diff --git a/src-web/components/ResponsePane.tsx b/src-web/components/ResponsePane.tsx
index 8716e7e9..b40a7c49 100644
--- a/src-web/components/ResponsePane.tsx
+++ b/src-web/components/ResponsePane.tsx
@@ -76,7 +76,7 @@ export const ResponsePane = memo(function ResponsePane({ className }: Props) {
                       label: viewMode === 'pretty' ? 'View Raw' : 'View Prettified',
                       onSelect: toggleViewMode,
                     },
-                    '-----',
+                    { type: 'separator' },
                     {
                       label: 'Clear Response',
                       onSelect: deleteResponse.mutate,
@@ -88,7 +88,7 @@ export const ResponsePane = memo(function ResponsePane({ className }: Props) {
                       hidden: responses.length <= 1,
                       disabled: responses.length === 0,
                     },
-                    '-----',
+                    { type: 'separator' },
                     ...responses.slice(0, 10).map((r) => ({
                       label: r.status + ' - ' + r.elapsed + ' ms',
                       leftSlot: activeResponse?.id === r.id ? <Icon icon="check" /> : <></>,
diff --git a/src-web/components/Sidebar.tsx b/src-web/components/Sidebar.tsx
index 378b09e8..b048824f 100644
--- a/src-web/components/Sidebar.tsx
+++ b/src-web/components/Sidebar.tsx
@@ -74,7 +74,6 @@ export const Sidebar = memo(function Sidebar({ className }: Props) {
   );
 
   const sidebarStyles = useMemo(() => ({ width: width.value }), [width.value]);
-  const sidebarWidth = width.value - 1; // Minus 1 for the border
 
   return (
     <div className="relative">
@@ -89,6 +88,7 @@ export const Sidebar = memo(function Sidebar({ className }: Props) {
       >
         <HStack as={WindowDragRegion} alignItems="center" justifyContent="end">
           <IconButton
+            size="sm"
             title="Add Request"
             className="mx-1"
             icon="plusCircle"
@@ -101,12 +101,8 @@ export const Sidebar = memo(function Sidebar({ className }: Props) {
             }}
           />
         </HStack>
-        <VStack as="ul" className="relative py-3" draggable={false}>
-          <SidebarItems
-            sidebarWidth={sidebarWidth}
-            activeRequestId={activeRequest?.id}
-            requests={requests}
-          />
+        <VStack as="ul" className="relative py-3 overflow-auto" draggable={false}>
+          <SidebarItems activeRequestId={activeRequest?.id} requests={requests} />
         </VStack>
         <HStack className="mx-1 pb-1" alignItems="center" justifyContent="end">
           <ToggleThemeButton />
@@ -119,11 +115,9 @@ export const Sidebar = memo(function Sidebar({ className }: Props) {
 function SidebarItems({
   requests,
   activeRequestId,
-  sidebarWidth,
 }: {
   requests: HttpRequest[];
   activeRequestId?: string;
-  sidebarWidth: number;
 }) {
   const [hoveredIndex, setHoveredIndex] = useState<number | null>(null);
   const updateRequest = useUpdateAnyRequest();
@@ -178,7 +172,6 @@ function SidebarItems({
             requestName={r.name}
             workspaceId={r.workspaceId}
             active={r.id === activeRequestId}
-            sidebarWidth={sidebarWidth}
             onMove={handleMove}
             onEnd={handleEnd}
           />
@@ -194,12 +187,11 @@ type SidebarItemProps = {
   requestId: string;
   requestName: string;
   workspaceId: string;
-  sidebarWidth: number;
   active?: boolean;
 };
 
 const _SidebarItem = forwardRef(function SidebarItem(
-  { className, requestName, requestId, workspaceId, active, sidebarWidth }: SidebarItemProps,
+  { className, requestName, requestId, workspaceId, active }: SidebarItemProps,
   ref: ForwardedRef<HTMLLIElement>,
 ) {
   const updateRequest = useUpdateRequest(requestId);
@@ -215,7 +207,6 @@ const _SidebarItem = forwardRef(function SidebarItem(
     el?.select();
   }, []);
 
-  const itemStyles = useMemo(() => ({ width: sidebarWidth }), [sidebarWidth]);
   const handleKeyDown = useCallback(
     (e: KeyboardEvent<HTMLElement>) => {
       // Hitting enter on active request during keyboard nav will start edit
@@ -242,12 +233,8 @@ const _SidebarItem = forwardRef(function SidebarItem(
   );
 
   return (
-    <li
-      ref={ref}
-      className={classnames(className, 'block group/item px-2 pb-0.5')}
-      style={itemStyles}
-    >
-      <div className="relative w-full">
+    <li ref={ref} className={classnames(className, 'block group/item px-2 pb-0.5')}>
+      <div className="relative">
         <Button
           color="custom"
           size="sm"
@@ -258,7 +245,6 @@ const _SidebarItem = forwardRef(function SidebarItem(
           justify="start"
           onKeyDown={handleKeyDown}
           className={classnames(
-            'w-full',
             editing && 'focus-within:border-focus',
             active
               ? 'bg-highlight text-gray-900'
@@ -315,7 +301,6 @@ const DraggableSidebarItem = memo(function DraggableSidebarItem({
   requestId,
   workspaceId,
   active,
-  sidebarWidth,
   onMove,
   onEnd,
 }: DraggableSidebarItemProps) {
@@ -358,7 +343,6 @@ const DraggableSidebarItem = memo(function DraggableSidebarItem({
       requestId={requestId}
       workspaceId={workspaceId}
       active={active}
-      sidebarWidth={sidebarWidth}
     />
   );
 });
diff --git a/src-web/components/WorkspaceDropdown.tsx b/src-web/components/WorkspaceDropdown.tsx
index cb6a90f7..f08246f7 100644
--- a/src-web/components/WorkspaceDropdown.tsx
+++ b/src-web/components/WorkspaceDropdown.tsx
@@ -1,8 +1,6 @@
 import classnames from 'classnames';
 import { memo, useMemo } from 'react';
-import { act } from 'react-dom/test-utils';
 import { useActiveWorkspace } from '../hooks/useActiveWorkspace';
-import { useActiveWorkspaceId } from '../hooks/useActiveWorkspaceId';
 import { useCreateWorkspace } from '../hooks/useCreateWorkspace';
 import { useDeleteWorkspace } from '../hooks/useDeleteWorkspace';
 import { useRoutes } from '../hooks/useRoutes';
@@ -36,17 +34,24 @@ export const WorkspaceDropdown = memo(function WorkspaceDropdown({ className }:
 
     return [
       ...workspaceItems,
-      '-----',
+      {
+        type: 'separator',
+        label: activeWorkspace?.name,
+      },
+      {
+        label: 'Delete',
+        leftSlot: <Icon icon="trash" />,
+        onSelect: () => deleteWorkspace.mutate(),
+      },
+      {
+        type: 'separator',
+        label: 'Actions',
+      },
       {
         label: 'New Workspace',
         leftSlot: <Icon icon="plus" />,
         onSelect: () => createWorkspace.mutate({ name: 'New Workspace' }),
       },
-      {
-        label: 'Delete Workspace',
-        leftSlot: <Icon icon="trash" />,
-        onSelect: () => deleteWorkspace.mutate(),
-      },
     ];
   }, [workspaces, activeWorkspaceId]);
 
diff --git a/src-web/components/core/Dropdown.tsx b/src-web/components/core/Dropdown.tsx
index 02c65763..c01340b4 100644
--- a/src-web/components/core/Dropdown.tsx
+++ b/src-web/components/core/Dropdown.tsx
@@ -8,6 +8,7 @@ import { VStack } from './Stacks';
 
 export type DropdownItem =
   | {
+      type?: 'default';
       label: string;
       disabled?: boolean;
       hidden?: boolean;
@@ -15,7 +16,10 @@ export type DropdownItem =
       rightSlot?: ReactNode;
       onSelect?: () => void;
     }
-  | '-----';
+  | {
+      type: 'separator';
+      label?: string;
+    };
 
 export interface DropdownProps {
   children: ReactElement<HTMLAttributes<HTMLButtonElement>>;
@@ -93,7 +97,7 @@ function Menu({ className, items, onClose, triggerRect }: MenuProps) {
       let nextIndex = (currIndex ?? 0) - 1;
       const maxTries = items.length;
       for (let i = 0; i < maxTries; i++) {
-        if (items[nextIndex] === '-----') {
+        if (items[nextIndex]?.type === 'separator') {
           nextIndex--;
         } else if (nextIndex < 0) {
           nextIndex = items.length - 1;
@@ -110,7 +114,7 @@ function Menu({ className, items, onClose, triggerRect }: MenuProps) {
       let nextIndex = (currIndex ?? -1) + 1;
       const maxTries = items.length;
       for (let i = 0; i < maxTries; i++) {
-        if (items[nextIndex] === '-----') {
+        if (items[nextIndex]?.type === 'separator') {
           nextIndex++;
         } else if (nextIndex >= items.length) {
           nextIndex = 0;
@@ -122,26 +126,29 @@ function Menu({ className, items, onClose, triggerRect }: MenuProps) {
     });
   });
 
-  const containerStyles: CSSProperties = useMemo(() => {
+  const { containerStyles, triangleStyles } = useMemo<{
+    containerStyles: CSSProperties;
+    triangleStyles: CSSProperties;
+  }>(() => {
     const docWidth = document.documentElement.getBoundingClientRect().width;
     const spaceRemaining = docWidth - triggerRect.left;
-    if (spaceRemaining < 200) {
-      return {
-        top: triggerRect?.bottom,
-        right: 0,
-      };
-    }
-    return {
-      top: triggerRect?.bottom,
-      left: triggerRect?.left,
-    };
+    const top = triggerRect?.bottom + 5;
+    const onRight = spaceRemaining < 200;
+    const containerStyles = onRight
+      ? { top, right: docWidth - triggerRect?.right }
+      : { top, left: triggerRect?.left };
+    const size = { top: '-0.2rem', width: '0.4rem', height: '0.4rem' };
+    const triangleStyles = onRight
+      ? { right: triggerRect.width / 2, marginRight: '-0.2rem', ...size }
+      : { left: triggerRect.width / 2, marginLeft: '-0.2rem', ...size };
+    return { containerStyles, triangleStyles };
   }, [triggerRect]);
 
   const handleSelect = useCallback(
     (i: DropdownItem) => {
       onClose();
       setSelectedIndex(null);
-      if (i !== '-----') {
+      if (i.type !== 'separator') {
         i.onSelect?.();
       }
     },
@@ -160,6 +167,11 @@ function Menu({ className, items, onClose, triggerRect }: MenuProps) {
         style={containerStyles}
         className={classnames(className, 'pointer-events-auto fixed z-50')}
       >
+        <span
+          style={triangleStyles}
+          aria-hidden
+          className="bg-gray-50 absolute rotate-45 border-gray-200 border-t border-l"
+        />
         {containerStyles && (
           <VStack
             space={0.5}
@@ -169,11 +181,12 @@ function Menu({ className, items, onClose, triggerRect }: MenuProps) {
             className={classnames(
               className,
               'h-auto bg-gray-50 rounded-md shadow-lg dark:shadow-gray-0 py-1.5 border',
-              'border-gray-200 overflow-auto m-1',
+              'border-gray-200 overflow-auto mb-1 mx-0.5',
             )}
           >
             {items.map((item, i) => {
-              if (item === '-----') return <Separator key={i} className="my-1.5" />;
+              if (item.type === 'separator')
+                return <Separator key={i} className="my-1.5" label={item.label} />;
               if (item.hidden) return null;
               return (
                 <MenuItem
@@ -211,7 +224,7 @@ function MenuItem({ className, focused, item, onSelect, ...props }: MenuItemProp
     [focused],
   );
 
-  if (item === '-----') return <Separator className="my-1.5" />;
+  if (item.type === 'separator') return <Separator className="my-1.5" />;
 
   return (
     <button
diff --git a/src-web/components/core/Separator.tsx b/src-web/components/core/Separator.tsx
index f9578a18..44b58f20 100644
--- a/src-web/components/core/Separator.tsx
+++ b/src-web/components/core/Separator.tsx
@@ -4,19 +4,26 @@ interface Props {
   orientation?: 'horizontal' | 'vertical';
   variant?: 'primary' | 'secondary';
   className?: string;
+  label?: string;
 }
 
-export function Separator({ className, variant = 'primary', orientation = 'horizontal' }: Props) {
+export function Separator({
+  className,
+  variant = 'primary',
+  orientation = 'horizontal',
+  label,
+}: Props) {
   return (
-    <div
-      role="separator"
-      className={classnames(
-        className,
-        variant === 'primary' && 'bg-highlight',
-        variant === 'secondary' && 'bg-highlightSecondary',
-        orientation === 'horizontal' && 'w-full h-[1px]',
-        orientation === 'vertical' && 'h-full w-[1px]',
-      )}
-    />
+    <div role="separator" className={classnames(className, 'flex items-center')}>
+      {label && <div className="text-xs text-gray-500 mx-2 whitespace-nowrap">{label}</div>}
+      <div
+        className={classnames(
+          variant === 'primary' && 'bg-highlight',
+          variant === 'secondary' && 'bg-highlightSecondary',
+          orientation === 'horizontal' && 'w-full h-[1px]',
+          orientation === 'vertical' && 'h-full w-[1px]',
+        )}
+      />
+    </div>
   );
 }
diff --git a/tailwind.config.cjs b/tailwind.config.cjs
index 935ef399..1bd38959 100644
--- a/tailwind.config.cjs
+++ b/tailwind.config.cjs
@@ -10,6 +10,9 @@ module.exports = {
       opacity: {
         "disabled": "0.3"
       },
+      fontSize: {
+        "xs": "0.8rem"
+      },
       height: {
         "xs": "1.5rem",
         "sm": "2.00rem",