diff --git a/Gemfile b/Gemfile
index 7fb1127a..3c6fe90e 100644
--- a/Gemfile
+++ b/Gemfile
@@ -9,6 +9,7 @@ gem 'rake', require: false
 group :test do
   gem 'codeclimate-test-reporter'
   gem 'pry'
+  gem 'rexml'
   gem 'rubocop'
 end
 
diff --git a/lib/moonshot/controller.rb b/lib/moonshot/controller.rb
index cc81250e..070b3edf 100644
--- a/lib/moonshot/controller.rb
+++ b/lib/moonshot/controller.rb
@@ -186,10 +186,13 @@ def ssh
       @config.ssh_instance ||= SSHTargetSelector.new(
         stack, asg_name: @config.ssh_auto_scaling_group_name
       ).choose!
-      cb = SSHCommandBuilder.new(@config.ssh_config, @config.ssh_instance)
+      teleport_config = TeleportConfig.new(
+        stack.name, @config.ssh_config.ssh_user, ENV['AWS_REGION']
+      )
+      cb = SSHCommandBuilder.new(@config.ssh_config, @config.ssh_instance, teleport_config)
       result = cb.build(@config.ssh_command)
 
-      warn "Opening SSH connection to #{@config.ssh_instance} (#{result.ip})..."
+      warn "Opening SSH connection to #{@config.ssh_instance} (#{result.host})..."
       exec(result.cmd)
     end
 
diff --git a/lib/moonshot/ssh_command_builder.rb b/lib/moonshot/ssh_command_builder.rb
index 40829e6f..9004f2bd 100644
--- a/lib/moonshot/ssh_command_builder.rb
+++ b/lib/moonshot/ssh_command_builder.rb
@@ -3,33 +3,30 @@
 require 'shellwords'
 
 module Moonshot
-  # Create an ssh command from configuration.
+  # Create a tsh ssh command from configuration.
   class SSHCommandBuilder
-    Result = Struct.new(:cmd, :ip)
+    Result = Struct.new(:cmd, :host)
 
-    def initialize(ssh_config, instance_id)
-      @config = ssh_config
-      @instance_id = instance_id
+    def initialize(ssh_config, instance_id, teleport_config)
+      @config          = ssh_config
+      @instance_id     = instance_id
+      @teleport_config = teleport_config
     end
 
     def build(command = nil)
-      cmd = ['ssh', '-t']
+      cmd = ['tsh', 'ssh']
       cmd << @config.ssh_options if @config.ssh_options
-      cmd << "-i #{@config.ssh_identity_file}" if @config.ssh_identity_file
-      cmd << "-l #{@config.ssh_user}" if @config.ssh_user
-      cmd << instance_ip
+      cmd << "--proxy=#{@teleport_config.proxy_url}"
+      cmd << "-i #{@teleport_config.identity_file}" if @teleport_config.bot_user?
+      cmd << "#{@teleport_config.ssh_user}@#{instance_host}"
       cmd << Shellwords.escape(command) if command
-      Result.new(cmd.join(' '), instance_ip)
+      Result.new(cmd.join(' '), instance_host)
     end
 
     private
 
-    def instance_ip
-      @instance_ip ||= Aws::EC2::Client.new
-                                       .describe_instances(instance_ids: [@instance_id])
-                                       .reservations.first.instances.first.public_ip_address
-    rescue StandardError
-      raise "Failed to determine public IP address for instance #{@instance_id}!"
+    def instance_host
+      @instance_host ||= @teleport_config.host_for(@instance_id)
     end
   end
 end
diff --git a/lib/moonshot/teleport_config.rb b/lib/moonshot/teleport_config.rb
new file mode 100644
index 00000000..b1a9015c
--- /dev/null
+++ b/lib/moonshot/teleport_config.rb
@@ -0,0 +1,57 @@
+# frozen_string_literal: true
+
+module Moonshot
+  # Encapsulates Teleport SSH configuration derived from the stack name,
+  # SSH user, and AWS region. Determines the correct proxy URL, account ID,
+  # and identity file path for both normal users and bot users.
+  class TeleportConfig
+    PROD_ACCOUNT_ID = '546349603759'
+    DEV_ACCOUNT_ID  = '672327909798'
+    BOT_USER        = 'clouddatabot'
+
+    PROD_PROXY_TEMPLATE = '%<region>s.teleport.cloudservices.acquia.io'
+    DEV_PROXY            = 'teleport.dev.cloudservices.acquia.io'
+
+    PROD_IDENTITY_TEMPLATE = '/opt/machine-id/%<region>s/identity'
+    DEV_IDENTITY           = '/opt/machine-id/dev-us-east-1/identity'
+
+    attr_reader :proxy_url, :account_id, :region, :ssh_user
+
+    def initialize(stack_name, ssh_user, region)
+      @stack_name = stack_name.to_s
+      @ssh_user   = ssh_user.to_s
+      @region     = region.to_s
+
+      if prod?
+        @account_id = PROD_ACCOUNT_ID
+        @proxy_url  = format(PROD_PROXY_TEMPLATE, region: @region)
+      else
+        @account_id = DEV_ACCOUNT_ID
+        @proxy_url  = DEV_PROXY
+      end
+    end
+
+    def bot_user?
+      @ssh_user == BOT_USER
+    end
+
+    # Returns the Teleport identity file path for bot users; nil for normal users.
+    def identity_file
+      return nil unless bot_user?
+
+      prod? ? format(PROD_IDENTITY_TEMPLATE, region: @region) : DEV_IDENTITY
+    end
+
+    # Constructs the Teleport node name used as SSH hostname.
+    # Format: <instance_id>.<region>.<account_id>
+    def host_for(instance_id)
+      "#{instance_id}.#{@region}.#{@account_id}"
+    end
+
+    private
+
+    def prod?
+      @stack_name.include?('prod')
+    end
+  end
+end
diff --git a/lib/plugins/rotate_asg_instances.rb b/lib/plugins/rotate_asg_instances.rb
index d8a341c4..50e8b283 100644
--- a/lib/plugins/rotate_asg_instances.rb
+++ b/lib/plugins/rotate_asg_instances.rb
@@ -1,6 +1,7 @@
 # frozen_string_literal: true
 
-require 'aws-sdk'
+require 'aws-sdk-autoscaling'
+require 'aws-sdk-ec2'
 
 module Moonshot
   module Plugins
diff --git a/lib/plugins/rotate_asg_instances/asg.rb b/lib/plugins/rotate_asg_instances/asg.rb
index 4031c9e2..0e5627ee 100644
--- a/lib/plugins/rotate_asg_instances/asg.rb
+++ b/lib/plugins/rotate_asg_instances/asg.rb
@@ -7,7 +7,7 @@ class ASG # rubocop:disable Metrics/ClassLength
 
       def initialize(resources)
         @resources = resources
-        @ssh = Moonshot::RotateAsgInstances::SSH.new
+        @ssh = Moonshot::RotateAsgInstances::SSH.new(@resources)
         @ilog = @resources.ilog
       end
 
diff --git a/lib/plugins/rotate_asg_instances/ssh.rb b/lib/plugins/rotate_asg_instances/ssh.rb
index ae29067a..1a41aee1 100644
--- a/lib/plugins/rotate_asg_instances/ssh.rb
+++ b/lib/plugins/rotate_asg_instances/ssh.rb
@@ -10,6 +10,10 @@ def initialize(response)
     end
 
     class SSH
+      def initialize(resources)
+        @resources = resources
+      end
+
       # As per the standard it is raising correctly but still giving an error.
       def test_ssh_connection(instance_id)
         Retriable.retriable(base_interval: 5, tries: 3) do
@@ -29,7 +33,12 @@ def exec(command, instance_id)
       private
 
       def build_command(command, instance_id)
-        cb = SSHCommandBuilder.new(Moonshot.config.ssh_config, instance_id)
+        teleport_config = Moonshot::TeleportConfig.new(
+          @resources.controller.stack.name,
+          Moonshot.config.ssh_config.ssh_user,
+          ENV['AWS_REGION']
+        )
+        cb = SSHCommandBuilder.new(Moonshot.config.ssh_config, instance_id, teleport_config)
         cb.build(command).cmd
       end
     end
diff --git a/spec/moonshot/plugins/rotate_asg_instances/asg_spec.rb b/spec/moonshot/plugins/rotate_asg_instances/asg_spec.rb
index 76e54af5..c00b44b5 100644
--- a/spec/moonshot/plugins/rotate_asg_instances/asg_spec.rb
+++ b/spec/moonshot/plugins/rotate_asg_instances/asg_spec.rb
@@ -113,26 +113,32 @@ def stub_cf_client
   end
 
   describe '#shutdown_instance' do
-    let(:public_ip_address) { '10.234.32.21' }
     let(:instance) { instance_double(Aws::EC2::Instance) }
     let(:command_builder) { Moonshot::SSHCommandBuilder }
     subject { super().send(:shutdown_instance, instance_id) }
 
     before(:each) do
+      ENV['AWS_REGION'] = 'us-east-1'
       moonshot_config.ssh_config.ssh_user = 'ci_user'
       moonshot_config.ssh_config.ssh_options = ssh_options
       allow(Aws::EC2::Instance).to receive(:new).and_return(instance)
-      allow_any_instance_of(command_builder).to receive(:instance_ip).and_return(public_ip_address)
+      allow(instance).to receive(:exists?).and_return(true)
+      allow(instance).to receive(:state).and_return({ name: 'running' })
       allow(instance).to receive(:wait_until_stopped)
+      allow(ilog).to receive(:info)
     end
 
+    after(:each) do
+      ENV.delete('AWS_REGION')
+    end
 
     context 'when ssh_options are not defined' do
       let(:ssh_options) { nil }
 
       it 'issues a shutdown without options to the instance' do
         expect_any_instance_of(ssh_executor).to receive(:run).with(
-          "ssh -t -l #{moonshot_config.ssh_config.ssh_user} #{public_ip_address} sudo\\ shutdown\\ -h\\ now"
+          'tsh ssh --proxy=teleport.dev.cloudservices.acquia.io -tA ' \
+          "ci_user@#{instance_id}.us-east-1.672327909798 sudo\\ shutdown\\ -h\\ now"
         )
         subject
       end
@@ -143,8 +149,9 @@ def stub_cf_client
 
       it 'issues a shutdown with options to the instance' do
         expect_any_instance_of(ssh_executor).to receive(:run).with(
-          'ssh -t -v -o UserKnownHostsFile=/dev/null ' \
-          "-l ci_user #{public_ip_address} sudo\\ shutdown\\ -h\\ now"
+          'tsh ssh -v -o UserKnownHostsFile=/dev/null ' \
+          '--proxy=teleport.dev.cloudservices.acquia.io -tA ' \
+          "ci_user@#{instance_id}.us-east-1.672327909798 sudo\\ shutdown\\ -h\\ now"
         )
         subject
       end
diff --git a/spec/moonshot/plugins/rotate_asg_instances/ssh_spec.rb b/spec/moonshot/plugins/rotate_asg_instances/ssh_spec.rb
index f6f897ee..dd3c7eb6 100644
--- a/spec/moonshot/plugins/rotate_asg_instances/ssh_spec.rb
+++ b/spec/moonshot/plugins/rotate_asg_instances/ssh_spec.rb
@@ -29,7 +29,7 @@
 
   let(:config) { resources.controller.config }
 
-  subject { described_class.new }
+  subject { described_class.new(resources) }
 
   describe '#test_ssh_connection' do
     it 'raise error if #test_ssh_connection fails' do
diff --git a/spec/moonshot/ssh_spec.rb b/spec/moonshot/ssh_spec.rb
index 56423c3d..4ace7bec 100644
--- a/spec/moonshot/ssh_spec.rb
+++ b/spec/moonshot/ssh_spec.rb
@@ -4,28 +4,33 @@
     c.app_name = 'MyApp'
     c.environment_name = 'prod'
     c.ssh_config.ssh_user = 'joeuser'
-    c.ssh_config.ssh_identity_file = '/Users/joeuser/.ssh/thegoods.key'
     c.ssh_command = 'cat /etc/passwd'
     Moonshot::Controller.new(c)
   end
 
+  let(:stack_double) { instance_double(Moonshot::Stack, name: 'MyApp-prod') }
+
   describe 'Moonshot::Controller#ssh' do
     before(:each) do
       ENV.delete('MOONSHOT_SSH_OPTIONS')
+      ENV['AWS_REGION'] = 'us-east-1'
+      allow(subject).to receive(:stack).and_return(stack_double)
+    end
+
+    after(:each) do
+      ENV.delete('AWS_REGION')
     end
 
     context 'normally' do
-      it 'should execute an ssh command with proper parameters' do
+      it 'should execute a tsh ssh command with proper parameters' do
         ts = instance_double(Moonshot::SSHTargetSelector)
         expect(Moonshot::SSHTargetSelector).to receive(:new).and_return(ts)
         expect(ts).to receive(:choose!).and_return('i-04683a82f2dddcc04')
 
-        expect_any_instance_of(Moonshot::SSHCommandBuilder).to receive(:instance_ip).exactly(2)
-          .and_return('123.123.123.123')
         expect(subject).to receive(:exec)
-          .with('ssh -t -i /Users/joeuser/.ssh/thegoods.key -l joeuser 123.123.123.123 cat\ /etc/passwd') # rubocop:disable LineLength
+          .with('tsh ssh --proxy=us-east-1.teleport.cloudservices.acquia.io -tA joeuser@i-04683a82f2dddcc04.us-east-1.546349603759 cat\ /etc/passwd') # rubocop:disable LineLength
         expect { subject.ssh }
-          .to output("Opening SSH connection to i-04683a82f2dddcc04 (123.123.123.123)...\n")
+          .to output("Opening SSH connection to i-04683a82f2dddcc04 (i-04683a82f2dddcc04.us-east-1.546349603759)...\n")
           .to_stderr
       end
     end
@@ -37,13 +42,11 @@
         c
       end
 
-      it 'should execute an ssh command with proper parameters' do
-        expect_any_instance_of(Moonshot::SSHCommandBuilder).to receive(:instance_ip).exactly(2)
-          .and_return('123.123.123.123')
+      it 'should execute a tsh ssh command with proper parameters' do
         expect(subject).to receive(:exec)
-          .with('ssh -t -i /Users/joeuser/.ssh/thegoods.key -l joeuser 123.123.123.123 cat\ /etc/passwd') # rubocop:disable LineLength
+          .with('tsh ssh --proxy=us-east-1.teleport.cloudservices.acquia.io -tA joeuser@i-012012012012012.us-east-1.546349603759 cat\ /etc/passwd') # rubocop:disable LineLength
         expect { subject.ssh }
-          .to output("Opening SSH connection to i-012012012012012 (123.123.123.123)...\n").to_stderr
+          .to output("Opening SSH connection to i-012012012012012 (i-012012012012012.us-east-1.546349603759)...\n").to_stderr
       end
     end
   end
diff --git a/spec/moonshot/teleport_config_spec.rb b/spec/moonshot/teleport_config_spec.rb
new file mode 100644
index 00000000..ec538761
--- /dev/null
+++ b/spec/moonshot/teleport_config_spec.rb
@@ -0,0 +1,75 @@
+describe Moonshot::TeleportConfig do
+  let(:instance_id) { 'i-0036e48e43b79740f' }
+
+  describe 'prod environment (stack name contains "prod")' do
+    subject { described_class.new('myapp-prod-us-east-1', 'joeuser', 'us-east-1') }
+
+    it 'uses region-based proxy URL' do
+      expect(subject.proxy_url).to eq('us-east-1.teleport.cloudservices.acquia.io')
+    end
+
+    it 'uses the prod account ID' do
+      expect(subject.account_id).to eq('546349603759')
+    end
+
+    it 'builds the Teleport hostname correctly' do
+      expect(subject.host_for(instance_id)).to eq(
+        'i-0036e48e43b79740f.us-east-1.546349603759'
+      )
+    end
+
+    it 'is not a bot user for a normal user' do
+      expect(subject.bot_user?).to be false
+    end
+
+    it 'returns nil identity_file for normal user' do
+      expect(subject.identity_file).to be_nil
+    end
+
+    context 'with bot user (clouddatabot)' do
+      subject { described_class.new('myapp-prod-us-east-1', 'clouddatabot', 'us-east-1') }
+
+      it 'is identified as a bot user' do
+        expect(subject.bot_user?).to be true
+      end
+
+      it 'uses the region-based identity file path' do
+        expect(subject.identity_file).to eq('/opt/machine-id/us-east-1/identity')
+      end
+    end
+  end
+
+  describe 'dev environment (stack name does not contain "prod")' do
+    subject { described_class.new('myapp-dev-jsmith', 'joeuser', 'us-east-1') }
+
+    it 'uses the shared dev proxy URL' do
+      expect(subject.proxy_url).to eq('teleport.dev.cloudservices.acquia.io')
+    end
+
+    it 'uses the dev account ID' do
+      expect(subject.account_id).to eq('672327909798')
+    end
+
+    it 'builds the Teleport hostname correctly' do
+      expect(subject.host_for(instance_id)).to eq(
+        'i-0036e48e43b79740f.us-east-1.672327909798'
+      )
+    end
+
+    it 'is not a bot user for a normal user' do
+      expect(subject.bot_user?).to be false
+    end
+
+    context 'with bot user (clouddatabot)' do
+      subject { described_class.new('myapp-dev-jsmith', 'clouddatabot', 'us-east-1') }
+
+      it 'is identified as a bot user' do
+        expect(subject.bot_user?).to be true
+      end
+
+      it 'uses the dev identity file path' do
+        expect(subject.identity_file).to eq('/opt/machine-id/dev-us-east-1/identity')
+      end
+    end
+  end
+end