diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 868aa85cec61b..2659fa7b335ed 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -3299,6 +3299,10 @@ export default function Sidebar({ routeReveal }: { routeReveal: SidebarRouteReve
                       "relative flex flex-col gap-px",
                       sidebarListItems.length > 0 && "flex-1",
                       actionSweep !== null && "**:pointer-events-none",
+                      // Projected rows (two boundary labels, two hints) extend the scroll range; a range that
+                      // shrinks as the target changes clamps scrollTop and flips the target under a still pointer.
+                      dragState !== null &&
+                        "after:pointer-events-none after:absolute after:inset-x-0 after:-bottom-30 after:h-px after:content-['']",
                     )}
                   >
                     {(() => {
diff --git a/apps/web/src/components/sidebar/SidebarListMarkers.tsx b/apps/web/src/components/sidebar/SidebarListMarkers.tsx
index 3416d80ff5e53..da9444a5c1b24 100644
--- a/apps/web/src/components/sidebar/SidebarListMarkers.tsx
+++ b/apps/web/src/components/sidebar/SidebarListMarkers.tsx
@@ -56,7 +56,10 @@ export function SidebarSectionPlaceholder(props: {
       marker={props.marker}
       data-testid={`sidebar-${props.marker}`}
       className="relative mx-0.5 -mb-px h-0"
-      revealOverflow={props.marker === "settled-placeholder" && props.showHint}
+      // Revealing on every drag scrolls the list out from under the pointer.
+      revealOverflow={
+        props.marker === "settled-placeholder" && props.showHint && props.isDropTarget
+      }
     >
       {props.showHint ? (
         <div