Make @ConditionalOn[Boolean]Property @Repeatable

Update `ConditionalOnProperty`, `ConditionalOnBooleanProperty`
and `OnPropertyCondition` to support `@Repeatable`.

Closes gh-2541

spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/ConditionalOnBooleanProperties.java

@@ -0,0 +1,48 @@
+/*
+ * 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.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.autoconfigure.condition;
+
+import java.lang.annotation.Documented;
+import java.lang.annotation.ElementType;
+import java.lang.annotation.Retention;
+import java.lang.annotation.RetentionPolicy;
+import java.lang.annotation.Target;
+
+import org.springframework.context.annotation.Conditional;
+
+/**
+ * Container annotation that aggregates several
+ * {@link ConditionalOnProperty @ConditionalOnProperty} annotations.
+ *
+ * @author Phillip Webb
+ * @since 3.5.0
+ * @see ConditionalOnBooleanProperty
+ */
+@Retention(RetentionPolicy.RUNTIME)
+@Target({ ElementType.TYPE, ElementType.METHOD })
+@Documented
+@Conditional(OnPropertyCondition.class)
+public @interface ConditionalOnBooleanProperties {
+
+	/**
+	 * Return the contained
+	 * {@link ConditionalOnBooleanProperty @ConditionalOnBooleanProperty} annotations.
+	 * @return the contained annotations
+	 */
+	ConditionalOnBooleanProperty[] value();
+
+}

spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/ConditionalOnBooleanProperty.java

@@ -18,6 +18,7 @@ package org.springframework.boot.autoconfigure.condition;
 
 import java.lang.annotation.Documented;
 import java.lang.annotation.ElementType;
+import java.lang.annotation.Repeatable;
 import java.lang.annotation.Retention;
 import java.lang.annotation.RetentionPolicy;
 import java.lang.annotation.Target;
@@ -43,6 +44,7 @@ import org.springframework.core.env.Environment;
 @Target({ ElementType.TYPE, ElementType.METHOD })
 @Documented
 @Conditional(OnPropertyCondition.class)
+@Repeatable(ConditionalOnBooleanProperties.class)
 public @interface ConditionalOnBooleanProperty {
 
 	/**

spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/ConditionalOnProperties.java

@@ -0,0 +1,48 @@
+/*
+ * 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.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.autoconfigure.condition;
+
+import java.lang.annotation.Documented;
+import java.lang.annotation.ElementType;
+import java.lang.annotation.Retention;
+import java.lang.annotation.RetentionPolicy;
+import java.lang.annotation.Target;
+
+import org.springframework.context.annotation.Conditional;
+
+/**
+ * Container annotation that aggregates several
+ * {@link ConditionalOnProperty @ConditionalOnProperty} annotations.
+ *
+ * @author Phillip Webb
+ * @since 3.5.0
+ * @see ConditionalOnProperty
+ */
+@Retention(RetentionPolicy.RUNTIME)
+@Target({ ElementType.TYPE, ElementType.METHOD })
+@Documented
+@Conditional(OnPropertyCondition.class)
+public @interface ConditionalOnProperties {
+
+	/**
+	 * Return the contained {@link ConditionalOnProperty @ConditionalOnProperty}
+	 * annotations.
+	 * @return the contained annotations
+	 */
+	ConditionalOnProperty[] value();
+
+}

spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/ConditionalOnProperty.java

@@ -18,6 +18,7 @@ package org.springframework.boot.autoconfigure.condition;
 
 import java.lang.annotation.Documented;
 import java.lang.annotation.ElementType;
+import java.lang.annotation.Repeatable;
 import java.lang.annotation.Retention;
 import java.lang.annotation.RetentionPolicy;
 import java.lang.annotation.Target;
@@ -94,6 +95,7 @@ import org.springframework.core.env.Environment;
 @Target({ ElementType.TYPE, ElementType.METHOD })
 @Documented
 @Conditional(OnPropertyCondition.class)
+@Repeatable(ConditionalOnProperties.class)
 public @interface ConditionalOnProperty {
 
 	/**

spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/condition/OnPropertyCondition.java

@@ -18,6 +18,7 @@ package org.springframework.boot.autoconfigure.condition;
 
 import java.lang.annotation.Annotation;
 import java.util.ArrayList;
+import java.util.Arrays;
 import java.util.List;
 import java.util.stream.Stream;
 
@@ -28,6 +29,7 @@ import org.springframework.core.Ordered;
 import org.springframework.core.annotation.AnnotationAttributes;
 import org.springframework.core.annotation.MergedAnnotation;
 import org.springframework.core.annotation.MergedAnnotationPredicates;
+import org.springframework.core.annotation.MergedAnnotations;
 import org.springframework.core.annotation.Order;
 import org.springframework.core.env.PropertyResolver;
 import org.springframework.core.type.AnnotatedTypeMetadata;
@@ -50,11 +52,8 @@ class OnPropertyCondition extends SpringBootCondition {
 
 	@Override
 	public ConditionOutcome getMatchOutcome(ConditionContext context, AnnotatedTypeMetadata metadata) {
-		List<MergedAnnotation<Annotation>> annotations = Stream
-			.concat(metadata.getAnnotations().stream(ConditionalOnProperty.class.getName()),
-					metadata.getAnnotations().stream(ConditionalOnBooleanProperty.class.getName()))
-			.filter(MergedAnnotationPredicates.unique(MergedAnnotation::getMetaTypes))
-			.toList();
+		MergedAnnotations mergedAnnotations = metadata.getAnnotations();
+		List<MergedAnnotation<Annotation>> annotations = stream(mergedAnnotations).toList();
 		List<ConditionMessage> noMatch = new ArrayList<>();
 		List<ConditionMessage> match = new ArrayList<>();
 		for (MergedAnnotation<Annotation> annotation : annotations) {
@@ -67,6 +66,34 @@ class OnPropertyCondition extends SpringBootCondition {
 		return ConditionOutcome.match(ConditionMessage.of(match));
 	}
 
+	private Stream<MergedAnnotation<Annotation>> stream(MergedAnnotations mergedAnnotations) {
+		return Stream.concat(stream(mergedAnnotations, ConditionalOnProperty.class, ConditionalOnProperties.class),
+				stream(mergedAnnotations, ConditionalOnBooleanProperty.class, ConditionalOnBooleanProperties.class));
+	}
+
+	private Stream<MergedAnnotation<Annotation>> stream(MergedAnnotations mergedAnnotations,
+			Class<? extends Annotation> type, Class<? extends Annotation> containerType) {
+		return Stream.concat(stream(mergedAnnotations, type), streamRepeated(mergedAnnotations, type, containerType));
+	}
+
+	private Stream<MergedAnnotation<Annotation>> streamRepeated(MergedAnnotations mergedAnnotations,
+			Class<? extends Annotation> type, Class<? extends Annotation> containerType) {
+		return stream(mergedAnnotations, containerType).flatMap((container) -> streamRepeated(container, type));
+	}
+
+	@SuppressWarnings("unchecked")
+	private Stream<MergedAnnotation<Annotation>> streamRepeated(MergedAnnotation<Annotation> container,
+			Class<? extends Annotation> type) {
+		MergedAnnotation<? extends Annotation>[] repeated = container.getAnnotationArray(MergedAnnotation.VALUE, type);
+		return Arrays.stream((MergedAnnotation<Annotation>[]) repeated);
+	}
+
+	private Stream<MergedAnnotation<Annotation>> stream(MergedAnnotations annotations,
+			Class<? extends Annotation> containerType) {
+		return annotations.stream(containerType.getName())
+			.filter(MergedAnnotationPredicates.unique(MergedAnnotation::getMetaTypes));
+	}
+
 	private ConditionOutcome determineOutcome(MergedAnnotation<Annotation> annotation, PropertyResolver resolver) {
 		Class<Annotation> annotationType = annotation.getType();
 		Spec spec = new Spec(annotationType, annotation.asAnnotationAttributes());

spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/condition/ConditionalOnBooleanPropertyTests.java

@@ -178,6 +178,22 @@ class ConditionalOnBooleanPropertyTests {
 			.contains("@ConditionalOnBooleanProperty (test=true) found different value in property 'test'");
 	}
 
+	@Test
+	void repeatablePropertiesConditionReportWhenMatched() {
+		load(RepeatablePropertiesRequiredConfiguration.class, "property1=true", "property2=true");
+		assertThat(this.context.containsBean("foo")).isTrue();
+		String report = getConditionEvaluationReport();
+		assertThat(report).contains("@ConditionalOnBooleanProperty (property1=true) matched");
+		assertThat(report).contains("@ConditionalOnBooleanProperty (property2=true) matched");
+	}
+
+	@Test
+	void repeatablePropertiesConditionReportWhenDoesNotMatch() {
+		load(RepeatablePropertiesRequiredConfiguration.class, "property1=true");
+		assertThat(getConditionEvaluationReport())
+			.contains("@ConditionalOnBooleanProperty (property2=true) did not find property 'property2'");
+	}
+
 	private <T extends Exception> Consumer<T> causeMessageContaining(String message) {
 		return (ex) -> assertThat(ex.getCause()).hasMessageContaining(message);
 	}
@@ -266,4 +282,16 @@ class ConditionalOnBooleanPropertyTests {
 
 	}
 
+	@Configuration(proxyBeanMethods = false)
+	@ConditionalOnBooleanProperty("property1")
+	@ConditionalOnBooleanProperty("property2")
+	static class RepeatablePropertiesRequiredConfiguration {
+
+		@Bean
+		String foo() {
+			return "foo";
+		}
+
+	}
+
 }

spring-boot-project/spring-boot-autoconfigure/src/test/java/org/springframework/boot/autoconfigure/condition/ConditionalOnPropertyTests.java

@@ -274,19 +274,35 @@ class ConditionalOnPropertyTests {
 	}
 
 	@Test
-	void conditionReportWhenMatched() {
+	void multiplePropertiesConditionReportWhenMatched() {
 		load(MultiplePropertiesRequiredConfiguration.class, "property1=value1", "property2=value2");
 		assertThat(this.context.containsBean("foo")).isTrue();
 		assertThat(getConditionEvaluationReport()).contains("@ConditionalOnProperty ([property1,property2]) matched");
 	}
 
 	@Test
-	void conditionReportWhenDoesNotMatch() {
+	void multiplePropertiesConditionReportWhenDoesNotMatch() {
 		load(MultiplePropertiesRequiredConfiguration.class, "property1=value1");
 		assertThat(getConditionEvaluationReport())
 			.contains("@ConditionalOnProperty ([property1,property2]) did not find property 'property2'");
 	}
 
+	@Test
+	void repeatablePropertiesConditionReportWhenMatched() {
+		load(RepeatablePropertiesRequiredConfiguration.class, "property1=value1", "property2=value2");
+		assertThat(this.context.containsBean("foo")).isTrue();
+		String report = getConditionEvaluationReport();
+		assertThat(report).contains("@ConditionalOnProperty (property1) matched");
+		assertThat(report).contains("@ConditionalOnProperty (property2) matched");
+	}
+
+	@Test
+	void repeatablePropertiesConditionReportWhenDoesNotMatch() {
+		load(RepeatablePropertiesRequiredConfiguration.class, "property1=value1");
+		assertThat(getConditionEvaluationReport())
+			.contains("@ConditionalOnProperty (property2) did not find property 'property2'");
+	}
+
 	private void load(Class<?> config, String... environment) {
 		TestPropertyValues.of(environment).applyTo(this.environment);
 		this.context = new SpringApplicationBuilder(config).environment(this.environment)
@@ -315,6 +331,18 @@ class ConditionalOnPropertyTests {
 
 	}
 
+	@Configuration(proxyBeanMethods = false)
+	@ConditionalOnProperty("property1")
+	@ConditionalOnProperty("property2")
+	static class RepeatablePropertiesRequiredConfiguration {
+
+		@Bean
+		String foo() {
+			return "foo";
+		}
+
+	}
+
 	@Configuration(proxyBeanMethods = false)
 	@ConditionalOnProperty(prefix = "spring.", name = "the-relaxed-property")
 	static class RelaxedPropertiesRequiredConfiguration {