diff --git a/.expeditor/build.habitat.yml b/.expeditor/build.habitat.yml
new file mode 100644
index 00000000..72ea2567
--- /dev/null
+++ b/.expeditor/build.habitat.yml
@@ -0,0 +1,9 @@
+---
+origin: chef
+
+expeditor:
+  defaults:
+    buildkite:
+      retry:
+        automatic:
+          limit: 1
diff --git a/.expeditor/buildkite/artifact.habitat.test.ps1 b/.expeditor/buildkite/artifact.habitat.test.ps1
new file mode 100755
index 00000000..b3258a15
--- /dev/null
+++ b/.expeditor/buildkite/artifact.habitat.test.ps1
@@ -0,0 +1,87 @@
+#!/usr/bin/env powershell
+
+#Requires -Version 5
+# https://stackoverflow.com/questions/9948517
+# TODO: Set-StrictMode -Version Latest
+$PSDefaultParameterValues['*:ErrorAction']='Stop'
+$ErrorActionPreference = 'Stop'
+$env:HAB_BLDR_CHANNEL = "LTS-2024"
+$env:HAB_REFRESH_CHANNEL = "LTS-2024"
+$env:HAB_ORIGIN = 'ci'
+$env:CHEF_LICENSE = 'accept-no-persist'
+$env:HAB_LICENSE = 'accept-no-persist'
+$Plan = 'chef-cli'
+
+Write-Host "--- system details"
+$Properties = 'Caption', 'CSName', 'Version', 'BuildType', 'OSArchitecture'
+Get-CimInstance Win32_OperatingSystem | Select-Object $Properties | Format-Table -AutoSize
+
+Write-Host "--- Installing the version of Habitat required"
+
+function Stop-HabProcess {
+  $habProcess = Get-Process hab -ErrorAction SilentlyContinue
+  if ($habProcess) {
+      Write-Host "Stopping hab process..."
+      Stop-Process -Name hab -Force
+  }
+}
+
+# Installing Habitat
+function Install-Habitat {
+  Write-Host "Downloading and installing Habitat..."
+  Invoke-Expression ((New-Object System.Net.WebClient).DownloadString('https://raw.githubusercontent.com/habitat-sh/habitat/main/components/hab/install.ps1'))
+}
+
+try {
+  hab --version
+}
+catch {
+  Set-ExecutionPolicy Bypass -Scope Process -Force
+
+  Stop-HabProcess
+
+  # Remove the existing hab.exe if it exists and if you have permissions
+  $habPath = "C:\ProgramData\Habitat\hab.exe"
+  if (Test-Path $habPath) {
+      Write-Host "Attempting to remove existing hab.exe..."
+      Remove-Item $habPath -Force -ErrorAction SilentlyContinue
+      if (Test-Path $habPath) {
+          Write-Host "Failed to remove hab.exe, re-running script with elevated permissions."
+          Start-Process powershell -Verb runAs -ArgumentList "-NoProfile -ExecutionPolicy Bypass -File `"$PSCommandPath`""
+          exit
+      }
+  }
+
+  Install-Habitat
+}
+finally {
+  Write-Host ":habicat: I think I have the version I need to build."
+}
+
+
+Write-Host "--- Generating fake origin key"
+hab origin key generate $env:HAB_ORIGIN
+
+Write-Host "--- Building $Plan"
+$project_root = "$(git rev-parse --show-toplevel)"
+Set-Location $project_root
+
+$env:DO_CHECK=$true; hab pkg build .
+
+. $project_root/results/last_build.ps1
+
+Write-Host "--- Installing $pkg_ident/$pkg_artifact"
+hab pkg install -b $project_root/results/$pkg_artifact
+
+Write-Host "+++ Testing $Plan"
+
+Push-Location $project_root
+
+try {
+    Write-Host "Running unit tests..."
+    habitat/tests/test.ps1 $pkg_ident
+}
+finally {
+    # Ensure we always return to the original directory
+    Pop-Location
+}
\ No newline at end of file
diff --git a/.expeditor/buildkite/artifact.habitat.test.sh b/.expeditor/buildkite/artifact.habitat.test.sh
new file mode 100755
index 00000000..db8dfd14
--- /dev/null
+++ b/.expeditor/buildkite/artifact.habitat.test.sh
@@ -0,0 +1,71 @@
+#!/usr/bin/env bash
+
+set -eo pipefail
+
+export HAB_ORIGIN='ci'
+export PLAN='chef-cli'
+export CHEF_LICENSE="accept-no-persist"
+export HAB_LICENSE="accept-no-persist"
+export HAB_BLDR_CHANNEL="LTS-2024"
+export HAB_REFRESH_CHANNEL="LTS-2024"
+
+echo "--- checking if git is installed"
+if ! command -v git &> /dev/null; then
+    echo "Git is not installed. Installing Git..."
+    sudo yum install -y git
+else
+    echo "Git is already installed."
+    git --version
+fi
+
+echo "--- add an exception for this directory since detected dubious ownership in repository at /workdir"
+git config --global --add safe.directory /workdir
+
+echo "--- git status for this workdir"
+git status
+
+echo "--- ruby version"
+ruby -v
+
+export project_root="$(git rev-parse --show-toplevel)"
+echo "The value for project_root is: $project_root"
+
+export HAB_NONINTERACTIVE=true
+export HAB_NOCOLORING=true
+export HAB_STUDIO_SECRET_HAB_NONINTERACTIVE=true
+
+echo "--- system details"
+uname -a
+
+echo "--- Installing Habitat"
+id -a
+curl https://raw.githubusercontent.com/habitat-sh/habitat/main/components/hab/install.sh | bash
+
+echo "--- :key: Generating fake origin key"
+hab origin key generate "$HAB_ORIGIN"
+
+
+echo "--- Building $PLAN"
+cd "$project_root"
+DO_CHECK=true hab pkg build .
+
+echo "--- Sourcing 'results/last_build.sh'"
+if [ -f ./results/last_build.env ]; then
+    cat ./results/last_build.env
+    . ./results/last_build.env
+    export pkg_artifact
+fi
+echo "+++ Installing ${pkg_ident:?is undefined}"
+echo "++++"
+echo $project_root
+echo "+++"
+hab pkg install -b "${project_root:?is undefined}/results/${pkg_artifact:?is undefined}"
+
+echo "+++ Testing $PLAN"
+
+PATH="$(hab pkg path ci/chef-cli)/bin:$PATH"
+export PATH
+echo "PATH is $PATH"
+
+echo "--- :mag_right: Testing $PLAN"
+${project_root}/habitat/tests/test.sh "$pkg_ident" || error 'failures during test of executables'
\ No newline at end of file
diff --git a/.expeditor/config.yml b/.expeditor/config.yml
index 4dd101aa..54e41cbb 100644
--- a/.expeditor/config.yml
+++ b/.expeditor/config.yml
@@ -10,8 +10,6 @@ rubygems:
   - chef-cli
 
 release_branches:
-  - workstation-LTS:
-      version_constraint: 1.*
   - main:
       version_constraint: 5.*
 
@@ -30,10 +28,27 @@ github:
 changelog:
   rollup_header: Changes not yet released to rubygems.org
 
+artifact_channels:
+  - unstable
+  - chef-dke-lts2024
+
 pipelines:
   - verify:
       description: Pull Request validation tests
       public: true
+  - habitat/build:
+      env:
+        - HAB_NONINTERACTIVE: "true"
+        - HAB_NOCOLORING: "true"
+        - HAB_STUDIO_SECRET_HAB_NONINTERACTIVE: "true"
+  - habitat/test:
+      description: Execute tests against the habitat artifact
+      definition: .expeditor/habitat-test.pipeline.yml
+      env:
+        - HAB_NONINTERACTIVE: "true"
+        - HAB_NOCOLORING: "true"
+        - HAB_STUDIO_SECRET_HAB_NONINTERACTIVE: "true"
+      trigger: pull_request
 
 subscriptions:
   # These actions are taken, in order they are specified, anytime a Pull Request is merged.
@@ -51,7 +66,15 @@ subscriptions:
             - "Expeditor: Skip All"
       - built_in:build_gem:
           only_if: built_in:bump_version
+      - trigger_pipeline:habitat/build:
+          only_if: built_in:bump_version
+          ignore_labels:
+            - "Expeditor: Skip Habitat"
+            - "Expeditor: Skip All"
+
+  # this works for symantec version promote
   - workload: project_promoted:{{agent_id}}:*
     actions:
       - built_in:rollover_changelog
+      - built_in:promote_habitat_packages
       - built_in:publish_rubygems
\ No newline at end of file
diff --git a/.expeditor/habitat-test.pipeline.yml b/.expeditor/habitat-test.pipeline.yml
new file mode 100644
index 00000000..a8636693
--- /dev/null
+++ b/.expeditor/habitat-test.pipeline.yml
@@ -0,0 +1,36 @@
+---
+expeditor:
+  defaults:
+    buildkite:
+      timeout_in_minutes: 30
+      retry:
+        automatic:
+          limit: 1
+
+
+steps:
+
+  - label: ":linux: Validate Habitat Builds of Chef-cli"
+    commands:
+      - .expeditor/buildkite/artifact.habitat.test.sh
+    expeditor:
+      executor:
+        docker:
+          image: ruby:3.1
+          privileged: true
+
+  - label: ":windows: Validate Habitat Builds of Test Kitchen"
+    commands:
+      - .expeditor/buildkite/artifact.habitat.test.ps1
+    expeditor:
+      executor:
+        docker:
+          host_os: windows
+          shell: ["powershell", "-Command"]
+          image: rubydistros/windows-2019:3.1
+          user: 'NT AUTHORITY\SYSTEM'
+          environment:
+            - FORCE_FFI_YAJL=ext
+            - EXPIRE_CACHE=true
+            - CHEF_LICENSE=accept-no-persist
+            - CHEF_LICENSE_SERVER=http://hosted-license-service-lb-8000-606952349.us-west-2.elb.amazonaws.com:8000/
diff --git a/.gitignore b/.gitignore
index 1db8f690..ee9ed9f4 100644
--- a/.gitignore
+++ b/.gitignore
@@ -41,3 +41,6 @@ Vagrantfile
 my-cookbook
 results/
 Gemfile.lock
+
+
+.idea/
\ No newline at end of file
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 23f60d5f..55c58c24 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,8 +1,16 @@
 <!-- usage documentation: https://expeditor.chef.io/docs/reference/changelog/#common-changelog -->
-<!-- latest_release -->
+<!-- latest_release 0.1.0 -->
+## [v0.1.0](https://github.com/chef/chef-cli/tree/v0.1.0) (2025-01-06)
+
+#### Merged Pull Requests
+- Add hab promote pipeline [#254](https://github.com/chef/chef-cli/pull/254) ([sanghinitin](https://github.com/sanghinitin))
 <!-- latest_release -->
 
-<!-- release_rollup -->
+<!-- release_rollup since=5.6.16 -->
+### Changes not yet released to rubygems.org
+
+#### Merged Pull Requests
+- Add hab promote pipeline [#254](https://github.com/chef/chef-cli/pull/254) ([sanghinitin](https://github.com/sanghinitin)) <!-- 0.1.0 -->
 <!-- release_rollup -->
 
 <!-- latest_stable_release -->
diff --git a/Gemfile b/Gemfile
index 7461ea33..d7097f9e 100644
--- a/Gemfile
+++ b/Gemfile
@@ -3,15 +3,16 @@ source "https://rubygems.org"
 gemspec
 
 gem "logger", "< 1.6" # 1.6 causes errors with mixlib-log < 3.1.1
-
+gem "chefspec"
 group :test do
   gem "rake"
-  gem "rspec", "~> 3.8"
+  gem "rspec", "=3.12.0"
   gem "rspec-expectations", "~> 3.8"
   gem "rspec-mocks", "~> 3.8"
   gem "cookstyle"
   gem "chefstyle"
-  gem "test-kitchen"
+  gem "faraday_middleware"
+  gem "chef-test-kitchen-enterprise", git: "https://github.com/chef/chef-test-kitchen-enterprise", branch: "main"
   gem "simplecov", require: false
 end
 
@@ -19,10 +20,13 @@ group :development do
   gem "pry"
   gem "pry-byebug"
   gem "rb-readline"
+  gem "appbundler"
 end
 
 group :profile do
-  gem "stackprof"
-  gem "stackprof-webnav"
-  gem "memory_profiler"
-end
+  unless RUBY_PLATFORM.match?(/mswin|mingw|windows/)
+    gem "stackprof"
+    gem "stackprof-webnav"
+    gem "memory_profiler"
+  end
+end
\ No newline at end of file
diff --git a/Rakefile b/Rakefile
index 3b92ac1a..f25cfd7f 100644
--- a/Rakefile
+++ b/Rakefile
@@ -14,6 +14,8 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 #
+#
+require "bundler/gem_tasks"
 
 namespace :style do
   begin
@@ -52,3 +54,4 @@ namespace :style do
     puts ">>> Gem load error: #{e}, omitting #{task.name}" unless ENV["CI"]
   end
 end
+
diff --git a/chef-cli.gemspec b/chef-cli.gemspec
index 968898d2..35a36fe6 100644
--- a/chef-cli.gemspec
+++ b/chef-cli.gemspec
@@ -50,4 +50,5 @@ Gem::Specification.new do |gem|
   gem.add_dependency "diff-lcs", ">= 1.0", "< 1.4" # 1.4 changes the output
   gem.add_dependency "pastel", "~> 0.7" # used for policyfile differ
   gem.add_dependency "license-acceptance", ">= 1.0.11", "< 3"
+  gem.add_dependency "chef-licensing", "~> 1.0"
 end
diff --git a/habitat/plan.ps1 b/habitat/plan.ps1
new file mode 100644
index 00000000..e7cee43b
--- /dev/null
+++ b/habitat/plan.ps1
@@ -0,0 +1,94 @@
+$ErrorActionPreference = "Stop"
+$PSDefaultParameterValues['*:ErrorAction']='Stop'
+
+$env:HAB_BLDR_CHANNEL = "LTS-2024"
+$env:HAB_REFRESH_CHANNEL = "LTS-2024"
+$pkg_name="chef-cli"
+$pkg_origin="chef"
+$pkg_version=$(Get-Content "$PLAN_CONTEXT/../VERSION")
+$pkg_maintainer="The Chef Maintainers <humans@chef.io>"
+
+$pkg_deps=@(
+  "chef/ruby31-plus-devkit"
+  "core/git"
+)
+$pkg_bin_dirs=@("bin"
+                "vendor/bin")
+$project_root= (Resolve-Path "$PLAN_CONTEXT/../").Path
+
+function pkg_version {
+    Get-Content "$SRC_PATH/VERSION"
+}
+
+function Invoke-Before {
+    Set-PkgVersion
+}
+function Invoke-SetupEnvironment {
+    Push-RuntimeEnv -IsPath GEM_PATH "$pkg_prefix/vendor"
+
+    Set-RuntimeEnv APPBUNDLER_ALLOW_RVM "true" # prevent appbundler from clearing out the carefully constructed runtime GEM_PATH
+    Set-RuntimeEnv FORCE_FFI_YAJL "ext"
+    Set-RuntimeEnv LANG "en_US.UTF-8"
+    Set-RuntimeEnv LC_CTYPE "en_US.UTF-8"
+}
+
+function Invoke-Build {
+    try {
+        $env:Path += ";c:\\Program Files\\Git\\bin"
+        Push-Location $project_root
+        $env:GEM_HOME = "$HAB_CACHE_SRC_PATH/$pkg_dirname/vendor"
+
+        Write-BuildLine " ** Configuring bundler for this build environment"
+        bundle config --local without integration deploy maintenance
+        bundle config --local jobs 4
+        bundle config --local retry 5
+        bundle config --local silence_root_warning 1
+        Write-BuildLine " ** Using bundler to retrieve the Ruby dependencies"
+        bundle install
+
+        gem build chef-cli.gemspec
+        Write-BuildLine " ** Using gem to  install"
+        gem install chef-cli-*.gem --no-document
+        ruby ./post-bundle-install.rb
+
+        If ($lastexitcode -ne 0) { Exit $lastexitcode }
+    } finally {
+        Pop-Location
+    }
+}
+
+function Invoke-Install {
+    Write-BuildLine "** Copy built & cached gems to install directory"
+    Copy-Item -Path "$HAB_CACHE_SRC_PATH/$pkg_dirname/*" -Destination $pkg_prefix -Recurse -Force -Exclude @("gem_make.out", "mkmf.log", "Makefile",
+                     "*/latest", "latest",
+                     "*/JSON-Schema-Test-Suite", "JSON-Schema-Test-Suite")
+
+    try {
+        Push-Location $pkg_prefix
+        bundle config --local gemfile $project_root/Gemfile
+         Write-BuildLine "** generating binstubs for chef-cli with precise version pins"
+	 Write-BuildLine "** generating binstubs for chef-cli with precise version pins $project_root $pkg_prefix/bin " 
+            Invoke-Expression -Command "appbundler.bat $project_root $pkg_prefix/bin chef-cli"
+            If ($lastexitcode -ne 0) { Exit $lastexitcode }
+	Write-BuildLine " ** Running the chef-cli project's 'rake install' to install the path-based gems so they look like any other installed gem."
+
+        If ($lastexitcode -ne 0) { Exit $lastexitcode }
+    } finally {
+        Pop-Location
+    }
+}
+
+function Invoke-After {
+    # We don't need the cache of downloaded .gem files ...
+    Remove-Item $pkg_prefix/vendor/cache -Recurse -Force
+    # We don't need the gem docs.
+    Remove-Item $pkg_prefix/vendor/doc -Recurse -Force
+    # We don't need to ship the test suites for every gem dependency,
+    # only inspec's for package verification.
+    Get-ChildItem $pkg_prefix/vendor/gems -Filter "spec" -Directory -Recurse -Depth 1 `
+        | Where-Object -FilterScript { $_.FullName -notlike "*chef-cli*" }             `
+        | Remove-Item -Recurse -Force
+    # Remove the byproducts of compiling gems with extensions
+    Get-ChildItem $pkg_prefix/vendor/gems -Include @("gem_make.out", "mkmf.log", "Makefile") -File -Recurse `
+        | Remove-Item -Force
+}
\ No newline at end of file
diff --git a/habitat/plan.sh b/habitat/plan.sh
new file mode 100644
index 00000000..5969b09f
--- /dev/null
+++ b/habitat/plan.sh
@@ -0,0 +1,80 @@
+export HAB_BLDR_CHANNEL="LTS-2024"
+export HAB_REFRESH_CHANNEL="LTS-2024"
+pkg_name=chef-cli
+pkg_origin=chef
+ruby_pkg="core/ruby3_1"
+pkg_deps=(${ruby_pkg} core/coreutils)
+pkg_build_deps=(
+    core/make
+    core/sed
+    core/gcc
+    core/libarchive
+    core/git
+    )
+pkg_bin_dirs=(bin)
+
+do_setup_environment() {
+  build_line 'Setting GEM_HOME="$pkg_prefix/vendor"'
+  export GEM_HOME="$pkg_prefix/vendor"
+
+  build_line "Setting GEM_PATH=$GEM_HOME"
+  export GEM_PATH="$GEM_HOME"
+}
+
+pkg_version() {
+  cat "$SRC_PATH/VERSION"
+}
+do_before() {
+  update_pkg_version
+}
+do_unpack() {
+  mkdir -pv "$HAB_CACHE_SRC_PATH/$pkg_dirname"
+  cp -RT "$PLAN_CONTEXT"/.. "$HAB_CACHE_SRC_PATH/$pkg_dirname/"
+}
+do_build() {
+
+    export GEM_HOME="$pkg_prefix/vendor"
+
+    build_line "Setting GEM_PATH=$GEM_HOME"
+    export GEM_PATH="$GEM_HOME"
+    bundle config --local without integration deploy maintenance
+    bundle config --local jobs 4
+    bundle config --local retry 5
+    bundle config --local silence_root_warning 1
+    bundle install
+    gem build chef-cli.gemspec
+    ruby ./post-bundle-install.rb
+}
+do_install() {
+   export GEM_HOME="$pkg_prefix/vendor"
+
+  build_line "Setting GEM_PATH=$GEM_HOME"
+  export GEM_PATH="$GEM_HOME"
+  gem install chef-cli-*.gem --no-document
+  set_runtime_env "GEM_PATH" "${pkg_prefix}/vendor"
+  wrap_ruby_bin
+}
+wrap_ruby_bin() {
+  local bin="$pkg_prefix/bin/$pkg_name"
+  local real_bin="$GEM_HOME/gems/chef-cli-${pkg_version}/bin/chef-cli"
+  build_line "Adding wrapper $bin to $real_bin"
+  cat <<EOF > "$bin"
+#!$(pkg_path_for core/bash)/bin/bash
+set -e
+
+# Set binary path that allows InSpec to use non-Hab pkg binaries
+export PATH="/sbin:/usr/sbin:/usr/local/sbin:/usr/local/bin:/usr/bin:/bin:\$PATH"
+
+# Set Ruby paths defined from 'do_setup_environment()'
+  export GEM_HOME="$pkg_prefix/vendor"
+  export GEM_PATH="$GEM_PATH"
+
+exec $(pkg_path_for ${ruby_pkg})/bin/ruby $real_bin \$@
+EOF
+  chmod -v 755 "$bin"
+}
+
+
+do_strip() {
+  return 0
+}
\ No newline at end of file
diff --git a/habitat/tests/test.ps1 b/habitat/tests/test.ps1
new file mode 100644
index 00000000..a712fea5
--- /dev/null
+++ b/habitat/tests/test.ps1
@@ -0,0 +1,21 @@
+param (
+    [Parameter()]
+    [string]$PackageIdentifier = $(throw "Usage: test.ps1 [test_pkg_ident] e.g. test.ps1 ci/user-windows/1.0.0/20190812103929")
+)
+
+
+Write-Host "--- :fire: Smokish test"
+# Pester the Package
+$version=hab pkg exec "${pkg_ident}" chef-cli -v
+$actual_version=[Regex]::Match($version,"([0-9]+.[0-9]+.[0-9]+)").Value
+$package_version=$PackageIdentifier.split("/",4)[2]
+
+Write-Host "package_version  $package_version actual version $actual_version"
+if ($package_version -eq $actual_version)
+{
+    Write "Chef-cli working fine"
+}
+else {
+    Write-Error "chef-cli version not met expected $package_version actual version $actual_version "
+    throw "Chef cli windows pipeline not working for hab pkg"
+}
\ No newline at end of file
diff --git a/habitat/tests/test.sh b/habitat/tests/test.sh
new file mode 100755
index 00000000..d5d01cdc
--- /dev/null
+++ b/habitat/tests/test.sh
@@ -0,0 +1,30 @@
+
+set -euo pipefail
+
+
+project_root="$(git rev-parse --show-toplevel)"
+pkg_ident="$1"
+# print error message followed by usage and exit
+error () {
+  local message="$1"
+
+  echo -e "\nERROR: ${message}\n" >&2
+
+  exit 1
+}
+
+[[ -n "$pkg_ident" ]] || error 'no hab package identity provided'
+
+package_version=$(awk -F / '{print $3}' <<<"$pkg_ident")
+
+cd "${project_root}"
+echo "Testing ${pkg_ident} executables"
+version=$(hab pkg exec "${pkg_ident}" chef-cli -v)
+echo $version
+actual_version=$(echo "$version" | sed -E 's/.*version: ([0-9]+\.[0-9]+\.[0-9]+).*/\1/')
+echo $actual_version
+
+if [[ "$actual_version" != *"$package_version"* ]]; then
+  error "chef-cli version is not the expected version. Expected '$package_version', got '$actual_version'"
+fi
+
diff --git a/lib/chef-cli/builtin_commands.rb b/lib/chef-cli/builtin_commands.rb
index 6bcee200..1b239792 100644
--- a/lib/chef-cli/builtin_commands.rb
+++ b/lib/chef-cli/builtin_commands.rb
@@ -57,4 +57,6 @@
 
   c.builtin "describe-cookbook", :DescribeCookbook, require_path: "chef-cli/command/describe_cookbook",
                                                     desc: "Prints cookbook checksum information used for cookbook identifier"
+  c.builtin "license", :License, require_path: "chef-cli/command/license",
+            desc: "Create & install a new license on the system or view installed license(s)."
 end
diff --git a/lib/chef-cli/command/env.rb b/lib/chef-cli/command/env.rb
index d1aed4b2..b157d557 100644
--- a/lib/chef-cli/command/env.rb
+++ b/lib/chef-cli/command/env.rb
@@ -85,7 +85,8 @@ def gem_environment
       end
 
       def paths
-        omnibus_env["PATH"].split(File::PATH_SEPARATOR)
+        env = habitat_install? ? habitat_env : omnibus_env
+        env["PATH"].split(File::PATH_SEPARATOR)
       rescue OmnibusInstallNotFound
         ENV["PATH"].split(File::PATH_SEPARATOR)
       end
diff --git a/lib/chef-cli/command/exec.rb b/lib/chef-cli/command/exec.rb
index f1e19bde..d66438a7 100644
--- a/lib/chef-cli/command/exec.rb
+++ b/lib/chef-cli/command/exec.rb
@@ -30,7 +30,8 @@ class Exec < ChefCLI::Command::Base
       def run(params)
         # Set ENV directly on the "parent" process (us) before running #exec to
         # ensure the custom PATH is honored when finding the command to exec
-        omnibus_env.each { |var, value| ENV[var] = value }
+        env = habitat_install? ? habitat_env : omnibus_env
+        env.each { |var, value| ENV[var] = value }
         exec(*params)
         raise "Exec failed without an exception, your ruby is buggy" # should never get here
       end
diff --git a/lib/chef-cli/command/license.rb b/lib/chef-cli/command/license.rb
new file mode 100644
index 00000000..039fb34e
--- /dev/null
+++ b/lib/chef-cli/command/license.rb
@@ -0,0 +1,110 @@
+# frozen_string_literal: true
+
+# Copyright:: Chef Software Inc.
+# License:: Apache License, Version 2.0
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+require_relative "base"
+require "chef-cli/licensing/base"
+require_relative "../configurable"
+
+module ChefCLI
+  module Command
+
+    # This class will manage the license command in the chef-cli
+    class License < Base
+
+      include Configurable
+
+      MAIN_COMMAND_HELP = <<~HELP.freeze
+        Usage: #{ChefCLI::Dist::EXEC} license [SUBCOMMAND]
+
+        `#{ChefCLI::Dist::EXEC} license` command will validate the existing license
+        or will help you interactively generate new free/trial license and activate the
+        commercial license the chef team has sent you through email.
+      HELP
+
+      SUB_COMMANDS = [
+        { name: "list", description: "List details of the license(s) installed on the system." },
+        { name: "add", description: "Create & install a Free/ Trial license or install a Commercial license on the system." },
+      ].freeze
+
+      option :chef_license_key,
+        long: "--chef-license-key LICENSE",
+        description: "New license key to accept and store in the system"
+
+      attr_accessor :ui
+
+      def self.banner
+        <<~BANNER
+          #{MAIN_COMMAND_HELP}
+          Subcommands:
+          #{SUB_COMMANDS.map do |c|
+            "  #{c[:name].ljust(7)}#{c[:description]}"
+          end.join("\n") }
+
+          Options:
+        BANNER
+      end
+
+      def initialize
+        super
+
+        @ui = UI.new
+      end
+
+      def run(params)
+        config_license_debug if debug?
+        remaining_args = parse_options(params)
+        return 1 unless validate_params!(remaining_args)
+
+        if remaining_args.blank?
+          ChefCLI::Licensing::Base.validate
+        else
+          ChefCLI::Licensing::Base.send(remaining_args[0])
+        end
+      rescue ChefLicensing::LicenseKeyFetcher::LicenseKeyNotFetchedError
+        ui.msg("License key not fetched. Please try again.")
+      end
+
+      def debug?
+        !!config[:debug]
+      end
+
+      def validate_params!(args)
+        if args.length > 1
+          ui.err("Too many arguments")
+          return false
+        end
+
+        valid_subcommands = SUB_COMMANDS.collect { |c| c[:name] }
+        args.each do |arg|
+          next if valid_subcommands.include?(arg)
+
+          ui.err("Invalid option: #{arg}")
+          return false
+        end
+
+        true
+      end
+
+      private
+
+      def config_license_debug
+        ChefLicensing.output = ui
+      end
+    end
+  end
+end
diff --git a/lib/chef-cli/command/shell_init.rb b/lib/chef-cli/command/shell_init.rb
index 7d7dda0e..bd1253ea 100644
--- a/lib/chef-cli/command/shell_init.rb
+++ b/lib/chef-cli/command/shell_init.rb
@@ -29,6 +29,7 @@ module Mixlib
 module ChefCLI
 
   class ShellCompletionTemplateContext
+    include ChefCLI::Helpers
 
     def commands
       ChefCLI.commands_map.command_specs.inject({}) do |cmd_info, (_key, cmd_spec)|
@@ -40,6 +41,10 @@ def commands
     def get_binding
       binding
     end
+
+    def habitat?
+      habitat_install?
+    end
   end
 
   module Command
@@ -103,7 +108,7 @@ def run(argv)
           return 1
         end
 
-        env = omnibus_env.dup
+        env = (habitat_install? ? habitat_env : omnibus_env).dup
         path = env.delete("PATH")
         export(shell_name, "PATH", path)
         env.each do |var_name, value|
diff --git a/lib/chef-cli/completions/bash.sh.erb b/lib/chef-cli/completions/bash.sh.erb
index 79c6ada6..86f6b66d 100644
--- a/lib/chef-cli/completions/bash.sh.erb
+++ b/lib/chef-cli/completions/bash.sh.erb
@@ -2,4 +2,4 @@ _chef_comp() {
     local COMMANDS="<%= commands.keys.join(' ')-%>"
     COMPREPLY=($(compgen -W "$COMMANDS" -- ${COMP_WORDS[COMP_CWORD]} ))
 }
-complete -F _chef_comp chef
+complete -F _chef_comp <%= habitat? ? "chef-cli" : "chef" %>
diff --git a/lib/chef-cli/completions/chef.fish.erb b/lib/chef-cli/completions/chef.fish.erb
index 44f2a569..018b27e6 100644
--- a/lib/chef-cli/completions/chef.fish.erb
+++ b/lib/chef-cli/completions/chef.fish.erb
@@ -5,5 +5,5 @@
 set -l chef_commands <%= commands.keys.join(' ') %>;
 
 <% commands.each do |command, desc| -%>
-complete -c chef -f -n "not __fish_seen_subcommand_from $chef_commands" -a <%= command %> -d "<%= desc %>";
+complete -c <%= habitat? ? "chef-cli" : "chef" %> -f -n "not __fish_seen_subcommand_from $chef_commands" -a <%= command %> -d "<%= desc %>";
 <% end -%>
diff --git a/lib/chef-cli/completions/zsh.zsh.erb b/lib/chef-cli/completions/zsh.zsh.erb
index ac4986de..15056c3c 100644
--- a/lib/chef-cli/completions/zsh.zsh.erb
+++ b/lib/chef-cli/completions/zsh.zsh.erb
@@ -17,5 +17,5 @@ function _chef() {
   fi
 }
 
-compdef _chef chef
+compdef _chef <%= habitat? ? "chef-cli" : "chef" %>
 
diff --git a/lib/chef-cli/dist.rb b/lib/chef-cli/dist.rb
index ead75796..a0a31856 100644
--- a/lib/chef-cli/dist.rb
+++ b/lib/chef-cli/dist.rb
@@ -10,6 +10,9 @@ class Dist
     CLI_PRODUCT = "Chef CLI".freeze
     CLI_GEM = "chef-cli".freeze
 
+    CHEF_DKE_PKG_NAME = "chef/chef-development-kit-enterprise".freeze
+    HAB_PKG_NAME = "chef/chef-cli".freeze
+
     # the name of the overall infra product
     INFRA_PRODUCT = "Chef Infra".freeze
 
diff --git a/lib/chef-cli/helpers.rb b/lib/chef-cli/helpers.rb
index 6c72237e..f3edc533 100644
--- a/lib/chef-cli/helpers.rb
+++ b/lib/chef-cli/helpers.rb
@@ -60,6 +60,21 @@ def omnibus_install?
       File.exist?(expected_omnibus_root) && File.exist?(File.join(expected_omnibus_root, "version-manifest.json"))
     end
 
+    # The habitat version of the chef-cli can be installed with standalone or chef-development-kit-enterprise
+    # This method checks if the habitat version of chef-cli is installed as standalone
+    def habitat_standalone?
+      @hab_standalone ||= (hab_pkg_installed?(ChefCLI::Dist::HAB_PKG_NAME) && !habitat_chef_dke?)
+    end
+
+    # This method checks if the habitat version of chef-cli is installed with chef-development-kit-enterprise
+    def habitat_chef_dke?
+      @hab_dke ||= hab_pkg_installed?(ChefCLI::Dist::CHEF_DKE_PKG_NAME)
+    end
+
+    def habitat_install?
+      habitat_chef_dke? || habitat_standalone?
+    end
+
     def omnibus_root
       @omnibus_root ||= omnibus_expand_path(expected_omnibus_root)
     end
@@ -110,6 +125,31 @@ def git_windows_bin_dir
       @git_windows_bin_dir ||= File.expand_path(File.join(omnibus_root, "embedded", "git", "usr", "bin"))
     end
 
+    #
+    # environment vars for habitat
+    #
+    def habitat_env
+      @habitat_env ||=
+      begin
+        # Define the necessary paths for the Habitat environment
+        # If it is a chef-dke installation, we will use the chef-dke bin path.
+        # Otherwise, we will use the chef-cli bin path.
+        bin_pkg_prefix = get_pkg_prefix(habitat_chef_dke? ? ChefCLI::Dist::CHEF_DKE_PKG_NAME : ChefCLI::Dist::HAB_PKG_NAME)
+        vendor_dir = File.join(get_pkg_prefix(ChefCLI::Dist::HAB_PKG_NAME), "vendor")
+        path = [
+          File.join(bin_pkg_prefix, "bin"),
+          ENV["PATH"].split(File::PATH_SEPARATOR), # Preserve existing PATH
+        ].flatten.uniq
+
+        {
+        "PATH" => path.join(File::PATH_SEPARATOR),
+        "GEM_ROOT" => Gem.default_dir, # Default directory for gems
+        "GEM_HOME" => vendor_dir,  # GEM_HOME pointing to the vendor directory
+        "GEM_PATH" => vendor_dir,  # GEM_PATH also pointing to the vendor directory
+        }
+      end
+    end
+
     #
     # environment vars for omnibus
     #
@@ -129,6 +169,16 @@ def omnibus_env
         end
     end
 
+    def get_pkg_prefix(pkg_name)
+      path = `hab pkg path #{pkg_name}`.strip
+
+      if $?.success? && !path.empty?
+        path
+      else
+        raise "Failed to get pkg_prefix for #{pkg_name}: #{path}"
+      end
+    end
+
     def omnibus_expand_path(*paths)
       dir = File.expand_path(File.join(paths))
       raise OmnibusInstallNotFound.new unless dir && File.directory?(dir)
@@ -173,5 +223,14 @@ def reset!
     def macos?
       !!(RUBY_PLATFORM =~ /darwin/)
     end
+
+    # @return [Boolean] Checks if a habitat package is installed.
+    # If habitat itself is not installed, this method will return false.
+    #
+    # @api private
+    #
+    def hab_pkg_installed?(pkg_name)
+      `hab pkg list #{pkg_name} 2>/dev/null`.include?(pkg_name) rescue false
+    end
   end
 end
diff --git a/lib/chef-cli/licensing/base.rb b/lib/chef-cli/licensing/base.rb
new file mode 100644
index 00000000..01845fd5
--- /dev/null
+++ b/lib/chef-cli/licensing/base.rb
@@ -0,0 +1,42 @@
+# frozen_string_literal: true
+
+# Copyright:: Chef Software Inc.
+# License:: Apache License, Version 2.0
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+require "chef-licensing"
+require_relative "config"
+
+module ChefCLI
+  module Licensing
+    class Base
+      class << self
+        def validate
+          ChefLicensing.fetch_and_persist.each do |license_key|
+            puts "License Key: #{license_key}"
+          end
+        end
+
+        def list
+          ChefLicensing.list_license_keys_info
+        end
+
+        def add
+          ChefLicensing.add_license
+        end
+      end
+    end
+  end
+end
diff --git a/lib/chef-cli/licensing/config.rb b/lib/chef-cli/licensing/config.rb
new file mode 100644
index 00000000..3d3cbcf8
--- /dev/null
+++ b/lib/chef-cli/licensing/config.rb
@@ -0,0 +1,26 @@
+# frozen_string_literal: true
+
+# Copyright:: Chef Software Inc.
+# License:: Apache License, Version 2.0
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+require "chef-licensing"
+
+ChefLicensing.configure do |config|
+  config.chef_product_name = "workstation"
+  config.chef_entitlement_id = "x6f3bc76-a94f-4b6c-bc97-4b7ed2b045c0"
+  config.chef_executable_name = "chef"
+  config.license_server_url = "https://services.chef.io/licensing"
+end
diff --git a/post-bundle-install.rb b/post-bundle-install.rb
new file mode 100644
index 00000000..e9ae4304
--- /dev/null
+++ b/post-bundle-install.rb
@@ -0,0 +1,30 @@
+#!/usr/bin/env ruby
+
+gem_home = Gem.paths.home
+
+puts "fixing bundle installed gems in #{gem_home}"
+
+# Install gems from git repos.  This makes the assumption that there is a <gem_name>.gemspec and
+# you can simply gem build + gem install the resulting gem, so nothing fancy.  This does not use
+# rake install since we need --conservative --minimal-deps in order to not install duplicate gems.
+#
+#
+puts "gem path #{gem_home}"
+
+Dir["#{gem_home}/bundler/gems/*"].each do |gempath|
+  puts "#{gempath}"
+  matches = File.basename(gempath).match(/.*-[A-Fa-f0-9]{12}/)
+  next unless matches
+
+  gem_name = File.basename(Dir["#{gempath}/*.gemspec"].first, ".gemspec")
+  # FIXME: should strip any valid ruby platform off of the gem_name if it matches
+
+  next unless gem_name
+
+  puts "re-installing #{gem_name}..."
+
+  Dir.chdir(gempath) do
+    system("gem build #{gem_name}.gemspec") or raise "gem build failed"
+    system("gem install #{gem_name}*.gem --conservative --minimal-deps --no-document") or raise "gem install failed"
+  end
+end
diff --git a/spec/unit/cli_spec.rb b/spec/unit/cli_spec.rb
index 51c7c18d..10e1515a 100644
--- a/spec/unit/cli_spec.rb
+++ b/spec/unit/cli_spec.rb
@@ -89,6 +89,8 @@ def mock_shell_out(exitstatus, stdout, stderr)
 
     commands_map.builtin "example", :TestCommand, require_path: "unit/fixtures/command/cli_test_command",
                                                   desc: "Example subcommand for testing"
+
+    allow(ChefCLI::Licensing::Base).to receive(:validate).and_return(true)
   end
 
   context "given no arguments or options" do
diff --git a/spec/unit/command/env_spec.rb b/spec/unit/command/env_spec.rb
index d614b397..4572ed97 100644
--- a/spec/unit/command/env_spec.rb
+++ b/spec/unit/command/env_spec.rb
@@ -35,6 +35,7 @@
 
   describe "when running from within an omnibus install" do
     before do
+      allow(command_instance).to receive(:habitat_install?).and_return false
       allow(command_instance).to receive(:omnibus_install?).and_return true
       allow(command_instance).to receive(:omnibus_embedded_bin_dir).and_return(omnibus_embedded_bin_dir)
       allow(command_instance).to receive(:omnibus_bin_dir).and_return(omnibus_bin_dir)
@@ -57,6 +58,7 @@
   end
   describe "when running locally" do
     before do
+      allow(command_instance).to receive(:habitat_install?).and_return false
       allow(command_instance).to receive(:omnibus_install?).and_return false
       command_instance.ui = ui
     end
diff --git a/spec/unit/command/exec_spec.rb b/spec/unit/command/exec_spec.rb
index 6cb99a79..15fcb46a 100644
--- a/spec/unit/command/exec_spec.rb
+++ b/spec/unit/command/exec_spec.rb
@@ -57,6 +57,7 @@ def run_command
     let(:ruby_path) { File.join(fixtures_path, "eg_omnibus_dir/valid/embedded/bin/ruby") }
 
     before do
+      allow(command_instance).to receive(:habitat_install?).and_return(false)
       allow(Gem).to receive(:ruby).and_return(ruby_path)
 
       # Using a fake path separator to keep to prevent people from accidentally
diff --git a/spec/unit/command/license_spec.rb b/spec/unit/command/license_spec.rb
new file mode 100644
index 00000000..a53a7e44
--- /dev/null
+++ b/spec/unit/command/license_spec.rb
@@ -0,0 +1,162 @@
+#
+# Copyright:: Chef Software Inc.
+# License:: Apache License, Version 2.0
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+require "spec_helper"
+require "chef-cli/command/license"
+require "shared/command_with_ui_object"
+require "chef-cli/licensing/base"
+
+describe ChefCLI::Command::License do
+  it_behaves_like "a command with a UI object"
+
+  let(:params) { [] }
+  let(:ui) { TestHelpers::TestUI.new }
+
+  before do
+    # Disable the access of local licenses
+    allow_any_instance_of(ChefLicensing::LicenseKeyFetcher).to receive(:fetch_license_key_from_arg).and_return([])
+    allow_any_instance_of(ChefLicensing::LicenseKeyFetcher).to receive(:fetch_license_key_from_env).and_return([])
+    allow_any_instance_of(ChefLicensing::LicensingService::Local).to receive(:detected?).and_return(false)
+  end
+
+  let(:command) do
+    c = described_class.new
+    c.validate_params!(params)
+    c.ui = ui
+    c
+  end
+
+  it "disables debug by default" do
+    expect(command.debug?).to be(false)
+  end
+
+  context "invalid parameters passed" do
+    let(:multiple_params) { %w{add list} }
+    let(:invalid_command) { %w{not_a_subcommand} }
+
+    it "should fail with errors when multiple subcommands passed" do
+      expect(command.run(multiple_params)).to eq(1)
+    end
+
+    it "should fail for invalid argument" do
+      expect(command.run(invalid_command)).to eq(1)
+    end
+  end
+
+  context "license command" do
+    context "when pre-accepted license exists" do
+      let(:license_keys) { %w{tsmc-abcd} }
+
+      before(:each) do
+        allow(ChefLicensing).to receive(:fetch_and_persist).and_return(license_keys)
+      end
+
+      it "should be successful" do
+        expect { command.run(params) }.not_to raise_exception
+      end
+
+      it "should return the correct license key" do
+        expect(command.run(params)).to eq(license_keys)
+      end
+    end
+
+    context "when no licenses are accepted previously" do
+      let(:new_key) { ["tsmc-123456789"] }
+      before(:each) do
+        ChefLicensing.configure do |config|
+          config.license_server_url = "https://license.test"
+          config.chef_product_name = "chef"
+          config.chef_entitlement_id = "chef-entitled-id"
+          config.chef_executable_name = "chef"
+        end
+
+        # Disable the active license check
+        allow_any_instance_of(ChefLicensing::LicenseKeyFetcher).to receive(:licenses_active?).and_return(false)
+        # Disable the UI engine
+        allow_any_instance_of(ChefLicensing::LicenseKeyFetcher).to receive(:append_extra_info_to_tui_engine)
+        # Disable the API call to fetch the license type
+        allow_any_instance_of(ChefLicensing::LicenseKeyFetcher).to receive(:get_license_type).and_return("free")
+        # Disable the overwriting to the license.yml file
+        allow_any_instance_of(ChefLicensing::LicenseKeyFetcher::File).to receive(:persist)
+
+        # Mocks the user prompt to enter the license
+        allow_any_instance_of(ChefLicensing::LicenseKeyFetcher::Prompt).to receive(:fetch).and_return(new_key)
+        allow(ChefLicensing).to receive(:fetch_and_persist).and_return(new_key)
+      end
+
+      it "should create and stores the new license" do
+        expect { command.run(params) }.not_to raise_exception
+      end
+
+      it "should be same as the user entered license" do
+        expect(command.run(params)).to include(new_key.first)
+      end
+    end
+  end
+
+  context "chef license list command" do
+    let(:params) { %w{list} }
+    let(:license_key) { "tsmn-123123" }
+
+    before do
+      command.ui = ui
+    end
+
+    context "when no licenses are accepted" do
+      before do
+        allow_any_instance_of(ChefLicensing::ListLicenseKeys).to receive(:fetch_license_keys).and_return([])
+        allow_any_instance_of(ChefLicensing::ListLicenseKeys).to receive(:fetch_licenses_metadata).and_return([])
+      end
+
+      it "should return the correct error message" do
+        expect(command.run(params)).to eq([])
+      end
+    end
+
+    context "when there is a valid license" do
+      before do
+        allow(ChefLicensing).to receive(:list_license_keys_info).and_return(license_key)
+      end
+
+      it "should print the license details" do
+        expect(command.run(params)).to eq(license_key)
+      end
+    end
+  end
+
+  context "chef license add command" do
+    let(:params) { %w{add} }
+    let(:license_key) { ["tsmn-123123"] }
+
+    before do
+      # Disable the API call to fetch the license type
+      allow_any_instance_of(ChefLicensing::LicenseKeyFetcher).to receive(:get_license_type).and_return("free")
+      # Disable the overwriting to the license.yml file
+      allow_any_instance_of(ChefLicensing::LicenseKeyFetcher::File).to receive(:persist)
+      # Mocks the user prompt to enter the license
+      allow_any_instance_of(ChefLicensing::LicenseKeyFetcher::Prompt).to receive(:fetch).and_return(license_key)
+    end
+
+    it "should not raise any errors" do
+      expect { command.run(params) }.not_to raise_exception
+    end
+
+    it "should create and store the new license" do
+      expect(command.run(params)).to include(license_key.first)
+    end
+  end
+end
diff --git a/spec/unit/command/shell_init_spec.rb b/spec/unit/command/shell_init_spec.rb
index fbe4c752..f82f9602 100644
--- a/spec/unit/command/shell_init_spec.rb
+++ b/spec/unit/command/shell_init_spec.rb
@@ -39,6 +39,7 @@
 
     before do
       allow(::Dir).to receive(:exist?).and_call_original
+      allow(command_instance).to receive(:habitat_install?).and_return(false)
     end
 
     context "with no explicit omnibus directory" do
@@ -98,6 +99,7 @@
   shared_examples "a posix shell script" do |shell|
     before do
       stub_const("File::PATH_SEPARATOR", ":")
+      allow(command_instance).to receive(:habitat_install?).and_return(false)
     end
 
     let(:expected_environment_commands) do
@@ -114,6 +116,7 @@
   shared_examples "a powershell script" do |shell|
     before do
       stub_const("File::PATH_SEPARATOR", ";")
+      allow(command_instance).to receive(:habitat_install?).and_return(false)
     end
 
     let(:expected_environment_commands) do
@@ -163,8 +166,10 @@
       before do
         # Stub this or else we'd have to update the test every time a new command
         # is added.
+        allow(command_instance).to receive(:habitat_install?).and_return(false)
         allow(command_instance.shell_completion_template_context).to receive(:commands)
           .and_return(command_descriptions)
+        allow(command_instance.shell_completion_template_context).to receive(:habitat?).and_return(false)
 
         allow(command_instance).to receive(:omnibus_embedded_bin_dir).and_return(omnibus_embedded_bin_dir)
         allow(command_instance).to receive(:omnibus_bin_dir).and_return(omnibus_bin_dir)
@@ -228,6 +233,7 @@
       before do
         # Stub this or else we'd have to update the test every time a new command
         # is added.
+        allow(command_instance).to receive(:habitat_install?).and_return(false)
         allow(command_instance.shell_completion_template_context).to receive(:commands)
           .and_return(command_descriptions)
 
@@ -244,8 +250,10 @@
 
   context "for fish" do
     before do
+      allow(command_instance).to receive(:habitat_install?).and_return(false)
       stub_const("File::PATH_SEPARATOR", ":")
     end
+
     let(:expected_path) { [omnibus_bin_dir, user_bin_dir, omnibus_embedded_bin_dir, ENV["PATH"], git_bin_dir].join(":").split(":").join('" "') }
     let(:expected_environment_commands) do
       <<~EOH
@@ -336,4 +344,94 @@
 
   end
 
+  context "habitat standalone shell-init on bash" do
+    let(:cli_hab_path) { "/hab/pkgs/chef/chef-cli/1.0.0/123" }
+
+    let(:argv) { ["bash"] }
+
+    before do
+      allow(command_instance).to receive(:habitat_chef_dke?).and_return(false)
+      allow(command_instance).to receive(:habitat_standalone?).and_return(true)
+    end
+
+    it "should return the correct paths" do
+      expect(command_instance).to receive(:get_pkg_prefix).with("chef/chef-cli").twice.and_return(cli_hab_path)
+
+      command_instance.run(argv)
+      expect(stdout_io.string).to include("export PATH=\"#{cli_hab_path}/bin")
+      expect(stdout_io.string).to include("export GEM_HOME=\"#{cli_hab_path}/vendor")
+      expect(stdout_io.string).to include("export GEM_PATH=\"#{cli_hab_path}/vendor")
+    end
+  end
+
+  context "with chef-development-kit-enterprise habitat pkg shell-init on bash" do
+
+    let(:chef_dke_path) { "/hab/pkgs/chef/chef-development-kit-enterprise/1.0.0/123" }
+    let(:cli_hab_path) { "/hab/pkgs/chef/chef-cli/1.0.0/123" }
+
+    let(:argv) { ["bash"] }
+
+    before do
+      allow(command_instance).to receive(:habitat_chef_dke?).and_return(true)
+      allow(command_instance).to receive(:habitat_standalone?).and_return(false)
+    end
+
+    it "should return the correct paths" do
+      expect(command_instance).to receive(:get_pkg_prefix).with("chef/chef-development-kit-enterprise").and_return(chef_dke_path)
+      expect(command_instance).to receive(:get_pkg_prefix).with("chef/chef-cli").and_return(cli_hab_path)
+
+      command_instance.run(argv)
+      expect(stdout_io.string).to include("export PATH=\"#{chef_dke_path}/bin")
+      expect(stdout_io.string).to include("export GEM_HOME=\"#{cli_hab_path}/vendor")
+      expect(stdout_io.string).to include("export GEM_PATH=\"#{cli_hab_path}/vendor")
+    end
+
+    describe "autocompletion" do
+      let(:command_descriptions) do
+        {
+          "exec" => "Runs the command in context of the embedded ruby",
+          "env" => "Prints environment variables used by #{ChefCLI::Dist::PRODUCT}",
+          "gem" => "Runs the `gem` command in context of the embedded ruby",
+          "generate" => "Generate a new app, cookbook, or component",
+        }
+      end
+
+      let(:omnibus_bin_dir) { "/foo/bin" }
+      let(:omnibus_embedded_bin_dir) { "/foo/embedded/bin" }
+
+      let(:argv) { [ "bash" ] }
+
+      let(:expected_completion_function) do
+        <<~END_COMPLETION
+          _chef_comp() {
+              local COMMANDS="exec env gem generate"
+              COMPREPLY=($(compgen -W "$COMMANDS" -- ${COMP_WORDS[COMP_CWORD]} ))
+          }
+          complete -F _chef_comp chef-cli
+        END_COMPLETION
+      end
+
+      before do
+        # Stub this or else we'd have to update the test every time a new command
+        # is added.
+        allow(command_instance).to receive(:get_pkg_prefix).with("chef/chef-development-kit-enterprise").and_return(chef_dke_path)
+        allow(command_instance).to receive(:get_pkg_prefix).with("chef/chef-cli").and_return(cli_hab_path)
+        allow(command_instance.shell_completion_template_context).to receive(:commands)
+          .and_return(command_descriptions)
+        allow(command_instance.shell_completion_template_context).to receive(:habitat?).and_return(true)
+
+        allow(command_instance).to receive(:omnibus_embedded_bin_dir).and_return(omnibus_embedded_bin_dir)
+        allow(command_instance).to receive(:omnibus_bin_dir).and_return(omnibus_bin_dir)
+      end
+
+      it "generates a completion function for the chef command" do
+        command_instance.run(argv)
+        expect(stdout_io.string).to include(expected_completion_function)
+      end
+
+      it "should generate the autocompletion" do
+
+      end
+    end
+  end
 end
diff --git a/spec/unit/helpers_spec.rb b/spec/unit/helpers_spec.rb
index 07f1dce2..0a71e312 100644
--- a/spec/unit/helpers_spec.rb
+++ b/spec/unit/helpers_spec.rb
@@ -19,6 +19,7 @@
 
 describe ChefCLI::Helpers do
   context "path_check!" do
+    let(:ruby_path) { "/opt/chef-workstation/embedded/bin/ruby" }
 
     before do
       allow(Gem).to receive(:ruby).and_return(ruby_path)
@@ -38,7 +39,7 @@
         let(:expected_GEM_ROOT) { Gem.default_dir }
         let(:expected_GEM_HOME) { Gem.user_dir }
         let(:expected_GEM_PATH) { Gem.path.join(File::PATH_SEPARATOR) }
-        let(:ruby_path) { "/opt/chef-workstation/embedded/bin/ruby" }
+
 
         it "#omnibus_env path" do
           allow(ChefCLI::Helpers).to receive(:omnibus_bin_dir).and_return("/opt/chef-workstation/bin")
@@ -107,5 +108,33 @@
       end
 
     end
+
+    context "when installed with habitat" do
+      let(:chef_dke_path) { "/hab/pkgs/chef/chef-development-kit-enterprise/1.0.0/123" }
+      let(:cli_hab_path) { "/hab/pkgs/chef/chef-cli/1.0.0/123" }
+      let(:expected_gem_root) { Gem.default_dir }
+      let(:expected_path) { %W{#{chef_dke_path}/bin /usr/bin:/bin} }
+      let(:expected_env) do
+        {
+          "PATH" =>  expected_path.join(File::PATH_SEPARATOR) ,
+          "GEM_ROOT" => expected_gem_root,
+          "GEM_HOME" => "#{cli_hab_path}/vendor",
+          "GEM_PATH" => "#{cli_hab_path}/vendor",
+        }
+      end
+
+      before do
+        allow(ChefCLI::Helpers).to receive(:habitat_chef_dke?).and_return true
+        allow(ChefCLI::Helpers).to receive(:habitat_standalone?).and_return false
+        allow(ENV).to receive(:[]).with("PATH").and_return("/usr/bin:/bin")
+      end
+
+      it "should return the habitat env" do
+        expect(ChefCLI::Helpers).to receive(:get_pkg_prefix).with("chef/chef-development-kit-enterprise").and_return(chef_dke_path)
+        expect(ChefCLI::Helpers).to receive(:get_pkg_prefix).with("chef/chef-cli").and_return(cli_hab_path)
+
+        expect(ChefCLI::Helpers.habitat_env).to eq(expected_env)
+      end
+    end
   end
 end
diff --git a/spec/unit/policyfile_services/clean_policies_spec.rb b/spec/unit/policyfile_services/clean_policies_spec.rb
index 6d462fc2..bf19081a 100644
--- a/spec/unit/policyfile_services/clean_policies_spec.rb
+++ b/spec/unit/policyfile_services/clean_policies_spec.rb
@@ -218,8 +218,8 @@
               - appserver (4444444444444444444444444444444444444444444444444444444444444444): Net::HTTPClientException 403 \"Unauthorized\"
             ERROR
 
-            expect { clean_policies_service.run }.to raise_error do |error|
-              expect(error.message).to eq(expected_message)
+            expect { clean_policies_service.run }.to raise_error(ChefCLI::PolicyfileCleanError) do |error|
+              expect(error.message).to include("403 \"Unauthorized\"")
             end
             expected_message = <<~MESSAGE
               DELETE appserver 4444444444444444444444444444444444444444444444444444444444444444