diff --git a/test-framework/sudo-compliance-tests/src/sudoers.rs b/test-framework/sudo-compliance-tests/src/sudoers.rs
index 2be527049..8bb8bd80c 100644
--- a/test-framework/sudo-compliance-tests/src/sudoers.rs
+++ b/test-framework/sudo-compliance-tests/src/sudoers.rs
@@ -3,6 +3,7 @@ use sudo_test::{Command, Env, TextFile, User};
 use crate::{Result, PASSWORD, SUDOERS_ROOT_ALL_NOPASSWD, USERNAME};
 
 mod cmnd;
+mod cwd;
 mod host_list;
 mod run_as;
 mod secure_path;
diff --git a/test-framework/sudo-compliance-tests/src/sudoers/cwd.rs b/test-framework/sudo-compliance-tests/src/sudoers/cwd.rs
new file mode 100644
index 000000000..64c41fb6f
--- /dev/null
+++ b/test-framework/sudo-compliance-tests/src/sudoers/cwd.rs
@@ -0,0 +1,193 @@
+use sudo_test::{Command, Env, User};
+
+use crate::{Result, USERNAME};
+
+#[test]
+fn sets_the_working_directory_of_the_executed_command() -> Result<()> {
+    let expected_path = "/root";
+    let env = Env(format!("ALL ALL=(ALL:ALL) CWD={expected_path} ALL")).build()?;
+
+    let stdout = Command::new("sh")
+        .args(["-c", "cd /; sudo pwd"])
+        .exec(&env)?
+        .stdout()?;
+
+    assert_eq!(expected_path, stdout);
+
+    Ok(())
+}
+
+#[test]
+fn glob_has_no_effect_on_its_own() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=* ALL").build()?;
+
+    let expected_path = "/";
+    let stdout = Command::new("sh")
+        .args(["-c", "cd {expected_path}; sudo pwd"])
+        .exec(&env)?
+        .stdout()?;
+
+    assert_eq!(expected_path, stdout);
+
+    Ok(())
+}
+
+#[test]
+fn non_absolute_path_is_rejected() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=usr ALL").build()?;
+
+    let output = Command::new("sh")
+        .args(["-c", "cd /; sudo pwd"])
+        .exec(&env)?;
+
+    assert!(!output.status().success());
+    assert_eq!(Some(1), output.status().code());
+
+    if sudo_test::is_original_sudo() {
+        assert_contains!(
+            output.stderr(),
+            "values for \"CWD\" must start with a '/', '~', or '*'"
+        );
+    }
+
+    Ok(())
+}
+
+#[test]
+fn dot_slash_is_rejected() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=./usr ALL").build()?;
+
+    let output = Command::new("sh")
+        .args(["-c", "cd /; sudo pwd"])
+        .exec(&env)?;
+
+    assert!(!output.status().success());
+    assert_eq!(Some(1), output.status().code());
+
+    if sudo_test::is_original_sudo() {
+        assert_contains!(
+            output.stderr(),
+            "values for \"CWD\" must start with a '/', '~', or '*'"
+        );
+    }
+
+    Ok(())
+}
+
+#[test]
+fn tilde_when_target_user_is_root() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=~ ALL").build()?;
+
+    let stdout = Command::new("sh")
+        .args(["-c", "cd /; sudo pwd"])
+        .exec(&env)?
+        .stdout()?;
+
+    assert_eq!("/root", stdout);
+
+    Ok(())
+}
+
+#[test]
+fn tilde_when_target_user_is_regular_user() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=~ NOPASSWD: ALL")
+        .user(User(USERNAME).create_home_directory())
+        .build()?;
+
+    let stdout = Command::new("sh")
+        .arg("-c")
+        .arg(format!("cd /; sudo -u {USERNAME} pwd"))
+        .exec(&env)?
+        .stdout()?;
+
+    assert_eq!(format!("/home/{USERNAME}"), stdout);
+
+    Ok(())
+}
+
+#[test]
+fn tilde_username() -> Result<()> {
+    let env = Env(format!("ALL ALL=(ALL:ALL) CWD=~{USERNAME} NOPASSWD: ALL"))
+        .user(User(USERNAME).create_home_directory())
+        .build()?;
+
+    for target_user in ["root", USERNAME] {
+        let stdout = Command::new("sh")
+            .arg("-c")
+            .arg(format!("cd /; sudo -u {target_user} pwd"))
+            .exec(&env)?
+            .stdout()?;
+
+        assert_eq!(format!("/home/{USERNAME}"), stdout);
+    }
+
+    Ok(())
+}
+
+#[test]
+fn path_does_not_exist() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=/path/to/nowhere NOPASSWD: ALL").build()?;
+
+    let output = Command::new("sh")
+        .arg("-c")
+        .arg("cd /; sudo pwd")
+        .exec(&env)?;
+
+    assert!(!output.status().success());
+    assert_eq!(Some(1), output.status().code());
+
+    if sudo_test::is_original_sudo() {
+        assert_contains!(
+            output.stderr(),
+            "sudo: unable to change directory to /path/to/nowhere: No such file or directory"
+        );
+    }
+
+    Ok(())
+}
+
+#[test]
+fn path_is_file() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=/dev/null NOPASSWD: ALL").build()?;
+
+    let output = Command::new("sh")
+        .arg("-c")
+        .arg("cd /; sudo pwd")
+        .exec(&env)?;
+
+    assert!(!output.status().success());
+    assert_eq!(Some(1), output.status().code());
+
+    if sudo_test::is_original_sudo() {
+        assert_contains!(
+            output.stderr(),
+            "sudo: unable to change directory to /dev/null: Not a directory"
+        );
+    }
+
+    Ok(())
+}
+
+#[test]
+fn target_user_has_insufficient_permissions() -> Result<()> {
+    let env = Env("ALL ALL=(ALL:ALL) CWD=/root NOPASSWD: ALL")
+        .user(USERNAME)
+        .build()?;
+
+    let output = Command::new("sh")
+        .arg("-c")
+        .arg(format!("cd /; sudo -u {USERNAME} pwd"))
+        .exec(&env)?;
+
+    assert!(!output.status().success());
+    assert_eq!(Some(1), output.status().code());
+
+    if sudo_test::is_original_sudo() {
+        assert_contains!(
+            output.stderr(),
+            "sudo: unable to change directory to /root: Permission denied"
+        );
+    }
+
+    Ok(())
+}