diff --git a/Tests/AK/TestString.cpp b/Tests/AK/TestString.cpp
index 38799ddb61a..6c40eba4887 100644
--- a/Tests/AK/TestString.cpp
+++ b/Tests/AK/TestString.cpp
@@ -211,7 +211,7 @@ TEST_CASE(to_titlecase)
     {
         auto string = MUST(String::from_utf8("f\"oo\" b'ar'"sv));
         auto result = MUST(string.to_titlecase());
-        EXPECT_EQ(result, "F\"Oo\" B'Ar'"sv);
+        EXPECT_EQ(result, "F\"Oo\" B'ar'"sv);
     }
     {
         auto string = MUST(String::from_utf8("123dollars"sv));
diff --git a/Tests/LibUnicode/TestUnicodeCharacterTypes.cpp b/Tests/LibUnicode/TestUnicodeCharacterTypes.cpp
index cc13963e272..211b4369df6 100644
--- a/Tests/LibUnicode/TestUnicodeCharacterTypes.cpp
+++ b/Tests/LibUnicode/TestUnicodeCharacterTypes.cpp
@@ -93,7 +93,7 @@ TEST_CASE(to_unicode_titlecase)
 
     EXPECT_EQ(MUST(Unicode::to_unicode_titlecase_full("foo bar baz"sv)), "Foo Bar Baz"sv);
     EXPECT_EQ(MUST(Unicode::to_unicode_titlecase_full("foo \n \r bar \t baz"sv)), "Foo \n \r Bar \t Baz"sv);
-    EXPECT_EQ(MUST(Unicode::to_unicode_titlecase_full("f\"oo\" b'ar'"sv)), "F\"Oo\" B'Ar'"sv);
+    EXPECT_EQ(MUST(Unicode::to_unicode_titlecase_full("f\"oo\" b'ar'"sv)), "F\"Oo\" B'ar'"sv);
     EXPECT_EQ(MUST(Unicode::to_unicode_titlecase_full("123dollars"sv)), "123Dollars"sv);
 }
 
diff --git a/Userland/Libraries/LibJS/Tests/builtins/Intl/Segmenter/Segmenter.prototype.segment.js b/Userland/Libraries/LibJS/Tests/builtins/Intl/Segmenter/Segmenter.prototype.segment.js
index 3db51e4e462..a1a527642c8 100644
--- a/Userland/Libraries/LibJS/Tests/builtins/Intl/Segmenter/Segmenter.prototype.segment.js
+++ b/Userland/Libraries/LibJS/Tests/builtins/Intl/Segmenter/Segmenter.prototype.segment.js
@@ -82,7 +82,6 @@ describe("correct behavior", () => {
         ];
         index = 0;
         for (const segment of wordSegments) {
-            console.log(JSON.stringify(segment));
             expect(segment.segment).toBe(expectedSegments[index].segment);
             expect(segment.index).toBe(expectedSegments[index].index);
             expect(segment.input).toBe(string);
@@ -103,4 +102,45 @@ describe("correct behavior", () => {
         }
         expect(index).toBe(1);
     });
+
+    test("word segmentation of string with mid-word punctuation", () => {
+        const string = "The quick (“brown”) fox can’t jump 32.3 feet, right?";
+
+        const segmenter = new Intl.Segmenter([], { granularity: "word" });
+        const segments = segmenter.segment(string);
+
+        const expectedSegments = [
+            { segment: "The", index: 0, isWordLike: true },
+            { segment: " ", index: 3, isWordLike: false },
+            { segment: "quick", index: 4, isWordLike: true },
+            { segment: " ", index: 9, isWordLike: false },
+            { segment: "(", index: 10, isWordLike: false },
+            { segment: "“", index: 11, isWordLike: false },
+            { segment: "brown", index: 12, isWordLike: true },
+            { segment: "”", index: 17, isWordLike: false },
+            { segment: ")", index: 18, isWordLike: false },
+            { segment: " ", index: 19, isWordLike: false },
+            { segment: "fox", index: 20, isWordLike: true },
+            { segment: " ", index: 23, isWordLike: false },
+            { segment: "can’t", index: 24, isWordLike: true },
+            { segment: " ", index: 29, isWordLike: false },
+            { segment: "jump", index: 30, isWordLike: true },
+            { segment: " ", index: 34, isWordLike: false },
+            { segment: "32.3", index: 35, isWordLike: true },
+            { segment: " ", index: 39, isWordLike: false },
+            { segment: "feet", index: 40, isWordLike: true },
+            { segment: ",", index: 44, isWordLike: false },
+            { segment: " ", index: 45, isWordLike: false },
+            { segment: "right", index: 46, isWordLike: true },
+            { segment: "?", index: 51, isWordLike: false },
+        ];
+
+        let index = 0;
+        for (const segment of segments) {
+            expect(segment.segment).toBe(expectedSegments[index].segment);
+            expect(segment.index).toBe(expectedSegments[index].index);
+            expect(segment.input).toBe(string);
+            index++;
+        }
+    });
 });
diff --git a/Userland/Libraries/LibUnicode/Segmentation.cpp b/Userland/Libraries/LibUnicode/Segmentation.cpp
index f843f1f5a06..47715efe845 100644
--- a/Userland/Libraries/LibUnicode/Segmentation.cpp
+++ b/Userland/Libraries/LibUnicode/Segmentation.cpp
@@ -215,7 +215,7 @@ static void for_each_word_segmentation_boundary_impl([[maybe_unused]] ViewType c
                 auto it_copy = it;
                 ++it_copy;
                 if (it_copy != view.end())
-                    next_next_code_point = *it;
+                    next_next_code_point = *it_copy;
             }
             bool next_next_code_point_is_hebrew_letter = next_next_code_point.has_value() && has_any_wbp(*next_next_code_point, WBP::Hebrew_Letter);
             bool next_next_code_point_is_ah_letter = next_next_code_point_is_hebrew_letter || (next_next_code_point.has_value() && has_any_wbp(*next_next_code_point, WBP::ALetter));
@@ -256,7 +256,7 @@ static void for_each_word_segmentation_boundary_impl([[maybe_unused]] ViewType c
             if (code_point_is_numeric && next_code_point_is_ah_letter)
                 continue;
 
-            auto previous_code_point_is_numeric = previous_code_point.has_value() && has_any_wbp(code_point, WBP::Numeric);
+            auto previous_code_point_is_numeric = previous_code_point.has_value() && has_any_wbp(*previous_code_point, WBP::Numeric);
 
             // WB11
             if (previous_code_point_is_numeric && next_code_point_is_numeric && (code_point_is_mid_num_let_q || has_any_wbp(code_point, WBP::MidNum)))