diff --git a/src/Transport/KubectlTransport.php b/src/Transport/KubectlTransport.php
index 988a12f..195d9da 100644
--- a/src/Transport/KubectlTransport.php
+++ b/src/Transport/KubectlTransport.php
@@ -4,6 +4,7 @@
 
 use Consolidation\SiteProcess\SiteProcess;
 use Consolidation\SiteAlias\SiteAliasInterface;
+use Consolidation\SiteProcess\Util\Escape;
 use Consolidation\SiteProcess\Util\Shell;
 
 /**
@@ -15,6 +16,9 @@ class KubectlTransport implements TransportInterface
     /** @var bool */
     protected $tty;
 
+    /** @var string */
+    protected $cd_remote;
+
     /** @var \Consolidation\SiteAlias\SiteAliasInterface */
     protected $siteAlias;
 
@@ -64,6 +68,21 @@ public function wrap($args)
             $transport = is_array($entrypoint) ? [...$transport, ...$entrypoint] : [...$transport, $entrypoint];
         }
 
+        if ($this->cd_remote) {
+            // Wrap the command in a subshell, to be able to prepend a `cd`.
+            $args = [
+                'sh',
+                '-c',
+                // Escape each argument for the target system and then join.
+                implode(' ', Escape::argsForSite($this->siteAlias, [
+                    'cd',
+                    $this->cd_remote,
+                    Shell::op('&&'),
+                    ...$args
+                ]))
+            ];
+        }
+
         return array_merge($transport, $args);
     }
 
@@ -72,13 +91,13 @@ public function wrap($args)
      */
     public function addChdir($cd_remote, $args)
     {
-        return array_merge(
-            [
-                'cd',
-                $cd_remote,
-                Shell::op('&&'),
-            ],
-            $args
-        );
+        // If the site alias specifies a root, and it matches the requested
+        // directory, there is no need to wrap the command in a subshell.
+        if ($cd_remote === $this->siteAlias->get('root') && $this->siteAlias->get('kubectl.cd_root') === false) {
+            return $args;
+        }
+
+        $this->cd_remote = $cd_remote;
+        return $args;
     }
 }
diff --git a/tests/Transport/KubectlTransportTest.php b/tests/Transport/KubectlTransportTest.php
index 628acc5..0cbc5ba 100644
--- a/tests/Transport/KubectlTransportTest.php
+++ b/tests/Transport/KubectlTransportTest.php
@@ -100,6 +100,37 @@ public function wrapTestValues()
                     ]
                 ],
             ],
+
+            // With root.
+            [
+                "kubectl --namespace=vv exec --tty=false --stdin=false deploy/drupal -- sh -c 'cd /path/to/drupal && ls'",
+                ['ls'],
+                [
+                    'root' => '/path/to/drupal',
+                    'kubectl' => [
+                        'tty' => false,
+                        'interactive' => false,
+                        'namespace' => 'vv',
+                        'resource' => 'deploy/drupal',
+                    ]
+                ],
+            ],
+
+            // With root and cd_root set to false.
+            [
+                'kubectl --namespace=vv exec --tty=false --stdin=false deploy/drupal -- ls',
+                ['ls'],
+                [
+                    'root' => '/path/to/drupal',
+                    'kubectl' => [
+                        'tty' => false,
+                        'interactive' => false,
+                        'namespace' => 'vv',
+                        'resource' => 'deploy/drupal',
+                        'cd_root' => false,
+                    ]
+                ],
+            ],
         ];
     }
 
@@ -110,6 +141,9 @@ public function testWrap($expected, $args, $siteAliasData)
     {
         $siteAlias = new SiteAlias($siteAliasData, '@alias.dev');
         $dockerTransport = new KubectlTransport($siteAlias);
+        if (isset($siteAliasData['root'])) {
+            $dockerTransport->addChdir($siteAliasData['root']);
+        }
         $actual = $dockerTransport->wrap($args);
         $this->assertEquals($expected, implode(' ', $actual));
     }