diff --git a/include/os/windows/zfs/sys/zfs_windows.h b/include/os/windows/zfs/sys/zfs_windows.h
index fce558209599..80ba0d732240 100644
--- a/include/os/windows/zfs/sys/zfs_windows.h
+++ b/include/os/windows/zfs/sys/zfs_windows.h
@@ -183,6 +183,8 @@ extern NTSTATUS set_file_rename_information(PDEVICE_OBJECT, PIRP,
     PIO_STACK_LOCATION);
 extern NTSTATUS set_file_valid_data_length_information(
     PDEVICE_OBJECT DeviceObject, PIRP Irp, PIO_STACK_LOCATION IrpSp);
+extern NTSTATUS set_file_case_sensitive_information(
+    PDEVICE_OBJECT DeviceObject, PIRP Irp, PIO_STACK_LOCATION IrpSp);
 extern NTSTATUS set_file_position_information(PDEVICE_OBJECT DeviceObject,
     PIRP Irp, PIO_STACK_LOCATION IrpSp);
 
diff --git a/include/os/windows/zfs/sys/zfs_znode_impl.h b/include/os/windows/zfs/sys/zfs_znode_impl.h
index 133a9bc204a3..c781ee0f5086 100644
--- a/include/os/windows/zfs/sys/zfs_znode_impl.h
+++ b/include/os/windows/zfs/sys/zfs_znode_impl.h
@@ -58,6 +58,8 @@ extern "C" {
 #define	ZFS_SIMMUTABLE	0x0040000000000000ull
 #define	ZFS_SAPPENDONLY	0x0080000000000000ull
 
+#define	ZFS_CASESENSITIVEDIR	0x0100000000000000ull
+
 #define	SA_ZPL_ADDTIME(z)	z->z_attr_table[ZPL_ADDTIME]
 #define	SA_ZPL_DOCUMENTID(z)	z->z_attr_table[ZPL_DOCUMENTID]
 
diff --git a/include/sys/xvattr.h b/include/sys/xvattr.h
index a7994db894b9..96bdbdd6e076 100644
--- a/include/sys/xvattr.h
+++ b/include/sys/xvattr.h
@@ -67,6 +67,10 @@ typedef struct xoptattr {
 	uint8_t		xoa_sparse;
 	uint8_t		xoa_projinherit;
 	uint64_t	xoa_projid;
+	uint8_t		xoa_tracked; /* macOS */;
+	uint8_t		xoa_sappendonly; /* macOS */;
+	uint8_t		xoa_simmutable; /* macOS */;
+	uint8_t		xoa_case_sensitive_dir; /* Win */
 } xoptattr_t;
 
 /*
@@ -174,12 +178,18 @@ typedef struct xvattr {
 #define	XAT0_SPARSE	0x00010000	/* sparse */
 #define	XAT0_PROJINHERIT	0x00020000	/* Create with parent projid */
 #define	XAT0_PROJID	0x00040000	/* Project ID */
+#define	XAT0_TRACKED	0x00080000	/* macOS UF_TRACKED */
+#define	XAT0_SAPPENDONLY	0x00100000	/* macOS SF_APPENDONLY */
+#define	XAT0_SIMMUTABLE	0x00200000	/* macOS SF_IMMUTABLE */
+#define	XAT0_CASESENSITIVEDIR	0x00400000	/* win */
+
 
 #define	XAT0_ALL_ATTRS	(XAT0_CREATETIME|XAT0_ARCHIVE|XAT0_SYSTEM| \
     XAT0_READONLY|XAT0_HIDDEN|XAT0_NOUNLINK|XAT0_IMMUTABLE|XAT0_APPENDONLY| \
     XAT0_NODUMP|XAT0_OPAQUE|XAT0_AV_QUARANTINED|  XAT0_AV_MODIFIED| \
-    XAT0_AV_SCANSTAMP|XAT0_REPARSE|XATO_GEN|XAT0_OFFLINE|XAT0_SPARSE| \
-    XAT0_PROJINHERIT | XAT0_PROJID)
+    XAT0_AV_SCANSTAMP|XAT0_REPARSE|XAT0_GEN|XAT0_OFFLINE|XAT0_SPARSE| \
+    XAT0_PROJINHERIT | XAT0_PROJID|XAT0_TRACKED|XAT0_SAPPENDONLY| \
+    XAT0_SIMMUTABLE|XAT0_CASESENSITIVEDIR)
 
 /* Support for XAT_* optional attributes */
 #define	XVA_MASK		0xffffffff	/* Used to mask off 32 bits */
@@ -218,6 +228,10 @@ typedef struct xvattr {
 #define	XAT_SPARSE		((XAT0_INDEX << XVA_SHFT) | XAT0_SPARSE)
 #define	XAT_PROJINHERIT		((XAT0_INDEX << XVA_SHFT) | XAT0_PROJINHERIT)
 #define	XAT_PROJID		((XAT0_INDEX << XVA_SHFT) | XAT0_PROJID)
+#define	XAT_TRACKED		((XAT0_INDEX << XVA_SHFT) | XAT0_TRACKED)
+#define	XAT_SAPPENDONLY		((XAT0_INDEX << XVA_SHFT) | XAT0_SAPPENDONLY)
+#define	XAT_SIMMUTABLE		((XAT0_INDEX << XVA_SHFT) | XAT0_SIMMUTABLE)
+#define	XAT_CASESENSITIVEDIR ((XAT0_INDEX << XVA_SHFT) | XAT0_CASESENSITIVEDIR)
 
 /*
  * The returned attribute map array (xva_rtnattrmap[]) is located past the
diff --git a/module/os/windows/zfs/zfs_dir.c b/module/os/windows/zfs/zfs_dir.c
index 36e2d923ff62..27f9d47ffa89 100644
--- a/module/os/windows/zfs/zfs_dir.c
+++ b/module/os/windows/zfs/zfs_dir.c
@@ -179,6 +179,18 @@ zfs_dirent_lock(zfs_dirlock_t **dlpp, znode_t *dzp, char *name, znode_t **zpp,
 	 * once so that simultaneous case-insensitive/case-sensitive
 	 * behaves as rationally as possible.
 	 */
+#ifdef _WIN32
+	/*
+	 * Windows lets you set Case-Sensitive on
+	 * a directory while the dataset as a whole
+	 * is insensitive.
+	 */
+	if (S_ISDIR(dzp->z_mode) &&
+	    (dzp->z_pflags & ZFS_CASESENSITIVEDIR)) {
+		flag &= ~ZCILOOK;
+		flag |= ZCIEXACT;
+	}
+#endif
 
 	/*
 	 * When matching we may need to normalize & change case according to
diff --git a/module/os/windows/zfs/zfs_vnops_os.c b/module/os/windows/zfs/zfs_vnops_os.c
index 436a93b90a2b..42d0e245bbb4 100644
--- a/module/os/windows/zfs/zfs_vnops_os.c
+++ b/module/os/windows/zfs/zfs_vnops_os.c
@@ -2012,6 +2012,16 @@ zfs_setattr(znode_t *zp, vattr_t *vap, int flags, cred_t *cr, zidmap_t *mnt_ns)
 			}
 		}
 
+		if (XVA_ISSET_REQ(xvap, XAT_CASESENSITIVEDIR)) {
+			if (xoap->xoa_case_sensitive_dir !=
+			    ((zp->z_pflags & ZFS_CASESENSITIVEDIR) != 0)) {
+				need_policy = TRUE;
+			} else {
+				XVA_CLR_REQ(xvap, XAT_CASESENSITIVEDIR);
+				XVA_SET_REQ(&tmpxvattr, XAT_CASESENSITIVEDIR);
+			}
+		}
+
 		if (XVA_ISSET_REQ(xvap, XAT_AV_MODIFIED)) {
 			if (xoap->xoa_av_modified !=
 			    ((zp->z_pflags & ZFS_AV_MODIFIED) != 0)) {
@@ -2404,6 +2414,9 @@ zfs_setattr(znode_t *zp, vattr_t *vap, int flags, cred_t *cr, zidmap_t *mnt_ns)
 		if (XVA_ISSET_REQ(&tmpxvattr, XAT_PROJINHERIT)) {
 			XVA_SET_REQ(xvap, XAT_PROJINHERIT);
 		}
+		if (XVA_ISSET_REQ(&tmpxvattr, XAT_CASESENSITIVEDIR)) {
+			XVA_SET_REQ(xvap, XAT_CASESENSITIVEDIR);
+		}
 
 		if (XVA_ISSET_REQ(xvap, XAT_AV_SCANSTAMP))
 			ASSERT(vp->v_type == VREG);
diff --git a/module/os/windows/zfs/zfs_vnops_windows.c b/module/os/windows/zfs/zfs_vnops_windows.c
index 24f435940a50..7dd0a7fe7c43 100644
--- a/module/os/windows/zfs/zfs_vnops_windows.c
+++ b/module/os/windows/zfs/zfs_vnops_windows.c
@@ -735,7 +735,7 @@ zfs_find_dvp_vp(zfsvfs_t *zfsvfs, char *filename, int finalpartmaynotexist,
  */
 int
 zfs_vnop_lookup_impl(PIRP Irp, PIO_STACK_LOCATION IrpSp, mount_t *zmo,
-    char *filename, vattr_t *vap)
+    char *filename, xvattr_t *xvap)
 {
 	int error;
 	cred_t *cr = NULL;
@@ -773,6 +773,7 @@ zfs_vnop_lookup_impl(PIRP Irp, PIO_STACK_LOCATION IrpSp, mount_t *zmo,
 	ACCESS_MASK DesiredAccess =
 	    IrpSp->Parameters.Create.SecurityContext->DesiredAccess;
 	zfs_ccb_t *zccb = NULL;
+	vattr_t *vap = &xvap->xva_vattr;
 
 	if (zfsvfs == NULL)
 		return (STATUS_OBJECT_PATH_NOT_FOUND);
@@ -1311,9 +1312,17 @@ zfs_vnop_lookup_impl(PIRP Irp, PIO_STACK_LOCATION IrpSp, mount_t *zmo,
 		vap->va_mode |= S_IFDIR;
 		vap->va_mask |= (ATTR_MODE | ATTR_TYPE);
 
+		/* If parent is CaseSensitive, sub-Dir should be too */
+		if (VTOZ(dvp)->z_pflags & ZFS_CASESENSITIVEDIR) {
+			xoptattr_t *xoap;
+			xoap = xva_getxoptattr(xvap);
+			xoap->xoa_case_sensitive_dir = 1;
+			XVA_SET_REQ(xvap, XAT_CASESENSITIVEDIR);
+		}
+
 		ASSERT(strchr(finalname, '\\') == NULL);
 		error = zfs_mkdir(VTOZ(dvp), finalname, vap, &zp, NULL,
-		    0, NULL, NULL);
+		    flags, NULL, NULL);
 		if (error == 0) {
 			vp = ZTOV(zp);
 			zfs_couplefileobject(vp, NULL, FileObject, 0ULL,
@@ -1572,7 +1581,7 @@ zfs_vnop_lookup_impl(PIRP Irp, PIO_STACK_LOCATION IrpSp, mount_t *zmo,
 		// O_EXCL only if FILE_CREATE
 		error = zfs_create(VTOZ(dvp), finalname, vap,
 		    CreateDisposition == FILE_CREATE, vap->va_mode,
-		    &zp, NULL, 0, NULL, NULL);
+		    &zp, NULL, flags, NULL, NULL);
 		if (error == 0) {
 			boolean_t reenter_for_xattr = B_FALSE;
 
@@ -1827,7 +1836,7 @@ zfs_vnop_lookup(PIRP Irp, PIO_STACK_LOCATION IrpSp, mount_t *zmo)
 	do {
 
 		// Call ZFS
-		status = zfs_vnop_lookup_impl(Irp, IrpSp, zmo, filename, vap);
+		status = zfs_vnop_lookup_impl(Irp, IrpSp, zmo, filename, &xva);
 
 	} while (status == EAGAIN);
 
@@ -4441,6 +4450,10 @@ set_information(PDEVICE_OBJECT DeviceObject, PIRP Irp,
 		Status = set_file_valid_data_length_information(DeviceObject,
 		    Irp, IrpSp);
 		break;
+	case FileCaseSensitiveInformation:
+		Status = set_file_case_sensitive_information(DeviceObject,
+		    Irp, IrpSp);
+		break;
 	default:
 		dprintf("* %s: unknown type NOTIMPLEMENTED\n", __func__);
 		break;
diff --git a/module/os/windows/zfs/zfs_vnops_windows_lib.c b/module/os/windows/zfs/zfs_vnops_windows_lib.c
index c51d742a950e..ab14d4c00682 100644
--- a/module/os/windows/zfs/zfs_vnops_windows_lib.c
+++ b/module/os/windows/zfs/zfs_vnops_windows_lib.c
@@ -4021,7 +4021,6 @@ set_file_valid_data_length_information(PDEVICE_OBJECT DeviceObject, PIRP Irp,
 	mount_t *zmo = DeviceObject->DeviceExtension;
 	int error;
 	CC_FILE_SIZES ccfs;
-	LIST_ENTRY rollback;
 	boolean_t set_size = B_FALSE;
 
 	dprintf("* FileValidDataLengthInformation: \n");
@@ -4105,6 +4104,65 @@ set_file_valid_data_length_information(PDEVICE_OBJECT DeviceObject, PIRP Irp,
 	return (Status);
 }
 
+NTSTATUS
+set_file_case_sensitive_information(PDEVICE_OBJECT DeviceObject, PIRP Irp,
+    PIO_STACK_LOCATION IrpSp)
+{
+	NTSTATUS Status;
+	FILE_CASE_SENSITIVE_INFORMATION *fcsi =
+	    Irp->AssociatedIrp.SystemBuffer;
+	mount_t *zmo = DeviceObject->DeviceExtension;
+	int error;
+
+	dprintf("* FileCaseSensitiveInformation: \n");
+
+	if (IrpSp->Parameters.SetFile.Length <
+	    sizeof (FILE_CASE_SENSITIVE_INFORMATION))
+		return (STATUS_INFO_LENGTH_MISMATCH);
+
+	if (IrpSp->FileObject == NULL ||
+	    IrpSp->FileObject->FsContext == NULL)
+		return (STATUS_INVALID_PARAMETER);
+
+	struct vnode *vp = IrpSp->FileObject->FsContext;
+	zfs_ccb_t *ccb = IrpSp->FileObject->FsContext2;
+	znode_t *zp = VTOZ(vp);
+
+	if (zmo == NULL || zp == NULL)
+		return (STATUS_INVALID_PARAMETER);
+
+	if (!vnode_isdir(vp))
+		return (STATUS_INVALID_PARAMETER);
+
+	zfsvfs_t *zfsvfs = vfs_fsprivate(zmo);
+	if (zfsvfs == NULL)
+		return (STATUS_INVALID_PARAMETER);
+
+	if ((error = zfs_enter(zfsvfs, FTAG)) != 0)
+		return (error);
+
+	xvattr_t xva = { 0 };
+	vattr_t *vap = &xva.xva_vattr;
+	xoptattr_t *xoap;
+
+	xva_init(&xva);
+	xoap = xva_getxoptattr(&xva);
+
+	/*
+	 * We need to check if there are case issues in this dir, if
+	 * the request is to make it case insensitive again. Return
+	 * the code: STATUS_CASE_DIFFERING_NAMES_IN_DIR
+	 */
+	xoap->xoa_case_sensitive_dir =
+	    (fcsi->Flags & FILE_CS_FLAG_CASE_SENSITIVE_DIR);
+	XVA_SET_REQ(&xva, XAT_CASESENSITIVEDIR);
+
+	Status = zfs_setattr(zp, vap, 0, NULL, NULL);
+
+	zfs_exit(zfsvfs, FTAG);
+	return (Status);
+}
+
 NTSTATUS
 set_file_position_information(PDEVICE_OBJECT DeviceObject, PIRP Irp,
     PIO_STACK_LOCATION IrpSp)
@@ -4677,13 +4735,9 @@ file_case_sensitive_information(PDEVICE_OBJECT DeviceObject, PIRP Irp,
 	struct vnode *vp = FileObject->FsContext;
 	if (vp != NULL) {
 		znode_t *zp = VTOZ(vp);
-		if (zp != NULL) {
-		zfsvfs_t *zfsvfs = zp->z_zfsvfs;
 
-		if (zfsvfs->z_case == ZFS_CASE_SENSITIVE)
+		if (zp && (zp->z_pflags & ZFS_CASESENSITIVEDIR))
 			fcsi->Flags |= FILE_CS_FLAG_CASE_SENSITIVE_DIR;
-
-		}
 	}
 
 	Irp->IoStatus.Information = sizeof (FILE_CASE_SENSITIVE_INFORMATION);
diff --git a/module/os/windows/zfs/zfs_znode.c b/module/os/windows/zfs/zfs_znode.c
index eff94188fffb..bd30a87b8dcb 100644
--- a/module/os/windows/zfs/zfs_znode.c
+++ b/module/os/windows/zfs/zfs_znode.c
@@ -1045,6 +1045,12 @@ zfs_xvattr_set(znode_t *zp, xvattr_t *xvap, dmu_tx_t *tx)
 		    zp->z_pflags, tx);
 		XVA_SET_RTN(xvap, XAT_SPARSE);
 	}
+	if (XVA_ISSET_REQ(xvap, XAT_CASESENSITIVEDIR)) {
+		ZFS_ATTR_SET(zp, ZFS_CASESENSITIVEDIR,
+		    xoap->xoa_case_sensitive_dir,
+		    zp->z_pflags, tx);
+		XVA_SET_RTN(xvap, XAT_CASESENSITIVEDIR);
+	}
 }
 
 int