diff --git a/web/components/nav-main.test.mjs b/web/components/nav-main.test.mjs
index e8525d4..a36d9a8 100644
--- a/web/components/nav-main.test.mjs
+++ b/web/components/nav-main.test.mjs
@@ -9,3 +9,12 @@ test("dashboard nav items expose full labels when visual text is truncated", ()
   assert.match(source, /tooltip=\{item\.title\}/)
   assert.match(source, /<span\s+title=\{item\.title\}>\{item\.title\}<\/span>/)
 })
+
+test("collapsed dashboard nav sections expose submenu flyouts on hover", () => {
+  assert.match(source, /useSidebar/)
+  assert.match(source, /state === "collapsed" && !isMobile/)
+  assert.match(source, /<DropdownMenuTrigger\s+openOnHover/)
+  assert.match(source, /render=\{<SidebarMenuButton \/>\}/)
+  assert.match(source, /<DropdownMenuContent[\s\S]*side="right"/)
+  assert.match(source, /<DropdownMenuGroup>[\s\S]*<DropdownMenuLabel/)
+})
diff --git a/web/components/nav-main.tsx b/web/components/nav-main.tsx
index fc970e1..312b614 100644
--- a/web/components/nav-main.tsx
+++ b/web/components/nav-main.tsx
@@ -15,6 +15,14 @@ import {
   CollapsibleContent,
   CollapsibleTrigger,
 } from "@/components/ui/collapsible"
+import {
+  DropdownMenu,
+  DropdownMenuContent,
+  DropdownMenuGroup,
+  DropdownMenuItem,
+  DropdownMenuLabel,
+  DropdownMenuTrigger,
+} from "@/components/ui/dropdown-menu"
 import {
   SidebarGroup,
   SidebarMenu,
@@ -23,6 +31,7 @@ import {
   SidebarMenuSub,
   SidebarMenuSubButton,
   SidebarMenuSubItem,
+  useSidebar,
 } from "@/components/ui/sidebar"
 
 export function NavMain({
@@ -41,6 +50,7 @@ export function NavMain({
   }>
 }) {
   const pathname = usePathname()
+  const { isMobile, state } = useSidebar()
   const storageKey = getDashboardNavSectionStorageKey(sectionKey)
   const [open, setOpen] = useState(() => {
     if (typeof window === "undefined") {
@@ -54,6 +64,49 @@ export function NavMain({
     window.localStorage.setItem(storageKey, String(nextOpen))
   }
 
+  if (state === "collapsed" && !isMobile) {
+    return (
+      <SidebarGroup className="px-2 py-0 first:pt-2 last:pb-2">
+        <SidebarMenu>
+          <SidebarMenuItem>
+            <DropdownMenu>
+              <DropdownMenuTrigger
+                openOnHover
+                render={<SidebarMenuButton />}
+              >
+                {icon}
+                <span title={title}>{title}</span>
+              </DropdownMenuTrigger>
+              <DropdownMenuContent
+                side="right"
+                align="start"
+                sideOffset={8}
+                className="w-56"
+              >
+                <DropdownMenuGroup>
+                  <DropdownMenuLabel className="truncate" title={title}>
+                    {title}
+                  </DropdownMenuLabel>
+                  {items.map((item) => (
+                    <DropdownMenuItem
+                      key={item.title}
+                      render={<Link href={item.url} />}
+                      className="cursor-pointer"
+                    >
+                      <span className="truncate" title={item.title}>
+                        {item.title}
+                      </span>
+                    </DropdownMenuItem>
+                  ))}
+                </DropdownMenuGroup>
+              </DropdownMenuContent>
+            </DropdownMenu>
+          </SidebarMenuItem>
+        </SidebarMenu>
+      </SidebarGroup>
+    )
+  }
+
   return (
     <SidebarGroup className="px-2 py-0 first:pt-2 last:pb-2">
       <SidebarMenu>