diff --git a/README.md b/README.md
index 9d60ad7..e985613 100644
--- a/README.md
+++ b/README.md
@@ -14,6 +14,7 @@ NOTE: This lab has not been hardened in any way and runs with default vagrant cr
 * Powershell transcript logging is enabled. All logs are saved to `\\wef\pslogs`
 * osquery comes installed on each host and is pre-configured to connect to a [Fleet](https://kolide.co/fleet) server via TLS. Fleet is preconfigured with the configuration from [Palantir's osquery Configuration](https://github.com/palantir/osquery-configuration)
 * Sysmon is installed and configured using SwiftOnSecurity’s open-sourced configuration
+* Mitre's [Caldera](https://github.com/mitre/caldera) server is built on the logger host and the Caldera agent gets pre-installed on all Windows hosts
 * All autostart items are logged to Windows Event Logs via [AutorunsToWinEventLog](https://github.com/palantir/windows-event-forwarding/tree/master/AutorunsToWinEventLog)
 * SMBv1 Auditing is enabled
 
@@ -84,8 +85,9 @@ Vagrant commands must be run from the "Vagrant" folder.
 ## Lab Information
 * Domain Name: windomain.local
 * Admininstrator login: vagrant:vagrant
-* Fleet login: admin:admin123#
-* Splunk login: admin:changeme
+* Fleet login: https://192.168.38.5:8412 - admin:admin123#
+* Splunk login: https://192.168.38.5:8000 - admin:changeme
+* Caldera login: https://192.168.38.5:8888 - admin:caldera
 
 ## Lab Hosts
 * DC - Windows 2016 Domain Controller
@@ -113,6 +115,7 @@ Vagrant commands must be run from the "Vagrant" folder.
 * Logger - Ubuntu 16.04
   * Splunk Enterprise
   * Fleet osquery Manager
+  * Mitre's Caldera Server
 
 ## Splunk Indexes
 Index Name | Description
@@ -127,6 +130,7 @@ wineventlog | Windows Event Logs
   * Sysmon
   * osquery
   * AutorunsToWinEventLog
+  * Caldera Agent
   * Process Monitor
   * Process Explorer
   * PsExec
@@ -193,6 +197,7 @@ A sizable percentage of this code was borrowed and adapted from [Stefan Scherer]
 * [Splunk](https://www.splunk.com)
 * [osquery](https://osquery.io)
 * [Fleet](https://kolide.co/fleet)
+* [Caldera](https://github.com/mitre/caldera)
 * [Windows Event Forwarding for Network Defense](https://medium.com/@palantir/windows-event-forwarding-for-network-defense-cb208d5ff86f)
 * [palantir/windows-event-forwarding](http://github.com/palantir/windows-event-forwarding)
 * [osquery Across the Enterprise](https://medium.com/@palantir/osquery-across-the-enterprise-3c3c9d13ec55)
diff --git a/Vagrant/Vagrantfile b/Vagrant/Vagrantfile
index 67c4931..68604cb 100644
--- a/Vagrant/Vagrantfile
+++ b/Vagrant/Vagrantfile
@@ -46,6 +46,7 @@ Vagrant.configure("2") do |config|
     cfg.vm.provision "shell", path: "scripts/install-inputsconf.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-utilities.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-osquery.ps1", privileged: true
+    cfg.vm.provision "shell", path: "scripts/install-caldera-agent.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-sysinternals.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/configure-ou.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/configure-wef-gpo.ps1", privileged: true
@@ -89,6 +90,7 @@ Vagrant.configure("2") do |config|
     cfg.vm.provision "shell", path: "scripts/install-windows_ta.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-utilities.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-osquery.ps1", privileged: true
+    cfg.vm.provision "shell", path: "scripts/install-caldera-agent.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-inputsconf.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-sysinternals.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/configure-pslogstranscriptsshare.ps1", privileged: true
@@ -128,6 +130,7 @@ Vagrant.configure("2") do |config|
     cfg.vm.provision "shell", path: "scripts/install-splunkuf.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-utilities.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-osquery.ps1", privileged: true
+    cfg.vm.provision "shell", path: "scripts/install-caldera-agent.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-inputsconf.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-sysinternals.ps1", privileged: true
     cfg.vm.provision "shell", path: "scripts/install-autorunstowineventlog.ps1", privileged: true
diff --git a/Vagrant/bootstrap.sh b/Vagrant/bootstrap.sh
index 75dbd23..4d6ccec 100644
--- a/Vagrant/bootstrap.sh
+++ b/Vagrant/bootstrap.sh
@@ -1,8 +1,12 @@
 #! /bin/bash
 
+# Install key and apt source for MongoDB
+apt-key adv --keyserver hkp://keyserver.ubuntu.com:80 --recv EA312927
+echo "deb http://repo.mongodb.org/apt/ubuntu "$(lsb_release -sc)"/mongodb-org/3.2 multiverse" | sudo tee /etc/apt/sources.list.d/mongodb-org-3.2.list
+
 # Install prerequisites and useful tools
 apt-get update
-apt-get install -y jq whois build-essential git docker docker-compose unzip
+apt-get install -y jq whois build-essential git docker docker-compose unzip python3-dev python3-pip mongodb-org
 
 # Install Golang v1.8
 wget https://storage.googleapis.com/golang/go1.8.linux-amd64.tar.gz
@@ -111,3 +115,27 @@ curl 'https://192.168.38.5:8412/api/v1/kolide/packs/5' -X PATCH -H 'origin: http
 # Add Splunk monitors for Fleet
 /opt/splunk/bin/splunk add monitor "/home/vagrant/kolide-quickstart/osquery_result" -index osquery -sourcetype 'osquery:json' -auth 'admin:changeme'
 /opt/splunk/bin/splunk add monitor "/home/vagrant/kolide-quickstart/osquery_status" -index osquery-status -sourcetype 'osquery:status' -auth 'admin:changeme'
+
+# Install Mitre's Caldera
+cd /home/vagrant
+git clone https://github.com/mitre/caldera.git
+cd /home/vagrant/caldera/caldera
+pip3 install -r requirements.txt
+pip3 install aiohttp==2.3.8 # See https://github.com/mitre/caldera/pull/13
+# Patch sslproto https://github.com/mitre/caldera/issues/14#issuecomment-358190888
+cd /usr/lib/python3.5/asyncio
+cp /vagrant/resources/caldera/sslproto.patch .
+patch < sslproto.patch
+# Add a Systemd service for MongoDB
+# https://www.howtoforge.com/tutorial/install-mongodb-on-ubuntu-16.04/
+cp /vagrant/resources/caldera/mongod.service /lib/systemd/system/mongod.service
+# Create Systemd service for Caldera
+cp /vagrant/resources/caldera/caldera.service /lib/systemd/system/caldera.service
+# Enable replication
+echo 'replication:
+   replSetName: caldera' >> /etc/mongod.conf
+service mongod start
+cd /home/vagrant/caldera
+mkdir -p dep/crater/crater
+wget https://github.com/mitre/caldera-crater/releases/download/v0.1.0/CraterMainWin8up.exe -O /home/vagrant/caldera/dep/crater/crater/CraterMain.exe
+service caldera start
diff --git a/Vagrant/resources/caldera/caldera.service b/Vagrant/resources/caldera/caldera.service
new file mode 100644
index 0000000..9e8524d
--- /dev/null
+++ b/Vagrant/resources/caldera/caldera.service
@@ -0,0 +1,11 @@
+[Unit]
+Description=My Script Service
+After=multi-user.target
+
+[Service]
+Type=idle
+WorkingDirectory=/home/vagrant/caldera/caldera
+ExecStart=/usr/bin/python3 caldera.py
+
+[Install]
+WantedBy=multi-user.target
diff --git a/Vagrant/resources/caldera/mongod.service b/Vagrant/resources/caldera/mongod.service
new file mode 100644
index 0000000..5a726a1
--- /dev/null
+++ b/Vagrant/resources/caldera/mongod.service
@@ -0,0 +1,12 @@
+[Unit]
+Description=High-performance, schema-free document-oriented database
+After=network.target
+Documentation=https://docs.mongodb.org/manual
+
+[Service]
+User=mongodb
+Group=mongodb
+ExecStart=/usr/bin/mongod --quiet --config /etc/mongod.conf
+
+[Install]
+WantedBy=multi-user.target
diff --git a/Vagrant/resources/caldera/sslproto.patch b/Vagrant/resources/caldera/sslproto.patch
new file mode 100644
index 0000000..66c1e76
--- /dev/null
+++ b/Vagrant/resources/caldera/sslproto.patch
@@ -0,0 +1,14 @@
+--- sslproto.py	2018-01-17 08:00:50.567571454 +0000
++++ sslproto.py.new	2018-01-17 08:03:31.996275969 +0000
+@@ -533,8 +533,10 @@
+     def _get_extra_info(self, name, default=None):
+         if name in self._extra:
+             return self._extra[name]
+-        else:
++        elif self._transport is not None:
+             return self._transport.get_extra_info(name, default)
++        else:
++            return default
+
+     def _start_shutdown(self):
+         if self._in_shutdown:
diff --git a/Vagrant/scripts/install-caldera-agent.ps1 b/Vagrant/scripts/install-caldera-agent.ps1
new file mode 100644
index 0000000..9ab10f2
--- /dev/null
+++ b/Vagrant/scripts/install-caldera-agent.ps1
@@ -0,0 +1,26 @@
+# Purpose: Installs the Caldera agent on the host
+
+# Add /etc/hosts entry
+Add-Content "c:\windows\system32\drivers\etc\hosts" "        192.168.38.5    logger"
+
+# Make the directory
+New-Item "c:\Program Files\cagent" -type directory
+
+# Install Visual Studio 2015 C++ Redistributable
+choco install -y vcredist2015
+
+# Download cagent and start the service
+If (-not (Test-Path "C:\Program Files\cagent\cagent.exe")) {
+  Write-Host "Downloading Caldera Agent (cagent.exe)"
+  $cagentPath = "C:\Program Files\cagent\cagent.exe"
+  $cagentConfPath = "C:\Program Files\cagent\conf.yml"
+  (New-Object System.Net.WebClient).DownloadFile('https://github.com/mitre/caldera-agent/releases/download/v0.1.0/cagent.exe', $cagentPath)
+  # Ignore SSL warning for conf file download
+  # https://stackoverflow.com/questions/34331206/ignore-ssl-warning-with-powershell-downloadstring
+  [System.Net.ServicePointManager]::ServerCertificateValidationCallback = {$true} ;(New-Object System.Net.WebClient).DownloadFile('https://logger:8888/conf.yml', $cagentConfPath)
+  Start-Process -FilePath $cagentPath -ArgumentList '--startup', 'auto', 'install' -Wait
+  Start-Process -FilePath $cagentPath -ArgumentList 'start' -Wait
+} Else {
+  Write-Host "Caldera Agent is already installed. Moving on."
+}
+Write-Host "Cagent installation complete!"
diff --git a/Vagrant/scripts/install-sysinternals.ps1 b/Vagrant/scripts/install-sysinternals.ps1
index 7885e14..20379b4 100755
--- a/Vagrant/scripts/install-sysinternals.ps1
+++ b/Vagrant/scripts/install-sysinternals.ps1
@@ -38,6 +38,9 @@ Invoke-WebRequest -Uri "https://raw.githubusercontent.com/SwiftOnSecurity/sysmon
 # Convert Sysmon config schema from 3.30 to 4.0 per GitHub Issue #38
 (Get-Content $sysmonConfigPath) -replace 'schemaversion="3.30"', 'schemaversion="4.00"' | Set-Content $sysmonConfigPath
 
+# Convert Schema from 3.30 to 4.0 per GitHub Issue #38
+(Get-Content $sysmonConfigPath) -replace 'schemaversion="3.30"', 'schemaversion="4.00"' | Set-Content $sysmonConfigPath
+
 # Startup Sysmon
 Write-Host "Starting Sysmon..."
 Start-Process -FilePath "$sysmonDir\Sysmon64.exe" -ArgumentList "-accepteula -i $sysmonConfigPath"
diff --git a/Vagrant/scripts/join-domain.ps1 b/Vagrant/scripts/join-domain.ps1
index 894abb5..009294f 100755
--- a/Vagrant/scripts/join-domain.ps1
+++ b/Vagrant/scripts/join-domain.ps1
@@ -18,7 +18,7 @@ $DomainCred = New-Object System.Management.Automation.PSCredential $user, $pass
 If ($hostname -eq "wef") {
   Add-Computer -DomainName "windomain.local" -credential $DomainCred -OUPath "ou=Servers,dc=windomain,dc=local" -PassThru
 } ElseIf ($hostname -eq "win10") {
-  Write-Host "Adding Win10 to the domain. Sometimes this step times out when using VMWare. If that happens, just run 'vagrant reload win10 --provision'" #debug
+  Write-Host "Adding Win10 to the domain. Sometimes this step times out. If that happens, just run 'vagrant reload win10 --provision'" #debug
   Add-Computer -DomainName "windomain.local" -credential $DomainCred -OUPath "ou=Workstations,dc=windomain,dc=local"
 } Else {
   Add-Computer -DomainName "windomain.local" -credential $DomainCred -PassThru