'username' command to define local users.
(config)# aaa authentication enable console LOCAL
WARNING: local database is empty! Use 'username' command to define local users.
(config)# username steve password MyP@ssw0rd! privilege 15

You got 2 warning messages here. The first command that warned you the local user database was empty was telling the ASA to look at the local user database for authentication. The second warning was for the same reason, but the command was telling the ASA that you also wanted user authentication for the “enable” command.


Perfect, now lets get out of this console connection and configure this thing over SSH.

ssh steve@
The authenticity of host ' (' can't be established.
RSA key fingerprint is 54:df:df:3e:we:5b:yj:20:ng:46:f4:a7:9p:a3:e6:8x.
Are you sure you want to continue connecting (yes/no)? yes
Warning: Permanently added '' (RSA) to the list of known hosts.
steve@'s password:
Type help or '?' for a list of available commands.
Erdmanor-ASA> en
Password: *********


Now that we’ve got management access setup, let’s get a real config going on this thing. The first way that’s going to be possible is if we give it a Default Gateway so that it knows where to send traffic. Your Internet Service Provider (ISP) should have given you a default gateway IP Address. If they haven’t, it is usually your ISP’s on-site equipment; usually some type of router.


Now lets start creating our Object groups. Beginning with ASA version 8.3, network objects are used to configure all forms of NAT. A network object is created and it is within this object that NAT is configured. In this step, network object “inside-net” is used to translate the inside network addresses to the global address of the outside ASA interface. Cisco says that this type of object configuration is called Auto-NAT.


You’re really going to want to create as MANY object groups as you can think of for all of your network segments. There’s a LOT of overhead here. You’re better off starting out making a list of all your servers, their functions, their open ports and what needs to be accessed from the Internet, then coming back and making your object groups. I went through all this crap when I put this together, you can do the same (it’s really not that difficult, and if you’re at a business and you dont already have this stuff documented, shame on you!).


Let’s start with the default “quad-zero” route and then specify the internal, external and DMZ networks. The “nat” statements we’re going to add to the DMZ and Internal network specify that all Internal traffic will leave through the “Outside-hide-nat” network, and be split up across the IP addresses in the range.

(config)# route outside
(config)# object network outside-hide-nat
(config-network-object)# range
(config-network-object)# exit
(config)# object network internal-network
(config-network-object)# subnet
(config-network-object)# nat (inside,outside) dynamic outside-hide-nat
(config-network-object)# exit
(config)# object network dmz-network
(config-network-object)# subnet
(config-network-object)# nat (DMZ,Outside) dynamic outside-hide-nat
(config-network-object)# end
# wr mem
Building configuration...
Cryptochecksum: 9a5cd00b 1dcb8169 b07905cf 8b7904ed

2961 bytes copied in 1.120 secs (2961 bytes/sec)


Alright, so now we have basic Internet access from both our networks (the DMZ and Internal). Now we need to configure our ASA to forward specific traffic to our DMZ servers. It is very important that you realize we’re using Port Address Translation (PAT) here. There are other ways to do NAT, but we have more ports to open up to internal servers than we have external IP addresses. We have over 5 Internal Servers and only 4 Public IP addresses we can use for inbound traffic.

What we’ll do here is create more objects first.

object network openvpn
object network https-exchange
object network dns-external-1
object network dns-external-2
object network external-rdp
object network external-ssh


Now we need to create the proper PAT NAT statements for all of our externally accessible services. To do this, first we need to identify a new network object and specify a unique name for each inbound service. Then we’ll specify the host that it’s talking to in our DMZ, then we can create the inbound NAT and tie it to a service.

(config)# object network client-openvpn
(config-network-object)# host
(config-network-object)# nat (Inside,Outside) static service tcp https https  
(config-network-object)# exit


See how easy that is? Let’s look at this stuff for a quick minute though. First there is the network object name, “Client-OpenVPN”. Then we specify the DMZ host IP Address that the name is attached to. Then we create the PAT. The NAT statement specifies the static address is a outside public address and then specifies that it’s a TCP service type and specifies its outside port is 443, mapping to the inside host port number 443.


Now, we’ve got one done, lets get the rest:

(config)# object network openvpn-site2site
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service udp 7777 7777
(config-network-object)# exit
(config)# object network http-20
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp www www
(config-network-object)# exit
(config)# object network http-25
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp www www
(config-network-object)# exit
(config)# object network https-25
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp https https
(config-network-object)# exit
(config)# object network https-exchange
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp https https
(config-network-object)# exit
(config)# object network smtp-in
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp smtp smtp
(config-network-object)# exit
(config)# object network dns-external-1
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service udp domain domain
(config-network-object)# exit
(config)# object network dns-external-2
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service udp domain domain
(config-network-object)# exit
(config)# object network external-rdp
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp 3389 3389
(config-network-object)# exit
(config)# object network external-ssh
(config-network-object)# host
(config-network-object)#  nat (Inside,Outside) static service tcp ssh ssh
(config-network-object)# exit
(config)# wr mem


Now that we have our internal objects created, as well as our PAT NAT objects created, now we can move
along and create our access list for our outside interface. This access list will control Internet
traffic inbound to our servers, specify the port number we’ll be using for each server service and then specify to log the event. Then we’ll place the access list on the external interface.

(config)# access-list outside-traffic-inbound extended permit udp any host eq domain log
(config)# access-list outside-traffic-inbound extended permit udp any host eq domain log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq www log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq www log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq 3389 log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq ssh log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq https log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq https log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq https log
(config)# access-list outside-traffic-inbound extended permit udp any host eq 5656 log
(config)# access-list outside-traffic-inbound extended permit tcp any host eq smtp log
(config)# access-list outside-traffic-inbound extended deny ip any any log
(config)# access-group outside-traffic-in in interface Outside
(config)# wr mem
Building configuration...
Cryptochecksum: 7f5a5aab aabeeafa dff03aeb ef264ed5

3404 bytes copied in 1.110 secs (3404 bytes/sec)



Fantastic. Now, the process we just ran through for creating inbound NATs for DNS traffic into the DMZ, that process can be repeated for any other service you are running on your network. Running Microsoft Exchange? You’ll want to allow TCP 443 into it. An SSH server? TCP 22 for that. An SMTP reverse proxy for SPAM filtering? TCP 25 into that.

Well… you get the picture. Just repeat process! 🙂



Now, to complete a network properly we shouldn’t just let anyone out over any port. There’s no egress filtering going on here. Let’s specify what ports our internal users, as well as our servers, are allowed to communicate on over the internet. The only way that’s going to be possible is to create more network objects and more access lists.



Obviously, there’s no reason to ever be browsing the Internet from a server. Don’t be lazy, just do it right. Start by creating a network object containing either the subnet your Windows servers are on, or, you can just specify the host IP addresses your Windows servers have.

object-group network Windows-Servers
 description Microsoft Windows Servers Group
 network-object host
 network-object host
 network-object host
 network-object host
 network-object host
 network-object host
 network-object host



Now let’s make a network object that contains the most common used IP ranges owned and operated by Microsoft:

object-group network Microsoft-Internet
 description Microsoft server networks External IP ranges



Now all we need is an ACL to allow the servers to talk outbound:

access-list inside-traffic-outbound extended permit tcp object-group Windows-Servers object-group Microsoft-Internet eq www
access-list inside-traffic-outbound extended permit tcp object-group Windows-Servers object-group Microsoft-Internet eq https



Let’s do the same thing for our Ubuntu Servers. We have Linux Mint, Debian, and Ubuntu on the network, so we’ll just tie them all together:

object-group network Linux-OS-Updates
 description Linux Mint - Debian - and Ubuntu server networks External IP ranges



And again we need to create our ACLs:

access-list inside-traffic-outbound extended permit tcp object-group Linux-Systems object-group Linux-OS-Updates eq www
access-list inside-traffic-outbound extended permit tcp object-group Linux-Systems object-group Linux-OS-Updates eq https



I also talk on a couple networks like AOL IM, ICQ and Facebook Chat so my computer needs access out to those servers.

So again create the object group, with the IP Ranges for AOL, ICQ and Facebook:

object-group network aim-icq-fb
 description networks for Facebook, AOL IM and ICQ Instant Messangers



And again, allow traffic out with an ACL:

access-list inside-traffic-outbound extended permit tcp host object-group aim-icq-fb eq aol
access-list inside-traffic-outbound extended permit tcp host object-group aim-icq-fb eq 5222


Also, if you’re running a Spam Filtering server in your DMZ, yet your mail server is in your Internal Network, then you’ll have to create a NAT from your DMZ to your internal, which you can use the same process again.


Also, dont forget to allow your Exchange server send mail and you DNS servers perform lookups!!


access-list inside-traffic-outbound extended permit tcp object https-exchange any eq smtp
access-list inside-traffic-outbound extended permit udp object-group Internal-DNS-Servers any eq domain



Lastly, if you want your DMZ or Internal to have access to the Internet, make sure to build an Access List to allow traffic out! Haha, wont get far without that!


Have fun with this. There’s a million ways to tweak what you’re trying to do!






References for this blog go to:




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Open Source: Managing Debian and Ubuntu Linux with Active Directory

I talked about this in my last blog post: We had a need for Authentication on our Linux/Unix systems to be done by Active Directory. So my co-worker and I set off on a mission to fulfill this request. We’d tried some software that wasn’t free, heard about some other software that wasn’t free and then is struck us. “Why Pay?”

All the work had previously been done for us in the Open Source community… why not leverage them directly? So this is my homage to the Open Source community. I’m going to try to give back by writing this blog about my trials and tribulations in setting up this functionality. I’ll forewarn you, this blog entry is very long and gets into a lot of detail, but I assure you, at the end of the day, this works!

My testbed here is my home network. I’m running a 2008 Server with AD installed. Nothing special, very vanilla, no crazy GPOs to deal with, no delegations to worry about and I’ve secured the environment fairly well (IMHO). There are virtually no extra roles, services or features installed other than a base install of AD Services, but I do have Exchange Server 2010 installed, so the schema has been extended for that. But it shouldn’t affect your environment if you aren’t running Exchange.

I want to get one last statement in here: I am by no means a Linux or Unix Expert, but I can troubleshoot and read. The way I have this setup here is the way I figured out to do it and the best I can say is that it works, it’s secure, and it doesn’t take long to do. I’ve done a bunch of research and I’m going to attempt to regurgitate that knowledge back into this blog as best I can. If you know how to do something better here, please contact me at my LinkedIn page 🙂 .

So lets get down to brass tacks here… I have some Debian based systems (Linux Mint 13, Debian 6 and two Ubuntu 10.04 Servers), a Red Hat server (REL 6), an Oracle Enterprise Linux 6 Server, 3 Windows Server 2008 domain controllers, an Exchange 2010 server and some other systems on my home network. I wanted to extend my AD capabilities by getting my Debian based systems to authenticate to my 2008 Domain Controllers (DCs).

To start, you’ll need to know a couple peices of information. You’ll need to know what DC is holding the PDC FSMO role. Easiest way to do that is to log onto a DC, fire up AD Users and Computers, right click on the domain name and then click on Operations Masters. In the window that appears on your screen click on the PDC tab and document the FQDN of the server that currently holds that role.

Operations Master

After you identify this system, the next best thing to do is create a DNS entry pointing to your PDC Server. This way if you ever need to decommission your current PDC server, you can just change the DNS record and not have to go back to all your Linux systems to update the system they authenticate to.

From here, everything you’re going to do, aside from creating new AD users and security groups, will all be done at the Linux command line. There’s a couple of conf files that we need to configure after installing some software on each of the systems. In one of my future blog posts, I’m (hopefully) going to be going over using Chef to distribute configuration files <>.

This whole process isnt all that difficult as long as you have a decent understanding of the services and subsystems that you’re relying on. Here they are:

  • Pluggable Authentication Modules (PAM)
  • Server Message Block (SMB, Samba)
  • WinBIND (part of Samba)
  • Kerberos 5 (By MIT, with Microsoft compatibility hacks)

SO, lets get some software installed. Below is the EXACT command line that I used on my Ubuntu servers (10.04).

sudo apt-get install krb5-user libkrb53 krb5-config winbind samba ntp ntpdate nss-updatedb libnss-db libpam-ccreds libnss-ldap ldap-utils


After installing that software, you’ll want to stop all the services while you configure them:

sudo /etc/init.d/samba stop
sudo /etc/init.d/winbind stop
sudo /etc/init.d/ntp-server stop


Each server in a Kerberos authentication realm must be assigned a Fully Qualified Domain Name (FQDN) that is both forward- and reverse-resolvable.

Note: Active Directory depends heavily on DNS, so it is likely that the Active Directory Domain Controller is also running the Microsoft DNS server package. If this is the case, verify that each server has a FQDN assigned to it before performing the tests outlined in this section.

If the server already has an FQDN assigned to it, test forward and reverse look-up with the following commands:

nslookup  (ip address of server)

The output of the first command should contain the IP address of the server. The output of the second command should contain the FQDN of the server. If this is not the case, Kerberos authentication will not function properly. Next, we’ll be configuring the Kerberos Config file which is located here: /etc/krb5.conf Here’s what mine looks like (Make sure to read the comments I put in there):

default_realm = ERDMANOR.COM #Kerberos is CASE sensitive; this must be all UPPERCASE!
default = FILE:/var/log/krb5.log
kdc = FILE:/var/log/krb5kdc.log
kdc = #You really only need 1 kerberos domain controller
kdc = #but in my network there are three, so I listed
kdc = #all of them in here.
admin_server = #This should be set to the DC that holds the PDC Role
default_domain = #

krb4_convert = true
krb4_get_tickets = false



Active Directory, for as long as I can remember, is time sensitive to about +/- 5 minutes. You can adjust that window to anything you want by editing your Domain Policies (Group Policies (GPOs)), but there’s no need to really do that. Anything outside that window of time and your Domain Controllers will deny any kerberos ticket requests. This is why you need to make sure and setup your NTP daemon to point at your domain controller. I recommend setting it up with a DNS name, but you can get by with an IP address. Reason is, if the PDC ever changes, you dont need to go back to all your old machines and update conf files. Run this command: “sudo nano /etc/ntp.conf”

# /etc/ntp.conf, configuration for ntpd; see ntp.conf(5) for help

driftfile /var/lib/ntp/ntp.drift
statistics loopstats peerstats clockstats
filegen loopstats file loopstats type day enable
filegen peerstats file peerstats type day enable
filegen clockstats file clockstats type day enable

# Specify one or more NTP servers.

server #insert your PDC here
server #secondary DC
server #third DC
server #fall back to Ubuntu's NTP
server #
server #


So, we’re on our way here. Without saying, you’re probably getting a DHCP address from a Domain Controller if you’re already on a Windows network. If you’re setting up a server with a Static address, then make sure to setup your DNS nameservers in your /etc/resolv.conf file so that you’re getting DNS from your PDC and any other Domain Controllers which host DNS. I DONT recommend using your “/etc/hosts” file for this.


So lets get to testing! From the command line issue this command:

kinit -p username@MYDOMAIN.COM
#obviously changing to your username and domain name on your network.
#Notice the UPPERCASE spelling of MYDOMAIN.COM?

After that command is entered you should be getting prompted for your DOMAIN password. From here just make sure that you’re not getting any errors (which you shouldn’t). If you’re looking to verify that you have a valid ticket, then issue this command:

klist -e

Now that we have Kerberos and NTP working properly, we can move onto the next portion of authentication: PAM. If you dont know anything about PAM then you can safely move on to the configuration portion of this part. But for those of you wanting more of an understanding, here you go. I got this information from, and it’s VERY good info. Also, verify that your “/etc/skel/” directory is setup properly. You can get creative with this and have some pretty neat options rolled out to all your users if you prefer.

#I took out all the #comments for this blog, but I HIGHLY recommend that you leave them in!

so here are what my PAM modules look like in /etc/pam.d/:

# /etc/pam.d/common-account - authorization settings common to all services
session required skel=/etc/skel/ umask=0022 #VERY IMPORTANT!
account [success=3 new_authtok_reqd=done default=ignore]
account [success=2 new_authtok_reqd=done default=ignore]
account [success=1 default=ignore]
account requisite
account required
account required minimum_uid=1000


# /etc/pam.d/common-auth - authentication settings common to all services
# here are the per-package modules (the "Primary" block)
session required skel=/etc/skel/ umask=0022
auth [success=6 default=ignore] minimum_uid=1000
auth [success=5 default=ignore] nullok_secure try_first_pass
auth [success=4 default=ignore] krb5_auth krb5_ccache_type=FILE cached_login try_first_pass
auth [success=3 default=ignore] use_first_pass
auth [success=2 default=ignore] minimum_uid=1000 action=validate use_first_pass
auth [default=ignore] minimum_uid=1000 action=update
auth requisite
auth required
auth optional minimum_uid=1000 action=store
auth optional
auth optional


# /etc/pam.d/common-password - password-related modules common to all services
password [success=4 default=ignore] minimum_uid=1000
password [success=3 default=ignore] obscure use_authtok try_first_pass sha512
password [success=2 default=ignore] use_authtok try_first_pass
password [success=1 user_unknown=ignore default=die] use_authtok try_first_pass
password requisite
password required
password optional


# /etc/pam.d/common-session - session-related modules common to all services
session [default=1]
session requisite
session required
session optional
session required skel=/etc/skel/ umask=0022
session optional minimum_uid=1000
session required
session optional
session optional
session optional
session optional nox11


# /etc/pam.d/common-session-noninteractive - session-related modules
# common to all non-interactive services
session [default=1]
session requisite
session required
session optional
session optional minimum_uid=1000
session required
session optional
session optional
session optional


This should be everything you need for PAM to work properly. Now we need to work on Samba. The Samba config is stored at “/etc/samba/smb.conf”. Again, I stripped my Samba config down and made a backup of the original. I dont want my end users sharing data between themselves, I want them using corporate file shares where I know that the data is backed up. Also, I want them using Print Servers, not hosting printers from their machines. So this smb.conf is pretty short compared to the original. If you visit the Samba website, you’ll even see that they want people to keep this file short and simple. According to the Samba Team, the longer this file is, the more it impacts performance of the system. Please heed the warnings in your smb.conf as well as the notes I post below:

# NOTE: Whenever you modify this file you should run the command
# "testparm" to check that you have not made any basic syntactic
# errors.
#======================= Global Settings =======================


security = ads
realm = MYDOMAIN.COM #Must be UPPER case
password server = #PDC that we mentioned earlier
workgroup = MYDOMAIN #This is the NetBIOS name of your Domain
idmap uid = 10000-20000
idmap gid = 10000-20000
winbind enum users = yes
winbind enum groups = yes
template homedir = /home/MYDOMAIN/%U #Dont forget to update this directory!
template shell = /bin/bash #You can use whatever shell you'd like
client use spnego = yes
client ntlmv2 auth = yes
encrypt passwords = yes
winbind use default domain = yes
restrict anonymous = 2

server string = %h server (Samba, Ubuntu)
dns proxy = no
log file = /var/log/samba/log.%m
max log size = 1000
syslog only = yes
syslog = 4
panic action = /usr/share/samba/panic-action %d
encrypt passwords = true
passdb backend = tdbsam
obey pam restrictions = yes
unix password sync = yes
passwd program = /usr/bin/passwd %u
passwd chat = *Enter\snew\s*\spassword:* %n\n *Retype\snew\s*\spassword:* %n\n *password\supdated\ssuccessfully* .
pam password change = yes
map to guest = bad user
domain logons = no #Extremely important that this is NO.
usershare allow guests = yes



Next we’ll be setting up the “/etc/nsswitch.conf” file. This file does a few things to help communications with your LDAP server (AD in this case) as well as tell your local Linux system where to look for password information.

When fiddling with /etc/nsswitch.conf, it is best to turn the Name Services Caching Daemon off or you will be confused by cached results. Turn it on afterwards.

/etc/init.d/nscd stop

Now edit the nsswitch.conf file:

# /etc/nsswitch.conf
passwd: files winbind
group: files winbind
shadow: compat
hosts: files mdns4_minimal [NOTFOUND=return] dns mdns4
networks: files
protocols: db files
services: db files
ethers: db files
rpc: db files
netgroup: nis

And Turn back on your service:

/etc/init.d/nscd start


Assuming that all goes well and Kerberos, Winbind and Samba are setup properly, you should be able to join your linux system to the domain. Due to restrictions in the NetBIOS protocol, the hostname must contain no more than 15 characters. If you see a STATUS_BUFFER_OVERFLOW message in the winbind log, odds are the hostname is invalid. Now would also be a good time to clear whatever cache files, if any, Winbind had previously generated. The Winbind cache is located in /var/lib/samba/. Backup this directory to /var/lib/samba.bak/ and delete all the files in the original. Now you can issue this command:

sudo net ads join -S MYDOMAIN.COM -U {domain-admin-user}

Couple things here.
First, you may need to change MYDOMAIN.COM to KERBEROS.MYDOMAIN.COM. If it doesn’t work the first way, try the next. Second is, {domain-admin-user} MUST be a Domain Admin account in Active Directory. Otherwise you’ll fail.

Now, I’ve gotten mixed results here… My Mint 12 and 13 boxes joined and I actually got a “Domain Joined!” message in the shell.

My Debian 6 machine threw an error:

steve @ mintdebianvm ~ :) ᛤ>   sudo net ads join -S ERDMANOR.COM -U administrator
[sudo] password for steve:
Enter administrator's password:
kinit succeeded but ads_sasl_spnego_krb5_bind failed: Server not found in Kerberos database
Failed to join domain: failed to connect to AD: Server not found in Kerberos database

I haven’t had much time to look into why this is happening, but I can assure you the system joined the domain, the computer account was created in AD and I’m able to SSH to this machine with domain creds… If anyone knows why this is happening, PLEASE contact me! Thanks!


Look up Windows Ports needed for Active Directory. Need Microsoft Link!
After your join to the domain is successfull, you can startup your services:

sudo /etc/init.d/samba start
sudo /etc/init.d/winbind start



From this point, you should be able to test some querys against the domain:

getent passwd
getent shadow
getent group

At this point, you should be able to resolve users and groups from the Windows Active Directory domain using getent passwd and getent group. If these commands don’t display your Windows accounts, try to resolve them using wbinfo -u and wbinfo -g. These commands query the Winbind service directly, bypassing the name service switch. If you can resolve users and groups with wbinfo, go back and make sure you configured /etc/nsswitch.conf properly.


Now with EVERYTHING setup properly, you *should* be able to fire up an SSH session to your linux box and log in with AD Credentals. BUT! Your Domain Users are NOT going to be able to “sudo” any commands. For the sake of security, you dont want ALL your domain users to be able to sudo commands, so what I did is create a domain security group, mine is named “linux-sudo”. Then I added in only the users I want to be able to sudo commands to that group. Then I edited my “sudoers” file to include the domain security group “linux-sudo”. So make sure to edit your “/etc/sudoers” file, and add this line:

%linux-sudo     ALL=(ALL:ALL) ALL

Now, I’m able to log into my Debian, Mint and Ubuntu Linux systems with Domain Credentials! 🙂

EDIT: In looking for information regarding this entire process on a RED HAT system. (RHEL 5 or 6), please refer to this guide:

Here are all the sites that I used in the making of this blog:

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Serious network architecture that works for everyone.

I started writing this blog post as a way to setup a reverse proxy for mail inspection, but it turned out that a network architecture blog focused on security of the perimeter was more important. I’ve gone over in my head with all the companies that have told me, “Ohhh we don’t need this” or, “this is too much administrative overhead” or, “We don’t need this much complexity, we’re just manufacturing “widgets” , or something like that. And to those people, I say this: “I am so sick and tired of hearing excuses of why you think it’s okay to be lazy. Do it right, do it now, and save yourself the headaches of a breach.” We’ll talk about the costs associated with being penetrated some other time, but it’s EXPENSIVE!

If you’re planning to do this right, then you’ll want/need to have a multi-tier DMZ for your public facing services. We’re not talking about internal servers or your internal network at this point (though after thinking about it, the exact same concept can be carried out on the Internal network too). In this blog, I’m merely trying to tell you about your externally facing services. This blog will go over proper placement for Internet facing services. The VAST majority of companies out there don’t go to this level of sophistication, but its totally possible for any company to do this and if you really want to secure your network infrastructure, then you’ll at least attempt this.

Before we start, I’ll say this. I’m going to try my best to describe this as granular as possible. There are a TON of intricacies here that need to be thought out. I’ll provide a rudimentary Visio diagram to help on this, but you’ll need to map out your own network and break it down in a way you can understand.

The main point of network segmentation and building a secure network architecture is based on one of the most talked about security areas: The Principle of Least Privilege. Do your end users need access to databases? How about other network services? How about filesharing with eachother? How about shared resources for just once specific department (should engineering folks be able to communicate with financial systems)? Please think about the level of access people should have to services while going through this blog.

You’re first level DMZ should house only your front end web servers (or load balancers in front of those servers), DNS servers and your proxy servers, nothing more. These systems are extremely visible to the public and will be processing thousands of requests per day, so if anything happens to them, trust me people will notice. Remember, these are front end systems, so you don’t need much of anything out there. I’ll be going over how to set those services up on a future blog, but for now just remember, least privilege. Internet users dont need direct access to the webserver, they do need access to a reverse proxy server that inspects the traffic going to the web server(s).

From here, you can create your second tier that will house your web servers (if you have load balancers or proxy servers in front of them out in tier one), mail servers, SFTP servers, if you’re using LDAP or AD you could add a read-only domain controller (RO-DC) for authentication (but NO Internet access), and things like that. These systems should be using local firewalls as well as network layer firewalls to control access to them. Web servers dont need to talk to anything except the back-end SQL BD and the end user. Both of those firewalls should specify that the only systems they’re allowed to talk to is the server in tier 1 that proxies data to it, and if there is a server behind it in tier three.

Then there is an optional third tier where you would house your back-end database servers and any other servers deemed unnecessary for tier two. when I say optional, I dont mean just throw it away and put SQL over in tier 2. I mean, if you dont have a SQL back-end you can eliminate tier 3. Another RO-DC could be posted here for authentication services(again, NO Internet access!). If you’re running MS-SQL or Oracle SQL servers here, you can have services level authentication (or any other services for that matter) authenticating to that RO-DC. Same goes for tier two.

Lastly, I’ll mention a Management network that will have access to all three tiers. You’ll obviously have admins (even if it’s just yourself) that will need to run updates on those boxes or perform other administrative functions on those systems. Don’t forget to allow yourself access to that. But that doesn’t mean “IP ANY ANY” from the management network into those tiers either! Dont be LAZY, be smart and do it right.

In my Visio diagram, I used some old hardware, and multiple physical switches, but don’t forget, you can trunk VLANs and do some pretty cool configurations with Cisco gear, especially the new ASA’s. See it here: DIAGRAM LINK

So from tier 1, your DNS server should only be servicing requests from your 3 DMZs, and the Internet. I would say, you shouldn’t open this up to your internal clients, because you should already have internal DNS servers for Active Directory (or what ever LDAP service you’re using). At most, you should only be allowing 53/udp inbound to that DNS server from the Internet, and allow SSH inbound to that server from your management network. That’s IT! For your proxy server or load balancer, you should allow 80/tcp and 443/tcp inbound from the Internet and allow in whatever port your load balancer needs from the management network. So in this scenario, you should have 80 and 443/tcp and 53/udp open from the Internet to tier 1. Simple, see?

Tier two only has ports open FROM tier 1 into tier 2 (and management network into tier 2). The people out on the Internet will NEVER communicate directly with tier 2, there’s just no need.

And lastly, tier 3 will only accept communications from tier 2 and the management tier. No end user needs to communicate with the SQL DB’s directly, so why let them?

The only thing I’ve left out here is the RO-DCs. What do they communicate with? Well, the way I would set them up is have the 2 real Domain Controllers in the management network. This should be a totally different domain than your internal network. Name the domain whatever you want (fubar.dmz or whatever). Your RO-DCs are only acting as a proxy to the domain. Nothing is stored on them, so you’ve got really nothing to lose.

So that’s really about it. If you’ve got any questions, contact me via my LinkedIn profile. There’s a link to that right on my home page near the bottom of the left column.


Enjoy!! 🙂

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