diff --git a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/AbstractBuildLog.java b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/AbstractBuildLog.java
index b870d30f9f6..7e4f26b62b5 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/AbstractBuildLog.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/AbstractBuildLog.java
@@ -102,6 +102,17 @@ public abstract class AbstractBuildLog implements BuildLog {
 		log();
 	}
 
+	@Override
+	public void failedCleaningWorkDir(Cache cache, Exception exception) {
+		StringBuilder message = new StringBuilder("Warning: Working location " + cache + " could not be cleaned");
+		if (exception != null) {
+			message.append(": ").append(exception.getMessage());
+		}
+		log();
+		log(message.toString());
+		log();
+	}
+
 	private String getDigest(Image image) {
 		List<String> digests = image.getDigests();
 		return (digests.isEmpty() ? "" : digests.get(0));
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/BuildLog.java b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/BuildLog.java
index e84054773f4..868a81a2300 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/BuildLog.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/BuildLog.java
@@ -114,6 +114,13 @@ public interface BuildLog {
 	 */
 	void taggedImage(ImageReference tag);
 
+	/**
+	 * Log that a cache cleanup step was not completed successfully.
+	 * @param cache the cache
+	 * @param exception any exception that caused the failure
+	 */
+	void failedCleaningWorkDir(Cache cache, Exception exception);
+
 	/**
 	 * Factory method that returns a {@link BuildLog} the outputs to {@link System#out}.
 	 * @return a build log instance that logs to system out
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/Lifecycle.java b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/Lifecycle.java
index 781d0aa7782..80322a0230a 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/Lifecycle.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-buildpack-platform/src/main/java/org/springframework/boot/buildpack/platform/build/Lifecycle.java
@@ -311,7 +311,7 @@ class Lifecycle implements Closeable {
 			deleteVolume(cache.getVolume().getVolumeName());
 		}
 		if (cache.getBind() != null) {
-			deleteBind(cache.getBind().getSource());
+			deleteBind(cache.getBind());
 		}
 	}
 
@@ -319,12 +319,12 @@ class Lifecycle implements Closeable {
 		this.docker.volume().delete(name, true);
 	}
 
-	private void deleteBind(String source) {
+	private void deleteBind(Cache.Bind bind) {
 		try {
-			FileSystemUtils.deleteRecursively(Path.of(source));
+			FileSystemUtils.deleteRecursively(Path.of(bind.getSource()));
 		}
 		catch (IOException ex) {
-			throw new IllegalStateException("Error cleaning bind mount directory '" + source + "'", ex);
+			this.log.failedCleaningWorkDir(bind, ex);
 		}
 	}
 
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java b/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java
index 5a0706ff108..b20924ad7d6 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-gradle-plugin/src/test/java/org/springframework/boot/gradle/tasks/bundling/BootBuildImageIntegrationTests.java
@@ -36,7 +36,6 @@ import org.apache.commons.compress.compressors.gzip.GzipCompressorOutputStream;
 import org.apache.commons.compress.utils.IOUtils;
 import org.gradle.testkit.runner.BuildResult;
 import org.gradle.testkit.runner.TaskOutcome;
-import org.junit.jupiter.api.Disabled;
 import org.junit.jupiter.api.TestTemplate;
 import org.junit.jupiter.api.condition.EnabledOnOs;
 import org.junit.jupiter.api.condition.OS;
@@ -301,10 +300,8 @@ class BootBuildImageIntegrationTests {
 	}
 
 	@TestTemplate
-	@EnabledOnOs(value = OS.LINUX,
-			disabledReason = "Works with Docker Engine on Linux but is not reliable with "
-					+ "Docker Desktop on other OSs")
-	@Disabled("gh-40760")
+	@EnabledOnOs(value = OS.LINUX, disabledReason = "Works with Docker Engine on Linux but is not reliable with "
+			+ "Docker Desktop on other OSs")
 	void buildsImageWithBindCaches() throws IOException {
 		writeMainClass();
 		writeLongNameResource();
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java
index a5e53a286b7..b4d0fffeb5b 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-maven-plugin/src/intTest/java/org/springframework/boot/maven/BuildImageTests.java
@@ -25,7 +25,6 @@ import java.time.OffsetDateTime;
 import java.util.Random;
 import java.util.stream.IntStream;
 
-import org.junit.jupiter.api.Disabled;
 import org.junit.jupiter.api.TestTemplate;
 import org.junit.jupiter.api.condition.EnabledOnOs;
 import org.junit.jupiter.api.condition.OS;
@@ -402,10 +401,8 @@ class BuildImageTests extends AbstractArchiveIntegrationTests {
 	}
 
 	@TestTemplate
-	@EnabledOnOs(value = OS.LINUX,
-			disabledReason = "Works with Docker Engine on Linux but is not reliable with "
-					+ "Docker Desktop on other OSs")
-	@Disabled("gh-40760")
+	@EnabledOnOs(value = OS.LINUX, disabledReason = "Works with Docker Engine on Linux but is not reliable with "
+			+ "Docker Desktop on other OSs")
 	void whenBuildImageIsInvokedWithBindCaches(MavenBuild mavenBuild) {
 		String testBuildId = randomString();
 		mavenBuild.project("build-image-bind-caches")