diff --git a/apps/planner/app/components/PlannerMap.tsx b/apps/planner/app/components/PlannerMap.tsx
index 73a5c27..5ee0ded 100644
--- a/apps/planner/app/components/PlannerMap.tsx
+++ b/apps/planner/app/components/PlannerMap.tsx
@@ -14,17 +14,21 @@ import { ColoredRoute, findSegmentForPoint, type ColorMode } from "./ColoredRout
 import { RouteInteraction } from "./RouteInteraction";
 import "leaflet/dist/leaflet.css";
 
-function waypointIcon(index: number, overnight?: boolean): L.DivIcon {
+function waypointIcon(index: number, overnight?: boolean, highlighted?: boolean): L.DivIcon {
   const bg = overnight ? "#8B6D3A" : "#2563eb";
+  const size = highlighted ? 30 : 24;
+  const offset = size / 2;
+  const ring = highlighted ? `outline:3px solid ${bg};outline-offset:2px;` : "";
   return L.divIcon({
     className: "",
     html: `<div style="
-      width:24px;height:24px;border-radius:50%;
+      width:${size}px;height:${size}px;border-radius:50%;
       background:${bg};color:white;
       display:flex;align-items:center;justify-content:center;
-      font-size:12px;font-weight:600;
+      font-size:${highlighted ? 14 : 12}px;font-weight:600;
       border:2px solid white;box-shadow:0 1px 4px rgba(0,0,0,0.3);
-      transform:translate(-12px,-12px);
+      transform:translate(-${offset}px,-${offset}px);
+      ${ring}transition:all 0.15s ease;
     ">${overnight ? "☾" : index + 1}</div>`,
     iconSize: [0, 0],
   });
@@ -66,6 +70,7 @@ interface PlannerMapProps {
   onRouteRequest?: (waypoints: WaypointData[]) => void;
   onImportError?: (message: string) => void;
   highlightPosition?: [number, number] | null;
+  highlightedWaypoint?: number | null;
   days?: DayStage[];
 }
 
@@ -228,7 +233,7 @@ function NoGoAreaButton({ active, onClick }: { active: boolean; onClick: () => v
   );
 }
 
-export function PlannerMap({ yjs, onRouteRequest, highlightPosition, onImportError, days }: PlannerMapProps) {
+export function PlannerMap({ yjs, onRouteRequest, highlightPosition, highlightedWaypoint, onImportError, days }: PlannerMapProps) {
   const { t } = useTranslation("planner");
   const [waypoints, setWaypoints] = useState<WaypointData[]>([]);
   const [draggingOver, setDraggingOver] = useState(false);
@@ -466,7 +471,7 @@ export function PlannerMap({ yjs, onRouteRequest, highlightPosition, onImportErr
           key={i}
           position={[wp.lat, wp.lon]}
           draggable
-          icon={waypointIcon(i, wp.overnight)}
+          icon={waypointIcon(i, wp.overnight, highlightedWaypoint === i)}
           eventHandlers={{
             mouseover: () => {
               routeInteractionSuspendedRef.current = true;
diff --git a/apps/planner/app/components/SessionView.tsx b/apps/planner/app/components/SessionView.tsx
index cadb4ef..c6c8f17 100644
--- a/apps/planner/app/components/SessionView.tsx
+++ b/apps/planner/app/components/SessionView.tsx
@@ -142,7 +142,7 @@ function ColorModeToggle({ yjs }: { yjs: YjsState }) {
   );
 }
 
-function SidebarTabs({ yjs, routeStats, days, onWaypointHover }: { yjs: YjsState; routeStats: ReturnType<typeof useRouting>["routeStats"]; days: ReturnType<typeof useDays>; onWaypointHover: (position: [number, number] | null) => void }) {
+function SidebarTabs({ yjs, routeStats, days, onWaypointHover }: { yjs: YjsState; routeStats: ReturnType<typeof useRouting>["routeStats"]; days: ReturnType<typeof useDays>; onWaypointHover: (index: number | null) => void }) {
   const { t } = useTranslation("planner");
   const [tab, setTab] = useState<"waypoints" | "notes">("waypoints");
 
@@ -193,6 +193,7 @@ export function SessionView({ sessionId, callbackUrl, callbackToken, returnUrl,
   useUndoShortcuts(yjs?.undoManager ?? null);
   const days = useDays(yjs);
   const [highlightPosition, setHighlightPosition] = useState<[number, number] | null>(null);
+  const [highlightedWaypoint, setHighlightedWaypoint] = useState<number | null>(null);
   const { toasts, addToast } = useToasts();
   useAwarenessToasts(yjs, t, addToast);
 
@@ -285,14 +286,14 @@ export function SessionView({ sessionId, callbackUrl, callbackToken, returnUrl,
                 </div>
               }
             >
-              <PlannerMap yjs={yjs} onRouteRequest={requestRoute} highlightPosition={highlightPosition} onImportError={(msg) => addToast(msg, "error")} days={days} />
+              <PlannerMap yjs={yjs} onRouteRequest={requestRoute} highlightPosition={highlightPosition} highlightedWaypoint={highlightedWaypoint} onImportError={(msg) => addToast(msg, "error")} days={days} />
             </Suspense>
           </div>
           <Suspense fallback={null}>
             <ElevationChart yjs={yjs} onHover={handleElevationHover} days={days} />
           </Suspense>
         </main>
-        <SidebarTabs yjs={yjs} routeStats={routeStats} days={days} onWaypointHover={setHighlightPosition} />
+        <SidebarTabs yjs={yjs} routeStats={routeStats} days={days} onWaypointHover={setHighlightedWaypoint} />
       </div>
       <YjsDebugPanel yjs={yjs} />
       {toasts.length > 0 && (
diff --git a/apps/planner/app/components/WaypointSidebar.tsx b/apps/planner/app/components/WaypointSidebar.tsx
index 5d53651..3c2d645 100644
--- a/apps/planner/app/components/WaypointSidebar.tsx
+++ b/apps/planner/app/components/WaypointSidebar.tsx
@@ -30,7 +30,7 @@ interface WaypointSidebarProps {
     elevationLoss?: number;
   };
   days: DayStage[];
-  onWaypointHover?: (position: [number, number] | null) => void;
+  onWaypointHover?: (index: number | null) => void;
 }
 
 export function WaypointSidebar({ yjs, routeStats, days, onWaypointHover }: WaypointSidebarProps) {
@@ -90,7 +90,7 @@ export function WaypointSidebar({ yjs, routeStats, days, onWaypointHover }: Wayp
     <li
       key={i}
       className="group flex items-center gap-2 px-4 py-2 hover:bg-gray-50"
-      onMouseEnter={() => onWaypointHover?.([wp.lat, wp.lon])}
+      onMouseEnter={() => onWaypointHover?.(i)}
       onMouseLeave={() => onWaypointHover?.(null)}
     >
       <span className="flex h-5 w-5 shrink-0 items-center justify-center rounded-full bg-blue-100 text-xs font-medium text-blue-700">