diff --git a/session.c b/session.c
index 7aec15d4208..39bede1d3dd 100644
--- a/session.c
+++ b/session.c
@@ -832,33 +832,45 @@ check_quietlogin(Session *s, const char *command)
 	return 0;
 }
 
+/*
+ * Check that any custom user environment/rc file is "safe" to run, i.e.
+ * - it belongs to either the superuser or to the logged in user, of which
+ *   the latter must also own the parent directory
+ * - if it belongs to the logged in user, either the file or its parent dir
+ *   is only accessible to the user
+ */
 static int
-safe_user_file(const char *filename, struct passwd *pw)
+safe_user_file(const char *filename, uid_t uid)
 {
 	struct stat st;
-	char *path;
+	char *lastsep;
+        uid_t dirowner;
+        mode_t dirmode;
 
+        /* Gather parent dir owner and mode first */
+        lastsep = strrchr(filename, '/');
+        *lastsep = '\0';
 	if (stat(filename, &st) == -1)
 		return 0;
-
-	path = realpath(filename, NULL);
-	if (strncmp(path, pw->pw_dir, strlen(pw->pw_dir)) == 0) {
-		if (st.st_uid != pw->pw_uid) {
-			fprintf(stderr, "Bad owner on %s, ignoring.\n",
-			    path);
-			return 0;
-		}
-		if ((st.st_mode & 077) != 0) {
-			fprintf(stderr,
-			    "Permissions too open (%3o) on %s, ignoring.\n",
-			    st.st_mode & 0777u, path);
-			return 0;
-		}
-		return 1;
-	}
-	if (st.st_uid != 0) {
-		fprintf(stderr, "%s not root-owned, ignoring.\n", path);
+        dirowner = st.st_uid;
+        dirmode = st.st_mode;
+        /* Then gather actual file info */
+        *lastsep = '/';
+        if (stat(filename, &st) == -1)
+                return 0;
+
+        if (st.st_uid != 0 && st.st_uid != uid && st.st_uid != dirowner) {
+                fprintf(stderr, "Bad owner on %s, ignoring.\n",
+		    filename);
 		return 0;
+        }
+
+	if (st.st_uid == uid &&
+            (st.st_mode & 077) != 0 && (dirmode & 077) != 0) {
+		fprintf(stderr,
+		    "Permissions too open on %s or its parent dir, ignoring.\n",
+    		    filename);
+                return 0;
 	}
 	return 1;
 }
@@ -1152,7 +1164,7 @@ do_setup_env(struct ssh *ssh, Session *s, const char *shell)
 		for (i = 0; i < options.num_user_env_files; i++) {
 			userenv = expand_user_file(options.user_env_files[i], pw,
 			    "UserEnvironment");
-			if (safe_user_file(userenv, pw))
+			if (safe_user_file(userenv, pw->pw_uid))
 				read_environment_file(&env, &envsize, userenv,
 				    options.permit_user_env_allowlist);
 		}
@@ -1250,7 +1262,7 @@ do_rc_files(struct ssh *ssh, Session *s, const char *shell)
 		for (i = 0; i < options.num_user_rc_files; i++) {
 			user_rc = expand_user_file(options.user_rc_files[i],
 			    s->pw, "UserRC");
-			if (safe_user_file(user_rc, s->pw)) {
+			if (safe_user_file(user_rc, s->pw->pw_uid)) {
 				if (xasprintf(&cmd, "%s -c '%s %s'", shell,
 				    _PATH_BSHELL, user_rc) == -1)
 					fatal_f("xasprintf: %s", strerror(errno));