diff --git a/habitat/plan.sh b/habitat/plan.sh
index 11445a80..52393bed 100644
--- a/habitat/plan.sh
+++ b/habitat/plan.sh
@@ -69,7 +69,8 @@ wrap_ruby_bin() {
 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:$pkg_prefix/vendor/bin:\$PATH"
+# Include Ruby bin directory so chef-cli exec can find gem, etc.
+export PATH="$(pkg_path_for ${ruby_pkg})/bin:/sbin:/usr/sbin:/usr/local/sbin:/usr/local/bin:/usr/bin:/bin:$pkg_prefix/vendor/bin:\$PATH"
 
 # Set Ruby paths defined from 'do_setup_environment()'
   export GEM_HOME="$pkg_prefix/vendor"
diff --git a/lib/chef-cli/helpers.rb b/lib/chef-cli/helpers.rb
index b2277d64..0eb23b37 100644
--- a/lib/chef-cli/helpers.rb
+++ b/lib/chef-cli/helpers.rb
@@ -173,10 +173,12 @@ def habitat_env(show_warning: false)
         raise "Error: Could not determine the vendor package prefix. Ensure #{ChefCLI::Dist::HAB_PKG_NAME} is installed and CHEF_CLI_VERSION is set correctly." unless vendor_pkg_prefix
 
         vendor_dir = File.join(vendor_pkg_prefix, "vendor")
-        # Construct PATH
+        # Construct PATH including Ruby bin directory for chef-cli exec command
+        ruby_bin_dir = File.dirname(RbConfig.ruby)
         path = [
           File.join(bin_pkg_prefix, "bin"),
           File.join(vendor_dir, "bin"),
+          ruby_bin_dir, # Add Ruby bin directory so exec can find gem etc.
           ENV["PATH"].split(File::PATH_SEPARATOR), # Preserve existing PATH
         ].flatten.uniq
 
diff --git a/spec/unit/helpers_spec.rb b/spec/unit/helpers_spec.rb
index b2280a3f..bd0f2bc7 100644
--- a/spec/unit/helpers_spec.rb
+++ b/spec/unit/helpers_spec.rb
@@ -112,8 +112,9 @@
     context "when installed with habitat" do
       let(:chef_dke_path) { "/hab/pkgs/chef/chef-workstation/1.0.0/123" }
       let(:cli_hab_path) { "/hab/pkgs/chef/chef-cli/1.0.0/123" }
+      let(:ruby_bin_dir) { File.dirname(RbConfig.ruby) }
       let(:expected_gem_root) { Gem.default_dir }
-      let(:expected_path) { [File.join(chef_dke_path, "bin"), File.join(cli_hab_path, "vendor", "bin"), "/usr/bin:/bin"].flatten }
+      let(:expected_path) { [File.join(chef_dke_path, "bin"), File.join(cli_hab_path, "vendor", "bin"), ruby_bin_dir, "/usr/bin:/bin"].flatten }
       let(:expected_env) do
         {
           "PATH" => expected_path.join(File::PATH_SEPARATOR),