diff --git a/studio/frontend/src/components/app-sidebar.tsx b/studio/frontend/src/components/app-sidebar.tsx
index f1a200b09..faa98abee 100644
--- a/studio/frontend/src/components/app-sidebar.tsx
+++ b/studio/frontend/src/components/app-sidebar.tsx
@@ -1099,7 +1099,7 @@ export function AppSidebar() {
                 side="top"
                 align="center"
                 sideOffset={8}
-                className="app-user-menu menu-soft-surface-up ring-0 w-[16rem] px-1.5 py-2.5 font-heading rounded-[20px] border-0"
+                className="app-user-menu menu-soft-surface-up ring-0 w-[16rem] px-2.5 py-2.5 font-heading rounded-[20px] border-0"
               >
                 <DropdownMenuGroup>
                   <DropdownMenuItem
diff --git a/studio/frontend/src/components/ui/dropdown-menu.tsx b/studio/frontend/src/components/ui/dropdown-menu.tsx
index a39651d93..ace3755a9 100644
--- a/studio/frontend/src/components/ui/dropdown-menu.tsx
+++ b/studio/frontend/src/components/ui/dropdown-menu.tsx
@@ -81,7 +81,7 @@ function DropdownMenuItem({
       data-inset={inset}
       data-variant={variant}
       className={cn(
-        "focus:bg-accent focus:text-accent-foreground data-[variant=destructive]:text-destructive data-[variant=destructive]:focus:bg-destructive/10 dark:data-[variant=destructive]:focus:bg-destructive/20 data-[variant=destructive]:focus:text-destructive data-[variant=destructive]:*:[svg]:text-destructive not-data-[variant=destructive]:focus:**:text-accent-foreground gap-2.5 rounded-full px-3 py-2 text-sm [&_svg:not([class*='size-'])]:size-4 group/dropdown-menu-item relative flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 data-[inset]:pl-8 [&_svg]:pointer-events-none [&_svg]:shrink-0",
+        "focus:bg-accent focus:text-accent-foreground data-[variant=destructive]:text-destructive data-[variant=destructive]:focus:bg-destructive/10 dark:data-[variant=destructive]:focus:bg-destructive/20 data-[variant=destructive]:focus:text-destructive data-[variant=destructive]:*:[svg]:text-destructive not-data-[variant=destructive]:focus:**:text-accent-foreground gap-2.5 rounded-[11px] px-3 py-2 text-sm [&_svg:not([class*='size-'])]:size-4 group/dropdown-menu-item relative flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 data-[inset]:pl-8 [&_svg]:pointer-events-none [&_svg]:shrink-0",
         className,
       )}
       {...props}
@@ -99,7 +99,7 @@ function DropdownMenuCheckboxItem({
     <DropdownMenuPrimitive.CheckboxItem
       data-slot="dropdown-menu-checkbox-item"
       className={cn(
-        "focus:bg-accent focus:text-accent-foreground focus:**:text-accent-foreground gap-2.5 rounded-full py-2 pr-8 pl-3 text-sm [&_svg:not([class*='size-'])]:size-4 relative flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 [&_svg]:pointer-events-none [&_svg]:shrink-0",
+        "focus:bg-accent focus:text-accent-foreground focus:**:text-accent-foreground gap-2.5 rounded-[11px] py-2 pr-8 pl-3 text-sm [&_svg:not([class*='size-'])]:size-4 relative flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 [&_svg]:pointer-events-none [&_svg]:shrink-0",
         className,
       )}
       checked={checked}
@@ -138,7 +138,7 @@ function DropdownMenuRadioItem({
     <DropdownMenuPrimitive.RadioItem
       data-slot="dropdown-menu-radio-item"
       className={cn(
-        "focus:bg-accent focus:text-accent-foreground focus:**:text-accent-foreground gap-2.5 rounded-full py-2 pr-8 pl-3 text-sm [&_svg:not([class*='size-'])]:size-4 relative flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 [&_svg]:pointer-events-none [&_svg]:shrink-0",
+        "focus:bg-accent focus:text-accent-foreground focus:**:text-accent-foreground gap-2.5 rounded-[11px] py-2 pr-8 pl-3 text-sm [&_svg:not([class*='size-'])]:size-4 relative flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 [&_svg]:pointer-events-none [&_svg]:shrink-0",
         className,
       )}
       {...props}
@@ -224,7 +224,7 @@ function DropdownMenuSubTrigger({
       data-slot="dropdown-menu-sub-trigger"
       data-inset={inset}
       className={cn(
-        "focus:bg-accent focus:text-accent-foreground data-open:bg-accent data-open:text-accent-foreground not-data-[variant=destructive]:focus:**:text-accent-foreground gap-2 rounded-full px-3 py-2 text-sm [&_svg:not([class*='size-'])]:size-4 flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 data-[inset]:pl-8 [&_svg]:pointer-events-none [&_svg]:shrink-0",
+        "focus:bg-accent focus:text-accent-foreground data-open:bg-accent data-open:text-accent-foreground not-data-[variant=destructive]:focus:**:text-accent-foreground gap-2 rounded-[11px] px-3 py-2 text-sm [&_svg:not([class*='size-'])]:size-4 flex cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 data-[inset]:pl-8 [&_svg]:pointer-events-none [&_svg]:shrink-0",
         className,
       )}
       {...props}
diff --git a/studio/frontend/src/components/ui/select.tsx b/studio/frontend/src/components/ui/select.tsx
index 0ec21850a..bb8e6e4e6 100644
--- a/studio/frontend/src/components/ui/select.tsx
+++ b/studio/frontend/src/components/ui/select.tsx
@@ -173,7 +173,7 @@ function SelectItem({
     <SelectPrimitive.Item
       data-slot="select-item"
       className={cn(
-        "focus:bg-accent focus:text-accent-foreground not-data-[variant=destructive]:focus:**:text-accent-foreground gap-2.5 rounded-full py-2 pr-8 pl-3 text-sm [&_svg:not([class*='size-'])]:size-4 *:[span]:last:flex *:[span]:last:items-center *:[span]:last:gap-2 relative flex w-full cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 [&_svg]:pointer-events-none [&_svg]:shrink-0",
+        "focus:bg-accent focus:text-accent-foreground not-data-[variant=destructive]:focus:**:text-accent-foreground gap-2.5 rounded-[11px] py-2 pr-8 pl-3 text-sm [&_svg:not([class*='size-'])]:size-4 *:[span]:last:flex *:[span]:last:items-center *:[span]:last:gap-2 relative flex w-full cursor-pointer items-center outline-hidden select-none data-[disabled]:pointer-events-none data-[disabled]:opacity-50 [&_svg]:pointer-events-none [&_svg]:shrink-0",
         className,
       )}
       {...props}
diff --git a/studio/frontend/src/index.css b/studio/frontend/src/index.css
index 9e394a31e..ecc0e0aeb 100644
--- a/studio/frontend/src/index.css
+++ b/studio/frontend/src/index.css
@@ -779,7 +779,7 @@
 		height: 36px;
 		padding: 0 0.75rem !important;
 		gap: 9.5px !important;
-		border-radius: 9999px;
+		border-radius: 12px;
 		font-weight: 500;
 		font-size: 15px;
 		line-height: 20px;
@@ -1294,18 +1294,33 @@
 
 	/* Soft elevation; [data-slot] outranks the component ring-1, dropping the border. */
 	.unsloth-plus-menu[data-slot] {
-		/* Pin radius so dark matches light (rounded-lg resolves smaller in dark).
+		/* Concentric with the item hover boxes, like Gemini: container radius =
+		   item radius (12px) + side gutter (10px), so the curves run parallel.
 		   !important beats the global 14px dropdown radius. */
-		border-radius: 18px !important;
+		border-radius: 22px !important;
 		padding-top: 0.5rem;
 		padding-bottom: 0.5rem;
+		/* Side gutter so item hover boxes sit inset from the menu edge, like
+		   Gemini's menus (more breathing room than a hairline gutter). */
+		padding-left: 10px;
+		padding-right: 10px;
 		box-shadow: 0 2px 8px -2px rgba(0, 0, 0, 0.16);
 	}
 
-	/* MCP menu is wider (232px), so nudge the radius up so it reads as round as
-	   the narrower + menu (18 * 232/212 ~= 20px). */
+	/* Width does not change the concentric radius; the MCP menu uses the same
+	   item radius + gutter, so it keeps the same container radius. */
 	.unsloth-plus-menu.mcp-menu[data-slot] {
-		border-radius: 20px !important;
+		border-radius: 22px !important;
+	}
+
+	/* One-line menus (a single item, e.g. "All saved prompts…" with nothing
+	   pinned, or a lone "Export as Markdown") read as fully rounded pills. */
+	.unsloth-plus-menu[data-slot]:not(:has(> :nth-child(2))) {
+		border-radius: 9999px !important;
+	}
+	.unsloth-plus-menu[data-slot]:not(:has(> :nth-child(2)))
+		:is([data-slot="dropdown-menu-item"], [data-slot="dropdown-menu-sub-trigger"]) {
+		border-radius: 9999px;
 	}
 
 	.dark .unsloth-plus-menu[data-slot] {
@@ -1319,14 +1334,15 @@
 			[data-slot="dropdown-menu-item"],
 			[data-slot="dropdown-menu-sub-trigger"]
 		) {
-		@apply gap-3 pl-4 pr-3 py-2 text-[14px];
+		@apply gap-3 pl-3 pr-3 py-2 text-[14px];
 		cursor: pointer;
-		/* Pin hover-box radius so dark matches light (same as the container). */
-		border-radius: 1.1rem;
+		/* Pin hover-box radius so dark matches light (container radius minus the
+		   side gutter keeps the curves concentric). */
+		border-radius: 12px;
 	}
 
 	.unsloth-plus-menu [data-slot="dropdown-menu-label"] {
-		@apply pl-4 pr-3 py-1.5 text-[12px];
+		@apply pl-3 pr-3 py-1.5 text-[12px];
 	}
 
 	/* Active (green) items keep their primary text and icon color on hover. */
@@ -1370,8 +1386,8 @@
 			[data-slot="dropdown-menu-sub-trigger"]
 		)
 		svg {
-		width: 1.05rem;
-		height: 1.05rem;
+		width: 1.15rem;
+		height: 1.15rem;
 	}
 
 	/* Destructive items keep red text and a red-tinted hover, not the grey one. */