diff --git a/frontend/src/components/layout/Sidebar.tsx b/frontend/src/components/layout/Sidebar.tsx
index f9454632..a6b69c36 100644
--- a/frontend/src/components/layout/Sidebar.tsx
+++ b/frontend/src/components/layout/Sidebar.tsx
@@ -2,10 +2,10 @@ import { useCallback, useEffect, useRef, useState, type PointerEvent as ReactPoi
 import { Link, useLocation } from 'react-router-dom'
 import type { LucideIcon } from 'lucide-react'
 import {
-  LayoutGrid, Clock, AlertTriangle, GitBranch, Layers, Code2, Wand2,
-  ListChecks, Download, BarChart3, Rocket,
+  LayoutGrid, Clock, AlertTriangle, GitBranch, Code2, Wand2,
+  ListChecks, Download, BarChart3,
   Settings, Pin, PinOff,
-  Zap, Database, HelpCircle,
+  Plus, History, FileText,
 } from 'lucide-react'
 import { cn } from '@/lib/utils'
 import { useUserPreferencesStore } from '@/store/userPreferencesStore'
@@ -71,44 +71,40 @@ export function Sidebar() {
       matchPaths: ['/'],
     },
     {
-      href: '/sessions', icon: Zap, label: 'Work', shortLabel: 'Work',
-      badge: (stats?.active_count || 0) + (stats?.escalation_count || 0) || undefined,
+      href: '/sessions', icon: History, label: 'History', shortLabel: 'History',
+      badge: stats?.active_count || undefined,
       matchPaths: ['/sessions', '/escalations', '/pilot'],
       children: [
-        { href: '/sessions', label: 'Active Sessions', count: stats?.active_count || undefined },
+        { href: '/sessions', label: 'Session History', count: stats?.active_count || undefined },
         { href: '/escalations', label: 'Escalations', count: stats?.escalation_count || undefined },
       ],
     },
     {
-      href: '/trees', icon: Database, label: 'Knowledge', shortLabel: 'Know',
+      href: '/trees', icon: GitBranch, label: 'Flows', shortLabel: 'Flows',
       badge: stats?.tree_counts.total || undefined,
-      matchPaths: ['/trees', '/flows', '/my-trees', '/step-library', '/scripts', '/script-builder', '/review-queue'],
+      matchPaths: ['/trees', '/flows', '/my-trees', '/step-library', '/review-queue'],
       children: [
-        { href: '/trees', label: 'All Flows', count: stats?.tree_counts.total || undefined },
+        { href: '/trees', label: 'Guided Flows', count: stats?.tree_counts.total || undefined },
         { href: '/trees?type=troubleshooting', label: 'Troubleshooting', count: stats?.tree_counts.troubleshooting || undefined },
         { href: '/trees?type=procedural', label: 'Projects', count: stats?.tree_counts.procedural || undefined },
-        { href: '/trees?type=maintenance', label: 'Maintenance', count: stats?.tree_counts.maintenance || undefined },
         { href: '/step-library', label: 'Step Library' },
-        { href: '/scripts', label: 'Scripts' },
-        { href: '/script-builder', label: 'Script Builder' },
         { href: '/review-queue', label: 'Review Queue' },
       ],
     },
+    {
+      href: '/scripts', icon: FileText, label: 'Scripts', shortLabel: 'Scripts',
+      matchPaths: ['/scripts', '/script-builder'],
+      children: [
+        { href: '/scripts', label: 'Script Library' },
+        { href: '/script-builder', label: 'Script Builder' },
+      ],
+    },
     {
       href: '/analytics', icon: BarChart3, label: 'Insights', shortLabel: 'Data',
       matchPaths: ['/analytics', '/shares'],
       children: [
-        { href: '/shares', label: 'Exports' },
         { href: '/analytics', label: 'Analytics' },
-        { href: '/analytics/flowpilot', label: 'FlowPilot Analytics' },
-      ],
-    },
-    {
-      href: '/guides', icon: HelpCircle, label: 'Help', shortLabel: 'Help',
-      matchPaths: ['/guides', '/feedback'],
-      children: [
-        { href: '/guides', label: 'User Guides' },
-        { href: '/feedback', label: 'Feedback' },
+        { href: '/shares', label: 'Exports' },
       ],
     },
   ]
@@ -119,7 +115,7 @@ export function Sidebar() {
       title: 'RESOLVE',
       items: [
         { href: '/', icon: LayoutGrid, label: 'Dashboard', shortLabel: 'Dash' },
-        { href: '/sessions', icon: Clock, label: 'Active Sessions', shortLabel: 'Sessions', badge: stats?.active_count || undefined, matchPaths: ['/sessions'] },
+        { href: '/sessions', icon: Clock, label: 'Session History', shortLabel: 'History', badge: stats?.active_count || undefined, matchPaths: ['/sessions'] },
         { href: '/escalations', icon: AlertTriangle, label: 'Escalations', shortLabel: 'Escal', badge: stats?.escalation_count || undefined },
       ],
     },
@@ -127,17 +123,15 @@ export function Sidebar() {
       title: 'KNOWLEDGE',
       items: [
         {
-          href: '/trees', icon: GitBranch, label: 'Flows', shortLabel: 'Flows',
+          href: '/trees', icon: GitBranch, label: 'Guided Flows', shortLabel: 'Flows',
           badge: stats?.tree_counts.total || undefined,
           matchPaths: ['/trees', '/flows', '/my-trees'],
           children: [
             { href: '/trees', label: 'All Flows' },
             { href: '/trees?type=troubleshooting', label: 'Troubleshooting', count: stats?.tree_counts.troubleshooting || undefined },
             { href: '/trees?type=procedural', label: 'Projects', count: stats?.tree_counts.procedural || undefined },
-            { href: '/trees?type=maintenance', label: 'Maintenance', count: stats?.tree_counts.maintenance || undefined },
           ],
         },
-        { href: '/step-library', icon: Layers, label: 'Step Library', shortLabel: 'Steps' },
         { href: '/scripts', icon: Code2, label: 'Scripts', shortLabel: 'Scripts' },
         { href: '/script-builder', icon: Wand2, label: 'Script Builder', shortLabel: 'Builder' },
         { href: '/review-queue', icon: ListChecks, label: 'Review Queue', shortLabel: 'Review' },
@@ -146,9 +140,8 @@ export function Sidebar() {
     {
       title: 'INSIGHTS',
       items: [
-        { href: '/shares', icon: Download, label: 'Exports', shortLabel: 'Export' },
         { href: '/analytics', icon: BarChart3, label: 'Analytics', shortLabel: 'Stats' },
-        { href: '/analytics/flowpilot', icon: Rocket, label: 'FlowPilot Analytics', shortLabel: 'FPilot' },
+        { href: '/shares', icon: Download, label: 'Exports', shortLabel: 'Export' },
       ],
     },
   ]
@@ -370,6 +363,17 @@ export function Sidebar() {
         style={{ background: 'var(--color-bg-sidebar)', borderRight: '1px solid var(--color-border-default)' }}
         onWheel={handleWheel}
       >
+        {/* New Session button */}
+        <div className="px-3 pt-3 pb-1">
+          <Link
+            to="/"
+            className="flex items-center justify-center gap-2 w-full rounded-lg bg-primary/15 py-2.5 text-sm font-semibold text-primary hover:bg-primary/25 transition-colors"
+          >
+            <Plus size={16} strokeWidth={2} />
+            New Session
+          </Link>
+        </div>
+
         {/* Pinned sidebar content */}
         <div className="px-3 py-2 space-y-0.5">
           {sections.map((section, si) => (
@@ -416,8 +420,20 @@ export function Sidebar() {
         style={{ background: 'var(--color-bg-sidebar)', borderRight: '1px solid var(--color-border-default)', width: '72px' }}
         onWheel={handleWheel}
       >
-        {/* Grouped nav items */}
-        <div className="flex flex-col items-center w-full px-1 pt-4 space-y-1.5">
+        {/* New Session button */}
+        <div className="w-full px-2 pt-4 pb-2">
+          <Link
+            to="/"
+            className="flex flex-col items-center justify-center w-full rounded-lg bg-primary/15 py-2.5 text-primary hover:bg-primary/25 transition-colors"
+            title="New Session"
+          >
+            <Plus size={20} strokeWidth={2} />
+            <span className="mt-1 text-[0.5625rem] font-sans font-semibold">New</span>
+          </Link>
+        </div>
+
+        {/* Nav items */}
+        <div className="flex flex-col items-center w-full px-1 space-y-1.5">
           {railGroups.map((item, i) => renderRailItem(item, `rail-${i}`))}
         </div>