diff --git a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/jdbc/DataSourceAutoConfiguration.java b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/jdbc/DataSourceAutoConfiguration.java
index 5ad8ff75ae83..74e9624ef27b 100644
--- a/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/jdbc/DataSourceAutoConfiguration.java
+++ b/spring-boot-project/spring-boot-autoconfigure/src/main/java/org/springframework/boot/autoconfigure/jdbc/DataSourceAutoConfiguration.java
@@ -42,6 +42,7 @@
 import org.springframework.core.env.Environment;
 import org.springframework.core.type.AnnotatedTypeMetadata;
 import org.springframework.jdbc.datasource.embedded.EmbeddedDatabaseType;
+import org.springframework.util.PlaceholderResolutionException;
 import org.springframework.util.StringUtils;
 
 /**
@@ -156,7 +157,7 @@ private boolean hasDataSourceUrlProperty(ConditionContext context) {
 				try {
 					return StringUtils.hasText(environment.getProperty(DATASOURCE_URL_PROPERTY));
 				}
-				catch (IllegalArgumentException ex) {
+				catch (PlaceholderResolutionException ex) {
 					// Ignore unresolvable placeholder errors
 				}
 			}
diff --git a/spring-boot-project/spring-boot-test/src/test/java/org/springframework/boot/test/web/SpringBootTestRandomPortEnvironmentPostProcessorTests.java b/spring-boot-project/spring-boot-test/src/test/java/org/springframework/boot/test/web/SpringBootTestRandomPortEnvironmentPostProcessorTests.java
index e3ee27b5e364..3f0bc86b84e9 100644
--- a/spring-boot-project/spring-boot-test/src/test/java/org/springframework/boot/test/web/SpringBootTestRandomPortEnvironmentPostProcessorTests.java
+++ b/spring-boot-project/spring-boot-test/src/test/java/org/springframework/boot/test/web/SpringBootTestRandomPortEnvironmentPostProcessorTests.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2023 the original author or authors.
+ * Copyright 2012-2024 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.
@@ -27,9 +27,10 @@
 import org.springframework.core.env.MutablePropertySources;
 import org.springframework.mock.env.MockEnvironment;
 import org.springframework.test.context.support.TestPropertySourceUtils;
+import org.springframework.util.PlaceholderResolutionException;
 
 import static org.assertj.core.api.Assertions.assertThat;
-import static org.assertj.core.api.Assertions.assertThatIllegalArgumentException;
+import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
 
 /**
  * Tests for {@link SpringBootTestRandomPortEnvironmentPostProcessor}.
@@ -169,7 +170,7 @@ void postProcessWhenManagementServerPortPlaceholderAbsentShouldFail() {
 		addTestPropertySource("0", null);
 		this.propertySources
 			.addLast(new MapPropertySource("other", Collections.singletonMap("management.server.port", "${port}")));
-		assertThatIllegalArgumentException()
+		assertThatExceptionOfType(PlaceholderResolutionException.class)
 			.isThrownBy(() -> this.postProcessor.postProcessEnvironment(this.environment, null))
 			.withMessage("Could not resolve placeholder 'port' in value \"${port}\"");
 	}
@@ -196,7 +197,7 @@ void postProcessWhenServerPortPlaceholderAbsentShouldFail() {
 		source.put("server.port", "${port}");
 		source.put("management.server.port", "9090");
 		this.propertySources.addLast(new MapPropertySource("other", source));
-		assertThatIllegalArgumentException()
+		assertThatExceptionOfType(PlaceholderResolutionException.class)
 			.isThrownBy(() -> this.postProcessor.postProcessEnvironment(this.environment, null))
 			.withMessage("Could not resolve placeholder 'port' in value \"${port}\"");
 	}
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/config/ConfigDataEnvironmentContributorPlaceholdersResolver.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/config/ConfigDataEnvironmentContributorPlaceholdersResolver.java
index c7a26a98fd63..4fcf79586032 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/config/ConfigDataEnvironmentContributorPlaceholdersResolver.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/config/ConfigDataEnvironmentContributorPlaceholdersResolver.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2023 the original author or authors.
+ * Copyright 2012-2024 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.
@@ -51,7 +51,8 @@ class ConfigDataEnvironmentContributorPlaceholdersResolver implements Placeholde
 		this.activeContributor = activeContributor;
 		this.failOnResolveFromInactiveContributor = failOnResolveFromInactiveContributor;
 		this.helper = new PropertyPlaceholderHelper(SystemPropertyUtils.PLACEHOLDER_PREFIX,
-				SystemPropertyUtils.PLACEHOLDER_SUFFIX, SystemPropertyUtils.VALUE_SEPARATOR, true);
+				SystemPropertyUtils.PLACEHOLDER_SUFFIX, SystemPropertyUtils.VALUE_SEPARATOR,
+				SystemPropertyUtils.ESCAPE_CHARACTER, true);
 	}
 
 	@Override
diff --git a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/PropertySourcesPlaceholdersResolver.java b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/PropertySourcesPlaceholdersResolver.java
index b6b6b9e10cdc..67e432fab521 100644
--- a/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/PropertySourcesPlaceholdersResolver.java
+++ b/spring-boot-project/spring-boot/src/main/java/org/springframework/boot/context/properties/bind/PropertySourcesPlaceholdersResolver.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2012-2022 the original author or authors.
+ * Copyright 2012-2024 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.
@@ -47,8 +47,10 @@ public PropertySourcesPlaceholdersResolver(Iterable<PropertySource<?>> sources)
 
 	public PropertySourcesPlaceholdersResolver(Iterable<PropertySource<?>> sources, PropertyPlaceholderHelper helper) {
 		this.sources = sources;
-		this.helper = (helper != null) ? helper : new PropertyPlaceholderHelper(SystemPropertyUtils.PLACEHOLDER_PREFIX,
-				SystemPropertyUtils.PLACEHOLDER_SUFFIX, SystemPropertyUtils.VALUE_SEPARATOR, true);
+		this.helper = (helper != null) ? helper
+				: new PropertyPlaceholderHelper(SystemPropertyUtils.PLACEHOLDER_PREFIX,
+						SystemPropertyUtils.PLACEHOLDER_SUFFIX, SystemPropertyUtils.VALUE_SEPARATOR,
+						SystemPropertyUtils.ESCAPE_CHARACTER, true);
 	}
 
 	@Override