From 6d236d83f60ab49dd47a010325e28372b404a8ba Mon Sep 17 00:00:00 2001
From: Cesar Berrospi Ramis <75900930+ceberam@users.noreply.github.com>
Date: Tue, 22 Jul 2025 16:52:18 +0200
Subject: [PATCH 1/2] fix(serializer): the HTML serializer should append nested
 lists to list items

For a valid HTML document, the serializer should ensure that sub-list items are indented
under their respective main list items.

Signed-off-by: Cesar Berrospi Ramis <75900930+ceberam@users.noreply.github.com>
---
 docling_core/transforms/serializer/html.py      | 17 +++++++++++++++++
 test/data/doc/constructed_doc.embedded.html.gt  | 15 ++++++++++-----
 test/data/doc/constructed_doc.html              | 15 ++++++++++-----
 .../doc/constructed_doc.placeholder.html.gt     | 15 ++++++++++-----
 .../data/doc/constructed_doc.referenced.html.gt | 15 ++++++++++-----
 test/data/doc/constructed_document.yaml.html    | 15 ++++++++++-----
 test/data/doc/constructed_orig_false.gt.html    | 15 ++++++++++-----
 test/data/doc/constructed_orig_true.gt.html     | 15 ++++++++++-----
 8 files changed, 87 insertions(+), 35 deletions(-)

diff --git a/docling_core/transforms/serializer/html.py b/docling_core/transforms/serializer/html.py
index 73a2fac7..7ef64847 100644
--- a/docling_core/transforms/serializer/html.py
+++ b/docling_core/transforms/serializer/html.py
@@ -713,6 +713,23 @@ def serialize(
             **kwargs,
         )
 
+        # Append nested list to parent list item:
+        i = 0
+        while i < len(parts):
+            prt = parts[i]
+            if prt.text.startswith(("<ul>", "<ol>")):
+                for j in range(i - 1, -1, -1):
+                    if parts[j].text.startswith(("<li>", "<li ")) and parts[
+                        j
+                    ].text.endswith("</li>"):
+                        before, _, _ = parts[j].text.rpartition("</li>")
+                        parts[j].text = f"{before}\n{prt.text}\n</li>"
+                        break
+                if j > -1:
+                    parts.pop(i)
+            else:
+                i += 1
+
         # Add all child parts
         text_res = "\n".join(
             [
diff --git a/test/data/doc/constructed_doc.embedded.html.gt b/test/data/doc/constructed_doc.embedded.html.gt
index 22c85c92..e87ad306 100644
--- a/test/data/doc/constructed_doc.embedded.html.gt
+++ b/test/data/doc/constructed_doc.embedded.html.gt
@@ -135,15 +135,17 @@
 <ul>
 <li style="list-style-type: '■ ';">list item 1</li>
 <li style="list-style-type: '■ ';">list item 2</li>
-<li style="list-style-type: '■ ';">list item 3</li>
+<li style="list-style-type: '■ ';">list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li style="list-style-type: '■ ';">list item 4</li>
 </ul>
 <table><caption><div class="caption">This is the caption of table 1.</div></caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -158,12 +160,13 @@
 </ul>
 <ul>
 <li style="list-style-type: '■ ';">item 1 of neighboring list</li>
-<li style="list-style-type: '■ ';">item 2 of neighboring list</li>
+<li style="list-style-type: '■ ';">item 2 of neighboring list
 <ul>
 <li style="list-style-type: '□ ';">item 1 of sub list</li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a code snippet: <code>print("Hello world")</code> (to be displayed inline)</span></li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -185,16 +188,18 @@
 <ol>
 <li style="list-style-type: '(i) ';">Item 1 in A</li>
 <li style="list-style-type: '(ii) ';">Item 2 in A</li>
-<li style="list-style-type: '(iii) ';">Item 3 in A</li>
+<li style="list-style-type: '(iii) ';">Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li style="list-style-type: '42. ';">Item 2 in B</li>
+<li style="list-style-type: '42. ';">Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li style="list-style-type: '(iv) ';">Item 4 in A</li>
 </ol>
 <ul>
diff --git a/test/data/doc/constructed_doc.html b/test/data/doc/constructed_doc.html
index c3b8b764..ff14a594 100644
--- a/test/data/doc/constructed_doc.html
+++ b/test/data/doc/constructed_doc.html
@@ -134,15 +134,17 @@ <h2>1. Introduction</h2>
 <ul>
 <li>list item 1</li>
 <li>list item 2</li>
-<li>list item 3</li>
+<li>list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li>list item 4</li>
 </ul>
 <table><caption>This is the caption of table 1.</caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -157,12 +159,13 @@ <h2>1. Introduction</h2>
 </ul>
 <ul>
 <li>item 1 of neighboring list</li>
-<li>item 2 of neighboring list</li>
+<li>item 2 of neighboring list
 <ul>
 <li>item 1 of sub list</li>
 <li><span class='inline-group'>Here a code snippet: <code>&lt;p&gt;Hello world&lt;/p&gt;</code> (to be displayed inline)</span></li>
 <li><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -186,16 +189,18 @@ <h2>1. Introduction</h2>
 <ol>
 <li>Item 1 in A</li>
 <li>Item 2 in A</li>
-<li>Item 3 in A</li>
+<li>Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li>Item 2 in B</li>
+<li>Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li>Item 4 in A</li>
 </ol>
 <p>The end.</p>
diff --git a/test/data/doc/constructed_doc.placeholder.html.gt b/test/data/doc/constructed_doc.placeholder.html.gt
index 55a9cee8..a4f0130a 100644
--- a/test/data/doc/constructed_doc.placeholder.html.gt
+++ b/test/data/doc/constructed_doc.placeholder.html.gt
@@ -135,15 +135,17 @@
 <ul>
 <li style="list-style-type: '■ ';">list item 1</li>
 <li style="list-style-type: '■ ';">list item 2</li>
-<li style="list-style-type: '■ ';">list item 3</li>
+<li style="list-style-type: '■ ';">list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li style="list-style-type: '■ ';">list item 4</li>
 </ul>
 <table><caption><div class="caption">This is the caption of table 1.</div></caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -158,12 +160,13 @@
 </ul>
 <ul>
 <li style="list-style-type: '■ ';">item 1 of neighboring list</li>
-<li style="list-style-type: '■ ';">item 2 of neighboring list</li>
+<li style="list-style-type: '■ ';">item 2 of neighboring list
 <ul>
 <li style="list-style-type: '□ ';">item 1 of sub list</li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a code snippet: <code>print("Hello world")</code> (to be displayed inline)</span></li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -185,16 +188,18 @@
 <ol>
 <li style="list-style-type: '(i) ';">Item 1 in A</li>
 <li style="list-style-type: '(ii) ';">Item 2 in A</li>
-<li style="list-style-type: '(iii) ';">Item 3 in A</li>
+<li style="list-style-type: '(iii) ';">Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li style="list-style-type: '42. ';">Item 2 in B</li>
+<li style="list-style-type: '42. ';">Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li style="list-style-type: '(iv) ';">Item 4 in A</li>
 </ol>
 <ul>
diff --git a/test/data/doc/constructed_doc.referenced.html.gt b/test/data/doc/constructed_doc.referenced.html.gt
index 0ccda7cf..43649aee 100644
--- a/test/data/doc/constructed_doc.referenced.html.gt
+++ b/test/data/doc/constructed_doc.referenced.html.gt
@@ -135,15 +135,17 @@
 <ul>
 <li style="list-style-type: '■ ';">list item 1</li>
 <li style="list-style-type: '■ ';">list item 2</li>
-<li style="list-style-type: '■ ';">list item 3</li>
+<li style="list-style-type: '■ ';">list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li style="list-style-type: '■ ';">list item 4</li>
 </ul>
 <table><caption><div class="caption">This is the caption of table 1.</div></caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -158,12 +160,13 @@
 </ul>
 <ul>
 <li style="list-style-type: '■ ';">item 1 of neighboring list</li>
-<li style="list-style-type: '■ ';">item 2 of neighboring list</li>
+<li style="list-style-type: '■ ';">item 2 of neighboring list
 <ul>
 <li style="list-style-type: '□ ';">item 1 of sub list</li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a code snippet: <code>print("Hello world")</code> (to be displayed inline)</span></li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -185,16 +188,18 @@
 <ol>
 <li style="list-style-type: '(i) ';">Item 1 in A</li>
 <li style="list-style-type: '(ii) ';">Item 2 in A</li>
-<li style="list-style-type: '(iii) ';">Item 3 in A</li>
+<li style="list-style-type: '(iii) ';">Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li style="list-style-type: '42. ';">Item 2 in B</li>
+<li style="list-style-type: '42. ';">Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li style="list-style-type: '(iv) ';">Item 4 in A</li>
 </ol>
 <ul>
diff --git a/test/data/doc/constructed_document.yaml.html b/test/data/doc/constructed_document.yaml.html
index 04754103..bc3e2333 100644
--- a/test/data/doc/constructed_document.yaml.html
+++ b/test/data/doc/constructed_document.yaml.html
@@ -135,15 +135,17 @@ <h2>1. Introduction</h2>
 <ul>
 <li style="list-style-type: '■ ';">list item 1</li>
 <li style="list-style-type: '■ ';">list item 2</li>
-<li style="list-style-type: '■ ';">list item 3</li>
+<li style="list-style-type: '■ ';">list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li style="list-style-type: '■ ';">list item 4</li>
 </ul>
 <table><caption><div class="caption">This is the caption of table 1.</div></caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -158,12 +160,13 @@ <h2>1. Introduction</h2>
 </ul>
 <ul>
 <li style="list-style-type: '■ ';">item 1 of neighboring list</li>
-<li style="list-style-type: '■ ';">item 2 of neighboring list</li>
+<li style="list-style-type: '■ ';">item 2 of neighboring list
 <ul>
 <li style="list-style-type: '□ ';">item 1 of sub list</li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a code snippet: <code>print("Hello world")</code> (to be displayed inline)</span></li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -185,16 +188,18 @@ <h2>1. Introduction</h2>
 <ol>
 <li style="list-style-type: '(i) ';">Item 1 in A</li>
 <li style="list-style-type: '(ii) ';">Item 2 in A</li>
-<li style="list-style-type: '(iii) ';">Item 3 in A</li>
+<li style="list-style-type: '(iii) ';">Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li style="list-style-type: '42. ';">Item 2 in B</li>
+<li style="list-style-type: '42. ';">Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li style="list-style-type: '(iv) ';">Item 4 in A</li>
 </ol>
 <ul>
diff --git a/test/data/doc/constructed_orig_false.gt.html b/test/data/doc/constructed_orig_false.gt.html
index 19f0398a..1f35636a 100644
--- a/test/data/doc/constructed_orig_false.gt.html
+++ b/test/data/doc/constructed_orig_false.gt.html
@@ -135,15 +135,17 @@ <h2>1. Introduction</h2>
 <ul>
 <li>list item 1</li>
 <li>list item 2</li>
-<li>list item 3</li>
+<li>list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li>list item 4</li>
 </ul>
 <table><caption><div class="caption">This is the caption of table 1.</div></caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -158,12 +160,13 @@ <h2>1. Introduction</h2>
 </ul>
 <ul>
 <li>item 1 of neighboring list</li>
-<li>item 2 of neighboring list</li>
+<li>item 2 of neighboring list
 <ul>
 <li>item 1 of sub list</li>
 <li><span class='inline-group'>Here a code snippet: <code>print("Hello world")</code> (to be displayed inline)</span></li>
 <li><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -185,16 +188,18 @@ <h2>1. Introduction</h2>
 <ol>
 <li>Item 1 in A</li>
 <li>Item 2 in A</li>
-<li>Item 3 in A</li>
+<li>Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li>Item 2 in B</li>
+<li>Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li>Item 4 in A</li>
 </ol>
 <ul>
diff --git a/test/data/doc/constructed_orig_true.gt.html b/test/data/doc/constructed_orig_true.gt.html
index 04754103..bc3e2333 100644
--- a/test/data/doc/constructed_orig_true.gt.html
+++ b/test/data/doc/constructed_orig_true.gt.html
@@ -135,15 +135,17 @@ <h2>1. Introduction</h2>
 <ul>
 <li style="list-style-type: '■ ';">list item 1</li>
 <li style="list-style-type: '■ ';">list item 2</li>
-<li style="list-style-type: '■ ';">list item 3</li>
+<li style="list-style-type: '■ ';">list item 3
 <ol>
 <li>list item 3.a</li>
 <li>list item 3.b</li>
-<li>list item 3.c</li>
+<li>list item 3.c
 <ol>
 <li>list item 3.c.i</li>
 </ol>
+</li>
 </ol>
+</li>
 <li style="list-style-type: '■ ';">list item 4</li>
 </ul>
 <table><caption><div class="caption">This is the caption of table 1.</div></caption><tbody><tr><td rowspan="2">Product</td><td colspan="2">Years</td></tr><tr><td>2016</td><td>2017</td></tr><tr><td>Apple</td><td>49823</td><td>695944</td></tr></tbody></table>
@@ -158,12 +160,13 @@ <h2>1. Introduction</h2>
 </ul>
 <ul>
 <li style="list-style-type: '■ ';">item 1 of neighboring list</li>
-<li style="list-style-type: '■ ';">item 2 of neighboring list</li>
+<li style="list-style-type: '■ ';">item 2 of neighboring list
 <ul>
 <li style="list-style-type: '□ ';">item 1 of sub list</li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a code snippet: <code>print("Hello world")</code> (to be displayed inline)</span></li>
 <li style="list-style-type: '□ ';"><span class='inline-group'>Here a formula: <math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><mrow><mi>E</mi><mo>&#x0003D;</mo><mi>m</mi><msup><mi>c</mi><mn>2</mn></msup></mrow><annotation encoding="TeX">E=mc^2</annotation></math> (to be displayed inline)</span></li>
 </ul>
+</li>
 </ul>
 <p>Here a code block:</p>
 <pre><code>print("Hello world")</code></pre>
@@ -185,16 +188,18 @@ <h2>1. Introduction</h2>
 <ol>
 <li style="list-style-type: '(i) ';">Item 1 in A</li>
 <li style="list-style-type: '(ii) ';">Item 2 in A</li>
-<li style="list-style-type: '(iii) ';">Item 3 in A</li>
+<li style="list-style-type: '(iii) ';">Item 3 in A
 <ol>
 <li>Item 1 in B</li>
-<li style="list-style-type: '42. ';">Item 2 in B</li>
+<li style="list-style-type: '42. ';">Item 2 in B
 <ol>
 <li>Item 1 in C</li>
 <li>Item 2 in C</li>
 </ol>
+</li>
 <li>Item 3 in B</li>
 </ol>
+</li>
 <li style="list-style-type: '(iv) ';">Item 4 in A</li>
 </ol>
 <ul>

From 175e5f6018d823630559a287b82c2ef1f90d9feb Mon Sep 17 00:00:00 2001
From: Cesar Berrospi Ramis <75900930+ceberam@users.noreply.github.com>
Date: Tue, 22 Jul 2025 17:08:27 +0200
Subject: [PATCH 2/2] test: address several warning messages

Signed-off-by: Cesar Berrospi Ramis <75900930+ceberam@users.noreply.github.com>
---
 test/test_base.py         |  4 ++--
 test/test_docling_doc.py  | 20 +++++++++++---------
 test/test_doctags_load.py | 12 ++++++++----
 3 files changed, 21 insertions(+), 15 deletions(-)

diff --git a/test/test_base.py b/test/test_base.py
index 0fe09ab5..d6f07f51 100644
--- a/test/test_base.py
+++ b/test/test_base.py
@@ -36,8 +36,8 @@ def test_identifier():
     )
 
     # schema_json(): no need to set by_alias since it is True by the default
-    tf = open("test/data/json_schemas/base_identifier.json", encoding="utf-8")
-    gold_json = json.load(tf)
+    with open("test/data/json_schemas/base_identifier.json", encoding="utf-8") as tf:
+        gold_json = json.load(tf)
 
     assert Identifier.model_json_schema() == gold_json
 
diff --git a/test/test_docling_doc.py b/test/test_docling_doc.py
index 1858f5f6..e0aa622f 100644
--- a/test/test_docling_doc.py
+++ b/test/test_docling_doc.py
@@ -1819,9 +1819,10 @@ def _verify(
 
     # Test the handling of list items in insert_* methods, both with and without parent groups
 
-    li_sibling = doc.insert_list_item(
-        sibling=node, text="Inserted List Item, Incorrect Parent", after=False
-    )
+    with pytest.warns(DeprecationWarning, match="ListItem parent must be a ListGroup"):
+        li_sibling = doc.insert_list_item(
+            sibling=node, text="Inserted List Item, Incorrect Parent", after=False
+        )
     doc.insert_list_item(
         sibling=li_sibling, text="Inserted List Item, Correct Parent", after=True
     )
@@ -1831,12 +1832,13 @@ def _verify(
         text="Inserted Text with LIST_ITEM Label, Correct Parent",
         after=False,
     )
-    doc.insert_text(
-        sibling=node,
-        label=DocItemLabel.LIST_ITEM,
-        text="Inserted Text with LIST_ITEM Label, Incorrect Parent",
-        after=True,
-    )
+    with pytest.warns(DeprecationWarning, match="ListItem parent must be a ListGroup"):
+        doc.insert_text(
+            sibling=node,
+            label=DocItemLabel.LIST_ITEM,
+            text="Inserted Text with LIST_ITEM Label, Incorrect Parent",
+            after=True,
+        )
 
     filename = Path(
         "test/data/doc/constructed_doc.inserted_list_items_with_insert_*.json"
diff --git a/test/test_doctags_load.py b/test/test_doctags_load.py
index 5f1d5733..a6bf5bea 100644
--- a/test/test_doctags_load.py
+++ b/test/test_doctags_load.py
@@ -60,7 +60,8 @@ def test_doctags_load_from_files():
 
 def test_doctags_load_from_memory():
 
-    doctags = Path("test/data/doc/page_with_pic.dt").open("r").read()
+    with Path("test/data/doc/page_with_pic.dt").open() as file:
+        doctags = file.read()
     image = PILImage.open(Path("test/data/doc/page_with_pic.png"))
 
     doctags_doc = DocTagsDocument.from_doctags_and_image_pairs([doctags], [image])
@@ -75,7 +76,8 @@ def test_doctags_load_from_memory():
 
 
 def test_doctags_load_without_image():
-    doctags = Path("test/data/doc/page_with_pic.dt").open("r").read()
+    with Path("test/data/doc/page_with_pic.dt").open() as file:
+        doctags = file.read()
     doctags_doc = DocTagsDocument.from_doctags_and_image_pairs([doctags], None)
     doc = DoclingDocument.load_from_doctags(doctags_doc)
     exp = "test/data/doc/page_without_pic.dt.json"
@@ -86,7 +88,8 @@ def test_doctags_load_without_image():
 
 
 def test_doctags_load_for_kv_region():
-    doctags = Path("test/data/doc/doc_with_kv.dt").open("r").read()
+    with Path("test/data/doc/doc_with_kv.dt").open() as file:
+        doctags = file.read()
     image = PILImage.open(Path("test/data/doc/doc_with_kv.png"))
     doctags_doc = DocTagsDocument.from_doctags_and_image_pairs([doctags], [image])
     doc = DoclingDocument.load_from_doctags(doctags_doc)
@@ -98,7 +101,8 @@ def test_doctags_load_for_kv_region():
 
 
 def test_multipage_doctags_load():
-    doctags = Path("test/data/doc/2206.01062.yaml.dt").open("r").read()
+    with Path("test/data/doc/2206.01062.yaml.dt").open() as file:
+        doctags = file.read()
     doctags_doc = DocTagsDocument.from_multipage_doctags_and_images(doctags, None)
     doc = DoclingDocument.load_from_doctags(doctags_doc)
     exp = "test/data/doc/2206.01062.yaml.dt.json"