diff --git a/packages/ui/src/components/session/sidebar/SessionNodeItem.tsx b/packages/ui/src/components/session/sidebar/SessionNodeItem.tsx
index f90e9d31..377c37e5 100644
--- a/packages/ui/src/components/session/sidebar/SessionNodeItem.tsx
+++ b/packages/ui/src/components/session/sidebar/SessionNodeItem.tsx
@@ -130,6 +130,30 @@ const treeContainsSessionId = (node: SessionNode, sessionId: string | null): boo
   return false;
 };
 
+const treeContainsMenuKey = (
+  node: SessionNode,
+  menuKey: string | null,
+  renderContext: 'project' | 'recent',
+  archivedBucket: boolean,
+): boolean => {
+  if (!menuKey) {
+    return false;
+  }
+
+  const nodeMenuKey = `${renderContext}:${archivedBucket ? 'archived' : 'active'}:${node.session.id}`;
+  if (nodeMenuKey === menuKey) {
+    return true;
+  }
+
+  for (const child of node.children) {
+    if (treeContainsMenuKey(child, menuKey, renderContext, archivedBucket)) {
+      return true;
+    }
+  }
+
+  return false;
+};
+
 const areEqual = (prev: Props, next: Props): boolean => {
   const prevSession = prev.node.session;
   const nextSession = next.node.session;
@@ -159,9 +183,9 @@ const areEqual = (prev: Props, next: Props): boolean => {
   if (prev.editTitle !== next.editTitle && ((prev.editingId === prevSessionId) || (next.editingId === nextSessionId))) return false;
   if ((prev.copiedSessionId === prevSessionId) !== (next.copiedSessionId === nextSessionId)) return false;
 
-  const prevMenuKey = `${prev.renderContext ?? 'project'}:${prev.archivedBucket ? 'archived' : 'active'}:${prevSessionId}`;
-  const nextMenuKey = `${next.renderContext ?? 'project'}:${next.archivedBucket ? 'archived' : 'active'}:${nextSessionId}`;
-  if ((prev.openSidebarMenuKey === prevMenuKey) !== (next.openSidebarMenuKey === nextMenuKey)) return false;
+  const prevMenuInTree = treeContainsMenuKey(prev.node, prev.openSidebarMenuKey, prev.renderContext ?? 'project', prev.archivedBucket ?? false);
+  const nextMenuInTree = treeContainsMenuKey(next.node, next.openSidebarMenuKey, next.renderContext ?? 'project', next.archivedBucket ?? false);
+  if (prevMenuInTree !== nextMenuInTree) return false;
 
   const prevDirectory = normalizePath((prevSession as Session & { directory?: string | null }).directory ?? null)
     ?? normalizePath(prev.groupDirectory ?? null);
@@ -426,6 +450,18 @@ function SessionNodeItemComponent(props: Props): React.ReactNode {
   };
 
   const handleMenuTriggerClick = (event: React.MouseEvent<HTMLButtonElement>) => {
+    event.preventDefault();
+    event.stopPropagation();
+    setOpenSidebarMenuKey(isMenuOpen ? null : menuInstanceKey);
+  };
+
+  const handleMenuTriggerPointerDown = (event: React.PointerEvent<HTMLButtonElement>) => {
+    event.preventDefault();
+    event.stopPropagation();
+  };
+
+  const handleMenuTriggerMouseDown = (event: React.MouseEvent<HTMLButtonElement>) => {
+    event.preventDefault();
     event.stopPropagation();
   };
 
@@ -568,7 +604,7 @@ function SessionNodeItemComponent(props: Props): React.ReactNode {
                       'flex min-w-0 flex-1 cursor-pointer flex-col gap-0 overflow-hidden rounded-sm text-left focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50 text-foreground select-none disabled:cursor-not-allowed transition-[padding]',
                       mobileVariant
                         ? (isVSCode ? revealPaddingClass : 'pr-7')
-                        : '',
+                        : revealPaddingClass,
                     )}
                   >
                     <div className={cn('flex w-full items-center min-w-0 flex-1 overflow-hidden', isMinimalMode ? 'gap-1' : 'gap-1')}>
@@ -585,25 +621,6 @@ function SessionNodeItemComponent(props: Props): React.ReactNode {
                           )}>
                             {sessionCompactUpdatedLabel}
                           </span>
-                          <DropdownMenu open={isMenuOpen} onOpenChange={handleMenuOpenChange}>
-                            <DropdownMenuTrigger asChild>
-                              <button
-                                type="button"
-                                className={cn(
-                                  'absolute inset-y-0 right-0 inline-flex h-4 w-4 items-center justify-center rounded-md text-muted-foreground hover:text-foreground focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50 transition-opacity',
-                                  isMenuOpen
-                                    ? 'opacity-100 pointer-events-auto'
-                                    : cn('opacity-0 pointer-events-none', revealOnHoverClass),
-                                )}
-                                aria-label="Session menu"
-                                onClick={handleMenuTriggerClick}
-                                onKeyDown={(event) => event.stopPropagation()}
-                              >
-                                <RiMore2Line className="h-2.5 w-2.5" />
-                              </button>
-                            </DropdownMenuTrigger>
-                            {sessionMenuContent}
-                          </DropdownMenu>
                         </div>
                       ) : null}
                       {pendingPermissionCount > 0 ? (
@@ -683,41 +700,38 @@ function SessionNodeItemComponent(props: Props): React.ReactNode {
             </div>
           ) : null}
 
-          {!isMinimalMode || mobileVariant ? (
-            <div className={cn(
-              'absolute right-0 top-1/2 z-10 -translate-y-1/2',
-              cn(
-                'transition-opacity',
-                isMenuOpen
-                  ? 'opacity-100 pointer-events-auto'
-                  : (mobileVariant && !isVSCode)
-                    ? 'opacity-100 pointer-events-auto'
-                    : cn('opacity-0 pointer-events-none', revealOnHoverClass),
-              ),
-            )}>
-              <DropdownMenu open={isMenuOpen} onOpenChange={handleMenuOpenChange}>
-                <DropdownMenuTrigger asChild>
-                  <button
-                    type="button"
-                    className={cn(
-                      'inline-flex items-center justify-center rounded-md text-muted-foreground hover:text-foreground focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50 transition-opacity',
-                      isMinimalMode && !mobileVariant
-                        ? (isMenuOpen
-                            ? 'h-4 w-4 opacity-100 pointer-events-auto'
-                            : cn('h-4 w-4 opacity-0 pointer-events-none', revealOnHoverClass))
-                        : 'h-6 w-6 opacity-100',
-                    )}
-                    aria-label="Session menu"
-                    onClick={handleMenuTriggerClick}
-                    onKeyDown={(event) => event.stopPropagation()}
-                    >
-                      <RiMore2Line className={cn(isMinimalMode && !mobileVariant ? 'h-2.5 w-2.5' : 'h-3.5 w-3.5')} />
-                  </button>
-                </DropdownMenuTrigger>
-                {sessionMenuContent}
-                </DropdownMenu>
-              </div>
-            ) : null}
+          <div className={cn(
+            'absolute right-0 top-1/2 z-10 -translate-y-1/2 transition-opacity',
+            isMenuOpen
+              ? 'opacity-100'
+              : (mobileVariant && !isVSCode)
+                ? 'opacity-100'
+                : cn('opacity-0', revealOnHoverClass),
+          )}>
+            <DropdownMenu open={isMenuOpen} onOpenChange={handleMenuOpenChange}>
+              <DropdownMenuTrigger asChild>
+                <button
+                  type="button"
+                  className={cn(
+                    'inline-flex items-center justify-center rounded-md text-muted-foreground hover:text-foreground focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-primary/50 transition-opacity',
+                    isMinimalMode && !mobileVariant
+                      ? (isMenuOpen
+                          ? 'h-4 w-4 opacity-100'
+                          : cn('h-4 w-4 opacity-0', revealOnHoverClass))
+                      : 'h-6 w-6 opacity-100',
+                  )}
+                  aria-label="Session menu"
+                  onPointerDown={handleMenuTriggerPointerDown}
+                  onMouseDown={handleMenuTriggerMouseDown}
+                  onClick={handleMenuTriggerClick}
+                  onKeyDown={(event) => event.stopPropagation()}
+                >
+                  <RiMore2Line className={cn(isMinimalMode && !mobileVariant ? 'h-2.5 w-2.5' : 'h-3.5 w-3.5')} />
+                </button>
+              </DropdownMenuTrigger>
+              {sessionMenuContent}
+            </DropdownMenu>
+          </div>
         </div>
       </DraggableSessionRow>
       {hasChildren && isExpanded
diff --git a/packages/ui/src/components/session/sidebar/sortableItems.tsx b/packages/ui/src/components/session/sidebar/sortableItems.tsx
index 46f6c383..d4fff7eb 100644
--- a/packages/ui/src/components/session/sidebar/sortableItems.tsx
+++ b/packages/ui/src/components/session/sidebar/sortableItems.tsx
@@ -118,6 +118,14 @@ export const SortableProjectItem: React.FC<SortableProjectItemProps> = ({
     event.stopPropagation();
   }, []);
 
+  const handleMenuTriggerPointerDown = React.useCallback((event: React.PointerEvent<HTMLButtonElement>) => {
+    event.stopPropagation();
+  }, []);
+
+  const handleMenuTriggerMouseDown = React.useCallback((event: React.MouseEvent<HTMLButtonElement>) => {
+    event.stopPropagation();
+  }, []);
+
   const handleToggleMouseDown = React.useCallback((event: React.MouseEvent<HTMLButtonElement>) => {
     if (event.button === 2 || (event.button === 0 && event.ctrlKey)) {
       suppressNextToggleRef.current = true;
@@ -250,6 +258,8 @@ export const SortableProjectItem: React.FC<SortableProjectItemProps> = ({
                               : 'opacity-0 pointer-events-none group-hover/project:opacity-100 group-hover/project:pointer-events-auto group-focus-within/project:opacity-100 group-focus-within/project:pointer-events-auto',
                         )}
                         aria-label="Project menu"
+                        onPointerDown={handleMenuTriggerPointerDown}
+                        onMouseDown={handleMenuTriggerMouseDown}
                         onClick={handleMenuTriggerClick}
                       >
                         <RiMore2Line className="h-3.5 w-3.5" />