diff --git a/tsc/internal/fswatch/fsevents_darwin_case_test.go b/tsc/internal/fswatch/fsevents_darwin_case_test.go
new file mode 100644
index 0000000000000..109a8e64b9a6e
--- /dev/null
+++ b/tsc/internal/fswatch/fsevents_darwin_case_test.go
@@ -0,0 +1,55 @@
+//go:build darwin && (amd64 || arm64)
+
+package fswatch
+
+import (
+	"errors"
+	"io/fs"
+	"os"
+	"path/filepath"
+	"testing"
+	"time"
+)
+
+func TestFSEventsDiskCasingDiffersFromSubscription(t *testing.T) {
+	t.Parallel()
+
+	runWithRetry(t, func(rt testingT) {
+		parent := newTmpDir(rt)
+		actualDir := filepath.Join(parent, "MixedCase")
+		requestedDir := filepath.Join(parent, "mixedcase")
+		if err := os.Mkdir(actualDir, 0o755); err != nil {
+			rt.Fatal(err)
+		}
+		if _, err := os.Stat(requestedDir); err != nil {
+			if errors.Is(err, fs.ErrNotExist) {
+				rt.Skip("filesystem is case-sensitive")
+			}
+			rt.Fatal(err)
+		}
+
+		r, _ := subscribeFor(rt, requestedDir, FSEvents())
+		requestedChild := filepath.Join(requestedDir, "hello.txt")
+		if err := os.WriteFile(requestedChild, []byte("hi"), 0o644); err != nil {
+			rt.Fatal(err)
+		}
+
+		got := r.waitForEvent(r.deadline(), func(event Event) bool {
+			return event.Path == requestedChild
+		})
+		got = append(got, r.next(500*time.Millisecond)...)
+		actualChild := filepath.Join(actualDir, "hello.txt")
+		foundRequested := false
+		for _, event := range got {
+			if event.Path == requestedChild {
+				foundRequested = true
+			}
+			if event.Path == actualChild {
+				rt.Fatalf("event path used filesystem casing instead of caller casing: %v", got)
+			}
+		}
+		if !foundRequested {
+			rt.Fatalf("event for %q not received: %v", requestedChild, got)
+		}
+	})
+}
diff --git a/tsc/internal/fswatch/watcher.go b/tsc/internal/fswatch/watcher.go
index fa8a7489841d7..9f6ec501cb383 100644
--- a/tsc/internal/fswatch/watcher.go
+++ b/tsc/internal/fswatch/watcher.go
@@ -72,6 +72,9 @@ type Watcher interface {
 	// dir must be an absolute path to an existing directory. If dir is a
 	// symlink or reparse point to a directory, the OS subscription follows
 	// the target directory but delivered event paths remain rooted at dir.
+	// On case-insensitive filesystems, dir may use different casing from the
+	// filesystem; the watch-root prefix in delivered paths retains the casing
+	// supplied by the caller.
 	// Userspace recursive traversal does not follow symlinked descendant
 	// directories.
 	// Returns [ErrUnavailable] if the watcher is not supported on
@@ -822,12 +825,13 @@ func newDirWatch(dir string, physicalDir string, db *debounce) *dirWatch {
 	return dw
 }
 
-// physicalDirFor returns the physical path to watch for dir. If dir, or an
-// ancestor of dir, is a symlink or reparse point, events are subscribed on its
-// realpath while callbacks still use dir.
+// physicalDirFor returns the physical path to watch for dir. It resolves
+// symlinks and reparse points in dir and its ancestors, and returns the
+// filesystem's path spelling where supported so it matches backend event paths.
+// Callbacks still use dir.
 func physicalDirFor(dir string) string {
-	realpath, err := nativepath.Realpath(dir)
-	if err != nil {
+	realpath, err := nativepath.RealpathDirectory(dir)
+	if err != nil || realpath == "" || !filepath.IsAbs(realpath) {
 		return dir
 	}
 	if realpath == dir {
diff --git a/tsc/internal/nativepath/eintr_unix.go b/tsc/internal/nativepath/eintr_unix.go
index 00adcf917b6e8..9e2df3108e075 100644
--- a/tsc/internal/nativepath/eintr_unix.go
+++ b/tsc/internal/nativepath/eintr_unix.go
@@ -1,4 +1,4 @@
-//go:build linux
+//go:build linux || darwin
 
 package nativepath
 
diff --git a/tsc/internal/nativepath/realpath_darwin_test.go b/tsc/internal/nativepath/realpath_darwin_test.go
index a606a8d77c2bc..8dac546178495 100644
--- a/tsc/internal/nativepath/realpath_darwin_test.go
+++ b/tsc/internal/nativepath/realpath_darwin_test.go
@@ -57,6 +57,10 @@ func TestRealpathHardlinkedFile(t *testing.T) {
 		got, err := Realpath(alias)
 		assert.NilError(t, err)
 		assert.Equal(t, got, want)
+
+		got, err = RealpathDirectory(alias)
+		assert.NilError(t, err)
+		assert.Equal(t, got, want)
 	}
 
 	stopWorker()
diff --git a/tsc/internal/nativepath/realpath_directory_darwin.go b/tsc/internal/nativepath/realpath_directory_darwin.go
new file mode 100644
index 0000000000000..d47817b3ec42a
--- /dev/null
+++ b/tsc/internal/nativepath/realpath_directory_darwin.go
@@ -0,0 +1,56 @@
+//go:build darwin
+
+package nativepath
+
+import (
+	"path/filepath"
+	"unsafe"
+
+	"golang.org/x/sys/unix"
+)
+
+func fcntlGetPath(fd int, buf *[unix.PathMax]byte) (int, error) {
+	return ignoringEINTR(func() (int, error) {
+		return fcntlGetPathPtr(uintptr(fd), uintptr(unsafe.Pointer(&buf[0])))
+	})
+}
+
+// Keep the pointer conversion in the call to this function. The compiler
+// directive below keeps the buffer alive across fcntl.
+//
+//go:uintptrescapes
+func fcntlGetPathPtr(fd uintptr, buf uintptr) (int, error) {
+	return unix.FcntlInt(fd, unix.F_GETPATH, int(buf))
+}
+
+// RealpathDirectory returns the kernel's path spelling for a directory.
+// F_GETPATH is restricted to directories because files with multiple hard
+// links can have multiple valid kernel paths. Other inputs and failures use
+// Realpath.
+func RealpathDirectory(path string) (string, error) {
+	fd, err := ignoringEINTR(func() (int, error) {
+		return unix.Open(path, unix.O_EVTONLY|unix.O_NONBLOCK|unix.O_CLOEXEC|unix.O_DIRECTORY, 0)
+	})
+	if err != nil {
+		return Realpath(path)
+	}
+	defer unix.Close(fd)
+
+	var stat unix.Stat_t
+	if err := unix.Fstat(fd, &stat); err != nil {
+		return Realpath(path)
+	}
+	if stat.Mode&unix.S_IFMT != unix.S_IFDIR {
+		return Realpath(path)
+	}
+
+	var buf [unix.PathMax]byte
+	if _, err := fcntlGetPath(fd, &buf); err != nil {
+		return Realpath(path)
+	}
+	realpath := unix.ByteSliceToString(buf[:])
+	if realpath == "" || !filepath.IsAbs(realpath) {
+		return Realpath(path)
+	}
+	return realpath, nil
+}
diff --git a/tsc/internal/nativepath/realpath_directory_darwin_test.go b/tsc/internal/nativepath/realpath_directory_darwin_test.go
new file mode 100644
index 0000000000000..13b7ebe8085cb
--- /dev/null
+++ b/tsc/internal/nativepath/realpath_directory_darwin_test.go
@@ -0,0 +1,34 @@
+//go:build darwin
+
+package nativepath
+
+import (
+	"errors"
+	"io/fs"
+	"os"
+	"path/filepath"
+	"testing"
+
+	"gotest.tools/v3/assert"
+)
+
+func TestRealpathDirectoryPreservesDiskCasing(t *testing.T) {
+	t.Parallel()
+
+	parent := t.TempDir()
+	parent, err := filepath.EvalSymlinks(parent)
+	assert.NilError(t, err)
+	actual := filepath.Join(parent, "MixedCase")
+	requested := filepath.Join(parent, "mixedcase")
+	assert.NilError(t, os.Mkdir(actual, 0o755))
+	if _, statErr := os.Stat(requested); statErr != nil {
+		if errors.Is(statErr, fs.ErrNotExist) {
+			t.Skip("filesystem is case-sensitive")
+		}
+		t.Fatal(statErr)
+	}
+
+	got, err := RealpathDirectory(requested)
+	assert.NilError(t, err)
+	assert.Equal(t, got, actual)
+}
diff --git a/tsc/internal/nativepath/realpath_directory_other.go b/tsc/internal/nativepath/realpath_directory_other.go
new file mode 100644
index 0000000000000..35a2da441a567
--- /dev/null
+++ b/tsc/internal/nativepath/realpath_directory_other.go
@@ -0,0 +1,9 @@
+//go:build !darwin
+
+package nativepath
+
+// RealpathDirectory delegates to Realpath without checking that path is a
+// directory. macOS provides a directory-specific implementation.
+func RealpathDirectory(path string) (string, error) {
+	return Realpath(path)
+}