diff --git a/spring-boot-project/spring-boot-properties-migrator/src/main/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporter.java b/spring-boot-project/spring-boot-properties-migrator/src/main/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporter.java
index d8d99d2c64ed..298f51610e38 100644
--- a/spring-boot-project/spring-boot-properties-migrator/src/main/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporter.java
+++ b/spring-boot-project/spring-boot-properties-migrator/src/main/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporter.java
@@ -25,6 +25,7 @@
 
 import org.springframework.boot.configurationmetadata.ConfigurationMetadataProperty;
 import org.springframework.boot.configurationmetadata.ConfigurationMetadataRepository;
+import org.springframework.boot.configurationmetadata.Deprecation;
 import org.springframework.boot.context.properties.source.ConfigurationProperty;
 import org.springframework.boot.context.properties.source.ConfigurationPropertyName;
 import org.springframework.boot.context.properties.source.ConfigurationPropertySource;
@@ -32,6 +33,7 @@
 import org.springframework.boot.env.OriginTrackedMapPropertySource;
 import org.springframework.boot.origin.OriginTrackedValue;
 import org.springframework.core.env.ConfigurableEnvironment;
+import org.springframework.core.env.MapPropertySource;
 import org.springframework.core.env.PropertySource;
 import org.springframework.util.LinkedMultiValueMap;
 import org.springframework.util.MultiValueMap;
@@ -105,10 +107,50 @@ private Map<String, List<PropertyMigration>> getMatchingProperties(
 				result.add(name,
 						new PropertyMigration(configurationProperty, metadata, determineReplacementMetadata(metadata)));
 			}
+			getMatchingPropertiesForMapEntries(name, source, metadata, result);
 		}));
 		return result;
 	}
 
+	private void getMatchingPropertiesForMapEntries(String name, ConfigurationPropertySource source, ConfigurationMetadataProperty metadata, MultiValueMap<String, PropertyMigration> result) {
+		if (source.getUnderlyingSource() instanceof MapPropertySource && name.equals(metadata.getName())) {
+			MapPropertySource mapSource = ((MapPropertySource) source.getUnderlyingSource());
+			for (String propertyName: mapSource.getPropertyNames()) {
+				ConfigurationProperty configurationProperty = source.getConfigurationProperty(ConfigurationPropertyName.of(propertyName));
+				if (configurationProperty != null) {
+					ConfigurationMetadataProperty entryMetadata = generateMetadataForMapEntry(propertyName, metadata);
+					result.add(name,
+							new PropertyMigration(configurationProperty, entryMetadata, determineReplacementMetadata(entryMetadata)));
+				}
+			}
+		}
+	}
+
+	private ConfigurationMetadataProperty generateMetadataForMapEntry(String propertyName, ConfigurationMetadataProperty mapMetadata) {
+		ConfigurationMetadataProperty newMetadata = new ConfigurationMetadataProperty();
+		newMetadata.setName(propertyName);
+		newMetadata.setId(propertyName);
+		String entryName = propertyName.substring(propertyName.lastIndexOf("."));
+		Deprecation oldDeprecation = mapMetadata.getDeprecation();
+		if (oldDeprecation != null) {
+			Deprecation deprecation = new Deprecation();
+			deprecation.setLevel(oldDeprecation.getLevel());
+			deprecation.setReason(oldDeprecation.getReason());
+			deprecation.setShortReason(oldDeprecation.getShortReason());
+			deprecation.setReplacement(oldDeprecation.getReplacement() + entryName);
+			newMetadata.setDeprecation(deprecation);
+		}
+
+		String type = mapMetadata.getType();
+		if (type.startsWith(Map.class.getName())) {
+			int lastComma = type.lastIndexOf(',');
+			if (lastComma != -1) {
+				newMetadata.setType(type.substring(lastComma + 1, type.length() - 1).trim());
+			}
+		}
+		return newMetadata;
+	}
+
 	private ConfigurationMetadataProperty determineReplacementMetadata(ConfigurationMetadataProperty metadata) {
 		String replacementId = metadata.getDeprecation().getReplacement();
 		if (StringUtils.hasText(replacementId)) {
diff --git a/spring-boot-project/spring-boot-properties-migrator/src/test/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporterTests.java b/spring-boot-project/spring-boot-properties-migrator/src/test/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporterTests.java
index 4fed9c1902fc..076f416c8a8b 100644
--- a/spring-boot-project/spring-boot-properties-migrator/src/test/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporterTests.java
+++ b/spring-boot-project/spring-boot-properties-migrator/src/test/java/org/springframework/boot/context/properties/migrator/PropertiesMigrationReporterTests.java
@@ -144,6 +144,30 @@ void invalidReplacementHandled() throws IOException {
 		assertThat(report).doesNotContain("null");
 	}
 
+	@Test
+	void detectDeprecatedPropertyInMap() {
+		MutablePropertySources propertySources = this.environment.getPropertySources();
+		Map<String, Object> content = new LinkedHashMap<>();
+		content.put("status.http-mapping.down", 500);
+		content.put("status.http-mapping.out-of-service", 503);
+		content.put("status.http-mapping.warning", 500);
+		propertySources.addFirst(new MapPropertySource("status.http-mapping", content));
+		assertThat(propertySources).hasSize(2);
+
+		String report = createWarningReport(loadRepository("metadata/map-deprecated-metadata.json"));
+		assertThat(report).isNotNull();
+		assertThat(report).contains("Property source 'status.http-mapping'", "Key: status.http-mapping.down",
+				"Replacement: endpoint.status.http-mapping.down", "Key: status.http-mapping.out-of-service",
+				"Replacement: endpoint.status.http-mapping.out-of-service", "Key: status.http-mapping.warning",
+				"Replacement: endpoint.status.http-mapping.warning");
+		assertThat(mapToNames(propertySources)).containsExactly("migrate-status.http-mapping", "status.http-mapping", "mockProperties");
+		PropertySource<?> propertySource = propertySources.get("migrate-status.http-mapping");
+		assertThat(propertySource).isNotNull();
+		assertMappedProperty(propertySource, "endpoint.status.http-mapping.down", 500, null);
+		assertMappedProperty(propertySource, "endpoint.status.http-mapping.out-of-service", 503, null);
+		assertMappedProperty(propertySource, "endpoint.status.http-mapping.warning", 500, null);
+	}
+
 	private List<String> mapToNames(PropertySources sources) {
 		List<String> names = new ArrayList<>();
 		for (PropertySource<?> source : sources) {
diff --git a/spring-boot-project/spring-boot-properties-migrator/src/test/resources/metadata/map-deprecated-metadata.json b/spring-boot-project/spring-boot-properties-migrator/src/test/resources/metadata/map-deprecated-metadata.json
new file mode 100644
index 000000000000..3e2356d1a71b
--- /dev/null
+++ b/spring-boot-project/spring-boot-properties-migrator/src/test/resources/metadata/map-deprecated-metadata.json
@@ -0,0 +1,17 @@
+{
+  "properties": [
+    {
+      "name": "status.http-mapping",
+      "type": "java.util.Map<java.lang.String,java.lang.Integer>",
+      "deprecated": true,
+      "deprecation": {
+        "replacement": "endpoint.status.http-mapping"
+      }
+    },
+    {
+      "name": "endpoint.status.http-mapping",
+      "type": "java.util.Map<java.lang.String,java.lang.Integer>",
+      "description": ""
+    }
+  ]
+}
\ No newline at end of file