diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointProperties.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointProperties.java
index 06a9223eaf62..2ecd45da2f2a 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointProperties.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/main/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointProperties.java
@@ -67,7 +67,7 @@ public void setBasePath(String basePath) {
 	}
 
 	private String cleanBasePath(String basePath) {
-		if (StringUtils.hasText(basePath) && basePath.endsWith("/")) {
+		if (StringUtils.hasText(basePath) && basePath.endsWith("/") && StringUtils.cleanPath(basePath).length() != 1) {
 			return basePath.substring(0, basePath.length() - 1);
 		}
 		return basePath;
diff --git a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointPropertiesTests.java b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointPropertiesTests.java
index 441d15bf6645..1e0e607175ec 100644
--- a/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointPropertiesTests.java
+++ b/spring-boot-project/spring-boot-actuator-autoconfigure/src/test/java/org/springframework/boot/actuate/autoconfigure/endpoint/web/WebEndpointPropertiesTests.java
@@ -16,10 +16,18 @@
 
 package org.springframework.boot.actuate.autoconfigure.endpoint.web;
 
+import org.junit.jupiter.api.Assertions;
 import org.junit.jupiter.api.Test;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.Arguments;
+import org.junit.jupiter.params.provider.MethodSource;
+import org.junit.jupiter.params.provider.ValueSource;
+
+import java.util.stream.Stream;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatIllegalArgumentException;
+import static org.junit.Assert.assertEquals;
 
 /**
  * Tests for {@link WebEndpointProperties}.
@@ -28,6 +36,8 @@
  */
 class WebEndpointPropertiesTests {
 
+	private static final String BLANK_ERR_MSG = "Base path must start with '/' or be empty";
+
 	@Test
 	void defaultBasePathShouldBeApplication() {
 		WebEndpointProperties properties = new WebEndpointProperties();
@@ -38,7 +48,7 @@ void defaultBasePathShouldBeApplication() {
 	void basePathShouldBeCleaned() {
 		WebEndpointProperties properties = new WebEndpointProperties();
 		properties.setBasePath("/");
-		assertThat(properties.getBasePath()).isEmpty();
+		assertThat(properties.getBasePath()).isNotEmpty();
 		properties.setBasePath("/actuator/");
 		assertThat(properties.getBasePath()).isEqualTo("/actuator");
 	}
@@ -57,4 +67,60 @@ void basePathCanBeEmpty() {
 		assertThat(properties.getBasePath()).isEmpty();
 	}
 
+	@ParameterizedTest
+	@MethodSource("notToBeCleanedArguments")
+	void basePathShouldNotBeCleaned(String path, String expected) {
+		WebEndpointProperties properties = new WebEndpointProperties();
+		properties.setBasePath(path);
+		assertThat(properties.getBasePath()).isNotEmpty();
+		assertEquals(properties.getBasePath(), expected);
+	}
+
+	private static Stream<Arguments> notToBeCleanedArguments() {
+		return Stream.of(
+				Arguments.of("/path", "/path"),
+				Arguments.of("/path/", "/path"),
+				Arguments.of("/", "/"),
+				Arguments.of("/path/path2", "/path/path2"),
+				Arguments.of("/path/path2/", "/path/path2"));
+	}
+
+	@ParameterizedTest
+	@MethodSource("notEmptyPaths")
+	void basePathShouldNotBeEmpty(String path) {
+		WebEndpointProperties properties = new WebEndpointProperties();
+		properties.setBasePath(path);
+		assertThat(properties.getBasePath()).isNotEmpty();
+	}
+
+	private static Stream<Arguments> notEmptyPaths() {
+		return Stream.of(Arguments.of("/path"), Arguments.of("/path/"));
+	}
+
+	@ParameterizedTest
+	@ValueSource(strings = {""})
+	void basePathShouldBeEmpty(String path) {
+		WebEndpointProperties properties = new WebEndpointProperties();
+		properties.setBasePath(path);
+		assertThat(properties.getBasePath()).isEmpty();
+	}
+
+	@ParameterizedTest
+	@MethodSource("argumentsForExceptions")
+	void basePathShouldThrowException(String input, Class<Exception> expectedEx, String expectedExMsg) {
+		Assertions.assertThrows(
+				expectedEx, () -> new WebEndpointProperties().setBasePath(input), expectedExMsg);
+	}
+
+	private static Stream<Arguments> argumentsForExceptions() {
+		return Stream.of(
+				Arguments.of(
+						"invalidpath",
+						IllegalArgumentException.class,
+						BLANK_ERR_MSG),
+				Arguments.of(
+						"  ", IllegalArgumentException.class, BLANK_ERR_MSG),
+				Arguments.of(
+						"null", IllegalArgumentException.class, BLANK_ERR_MSG));
+	}
 }