diff --git a/debian/changelog b/debian/changelog
index 1b722908..6afe1053 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -3,6 +3,8 @@ byobu (4.35) unreleased; urgency=low
   * usr/bin/byobu-janitor, usr/share/byobu/status/status: LP: #856467
     - cleaner fix for ensuring ec2_cost is enabled in ec2 instances;
       previous fix just enabled it everywhere
+  * debian/postinst, usr/bin/byobu-janitor:
+    - smooth upgrades from older byobu (<= 4.0)
 
  -- Dustin Kirkland <kirkland@ubuntu.com>  Wed, 21 Sep 2011 18:49:00 -0500
 
diff --git a/debian/postinst b/debian/postinst
index 40f34906..4376afe2 100644
--- a/debian/postinst
+++ b/debian/postinst
@@ -25,14 +25,21 @@ fi
 rm -f /etc/update-motd.d/55-window-manager
 
 # Notify users that they should reload their profile
+touch_flag() {
+	touch "$1"
+	chown --reference $(dirname "$1") "$1" || true
+	chmod 700 "$1"
+}
 [ -r "/etc/$PKG/socketdir" ] && . "/etc/$PKG/socketdir"
 if [ -d "$SOCKETDIR" ]; then
-	for d in "$SOCKETDIR"/*/"$PKG"; do
-		[ -d "$d" ] || continue
-		flag="$d/reload-required"
-		touch "$flag"
-		chown --reference "$d" "$flag" || true
-		chmod 700 "$flag"
+	for d in "$SOCKETDIR"/*; do
+		if [ -d "$d/$PKG" ]; then
+			# New location of the reload flag
+			touch_flag "$d/$PKG/reload-required"
+		elif [ -d "$d" ]; then
+			# Old location of the reload flag
+			touch_flag "$d/$PKG.reload-required"
+		fi
 	done
 fi
 
diff --git a/usr/bin/byobu-janitor b/usr/bin/byobu-janitor
index f2bce1d3..14bf0262 100755
--- a/usr/bin/byobu-janitor
+++ b/usr/bin/byobu-janitor
@@ -46,6 +46,12 @@ if [ -d "$BYOBU_CONFIG_DIR" ] && [ ! -w "$BYOBU_CONFIG_DIR" ]; then
 	exit 1
 fi
 
+# Affects: Upgrades from <= byobu 4.30
+# Clear out old style status configuration
+if ! grep -qs "^screen_upper_left=" "$BYOBU_CONFIG_DIR/status"; then
+	rm -f "$BYOBU_CONFIG_DIR/status" "$BYOBU_CONFIG_DIR/statusrc"
+fi
+
 # Affects: First runs with no configuration
 # Seed the configuration
 # Setup initial local user configuration
@@ -127,7 +133,7 @@ fi
 # Affects: Upgrades from <= byobu 4.22
 killall -u $USER byobu-statusd >/dev/null 2>&1 || true
 
-# Clean up flag
-rm -f "$FLAG"
+# Clean up flag (new and old)
+rm -f "$FLAG" "/var/run/screen/S-$USER/$PKG.reload-required"
 
 # vi: syntax=sh ts=4 noexpandtab