diff --git a/libc-test/semver/apple.txt b/libc-test/semver/apple.txt
index 7c4356432f5a7..10e505ed46dd0 100644
--- a/libc-test/semver/apple.txt
+++ b/libc-test/semver/apple.txt
@@ -245,6 +245,19 @@ COPYFILE_SECURITY
 COPYFILE_SKIP
 COPYFILE_START
 COPYFILE_STAT
+COPYFILE_STATE_BSIZE
+COPYFILE_STATE_COPIED
+COPYFILE_STATE_DST_BSIZE
+COPYFILE_STATE_DST_FD
+COPYFILE_STATE_DST_FILENAME
+COPYFILE_STATE_QUARANTINE
+COPYFILE_STATE_SRC_BSIZE
+COPYFILE_STATE_SRC_FD
+COPYFILE_STATE_SRC_FILENAME
+COPYFILE_STATE_STATUS_CB
+COPYFILE_STATE_STATUS_CTX
+COPYFILE_STATE_XATTRNAME
+COPYFILE_STATE_WAS_CLONED
 COPYFILE_VERBOSE
 COPYFILE_UNLINK
 COPYFILE_XATTR
@@ -1844,7 +1857,12 @@ cmsghdr
 confstr
 connectx
 copyfile
+copyfile_callback_t
 copyfile_flags_t
+copyfile_state_alloc
+copyfile_state_free
+copyfile_state_get
+copyfile_state_set
 cpu_subtype_t
 cpu_type_t
 ctime
diff --git a/src/unix/bsd/apple/mod.rs b/src/unix/bsd/apple/mod.rs
index a2fbf876731ba..bf571aeb738ff 100644
--- a/src/unix/bsd/apple/mod.rs
+++ b/src/unix/bsd/apple/mod.rs
@@ -145,6 +145,16 @@ pub type CCRNGStatus = ::CCCryptorStatus;
 
 pub type copyfile_state_t = *mut ::c_void;
 pub type copyfile_flags_t = u32;
+pub type copyfile_callback_t = ::Option<
+    extern "C" fn(
+        ::c_int,
+        ::c_int,
+        copyfile_state_t,
+        *const ::c_char,
+        *const ::c_char,
+        *mut ::c_void,
+    ) -> ::c_int,
+>;
 
 pub type attrgroup_t = u32;
 pub type vol_capabilities_set_t = [u32; 4];
@@ -4911,6 +4921,19 @@ pub const COPYFILE_PROGRESS: ::c_int = 4;
 pub const COPYFILE_CONTINUE: ::c_int = 0;
 pub const COPYFILE_SKIP: ::c_int = 1;
 pub const COPYFILE_QUIT: ::c_int = 2;
+pub const COPYFILE_STATE_SRC_FD: ::c_int = 1;
+pub const COPYFILE_STATE_SRC_FILENAME: ::c_int = 2;
+pub const COPYFILE_STATE_DST_FD: ::c_int = 3;
+pub const COPYFILE_STATE_DST_FILENAME: ::c_int = 4;
+pub const COPYFILE_STATE_QUARANTINE: ::c_int = 5;
+pub const COPYFILE_STATE_STATUS_CB: ::c_int = 6;
+pub const COPYFILE_STATE_STATUS_CTX: ::c_int = 7;
+pub const COPYFILE_STATE_COPIED: ::c_int = 8;
+pub const COPYFILE_STATE_XATTRNAME: ::c_int = 9;
+pub const COPYFILE_STATE_WAS_CLONED: ::c_int = 10;
+pub const COPYFILE_STATE_SRC_BSIZE: ::c_int = 11;
+pub const COPYFILE_STATE_DST_BSIZE: ::c_int = 12;
+pub const COPYFILE_STATE_BSIZE: ::c_int = 13;
 
 // <sys/attr.h>
 pub const ATTR_BIT_MAP_COUNT: ::c_ushort = 5;
@@ -5819,6 +5842,10 @@ extern "C" {
         state: copyfile_state_t,
         flags: copyfile_flags_t,
     ) -> ::c_int;
+    pub fn copyfile_state_free(s: copyfile_state_t) -> ::c_int;
+    pub fn copyfile_state_alloc() -> copyfile_state_t;
+    pub fn copyfile_state_get(s: copyfile_state_t, flags: u32, dst: *mut ::c_void) -> ::c_int;
+    pub fn copyfile_state_set(s: copyfile_state_t, flags: u32, src: *const ::c_void) -> ::c_int;
 
     // Added in macOS 10.13
     // ISO/IEC 9899:2011 ("ISO C11") K.3.7.4.1