diff --git a/frontend/src/components/layout/Header.js b/frontend/src/components/layout/Header.js
index b1692ad196..9b661146ab 100644
--- a/frontend/src/components/layout/Header.js
+++ b/frontend/src/components/layout/Header.js
@@ -182,8 +182,44 @@ function OEHeader(props) {
     setSearchBar(!searchBar);
   };
   const generateMenuItems = (menuItem, index, level, path) => {
-    if (menuItem.menu.isActive) {
-      if (level === 0 && menuItem.childMenus.length > 0) {
+    if (!menuItem.menu.isActive) {
+      return <React.Fragment key={path}></React.Fragment>;
+    }
+
+    const activeChildMenus = menuItem.childMenus.filter(
+      (child) => child.menu.isActive,
+    );
+
+    if (level === 0) {
+      // For top level items with exactly one active child, render direct link
+      if (activeChildMenus.length === 1) {
+        const singleChildMenu = activeChildMenus[0];
+        return (
+          <span
+            key={path}
+            id={menuItem.menu.elementId}
+            style={{ position: "relative", zIndex: 10 }}
+          >
+            <span
+              id={menuItem.menu.elementId + "_dropdown"}
+              style={{ position: "relative", zIndex: 5 }}
+            >
+              <SideNavMenuItem
+                id={menuItem.menu.elementId + "dashboard_nav"}
+                href={singleChildMenu.menu.actionURL}
+                target={singleChildMenu.menu.openInNewWindow ? "_blank" : ""}
+                className="top-level-menu-item"
+                style={{ position: "relative", zIndex: 15 }}
+              >
+                {renderSideNavMenuItemLabel(menuItem, level)}
+              </SideNavMenuItem>
+            </span>
+          </span>
+        );
+      }
+
+      // Multiple active children - show dropdown
+      if (menuItem.childMenus.length > 0) {
         return (
           <span id={menuItem.menu.elementId} key={path}>
             <span
@@ -202,9 +238,6 @@ function OEHeader(props) {
                 })}
                 key={"menu_" + index + "_" + level}
                 defaultExpanded={menuItem.expanded}
-                // onClick={(e) => { // not supported yet, but if it becomes so we can simplify the functionality here by having this here and not have a span around it
-                //   setMenuItemExpanded(e, menuItem, path);
-                // }}
               >
                 <span
                   onClick={(e) => {
@@ -225,7 +258,7 @@ function OEHeader(props) {
             </span>
           </span>
         );
-      } else if (level === 0) {
+      } else {
         return (
           <span key={path} id={menuItem.menu.elementId}>
             <SideNavMenuItem
@@ -238,53 +271,50 @@ function OEHeader(props) {
             </SideNavMenuItem>
           </span>
         );
-      } else {
-        return (
-          <span id={menuItem.menu.elementId} key={path}>
-            <SideNavMenuItem
-              className="reduced-padding-nav-menu-item"
-              href={menuItem.menu.actionURL}
-              target={menuItem.menu.openInNewWindow ? "_blank" : ""}
-              style={{ width: "100%" }}
-              rel="noreferrer"
-            >
-              <span style={{ display: "flex", width: "100%" }}>
-                {!menuItem.menu.actionURL &&
-                  !hasActiveChildMenu(menuItem) &&
-                  console.warn("menu entry has no action url and no child")}
-                {!hasActiveChildMenu(menuItem) &&
-                  renderSingleNavButton(menuItem, index, level, path)}
-                {!menuItem.menu.actionURL &&
-                  hasActiveChildMenu(menuItem) &&
-                  renderSingleDropdownButton(menuItem, index, level, path)}
-                {menuItem.menu.actionURL &&
-                  hasActiveChildMenu(menuItem) &&
-                  renderDualNavDropdownButton(menuItem, index, level, path)}
-              </span>
-            </SideNavMenuItem>
-            {menuItem.childMenus.map((childMenuItem, index) => {
-              return (
-                <span
-                  key={path + ".childMenus[" + index + "].span"}
-                  style={{ display: menuItem.expanded ? "" : "none" }}
-                >
-                  {generateMenuItems(
-                    childMenuItem,
-                    index,
-                    level + 1,
-                    path + ".childMenus[" + index + "]",
-                  )}
-                </span>
-              );
-            })}
-          </span>
-        );
       }
     } else {
-      return <React.Fragment key={path}></React.Fragment>;
+      return (
+        <span id={menuItem.menu.elementId} key={path}>
+          <SideNavMenuItem
+            className="reduced-padding-nav-menu-item"
+            href={menuItem.menu.actionURL}
+            target={menuItem.menu.openInNewWindow ? "_blank" : ""}
+            style={{ width: "100%" }}
+            rel="noreferrer"
+          >
+            <span style={{ display: "flex", width: "100%" }}>
+              {!menuItem.menu.actionURL &&
+                !hasActiveChildMenu(menuItem) &&
+                console.warn("menu entry has no action url and no child")}
+              {!hasActiveChildMenu(menuItem) &&
+                renderSingleNavButton(menuItem, index, level, path)}
+              {!menuItem.menu.actionURL &&
+                hasActiveChildMenu(menuItem) &&
+                renderSingleDropdownButton(menuItem, index, level, path)}
+              {menuItem.menu.actionURL &&
+                hasActiveChildMenu(menuItem) &&
+                renderDualNavDropdownButton(menuItem, index, level, path)}
+            </span>
+          </SideNavMenuItem>
+          {menuItem.childMenus.map((childMenuItem, index) => {
+            return (
+              <span
+                key={path + ".childMenus[" + index + "].span"}
+                style={{ display: menuItem.expanded ? "" : "none" }}
+              >
+                {generateMenuItems(
+                  childMenuItem,
+                  index,
+                  level + 1,
+                  path + ".childMenus[" + index + "]",
+                )}
+              </span>
+            );
+          })}
+        </span>
+      );
     }
   };
-
   const hasActiveChildMenu = (menuItem) => {
     if (menuItem.menu.elementId === "menu_reports_routine") {
       console.log("reports");