From 4318fa048f40c8394db1099b015534d9551f2477 Mon Sep 17 00:00:00 2001
From: ryo kamei <r-kamei@sixsquare.co.jp>
Date: Mon, 7 Oct 2024 01:54:02 +0900
Subject: [PATCH 1/3] BUG: The font list order of pypdf.annotations.FreeText is
 different(#1435)

---
 pypdf/annotations/_markup_annotations.py | 11 ++++++++---
 1 file changed, 8 insertions(+), 3 deletions(-)

diff --git a/pypdf/annotations/_markup_annotations.py b/pypdf/annotations/_markup_annotations.py
index 580b8bf58..5d7da5659 100644
--- a/pypdf/annotations/_markup_annotations.py
+++ b/pypdf/annotations/_markup_annotations.py
@@ -103,12 +103,17 @@ def __init__(
         self[NameObject("/Subtype")] = NameObject("/FreeText")
         self[NameObject("/Rect")] = RectangleObject(rect)
 
+        # Table 225 of the 1.7 reference ("CSS2 style attributes used in rich text strings")
         font_str = "font: "
-        if bold:
-            font_str = f"{font_str}bold "
         if italic:
             font_str = f"{font_str}italic "
-        font_str = f"{font_str}{font} {font_size}"
+        else:
+            font_str = f"{font_str}normal "
+        if bold:
+            font_str = f"{font_str}bold "
+        else:
+            font_str = f"{font_str}normal "
+        font_str = f"{font_str}{font_size} {font}"
         font_str = f"{font_str};text-align:left;color:#{font_color}"
 
         default_appearance_string = ""

From c77a0f5c4f1d643a10ad14fb29bd2caa81f2a62e Mon Sep 17 00:00:00 2001
From: Ryo Kamei <r-kamei@sixsquare.co.jp>
Date: Mon, 7 Oct 2024 10:39:58 +0900
Subject: [PATCH 2/3] Add tests

---
 tests/test_annotations.py | 18 ++++++++++++++++++
 1 file changed, 18 insertions(+)

diff --git a/tests/test_annotations.py b/tests/test_annotations.py
index f6d14c5e4..6c8c83f6b 100644
--- a/tests/test_annotations.py
+++ b/tests/test_annotations.py
@@ -93,6 +93,24 @@ def test_text_annotation(pdf_file_path):
 
 
 def test_free_text_annotation(pdf_file_path):
+    free_text_annotation = FreeText(
+        text="Hello World",
+        rect=(0, 0, 0, 0),
+    )
+    assert free_text_annotation["/DS"] == "font: normal normal 14pt Helvetica;text-align:left;color:#000000"
+    free_text_annotation = FreeText(
+        text="Hello World",
+        rect=(50, 550, 200, 650),
+        font="Arial",
+        bold=True,
+        italic=True,
+        font_size="20pt",
+        font_color="00ff00",
+        border_color=None,
+        background_color=None,
+    )
+    assert free_text_annotation["/DS"] == "font: italic bold 20pt Arial;text-align:left;color:#00ff00"
+
     # Arrange
     pdf_path = RESOURCE_ROOT / "crazyones.pdf"
     reader = PdfReader(pdf_path)

From 423876d757598f29ec92c21418b93cdb027e9902 Mon Sep 17 00:00:00 2001
From: Ryo Kamei <r-kamei@sixsquare.co.jp>
Date: Mon, 7 Oct 2024 16:37:27 +0900
Subject: [PATCH 3/3] Split the test

---
 tests/test_annotations.py | 38 ++++++++++++++++++++------------------
 1 file changed, 20 insertions(+), 18 deletions(-)

diff --git a/tests/test_annotations.py b/tests/test_annotations.py
index 6c8c83f6b..c5df2328d 100644
--- a/tests/test_annotations.py
+++ b/tests/test_annotations.py
@@ -93,24 +93,6 @@ def test_text_annotation(pdf_file_path):
 
 
 def test_free_text_annotation(pdf_file_path):
-    free_text_annotation = FreeText(
-        text="Hello World",
-        rect=(0, 0, 0, 0),
-    )
-    assert free_text_annotation["/DS"] == "font: normal normal 14pt Helvetica;text-align:left;color:#000000"
-    free_text_annotation = FreeText(
-        text="Hello World",
-        rect=(50, 550, 200, 650),
-        font="Arial",
-        bold=True,
-        italic=True,
-        font_size="20pt",
-        font_color="00ff00",
-        border_color=None,
-        background_color=None,
-    )
-    assert free_text_annotation["/DS"] == "font: italic bold 20pt Arial;text-align:left;color:#00ff00"
-
     # Arrange
     pdf_path = RESOURCE_ROOT / "crazyones.pdf"
     reader = PdfReader(pdf_path)
@@ -150,6 +132,26 @@ def test_free_text_annotation(pdf_file_path):
         writer.write(fp)
 
 
+def test_free_text_annotation__font_specifier():
+    free_text_annotation = FreeText(
+        text="Hello World",
+        rect=(0, 0, 0, 0),
+    )
+    assert free_text_annotation["/DS"] == "font: normal normal 14pt Helvetica;text-align:left;color:#000000"
+    free_text_annotation = FreeText(
+        text="Hello World",
+        rect=(50, 550, 200, 650),
+        font="Arial",
+        bold=True,
+        italic=True,
+        font_size="20pt",
+        font_color="00ff00",
+        border_color=None,
+        background_color=None,
+    )
+    assert free_text_annotation["/DS"] == "font: italic bold 20pt Arial;text-align:left;color:#00ff00"
+
+
 def test_annotationdictionary():
     a = AnnotationDictionary()
     a.flags = 123