diff --git a/usr.sbin/pw/pw.8 b/usr.sbin/pw/pw.8
--- a/usr.sbin/pw/pw.8
+++ b/usr.sbin/pw/pw.8
@@ -741,6 +741,9 @@
 the user, or symbolic links owned by anyone under the user's home directory.
 Finally, after deleting all contents owned by the user only empty directories
 will be removed.
+If the home directory is a ZFS dataset and has been emptied,
+the dataset will be destroyed.
+ZFS datasets within the home directory and snapshots are not handled.
 If any additional cleanup work is required, this is left to the administrator.
 .El
 .Pp
@@ -1077,7 +1080,8 @@
 .Xr passwd 5 ,
 .Xr pw.conf 5 ,
 .Xr pwd_mkdb 8 ,
-.Xr vipw 8
+.Xr vipw 8 ,
+.Xr zfs 8
 .Sh HISTORY
 The
 .Nm
diff --git a/usr.sbin/pw/pw_user.c b/usr.sbin/pw/pw_user.c
--- a/usr.sbin/pw/pw_user.c
+++ b/usr.sbin/pw/pw_user.c
@@ -28,7 +28,7 @@
  */
 
 #include <sys/param.h>
-#include <sys/types.h>
+#include <sys/wait.h>
 
 #include <assert.h>
 #include <ctype.h>
@@ -669,6 +669,7 @@
 
 		while ((e = readdir(d)) != NULL) {
 			struct stat     st;
+			pid_t		pid;
 
 			if (strncmp(e->d_name, ".lock", 5) != 0 &&
 			    stat(e->d_name, &st) == 0 &&
@@ -679,11 +680,12 @@
 					e->d_name,
 					NULL
 				};
-				if (posix_spawn(NULL, argv[0], NULL, NULL,
+				if (posix_spawn(&pid, argv[0], NULL, NULL,
 				    (char *const *) argv, environ)) {
 					warn("Failed to execute '%s %s'",
 					    argv[0], argv[1]);
-				}
+				} else
+					(void) waitpid(pid, NULL, 0);
 			}
 		}
 		closedir(d);
@@ -919,11 +921,14 @@
 				"-r",
 				NULL
 			};
-			if (posix_spawnp(NULL, argv[0], NULL, NULL,
+			pid_t pid;
+
+			if (posix_spawnp(&pid, argv[0], NULL, NULL,
 						(char *const *) argv, environ)) {
 				warn("Failed to execute '%s %s'",
 						argv[0], argv[1]);
-			}
+			} else
+				(void) waitpid(pid, NULL, 0);
 		}
 	}
 
diff --git a/usr.sbin/pw/pwupd.h b/usr.sbin/pw/pwupd.h
--- a/usr.sbin/pw/pwupd.h
+++ b/usr.sbin/pw/pwupd.h
@@ -139,7 +139,7 @@
 
 void copymkdir(int rootfd, char const * dir, int skelfd, mode_t mode, uid_t uid,
     gid_t gid, int flags);
-void rm_r(int rootfd, char const * dir, uid_t uid);
+bool rm_r(int rootfd, char const * dir, uid_t uid);
 __END_DECLS
 
 #endif				/* !_PWUPD_H */
diff --git a/usr.sbin/pw/rm_r.c b/usr.sbin/pw/rm_r.c
--- a/usr.sbin/pw/rm_r.c
+++ b/usr.sbin/pw/rm_r.c
@@ -26,35 +26,58 @@
  * SUCH DAMAGE.
  */
 
+#include <sys/param.h>
+#include <sys/mount.h>
 #include <sys/stat.h>
+#include <sys/wait.h>
 
 #include <dirent.h>
+#include <err.h>
+#include <errno.h>
 #include <fcntl.h>
+#include <libgen.h>
+#include <libutil.h>
+#include <spawn.h>
+#include <stdbool.h>
+#include <stdio.h>
+#include <stdlib.h>
 #include <string.h>
 #include <unistd.h>
 
 #include "pwupd.h"
 
-void
+static bool try_dataset_remove(const char *home);
+extern char **environ;
+
+/*
+ * "rm -r" a directory tree.  If the top-level directory cannot be removed
+ * due to EBUSY, indicating that it is a ZFS dataset, and we have emptied
+ * it, destroy the dataset.  Return true if any files or directories
+ * remain.
+ */
+bool
 rm_r(int rootfd, const char *path, uid_t uid)
 {
 	int dirfd;
 	DIR *d;
 	struct dirent  *e;
 	struct stat     st;
+	const char     *fullpath;
+	bool skipped = false;
 
+	fullpath = path;
 	if (*path == '/')
 		path++;
 
 	dirfd = openat(rootfd, path, O_DIRECTORY);
 	if (dirfd == -1) {
-		return;
+		return (true);
 	}
 
 	d = fdopendir(dirfd);
 	if (d == NULL) {
 		(void)close(dirfd);
-		return;
+		return (true);
 	}
 	while ((e = readdir(d)) != NULL) {
 		if (strcmp(e->d_name, ".") == 0 || strcmp(e->d_name, "..") == 0)
@@ -62,16 +85,84 @@
 
 		if (fstatat(dirfd, e->d_name, &st, AT_SYMLINK_NOFOLLOW) != 0)
 			continue;
-		if (S_ISDIR(st.st_mode))
-			rm_r(dirfd, e->d_name, uid);
-		else if (S_ISLNK(st.st_mode) || st.st_uid == uid)
+		if (S_ISDIR(st.st_mode)) {
+			if (rm_r(dirfd, e->d_name, uid) == true)
+				skipped = true;
+		} else if (S_ISLNK(st.st_mode) || st.st_uid == uid)
 			unlinkat(dirfd, e->d_name, 0);
+		else
+			skipped = true;
 	}
 	closedir(d);
 	if (fstatat(rootfd, path, &st, AT_SYMLINK_NOFOLLOW) != 0)
-		return;
-	if (S_ISLNK(st.st_mode))
-		unlinkat(rootfd, path, 0);
-	else if (st.st_uid == uid)
-		unlinkat(rootfd, path, AT_REMOVEDIR);
+		return (skipped);
+	if (S_ISLNK(st.st_mode)) {
+		if (unlinkat(rootfd, path, 0) == -1)
+			skipped = true;
+	} else if (st.st_uid == uid) {
+		if (unlinkat(rootfd, path, AT_REMOVEDIR) == -1) {
+			if (errno == EBUSY && skipped == false)
+				skipped = try_dataset_remove(fullpath);
+			else
+				skipped = true;
+		}
+	} else
+		skipped = true;
+
+	return (skipped);
+}
+
+/*
+ * If the home directory is a ZFS dataset, attempt to destroy it.
+ * Return true if the dataset is not destroyed.
+ * This would be more straightforward as a shell script.
+ */
+static bool
+try_dataset_remove(const char *path)
+{
+	bool skipped = true;
+	struct statfs stat;
+	const char *argv[] = {
+		"/sbin/zfs",
+		"destroy",
+		NULL,
+		NULL
+	};
+	int status;
+	pid_t pid;
+
+	/* see if this is an absolute path (top-level directory) */
+	if (*path != '/')
+		return (skipped);
+	/* see if ZFS is loaded */
+	if (kld_isloaded("zfs") == 0)
+		return (skipped);
+	/* This won't work if root dir is not / (-R option) */
+	if (strcmp(conf.rootdir, "/") != 0) {
+		warnx("cannot destroy home dataset when -R was used");
+		return (skipped);
+	}
+	/* if so, find dataset name */
+	if (statfs(path, &stat) != 0) {
+		warn("statfs %s", path);
+		return (skipped);
+	}
+	/*
+	 * Check that the path refers to the dataset itself,
+	 * not a subdirectory.
+	 */
+	if (strcmp(stat.f_mntonname, path) != 0)
+		return (skipped);
+	argv[2] = stat.f_mntfromname;
+	if ((skipped = posix_spawn(&pid, argv[0], NULL, NULL,
+	    (char *const *) argv, environ)) != 0) {
+		warn("Failed to execute '%s %s %s'",
+		    argv[0], argv[1], argv[2]);
+	} else {
+		if (waitpid(pid, &status, 0) != -1 && status != 0) {
+			warnx("'%s %s %s' exit status %d\n",
+			    argv[0], argv[1], argv[2], status);
+		}
+	}
+	return (skipped);
 }