diff --git a/ldap/src/integration-test/java/org/springframework/security/ldap/server/UnboundIdContainerLdifTests.java b/ldap/src/integration-test/java/org/springframework/security/ldap/server/UnboundIdContainerLdifTests.java
new file mode 100644
index 0000000000..a407a244e8
--- /dev/null
+++ b/ldap/src/integration-test/java/org/springframework/security/ldap/server/UnboundIdContainerLdifTests.java
@@ -0,0 +1,144 @@
+/*
+ * Copyright 2002-2020 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.security.ldap.server;
+
+import org.junit.After;
+import org.junit.Test;
+import org.springframework.context.annotation.AnnotationConfigApplicationContext;
+import org.springframework.context.annotation.Bean;
+import org.springframework.context.annotation.Configuration;
+import org.springframework.ldap.core.ContextSource;
+import org.springframework.security.ldap.DefaultSpringSecurityContextSource;
+import org.springframework.security.ldap.SpringSecurityLdapTemplate;
+
+import javax.annotation.PreDestroy;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.failBecauseExceptionWasNotThrown;
+
+/**
+ * Tests for {@link UnboundIdContainer}, specifically relating to LDIF file detection.
+ *
+ * @author Eleftheria Stein
+ */
+public class UnboundIdContainerLdifTests {
+
+	AnnotationConfigApplicationContext appCtx;
+
+	@After
+	public void closeAppContext() {
+		if (appCtx != null) {
+			appCtx.close();
+			appCtx = null;
+		}
+	}
+
+	@Test
+	public void unboundIdContainerWhenCustomLdifNameThenLdifLoaded() {
+		appCtx = new AnnotationConfigApplicationContext(CustomLdifConfig.class);
+
+		DefaultSpringSecurityContextSource contextSource = (DefaultSpringSecurityContextSource) appCtx
+				.getBean(ContextSource.class);
+
+		SpringSecurityLdapTemplate template = new SpringSecurityLdapTemplate(contextSource);
+		assertThat(template.compare("uid=bob,ou=people", "uid", "bob")).isTrue();
+	}
+
+	@Configuration
+	static class CustomLdifConfig {
+		private UnboundIdContainer container = new UnboundIdContainer("dc=springframework,dc=org",
+				"classpath:test-server.ldif");
+
+		@Bean
+		UnboundIdContainer ldapContainer() {
+			this.container.setPort(0);
+			return this.container;
+		}
+
+		@Bean
+		ContextSource contextSource(UnboundIdContainer container) {
+			return new DefaultSpringSecurityContextSource("ldap://127.0.0.1:"
+					+ container.getPort() + "/dc=springframework,dc=org");
+		}
+
+		@PreDestroy
+		void shutdown() {
+			this.container.stop();
+		}
+	}
+
+	@Test
+	public void unboundIdContainerWhenWildcardLdifNameThenLdifLoaded() {
+		appCtx = new AnnotationConfigApplicationContext(WildcardLdifConfig.class);
+
+		DefaultSpringSecurityContextSource contextSource = (DefaultSpringSecurityContextSource) appCtx
+				.getBean(ContextSource.class);
+
+		SpringSecurityLdapTemplate template = new SpringSecurityLdapTemplate(contextSource);
+		assertThat(template.compare("uid=bob,ou=people", "uid", "bob")).isTrue();
+	}
+
+	@Configuration
+	static class WildcardLdifConfig {
+		private UnboundIdContainer container = new UnboundIdContainer("dc=springframework,dc=org",
+				"classpath*:test-server.ldif");
+
+		@Bean
+		UnboundIdContainer ldapContainer() {
+			this.container.setPort(0);
+			return this.container;
+		}
+
+		@Bean
+		ContextSource contextSource(UnboundIdContainer container) {
+			return new DefaultSpringSecurityContextSource("ldap://127.0.0.1:"
+					+ container.getPort() + "/dc=springframework,dc=org");
+		}
+
+		@PreDestroy
+		void shutdown() {
+			this.container.stop();
+		}
+	}
+
+	@Test
+	public void unboundIdContainerWhenMalformedLdifThenException() {
+		try {
+			appCtx = new AnnotationConfigApplicationContext(MalformedLdifConfig.class);
+			failBecauseExceptionWasNotThrown(IllegalStateException.class);
+		} catch (Exception e) {
+			assertThat(e.getCause()).isInstanceOf(IllegalStateException.class);
+			assertThat(e.getMessage()).contains("Unable to load LDIF classpath:test-server-malformed.txt");
+		}
+	}
+
+	@Configuration
+	static class MalformedLdifConfig {
+		private UnboundIdContainer container = new UnboundIdContainer("dc=springframework,dc=org",
+				"classpath:test-server-malformed.txt");
+
+		@Bean
+		UnboundIdContainer ldapContainer() {
+			this.container.setPort(0);
+			return this.container;
+		}
+
+		@PreDestroy
+		void shutdown() {
+			this.container.stop();
+		}
+	}
+}
diff --git a/ldap/src/integration-test/resources/test-server-malformed.txt b/ldap/src/integration-test/resources/test-server-malformed.txt
new file mode 100644
index 0000000000..e24b511f76
--- /dev/null
+++ b/ldap/src/integration-test/resources/test-server-malformed.txt
@@ -0,0 +1,9 @@
+dn: ou=groups,dc=springframework,dc=org
+objectclass: top
+objectclass: organizationalUnit
+ou: groups
+
+dn ou=subgroups,ou=groups,dc=springframework,dc=org
+objectclass: top
+objectclass: organizationalUnit
+ou: subgroups
diff --git a/ldap/src/main/java/org/springframework/security/ldap/server/UnboundIdContainer.java b/ldap/src/main/java/org/springframework/security/ldap/server/UnboundIdContainer.java
index a533b029cb..aaa54ee413 100644
--- a/ldap/src/main/java/org/springframework/security/ldap/server/UnboundIdContainer.java
+++ b/ldap/src/main/java/org/springframework/security/ldap/server/UnboundIdContainer.java
@@ -114,10 +114,10 @@ public class UnboundIdContainer implements InitializingBean, DisposableBean, Lif
 
 	private void importLdif(InMemoryDirectoryServer directoryServer) {
 		if (StringUtils.hasText(this.ldif)) {
-			Resource resource = this.context.getResource(this.ldif);
 			try {
-				if (resource.exists()) {
-					try (InputStream inputStream = resource.getInputStream()) {
+				Resource[] resources = this.context.getResources(this.ldif);
+				if (resources.length > 0 && resources[0].exists()) {
+					try (InputStream inputStream = resources[0].getInputStream()) {
 						directoryServer.importFromLDIF(false, new LDIFReader(inputStream));
 					}
 				}