diff --git a/routers/web/repo/view.go b/routers/web/repo/view.go
index 8e85cc3278..80148ecdf9 100644
--- a/routers/web/repo/view.go
+++ b/routers/web/repo/view.go
@@ -35,6 +35,7 @@ import (
 	"code.gitea.io/gitea/modules/lfs"
 	"code.gitea.io/gitea/modules/log"
 	"code.gitea.io/gitea/modules/markup"
+	"code.gitea.io/gitea/modules/markup/markdown"
 	"code.gitea.io/gitea/modules/setting"
 	"code.gitea.io/gitea/modules/structs"
 	"code.gitea.io/gitea/modules/templates"
@@ -179,6 +180,18 @@ func markupRender(ctx *context.Context, renderCtx *markup.RenderContext, input i
 	return escaped, output, err
 }
 
+func renderSidebarTocHTML(rctx *markup.RenderContext) template.HTML {
+	if rctx.SidebarTocNode == nil {
+		return ""
+	}
+	sb := &strings.Builder{}
+	if err := markdown.SpecializedMarkdown(rctx).Renderer().Render(sb, nil, rctx.SidebarTocNode); err != nil {
+		log.Error("Failed to render sidebar TOC: %v", err)
+		return ""
+	}
+	return templates.SanitizeHTML(sb.String())
+}
+
 func checkHomeCodeViewable(ctx *context.Context) {
 	if ctx.Repo.HasUnits() {
 		if ctx.Repo.Repository.IsBeingCreated() {
diff --git a/routers/web/repo/view_file.go b/routers/web/repo/view_file.go
index 167cd5f927..d505ce982b 100644
--- a/routers/web/repo/view_file.go
+++ b/routers/web/repo/view_file.go
@@ -92,6 +92,8 @@ func handleFileViewRenderMarkup(ctx *context.Context, filename string, sniffedTy
 		ctx.ServerError("Render", err)
 		return true
 	}
+
+	ctx.Data["FileTocHTML"] = renderSidebarTocHTML(rctx)
 	return true
 }
 
diff --git a/routers/web/repo/view_readme.go b/routers/web/repo/view_readme.go
index f1fa5732f0..8999339bab 100644
--- a/routers/web/repo/view_readme.go
+++ b/routers/web/repo/view_readme.go
@@ -206,6 +206,8 @@ func prepareToRenderReadmeFile(ctx *context.Context, subfolder string, readmeFil
 			log.Error("Render failed for %s in %-v: %v Falling back to rendering source", readmeFile.Name(), ctx.Repo.Repository, err)
 			delete(ctx.Data, "IsMarkup")
 		}
+
+		ctx.Data["ReadmeTocHTML"] = renderSidebarTocHTML(rctx)
 	}
 
 	if ctx.Data["IsMarkup"] != true {
diff --git a/templates/repo/view_file.tmpl b/templates/repo/view_file.tmpl
index 809b1e9677..f15b932b2b 100644
--- a/templates/repo/view_file.tmpl
+++ b/templates/repo/view_file.tmpl
@@ -35,6 +35,11 @@
 			{{end}}
 		</div>
 		<div class="file-header-right file-actions flex-text-block tw-flex-wrap">
+			{{if or .ReadmeTocHTML .FileTocHTML}}
+			<button class="btn-octicon" id="toggle-toc-btn" data-tooltip-content="{{ctx.Locale.Tr "toc"}}">
+				{{svg "octicon-list-unordered" 16}}
+			</button>
+			{{end}}
 			{{/* this componment is also controlled by frontend plugin renders */}}
 			<div class="ui compact icon buttons file-view-toggle-buttons {{Iif .HasSourceRenderedToggle "" "tw-hidden"}}">
 				{{if .IsRepresentableAsText}}
@@ -93,50 +98,57 @@
 		{{if not .IsMarkup}}
 			{{template "repo/unicode_escape_prompt" dict "EscapeStatus" .EscapeStatus}}
 		{{end}}
-		<div class="file-view {{if .IsMarkup}}markup {{.MarkupType}}{{else if .IsPlainText}}plain-text{{else if .IsDisplayingSource}}code-view{{end}}">
-			{{if .IsFileTooLarge}}
-				{{template "shared/filetoolarge" dict "RawFileLink" .RawFileLink}}
-			{{else if not .FileSize}}
-				{{template "shared/fileisempty"}}
-			{{else if .IsMarkup}}
-				{{.FileContent}}
-			{{else if .IsPlainText}}
-				<pre>{{if .FileContent}}{{.FileContent}}{{end}}</pre>
-			{{else if .FileContent}}
-				<table>
-					<tbody>
-					{{range $idx, $code := .FileContent}}
-						{{$line := Eval $idx "+" 1}}
-						<tr>
-							<td class="lines-num"><span id="L{{$line}}" data-line-number="{{$line}}"></span></td>
-							{{if $.EscapeStatus.Escaped}}
-								<td class="lines-escape">{{if (index $.LineEscapeStatus $idx).Escaped}}<button class="toggle-escape-button btn interact-bg" title="{{if (index $.LineEscapeStatus $idx).HasInvisible}}{{ctx.Locale.Tr "repo.invisible_runes_line"}} {{end}}{{if (index $.LineEscapeStatus $idx).HasAmbiguous}}{{ctx.Locale.Tr "repo.ambiguous_runes_line"}}{{end}}"></button>{{end}}</td>
-							{{end}}
-							<td rel="L{{$line}}" class="lines-code chroma"><code class="code-inner">{{$code}}</code></td>
-						</tr>
-					{{end}}
-					</tbody>
-				</table>
-			{{else}}
-				<div class="view-raw">
-					{{if .IsImageFile}}
-						<img alt="{{$.RawFileLink}}" src="{{$.RawFileLink}}">
-					{{else if .IsVideoFile}}
-						<video controls src="{{$.RawFileLink}}">
-							<strong>{{ctx.Locale.Tr "repo.video_not_supported_in_browser"}}</strong>
-						</video>
-					{{else if .IsAudioFile}}
-						<audio controls src="{{$.RawFileLink}}">
-							<strong>{{ctx.Locale.Tr "repo.audio_not_supported_in_browser"}}</strong>
-						</audio>
-					{{else}}
-						<div class="file-view-render-container">
-							<div class="file-view-raw-prompt tw-p-4">
-								<a href="{{$.RawFileLink}}" rel="nofollow">{{ctx.Locale.Tr "repo.file_view_raw"}}</a>
+		<div class="file-view-container">
+			<div class="file-view {{if .IsMarkup}}markup {{.MarkupType}}{{else if .IsPlainText}}plain-text{{else if .IsDisplayingSource}}code-view{{end}}">
+				{{if .IsFileTooLarge}}
+					{{template "shared/filetoolarge" dict "RawFileLink" .RawFileLink}}
+				{{else if not .FileSize}}
+					{{template "shared/fileisempty"}}
+				{{else if .IsMarkup}}
+					{{.FileContent}}
+				{{else if .IsPlainText}}
+					<pre>{{if .FileContent}}{{.FileContent}}{{end}}</pre>
+				{{else if .FileContent}}
+					<table>
+						<tbody>
+						{{range $idx, $code := .FileContent}}
+							{{$line := Eval $idx "+" 1}}
+							<tr>
+								<td class="lines-num"><span id="L{{$line}}" data-line-number="{{$line}}"></span></td>
+								{{if $.EscapeStatus.Escaped}}
+									<td class="lines-escape">{{if (index $.LineEscapeStatus $idx).Escaped}}<button class="toggle-escape-button btn interact-bg" title="{{if (index $.LineEscapeStatus $idx).HasInvisible}}{{ctx.Locale.Tr "repo.invisible_runes_line"}} {{end}}{{if (index $.LineEscapeStatus $idx).HasAmbiguous}}{{ctx.Locale.Tr "repo.ambiguous_runes_line"}}{{end}}"></button>{{end}}</td>
+								{{end}}
+								<td rel="L{{$line}}" class="lines-code chroma"><code class="code-inner">{{$code}}</code></td>
+							</tr>
+						{{end}}
+						</tbody>
+					</table>
+				{{else}}
+					<div class="view-raw">
+						{{if .IsImageFile}}
+							<img alt="{{$.RawFileLink}}" src="{{$.RawFileLink}}">
+						{{else if .IsVideoFile}}
+							<video controls src="{{$.RawFileLink}}">
+								<strong>{{ctx.Locale.Tr "repo.video_not_supported_in_browser"}}</strong>
+							</video>
+						{{else if .IsAudioFile}}
+							<audio controls src="{{$.RawFileLink}}">
+								<strong>{{ctx.Locale.Tr "repo.audio_not_supported_in_browser"}}</strong>
+							</audio>
+						{{else}}
+							<div class="file-view-render-container">
+								<div class="file-view-raw-prompt tw-p-4">
+									<a href="{{$.RawFileLink}}" rel="nofollow">{{ctx.Locale.Tr "repo.file_view_raw"}}</a>
+								</div>
 							</div>
-						</div>
-					{{end}}
-				</div>
+						{{end}}
+					</div>
+				{{end}}
+			</div>
+			{{if or .ReadmeTocHTML .FileTocHTML}}
+			<div class="file-view-toc markup toc-panel-hidden">
+				{{or .ReadmeTocHTML .FileTocHTML}}
+			</div>
 			{{end}}
 		</div>
 
diff --git a/web_src/css/repo/home.css b/web_src/css/repo/home.css
index 60bf1f17f9..c43afe826c 100644
--- a/web_src/css/repo/home.css
+++ b/web_src/css/repo/home.css
@@ -105,3 +105,92 @@
   padding: 0 0.5em; /* make the UI look better for narrow (mobile) view */
   text-decoration: none;
 }
+
+/* File view with TOC sidebar */
+.file-view-container {
+  position: relative;
+}
+
+.file-view-container .file-view {
+  width: 100%;
+}
+
+/* TOC as a floating sidebar panel */
+.file-view-toc {
+  position: fixed;
+  top: 60px;
+  right: 0;
+  width: 280px;
+  max-height: calc(100vh - 80px);
+  overflow-y: auto;
+  padding: 1rem;
+  background: var(--color-body);
+  border: 1px solid var(--color-secondary);
+  border-right: none;
+  border-radius: var(--border-radius) 0 0 var(--border-radius);
+  box-shadow: -4px 0 12px rgba(0, 0, 0, 0.15);
+  z-index: 100;
+  transform: translateX(0);
+  transition: transform 0.25s ease-in-out;
+}
+
+/* Hidden state - using custom class to avoid Tailwind conflicts */
+.file-view-toc.toc-panel-hidden {
+  transform: translateX(100%);
+}
+
+.file-view-toc details {
+  font-size: 13px;
+}
+
+.file-view-toc summary {
+  font-weight: 600;
+  cursor: pointer;
+  padding: 8px 0;
+  color: var(--color-text);
+  border-bottom: 1px solid var(--color-secondary);
+  margin-bottom: 8px;
+}
+
+.file-view-toc ul {
+  margin: 0;
+  list-style: none;
+  padding: 5px 0 5px 1em;
+}
+
+.file-view-toc ul ul {
+  border-left: 1px dashed var(--color-secondary);
+}
+
+.file-view-toc a {
+  display: block;
+  padding: 6px 10px;
+  color: var(--color-text);
+  text-decoration: none;
+  font-size: 13px;
+  line-height: 1.4;
+  border-radius: var(--border-radius);
+}
+
+.file-view-toc a:hover {
+  color: var(--color-primary);
+  background: var(--color-hover);
+}
+
+/* TOC toggle button active state - when TOC is visible */
+#toggle-toc-btn.active {
+  color: var(--color-primary);
+  background: var(--color-hover);
+}
+
+/* Hide TOC sidebar on small screens */
+@media (max-width: 768px) {
+  .file-view-toc {
+    width: 100%;
+    max-width: 300px;
+  }
+
+  #toggle-toc-btn {
+    display: none;
+  }
+}
diff --git a/web_src/js/features/file-view.ts b/web_src/js/features/file-view.ts
index ff9e8cfa26..74e3d042b2 100644
--- a/web_src/js/features/file-view.ts
+++ b/web_src/js/features/file-view.ts
@@ -59,9 +59,47 @@ async function renderRawFileToContainer(container: HTMLElement, rawFileLink: str
   }
 }
 
+function initTocToggle(elFileView: HTMLElement): void {
+  const toggleBtn = elFileView.querySelector('#toggle-toc-btn');
+  const tocSidebar = elFileView.querySelector('.file-view-toc');
+  if (!toggleBtn || !tocSidebar) return;
+
+  // Restore saved state from localStorage (default to hidden)
+  const savedState = localStorage.getItem('file-view-toc-visible');
+  const isVisible = savedState === 'true'; // default to hidden
+
+  // Apply initial state
+  if (isVisible) {
+    tocSidebar.classList.remove('toc-panel-hidden');
+    toggleBtn.classList.add('active');
+  } else {
+    tocSidebar.classList.add('toc-panel-hidden');
+    toggleBtn.classList.remove('active');
+  }
+
+  toggleBtn.addEventListener('click', () => {
+    const isCurrentlyVisible = !tocSidebar.classList.contains('toc-panel-hidden');
+    if (isCurrentlyVisible) {
+      // Hide TOC
+      tocSidebar.classList.add('toc-panel-hidden');
+      toggleBtn.classList.remove('active');
+      localStorage.setItem('file-view-toc-visible', 'false');
+    } else {
+      // Show TOC
+      tocSidebar.classList.remove('toc-panel-hidden');
+      toggleBtn.classList.add('active');
+      localStorage.setItem('file-view-toc-visible', 'true');
+    }
+  });
+}
+
 export function initRepoFileView(): void {
   registerGlobalInitFunc('initRepoFileView', async (elFileView: HTMLElement) => {
     initPluginsOnce();
+
+    // Initialize TOC toggle functionality
+    initTocToggle(elFileView);
+
     const rawFileLink = elFileView.getAttribute('data-raw-file-link')!;
     const mimeType = elFileView.getAttribute('data-mime-type') || ''; // not used yet
     // TODO: we should also provide the prefetched file head bytes to let the plugin decide whether to render or not