diff --git a/libc-test/build.rs b/libc-test/build.rs
index b397a83b19e2f..f568affc7d4fc 100644
--- a/libc-test/build.rs
+++ b/libc-test/build.rs
@@ -234,6 +234,7 @@ fn test_apple(target: &str) {
         "stdio.h",
         "stdlib.h",
         "string.h",
+        "sysdir.h",
         "sys/attr.h",
         "sys/clonefile.h",
         "sys/event.h",
diff --git a/libc-test/semver/apple.txt b/libc-test/semver/apple.txt
index e67830880f3c0..1814d73ffc06d 100644
--- a/libc-test/semver/apple.txt
+++ b/libc-test/semver/apple.txt
@@ -1920,6 +1920,10 @@ syscall
 sysctl
 sysctlbyname
 sysctlnametomib
+sysdir_get_next_search_path_enumeration
+sysdir_search_path_directory_t
+sysdir_search_path_domain_mask_t
+sysdir_start_search_path_enumeration
 telldir
 thread_basic_info_t
 thread_extended_info_t
diff --git a/src/unix/bsd/apple/mod.rs b/src/unix/bsd/apple/mod.rs
index 33a0c4a69e595..e63d26dc7f12e 100644
--- a/src/unix/bsd/apple/mod.rs
+++ b/src/unix/bsd/apple/mod.rs
@@ -105,6 +105,8 @@ pub type vm_statistics_data_t = vm_statistics;
 pub type vm_statistics64_t = *mut vm_statistics64;
 pub type vm_statistics64_data_t = vm_statistics64;
 
+pub type sysdir_search_path_enumeration_state = ::c_uint;
+
 pub type CCStatus = i32;
 pub type CCCryptorStatus = i32;
 pub type CCRNGStatus = ::CCCryptorStatus;
@@ -140,6 +142,57 @@ impl ::Clone for qos_class_t {
     }
 }
 
+#[cfg_attr(feature = "extra_traits", derive(Debug))]
+#[repr(u32)]
+pub enum sysdir_search_path_directory_t {
+    SYSDIR_DIRECTORY_APPLICATION = 1,
+    SYSDIR_DIRECTORY_DEMO_APPLICATION = 2,
+    SYSDIR_DIRECTORY_DEVELOPER_APPLICATION = 3,
+    SYSDIR_DIRECTORY_ADMIN_APPLICATION = 4,
+    SYSDIR_DIRECTORY_LIBRARY = 5,
+    SYSDIR_DIRECTORY_DEVELOPER = 6,
+    SYSDIR_DIRECTORY_USER = 7,
+    SYSDIR_DIRECTORY_DOCUMENTATION = 8,
+    SYSDIR_DIRECTORY_DOCUMENT = 9,
+    SYSDIR_DIRECTORY_CORESERVICE = 10,
+    SYSDIR_DIRECTORY_AUTOSAVED_INFORMATION = 11,
+    SYSDIR_DIRECTORY_DESKTOP = 12,
+    SYSDIR_DIRECTORY_CACHES = 13,
+    SYSDIR_DIRECTORY_APPLICATION_SUPPORT = 14,
+    SYSDIR_DIRECTORY_DOWNLOADS = 15,
+    SYSDIR_DIRECTORY_INPUT_METHODS = 16,
+    SYSDIR_DIRECTORY_MOVIES = 17,
+    SYSDIR_DIRECTORY_MUSIC = 18,
+    SYSDIR_DIRECTORY_PICTURES = 19,
+    SYSDIR_DIRECTORY_PRINTER_DESCRIPTION = 20,
+    SYSDIR_DIRECTORY_SHARED_PUBLIC = 21,
+    SYSDIR_DIRECTORY_PREFERENCE_PANES = 22,
+    SYSDIR_DIRECTORY_ALL_APPLICATIONS = 100,
+    SYSDIR_DIRECTORY_ALL_LIBRARIES = 101,
+}
+impl ::Copy for sysdir_search_path_directory_t {}
+impl ::Clone for sysdir_search_path_directory_t {
+    fn clone(&self) -> sysdir_search_path_directory_t {
+        *self
+    }
+}
+
+#[cfg_attr(feature = "extra_traits", derive(Debug))]
+#[repr(u32)]
+pub enum sysdir_search_path_domain_mask_t {
+    SYSDIR_DOMAIN_MASK_USER = (1 << 0),
+    SYSDIR_DOMAIN_MASK_LOCAL = (1 << 1),
+    SYSDIR_DOMAIN_MASK_NETWORK = (1 << 2),
+    SYSDIR_DOMAIN_MASK_SYSTEM = (1 << 3),
+    SYSDIR_DOMAIN_MASK_ALL = 0x0ffff,
+}
+impl ::Copy for sysdir_search_path_domain_mask_t {}
+impl ::Clone for sysdir_search_path_domain_mask_t {
+    fn clone(&self) -> sysdir_search_path_domain_mask_t {
+        *self
+    }
+}
+
 s! {
     pub struct ip_mreq {
         pub imr_multiaddr: in_addr,
@@ -4971,6 +5024,16 @@ extern "C" {
     ) -> ::kern_return_t;
 
     pub static mut mach_task_self_: mach_port_t;
+
+    // sysdir.h
+    pub fn sysdir_start_search_path_enumeration(
+        dir: sysdir_search_path_directory_t,
+        domainMask: sysdir_search_path_domain_mask_t,
+    ) -> ::sysdir_search_path_enumeration_state;
+    pub fn sysdir_get_next_search_path_enumeration(
+        state: ::sysdir_search_path_enumeration_state,
+        path: *mut ::c_char,
+    ) -> ::sysdir_search_path_enumeration_state;
 }
 
 pub unsafe fn mach_task_self() -> mach_port_t {