diff --git a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/main/java/org/springframework/boot/configurationmetadata/changelog/Changelog.java b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/main/java/org/springframework/boot/configurationmetadata/changelog/Changelog.java
index 964298fe567..61217687e4e 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/main/java/org/springframework/boot/configurationmetadata/changelog/Changelog.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/main/java/org/springframework/boot/configurationmetadata/changelog/Changelog.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2023 the original author or authors.
+ * Copyright 2012-2025 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -21,6 +21,7 @@ import java.util.List;
 
 import org.springframework.boot.configurationmetadata.ConfigurationMetadataProperty;
 import org.springframework.boot.configurationmetadata.ConfigurationMetadataRepository;
+import org.springframework.boot.configurationmetadata.Deprecation;
 
 /**
  * A changelog containing differences computed from two repositories of configuration
@@ -32,6 +33,7 @@ import org.springframework.boot.configurationmetadata.ConfigurationMetadataRepos
  * @author Stephane Nicoll
  * @author Andy Wilkinson
  * @author Phillip Webb
+ * @author Yoobin Yoon
  */
 record Changelog(String oldVersionNumber, String newVersionNumber, List<Difference> differences) {
 
@@ -48,14 +50,24 @@ record Changelog(String oldVersionNumber, String newVersionNumber, List<Differen
 			String id = oldProperty.getId();
 			seenIds.add(id);
 			ConfigurationMetadataProperty newProperty = newMetadata.getAllProperties().get(id);
-			Difference difference = Difference.compute(oldProperty, newProperty);
-			if (difference != null) {
-				differences.add(difference);
+			if (newProperty == null) {
+				differences.add(new Difference(DifferenceType.DELETED, oldProperty, null));
+			}
+			else {
+				Difference difference = Difference.compute(oldProperty, newProperty);
+				if (difference != null) {
+					differences.add(difference);
+				}
 			}
 		}
 		for (ConfigurationMetadataProperty newProperty : newMetadata.getAllProperties().values()) {
-			if ((!seenIds.contains(newProperty.getId())) && (!newProperty.isDeprecated())) {
-				differences.add(new Difference(DifferenceType.ADDED, null, newProperty));
+			if (!seenIds.contains(newProperty.getId())) {
+				if (newProperty.isDeprecated() && newProperty.getDeprecation().getLevel() == Deprecation.Level.ERROR) {
+					differences.add(new Difference(DifferenceType.DELETED, null, newProperty));
+				}
+				else if (!newProperty.isDeprecated()) {
+					differences.add(new Difference(DifferenceType.ADDED, null, newProperty));
+				}
 			}
 		}
 		return List.copyOf(differences);
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/java/org/springframework/boot/configurationmetadata/changelog/ChangelogTests.java b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/java/org/springframework/boot/configurationmetadata/changelog/ChangelogTests.java
index 5057cb8087e..8d59cb65ade 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/java/org/springframework/boot/configurationmetadata/changelog/ChangelogTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/java/org/springframework/boot/configurationmetadata/changelog/ChangelogTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2023 the original author or authors.
+ * Copyright 2012-2025 the original author or authors.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -29,6 +29,7 @@ import static org.assertj.core.api.Assertions.assertThat;
  *
  * @author Stephane Nicoll
  * @author Andy Wilkinson
+ * @author Yoobin Yoon
  */
 class ChangelogTests {
 
@@ -38,7 +39,7 @@ class ChangelogTests {
 		assertThat(differences).isNotNull();
 		assertThat(differences.oldVersionNumber()).isEqualTo("1.0");
 		assertThat(differences.newVersionNumber()).isEqualTo("2.0");
-		assertThat(differences.differences()).hasSize(4);
+		assertThat(differences.differences()).hasSize(5);
 		List<Difference> added = differences.differences()
 			.stream()
 			.filter((difference) -> difference.type() == DifferenceType.ADDED)
@@ -49,10 +50,12 @@ class ChangelogTests {
 			.stream()
 			.filter((difference) -> difference.type() == DifferenceType.DELETED)
 			.toList();
-		assertThat(deleted).hasSize(2)
+		assertThat(deleted).hasSize(3)
 			.anySatisfy((entry) -> assertProperty(entry.oldProperty(), "test.delete", String.class, "delete"))
 			.anySatisfy(
-					(entry) -> assertProperty(entry.newProperty(), "test.delete.deprecated", String.class, "delete"));
+					(entry) -> assertProperty(entry.newProperty(), "test.delete.deprecated", String.class, "delete"))
+			.anySatisfy((entry) -> assertProperty(entry.newProperty(), "test.removed.directly", String.class,
+					"directlyRemoved"));
 		List<Difference> deprecated = differences.differences()
 			.stream()
 			.filter((difference) -> difference.type() == DifferenceType.DEPRECATED)
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample-2.0.json b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample-2.0.json
index ef959d39c9e..897c7b6dbc3 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample-2.0.json
+++ b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample-2.0.json
@@ -31,6 +31,17 @@
         "replacement": "test.add",
         "reason": "it was just bad"
       }
+    },
+    {
+      "name": "test.removed.directly",
+      "type": "java.lang.String",
+      "description": "Test property removed without prior deprecation.",
+      "defaultValue": "directlyRemoved",
+      "deprecation": {
+        "level": "error",
+        "replacement": "test.new.property",
+        "reason": "Removed in Upgrade 10"
+      }
     }
   ]
-}
\ No newline at end of file
+}
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample.adoc b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample.adoc
index 26876aa8542..21963bffaa0 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample.adoc
+++ b/spring-boot-project/spring-boot-tools/spring-boot-configuration-metadata-changelog-generator/src/test/resources/sample.adoc
@@ -32,4 +32,8 @@ _None_.
 | `test.delete.deprecated`
 | `test.add`
 | it was just bad
+
+| `test.removed.directly`
+| `test.new.property`
+| Removed in Upgrade 10
 |======================