diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/BindConverter.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/BindConverter.java
index cdabe1d990d5..d98c31135c7a 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/BindConverter.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/BindConverter.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2022 the original author or authors.
+ * Copyright 2012-2023 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.
@@ -42,6 +42,7 @@
 import org.springframework.core.convert.TypeDescriptor;
 import org.springframework.core.convert.converter.ConditionalGenericConverter;
 import org.springframework.core.convert.support.GenericConversionService;
+import org.springframework.core.io.Resource;
 import org.springframework.util.CollectionUtils;
 
 /**
@@ -154,8 +155,8 @@ private static class ResolvableTypeDescriptor extends TypeDescriptor {
 	private static class TypeConverterConversionService extends GenericConversionService {
 
 		TypeConverterConversionService(Consumer<PropertyEditorRegistry> initializer) {
-			addConverter(new TypeConverterConverter(initializer));
 			ApplicationConversionService.addDelimitedStringConverters(this);
+			addConverter(new TypeConverterConverter(initializer));
 		}
 
 		@Override
@@ -196,16 +197,23 @@ private static class TypeConverterConverter implements ConditionalGenericConvert
 
 		@Override
 		public Set<ConvertiblePair> getConvertibleTypes() {
-			return Collections.singleton(new ConvertiblePair(String.class, Object.class));
+			return Set.of(new ConvertiblePair(String.class, Object.class),
+					new ConvertiblePair(String.class, Object[].class),
+					new ConvertiblePair(String.class, Collection.class));
 		}
 
 		@Override
 		public boolean matches(TypeDescriptor sourceType, TypeDescriptor targetType) {
 			Class<?> type = targetType.getType();
-			if (type == null || type == Object.class || Collection.class.isAssignableFrom(type)
-					|| Map.class.isAssignableFrom(type)) {
+			if (type == null || type == Object.class || Map.class.isAssignableFrom(type)) {
 				return false;
 			}
+			if (Collection.class.isAssignableFrom(type)) {
+				TypeDescriptor elementType = targetType.getElementTypeDescriptor();
+				if (elementType == null || (!Resource.class.isAssignableFrom(elementType.getType()))) {
+					return false;
+				}
+			}
 			PropertyEditor editor = this.matchesOnlyTypeConverter.getDefaultEditor(type);
 			if (editor == null) {
 				editor = this.matchesOnlyTypeConverter.findCustomEditor(type, null);
@@ -218,7 +226,7 @@ public boolean matches(TypeDescriptor sourceType, TypeDescriptor targetType) {
 
 		@Override
 		public Object convert(Object source, TypeDescriptor sourceType, TypeDescriptor targetType) {
-			return createTypeConverter().convertIfNecessary(source, targetType.getType());
+			return createTypeConverter().convertIfNecessary(source, targetType.getType(), targetType);
 		}
 
 		private SimpleTypeConverter createTypeConverter() {
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/context/properties/ConfigurationPropertiesTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/context/properties/ConfigurationPropertiesTests.java
index 3ae3dd2c2a7b..9f7c97f7a317 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/context/properties/ConfigurationPropertiesTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/context/properties/ConfigurationPropertiesTests.java
@@ -23,6 +23,7 @@
 import java.time.Period;
 import java.time.temporal.ChronoUnit;
 import java.util.ArrayList;
+import java.util.Collection;
 import java.util.Collections;
 import java.util.HashMap;
 import java.util.LinkedHashMap;
@@ -1173,6 +1174,22 @@ void loadWhenPotentiallyConstructorBoundPropertiesAreImportedUsesJavaBeanBinding
 		assertThat(properties.getProp()).isEqualTo("alpha");
 	}
 
+	@Test
+	void loadWhenBindingClasspathPatternToResourceArrayShouldBindMultipleValues() {
+		load(ResourceArrayPropertiesConfiguration.class,
+				"test.resources=classpath*:org/springframework/boot/context/properties/*.class");
+		ResourceArrayProperties properties = this.context.getBean(ResourceArrayProperties.class);
+		assertThat(properties.getResources()).hasSizeGreaterThan(1);
+	}
+
+	@Test
+	void loadWhenBindingClasspathPatternToResourceCollectionShouldBindMultipleValues() {
+		load(ResourceCollectionPropertiesConfiguration.class,
+				"test.resources=classpath*:org/springframework/boot/context/properties/*.class");
+		ResourceCollectionProperties properties = this.context.getBean(ResourceCollectionProperties.class);
+		assertThat(properties.getResources()).hasSizeGreaterThan(1);
+	}
+
 	private AnnotationConfigApplicationContext load(Class<?> configuration, String... inlinedProperties) {
 		return load(new Class<?>[] { configuration }, inlinedProperties);
 	}
@@ -3058,4 +3075,44 @@ void setProp(String prop) {
 
 	}
 
+	@EnableConfigurationProperties(ResourceArrayProperties.class)
+	static class ResourceArrayPropertiesConfiguration {
+
+	}
+
+	@ConfigurationProperties("test")
+	static class ResourceArrayProperties {
+
+		private Resource[] resources;
+
+		Resource[] getResources() {
+			return this.resources;
+		}
+
+		void setResources(Resource[] resources) {
+			this.resources = resources;
+		}
+
+	}
+
+	@EnableConfigurationProperties(ResourceCollectionProperties.class)
+	static class ResourceCollectionPropertiesConfiguration {
+
+	}
+
+	@ConfigurationProperties("test")
+	static class ResourceCollectionProperties {
+
+		private Collection<Resource> resources;
+
+		Collection<Resource> getResources() {
+			return this.resources;
+		}
+
+		void setResources(Collection<Resource> resources) {
+			this.resources = resources;
+		}
+
+	}
+
 }