diff --git a/src/crate/theme/rtd/crate/static/css/custom.css b/src/crate/theme/rtd/crate/static/css/custom.css
index 5d497f20..f247735c 100644
--- a/src/crate/theme/rtd/crate/static/css/custom.css
+++ b/src/crate/theme/rtd/crate/static/css/custom.css
@@ -1865,3 +1865,4 @@ div.cell_output tbody tr:nth-child(odd):hover,
 div.cell_output tbody tr:nth-child(even):hover {
   background: rgba(66, 165, 245, 0.2);
 }
+
diff --git a/src/crate/theme/rtd/crate/static/css/furo-collapsible-toc.scss b/src/crate/theme/rtd/crate/static/css/furo-collapsible-toc.scss
index 0a7db2f5..468190a6 100644
--- a/src/crate/theme/rtd/crate/static/css/furo-collapsible-toc.scss
+++ b/src/crate/theme/rtd/crate/static/css/furo-collapsible-toc.scss
@@ -2,6 +2,24 @@
  * Furo-Compatible Collapsible Navigation styling for CrateDB Theme
  */
 
+/* TOC section captions */
+ul.toctree.nav p.caption {
+  margin-top: 1.25rem;
+  margin-bottom: 0.25rem;
+  padding-top: 0;
+  padding-bottom: 0;
+  font-size: 13px;  /* Match TOC link size */
+}
+
+/* Caption icons in navigation */
+.caption-icon {
+  width: 14px;
+  height: 14px;
+  margin-right: 6px;
+  vertical-align: -1px;
+  display: inline-block;
+}
+
 .bs-docs-sidenav.sidebar-tree {
   /* Match label height to our link height */
   li.has-children > label {
diff --git a/src/crate/theme/rtd/crate/static/js/custom.js b/src/crate/theme/rtd/crate/static/js/custom.js
index ed542ff7..b69c4095 100644
--- a/src/crate/theme/rtd/crate/static/js/custom.js
+++ b/src/crate/theme/rtd/crate/static/js/custom.js
@@ -160,4 +160,13 @@ document.addEventListener('DOMContentLoaded', () => {
             // If <ul> has children, default behavior (toggle checkbox) applies
         });
     });
+
+    // Mark Overview as current on root page. The overview content lives in
+    // index.md but Sphinx only marks toctree entries as "current" when the
+    // pagename matches. Since the Overview href is rewritten to "#" (self)
+    // on the root page, we detect that and add the current class.
+    document.querySelectorAll('.sidebar-tree .toctree-l1 > a[href="#"]').forEach((a) => {
+        a.classList.add('current');
+        a.closest('li').classList.add('current');
+    });
 });
diff --git a/src/crate/theme/rtd/icons.py b/src/crate/theme/rtd/icons.py
new file mode 100644
index 00000000..5bee8b0d
--- /dev/null
+++ b/src/crate/theme/rtd/icons.py
@@ -0,0 +1,30 @@
+# Caption icons for sidebar navigation (inline SVGs with color accents)
+# Using primary brand color #19c0ea for accent elements
+
+ICON_BUILD = '''<svg class="caption-icon" viewBox="1 4 22 19" fill="none" stroke-width="1.5">
+  <path d="M3 21h18M6 21V12l6-5 6 5v9" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round"/>
+  <path d="M9 21v-6h6v6" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round"/>
+  <rect x="10" y="8" width="4" height="3" rx="0.5" fill="#19c0ea" stroke="#19c0ea"/>
+</svg>'''
+
+ICON_OPERATIONS = '''<svg class="caption-icon" viewBox="0 0 24 24" fill="none" stroke-width="1.5">
+  <rect x="3" y="4" width="18" height="6" rx="1" stroke="currentColor"/>
+  <rect x="3" y="14" width="18" height="6" rx="1" stroke="currentColor"/>
+  <circle cx="7" cy="7" r="1.5" fill="#19c0ea"/>
+  <circle cx="7" cy="17" r="1.5" fill="#19c0ea"/>
+  <line x1="11" y1="7" x2="17" y2="7" stroke="currentColor" stroke-linecap="round"/>
+  <line x1="11" y1="17" x2="17" y2="17" stroke="currentColor" stroke-linecap="round"/>
+</svg>'''
+
+ICON_REFERENCE = '''<svg class="caption-icon" viewBox="0 0 24 24" fill="none" stroke-width="1.5">
+  <path d="M4 19.5A2.5 2.5 0 0 1 6.5 17H19" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round"/>
+  <path d="M6.5 2H19v20H6.5A2.5 2.5 0 0 1 4 19.5v-15A2.5 2.5 0 0 1 6.5 2z" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round"/>
+  <rect x="17" y="4" width="2" height="8" rx="0.5" fill="#19c0ea"/>
+  <line x1="8" y1="7" x2="14" y2="7" stroke="currentColor" stroke-linecap="round"/>
+  <line x1="8" y1="11" x2="14" y2="11" stroke="currentColor" stroke-linecap="round"/>
+</svg>'''
+
+ICON_TOOLS = '''<svg class="caption-icon" viewBox="0 0 24 24" fill="none" stroke-width="1.5">
+  <path d="M14.7 6.3a1 1 0 0 0 0 1.4l1.6 1.6a1 1 0 0 0 1.4 0l3.77-3.77a6 6 0 0 1-7.94 7.94l-6.91 6.91a2.12 2.12 0 0 1-3-3l6.91-6.91a6 6 0 0 1 7.94-7.94l-3.76 3.76z" stroke="currentColor" stroke-linecap="round" stroke-linejoin="round"/>
+  <circle cx="17" cy="7" r="2" fill="#19c0ea" opacity="0.6"/>
+</svg>'''
diff --git a/src/crate/theme/rtd/sidebartoc.py b/src/crate/theme/rtd/sidebartoc.py
index 079445b8..cef5089c 100644
--- a/src/crate/theme/rtd/sidebartoc.py
+++ b/src/crate/theme/rtd/sidebartoc.py
@@ -24,6 +24,8 @@
 import os
 import re
 
+from crate.theme.rtd.icons import ICON_BUILD, ICON_OPERATIONS, ICON_REFERENCE, ICON_TOOLS
+
 
 def _slugify_id(text):
     """Normalize text to a safe HTML ID: alphanumerics and hyphens only."""
@@ -124,6 +126,7 @@ def _get_toctree(maxdepth=-1, titles_only=True, collapse=False):
         parts.append('<li class="navleft-item border-top"><a href="https://cratedb.com/docs/guide/connect/">All database drivers</a></li>')
         return ''.join(parts)
 
+
     # Start CrateDB docs TOC with a Search box
     parts.append('<li>')
     parts.append('<div class="search-link">')
@@ -131,31 +134,54 @@ def _get_toctree(maxdepth=-1, titles_only=True, collapse=False):
     parts.append('</div>')
     parts.append('</li>')
 
-    # Add Overview and top level entries defined in the Guide's toctree.
-    # The Guide project is the only one that has multiple top-level entries.
+    # Add Guide's toctree entries (Overview, Getting Started, captions, etc.)
     if project == 'CrateDB: Guide':
-        if pagename == 'index':
-            parts.append('<li class="current">')
-            parts.append(f'<a class="current-active" href="{master_path}">Overview</a>')
-            parts.append('</li>')
-        else:
-            parts.append('<li class="navleft-item">')
-            parts.append(f'<a href="{master_path}">Overview</a>')
-            parts.append('</li>')
-        parts.append(_get_toctree())
+        toctree_html = _get_toctree()
+        # Rewrite the Overview sidebar link to point to root (index.md)
+        # instead of overview/. The overview content lives in index.md;
+        # overview/index.md is only kept for toctree structure.
+        toctree_html = re.sub(
+            r'href="([^"]*overview/(?:index\.html)?)"',
+            f'href="{master_path}"',
+            toctree_html
+        )
+        # Add icons to captions
+        toctree_html = toctree_html.replace(
+            '<span class="caption-text">Build</span>',
+            f'{ICON_BUILD}<span class="caption-text">Build</span>'
+        )
+        toctree_html = toctree_html.replace(
+            '<span class="caption-text">Operations</span>',
+            f'{ICON_OPERATIONS}<span class="caption-text">Operations</span>'
+        )
+        parts.append(toctree_html)
     else:
-        # Show Overview link to Guide's index (no icon - it's just an index page)
-        parts.append('<li class="navleft-item"><a href="/docs/guide/">Overview</a></li>')
-        # Add Guide's level 1 entries with icons
-        builder.add_nav_link('Getting Started','/docs/guide/start/')
-        builder.add_nav_link('Handbook', '/docs/guide/handbook/')
-
-    # Add individual projects
+        # Show Guide's navigation structure when viewing other projects
+        # This must be kept in sync with the Guide's index.md toctree
+        builder.add_nav_link('Overview', '/docs/guide/')
+        builder.add_nav_link('Getting Started', '/docs/guide/start/')
+
+        # BUILD section
+        parts.append(f'<p class="caption" role="heading">{ICON_BUILD}<span class="caption-text">Build</span></p>')
+        builder.add_nav_link('Load data into CrateDB', '/docs/guide/ingest/')
+        builder.add_nav_link('Connect / Drivers', '/docs/guide/connect/')
+        builder.add_nav_link('Integrations', '/docs/guide/integrate/')
+        builder.add_nav_link('All Features', '/docs/guide/feature/')
+
+        # OPERATIONS section
+        parts.append(f'<p class="caption" role="heading">{ICON_OPERATIONS}<span class="caption-text">Operations</span></p>')
+        builder.add_nav_link('Installation', '/docs/guide/install/')
+        builder.add_nav_link('Administration', '/docs/guide/admin/')
+        builder.add_nav_link('Performance guides', '/docs/guide/performance/')
+
+    # Add Reference section with caption
+    parts.append(f'<p class="caption" role="heading">{ICON_REFERENCE}<span class="caption-text">References</span></p>')
     builder.add_project_nav_item('CrateDB Cloud', 'CrateDB Cloud', '/docs/cloud/')
-    builder.add_project_nav_item('CrateDB: Reference', 'Reference Manual', '/docs/crate/reference/')
+    builder.add_project_nav_item('CrateDB: Reference', 'CrateDB', '/docs/crate/reference/')
 
-    # Start new section with a border
-    builder.add_project_nav_item('CrateDB: Admin UI', 'Admin UI', '/docs/crate/admin-ui/', border_top=True)
+    # Add Tools section with caption
+    parts.append(f'<p class="caption" role="heading">{ICON_TOOLS}<span class="caption-text">Tools</span></p>')
+    builder.add_project_nav_item('CrateDB: Admin UI', 'Admin UI', '/docs/crate/admin-ui/')
     builder.add_project_nav_item('CrateDB: Crash CLI', 'CrateDB CLI', '/docs/crate/crash/')
     builder.add_project_nav_item('CrateDB Cloud: Croud CLI', 'Cloud CLI', '/docs/cloud/cli/')