diff --git a/.changeset/fix-dollar-replacement.md b/.changeset/fix-dollar-replacement.md
new file mode 100644
index 00000000..26d88d4d
--- /dev/null
+++ b/.changeset/fix-dollar-replacement.md
@@ -0,0 +1,7 @@
+---
+'@node-core/doc-kit-legacy': patch
+'@node-core/doc-kit': patch
+'@doc-kit/generator-react': patch
+---
+
+Fix `$$`, `$&`, `` $` `` and `$'` in page content being treated as `String.prototype.replace` replacement patterns instead of literal text. This affected the legacy HTML generator's page and navigation content, the man page generator's options/environment sections, and the sitemap generator's URL entries.
diff --git a/packages/node-legacy/src/legacy-html/utils/__tests__/replaceTemplateValues.test.mjs b/packages/node-legacy/src/legacy-html/utils/__tests__/replaceTemplateValues.test.mjs
new file mode 100644
index 00000000..1cb51bbf
--- /dev/null
+++ b/packages/node-legacy/src/legacy-html/utils/__tests__/replaceTemplateValues.test.mjs
@@ -0,0 +1,57 @@
+'use strict';
+
+import assert from 'node:assert/strict';
+import { before, describe, it } from 'node:test';
+
+import { setConfig } from '@doc-kit/core/utils/configuration/index.mjs';
+
+import { replaceTemplateValues } from '../replaceTemplateValues.mjs';
+
+describe('replaceTemplateValues', () => {
+  before(() => setConfig({}));
+
+  const baseValues = {
+    path: '/test',
+    api: 'test',
+    added: undefined,
+    section: 'section',
+    toc: [],
+    nav: 'nav',
+    content: 'content',
+  };
+
+  const config = { version: { version: '1.0.0' }, changelog: [] };
+
+  it('does not treat `$$`, `$&`, "$`" and `$\'` in content as replacement patterns', () => {
+    const template = '<main>__CONTENT__</main><nav>__GTOC__</nav>';
+
+    const dollarContent = 'dirname "$$(command -v node)" $& $` $\'';
+
+    const output = replaceTemplateValues(
+      template,
+      { ...baseValues, content: dollarContent },
+      config,
+      { skipGitHub: true }
+    );
+
+    assert.match(
+      output,
+      /<main>dirname "\$\$\(command -v node\)" \$& \$` \$'<\/main>/
+    );
+  });
+
+  it('does not treat `$$`, `$&`, "$`" and `$\'` in nav as replacement patterns', () => {
+    const template = '<main>__CONTENT__</main><nav>__GTOC__</nav>';
+
+    const dollarNav = "nav $$ $& $` $'";
+
+    const output = replaceTemplateValues(
+      template,
+      { ...baseValues, nav: dollarNav },
+      config,
+      { skipGitHub: true }
+    );
+
+    assert.match(output, /<nav>nav \$\$ \$& \$` \$'<\/nav>/);
+  });
+});
diff --git a/packages/node-legacy/src/legacy-html/utils/replaceTemplateValues.mjs b/packages/node-legacy/src/legacy-html/utils/replaceTemplateValues.mjs
index 4d434ea7..5e73fc3b 100644
--- a/packages/node-legacy/src/legacy-html/utils/replaceTemplateValues.mjs
+++ b/packages/node-legacy/src/legacy-html/utils/replaceTemplateValues.mjs
@@ -27,16 +27,17 @@ export const replaceTemplateValues = (
   return apiTemplate
     .replace('__ID__', api)
     .replace(/__FILENAME__/g, api)
-    .replace('__SECTION__', section)
+    .replace('__SECTION__', () => section)
     .replace(/__VERSION__/g, `v${config.version.version}`)
-    .replace(/__TOC__/g, tableOfContents.wrapToC(toc))
-    .replace(/__GTOC__/g, nav)
-    .replace('__CONTENT__', content)
-    .replace(/__TOC_PICKER__/g, buildToC(toc))
-    .replace(/__GTOC_PICKER__/g, skipGtocPicker ? '' : buildNavigation(nav))
-    .replace('__ALTDOCS__', buildVersions(path, added, config.changelog))
-    .replace(
-      '__EDIT_ON_GITHUB__',
+    .replace(/__TOC__/g, () => tableOfContents.wrapToC(toc))
+    .replace(/__GTOC__/g, () => nav)
+    .replace('__CONTENT__', () => content)
+    .replace(/__TOC_PICKER__/g, () => buildToC(toc))
+    .replace(/__GTOC_PICKER__/g, () =>
+      skipGtocPicker ? '' : buildNavigation(nav)
+    )
+    .replace('__ALTDOCS__', () => buildVersions(path, added, config.changelog))
+    .replace('__EDIT_ON_GITHUB__', () =>
       skipGitHub
         ? ''
         : buildGitHub(populate(config.editURL, { ...config, path }))
diff --git a/packages/node/src/man-page/generate.mjs b/packages/node/src/man-page/generate.mjs
index 1b75fc9d..e6a75054 100644
--- a/packages/node/src/man-page/generate.mjs
+++ b/packages/node/src/man-page/generate.mjs
@@ -68,8 +68,8 @@ export async function generate(input) {
   const template = await readFile(config.templatePath, 'utf-8');
 
   const filledTemplate = template
-    .replace('__OPTIONS__', output.options)
-    .replace('__ENVIRONMENT__', output.env);
+    .replace('__OPTIONS__', () => output.options)
+    .replace('__ENVIRONMENT__', () => output.env);
 
   if (config.output) {
     await writeFile(join(config.output, config.fileName), filledTemplate);
diff --git a/packages/react/src/sitemap/generate.mjs b/packages/react/src/sitemap/generate.mjs
index 8b87b9ed..dc6695fd 100644
--- a/packages/react/src/sitemap/generate.mjs
+++ b/packages/react/src/sitemap/generate.mjs
@@ -50,14 +50,14 @@ export async function generate(entries) {
   const urlset = apiPages
     .map(page =>
       entryTemplate
-        .replace('__LOC__', page.loc)
-        .replace('__LASTMOD__', page.lastmod)
-        .replace('__CHANGEFREQ__', page.changefreq)
-        .replace('__PRIORITY__', page.priority)
+        .replace('__LOC__', () => page.loc)
+        .replace('__LASTMOD__', () => page.lastmod)
+        .replace('__CHANGEFREQ__', () => page.changefreq)
+        .replace('__PRIORITY__', () => page.priority)
     )
     .join('');
 
-  const sitemap = template.replace('__URLSET__', urlset);
+  const sitemap = template.replace('__URLSET__', () => urlset);
 
   if (config.output) {
     await writeFile(join(config.output, 'sitemap.xml'), sitemap, 'utf-8');