diff --git a/packages/guides/src/Compiler/NodeTransformers/MenuNodeTransformers/GlobMenuEntryNodeTransformer.php b/packages/guides/src/Compiler/NodeTransformers/MenuNodeTransformers/GlobMenuEntryNodeTransformer.php
index 16484f525..5ed5fec51 100644
--- a/packages/guides/src/Compiler/NodeTransformers/MenuNodeTransformers/GlobMenuEntryNodeTransformer.php
+++ b/packages/guides/src/Compiler/NodeTransformers/MenuNodeTransformers/GlobMenuEntryNodeTransformer.php
@@ -27,8 +27,9 @@
 use function explode;
 use function implode;
 use function in_array;
+use function is_string;
 use function preg_match;
-use function str_replace;
+use function preg_replace;
 
 final class GlobMenuEntryNodeTransformer extends AbstractMenuEntryNodeTransformer
 {
@@ -137,7 +138,9 @@ private static function matches(string $actualFile, GlobMenuEntryNode $parsedMen
     private static function isGlob(string $documentEntryFile, string $currentPath, string $file, string $prefix, array $globExclude): bool
     {
         if (!in_array($documentEntryFile, $globExclude, true)) {
-            $file = str_replace('*', '[^\/]*', $file);
+            $file = preg_replace('/(?<!\*)\*(?!\*)/', '[^\/]*', $file);
+            assert(is_string($file));
+            $file = preg_replace('/\*{2}/', '.*', $file);
             $pattern = '`^' . $file . '$`';
 
             return preg_match($pattern, $prefix . $documentEntryFile) > 0;
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/expected/index.html b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/expected/index.html
new file mode 100644
index 000000000..7f33b6846
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/expected/index.html
@@ -0,0 +1,118 @@
+<!-- content start -->
+<div class="section" id="document-title">
+    <h1>Document Title</h1>
+
+    <p>Lorem Ipsum Dolor.</p>
+
+    <div class="toc">
+        <ul class="menu-level">
+            <li class="toc-item">
+                <a href="/level-1-1/index.html#level-1-1">Level 1-1</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/level-2-1/index.html#level-2-1">Level 2-1</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/level-2-1/subpage1.html#subpage-1-level-2-1">Subpage 1, Level 2-1</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/level-2-1/subpage2.html#subpage-2-level-2-1">Subpage 2, Level 2-1</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/level-2-2/index.html#level-2-2">Level 2-2</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/level-2-2/subpage1.html#subpage-1-level-2-2">Subpage 1, Level 2-2</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/level-2-2/subpage2.html#subpage-1-level-2-2">Subpage 1, Level 2-2</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/subpage1.html#subpage-1-level-1-1">Subpage 1, Level 1-1</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-1/subpage2.html#subpage-2-level-1-1">Subpage 2, Level 1-1</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-2/index.html#level-1-2">Level 1-2</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-2/subpage1.html#subpage-1-level-1-2">Subpage 1, Level 1-2</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/level-1-2/subpage2.html#subpage-1-level-1-2">Subpage 1, Level 1-2</a>
+
+
+            </li>
+            <li class="toc-item">
+                <a href="/page1.html#page-1">Page 1</a>
+
+                <ul class="section-level-1">
+                    <li class="toc-item">
+                        <a href="/page1.html#page-1-level-2">Page 1 Level 2</a>
+
+                        <ul class="section-level-2">
+                            <li class="toc-item">
+                                <a href="/page1.html#page-1-level-3">Page 1 Level 3</a>
+
+                                <ul class="section-level-2">
+                                    <li class="toc-item">
+                                        <a href="/page1.html#page-1-level-4">Page 1 Level 4</a>
+
+
+                                    </li>
+                                </ul>
+                            </li>
+                        </ul>
+                    </li>
+                </ul>
+            </li>
+            <li class="toc-item">
+                <a href="/page2.html#page-2">Page 2</a>
+
+                <ul class="section-level-1">
+                    <li class="toc-item">
+                        <a href="/page2.html#page-2-level-2">Page 2 Level 2</a>
+
+                        <ul class="section-level-2">
+                            <li class="toc-item">
+                                <a href="/page2.html#page-2-level-3">Page 2 Level 3</a>
+
+                                <ul class="section-level-2">
+                                    <li class="toc-item">
+                                        <a href="/page2.html#page-2-level-4">Page 2 Level 4</a>
+
+
+                                    </li>
+                                </ul>
+                            </li>
+                        </ul>
+                    </li>
+                </ul>
+            </li>
+        </ul>
+    </div>
+</div>
+<!-- content end -->
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/index.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/index.rst
new file mode 100644
index 000000000..0f2651c64
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/index.rst
@@ -0,0 +1,10 @@
+==============
+Document Title
+==============
+
+Lorem Ipsum Dolor.
+
+..  toctree::
+    :glob:
+
+    **
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/index.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/index.rst
new file mode 100644
index 000000000..761253b85
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/index.rst
@@ -0,0 +1,8 @@
+=========
+Level 1-1
+=========
+
+Lorem Ipsum Dolor.
+
+A Definition List
+    Some definition.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/index.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/index.rst
new file mode 100644
index 000000000..6d2c3be7c
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/index.rst
@@ -0,0 +1,5 @@
+=========
+Level 2-1
+=========
+
+A Toctree with multiple whitespaces in the directive:
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/subpage1.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/subpage1.rst
new file mode 100644
index 000000000..cb49d6baa
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/subpage1.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 1, Level 2-1
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/subpage2.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/subpage2.rst
new file mode 100644
index 000000000..ceea6a3d4
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-1/subpage2.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 2, Level 2-1
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/index.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/index.rst
new file mode 100644
index 000000000..bbd7723d3
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/index.rst
@@ -0,0 +1,6 @@
+=========
+Level 2-2
+=========
+
+A Toctree with multiple whitespaces in the directive:
+
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/subpage1.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/subpage1.rst
new file mode 100644
index 000000000..fb4915895
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/subpage1.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 1, Level 2-2
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/subpage2.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/subpage2.rst
new file mode 100644
index 000000000..fb4915895
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/level-2-2/subpage2.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 1, Level 2-2
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/subpage1.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/subpage1.rst
new file mode 100644
index 000000000..ba6aa0052
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/subpage1.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 1, Level 1-1
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/subpage2.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/subpage2.rst
new file mode 100644
index 000000000..06615899a
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-1/subpage2.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 2, Level 1-1
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/index.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/index.rst
new file mode 100644
index 000000000..3fd821de6
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/index.rst
@@ -0,0 +1,5 @@
+=========
+Level 1-2
+=========
+
+A Toctree with multiple whitespaces in the directive:
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/subpage1.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/subpage1.rst
new file mode 100644
index 000000000..0371975a0
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/subpage1.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 1, Level 1-2
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/subpage2.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/subpage2.rst
new file mode 100644
index 000000000..0371975a0
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/level-1-2/subpage2.rst
@@ -0,0 +1,5 @@
+====================
+Subpage 1, Level 1-2
+====================
+
+Lorem Ipsum Dolor.
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/page1.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/page1.rst
new file mode 100644
index 000000000..9a1df3ce9
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/page1.rst
@@ -0,0 +1,14 @@
+======
+Page 1
+======
+
+Lorem Ipsum Dolor.
+
+Page 1 Level 2
+--------------
+
+Page 1 Level 3
+~~~~~~~~~~~~~~
+
+Page 1 Level 4
+""""""""""""""
diff --git a/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/page2.rst b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/page2.rst
new file mode 100644
index 000000000..cdd19d739
--- /dev/null
+++ b/tests/Integration/tests/toctree/toctree-glob-deep-level-3/input/page2.rst
@@ -0,0 +1,14 @@
+======
+Page 2
+======
+
+Lorem Ipsum Dolor.
+
+Page 2 Level 2
+--------------
+
+Page 2 Level 3
+~~~~~~~~~~~~~~
+
+Page 2 Level 4
+""""""""""""""