diff --git a/core/src/main/java/hudson/FilePath.java b/core/src/main/java/hudson/FilePath.java
index 2f3c08fcbad6592e2889ec2bcb1154ca969a3711..fb6a09a2d51a53e2e13dbdb98596f3183a131b7f 100644
--- a/core/src/main/java/hudson/FilePath.java
+++ b/core/src/main/java/hudson/FilePath.java
@@ -1271,7 +1271,7 @@ public final class FilePath implements Serializable {
         private static final long serialVersionUID = 1L;
         @Override
         public Void invoke(File f, VirtualChannel channel) throws IOException {
-            Util.deleteRecursive(deleting(f));
+            Util.deleteRecursive(fileToPath(f), path -> deleting(path.toFile()).delete());
             return null;
         }
     }
@@ -1286,7 +1286,7 @@ public final class FilePath implements Serializable {
         private static final long serialVersionUID = 1L;
         @Override
         public Void invoke(File f, VirtualChannel channel) throws IOException {
-            Util.deleteContentsRecursive(deleting(f));
+            Util.deleteContentsRecursive(fileToPath(f), path -> deleting(path.toFile()).delete());
             return null;
         }
     }
diff --git a/core/src/main/java/hudson/Util.java b/core/src/main/java/hudson/Util.java
index 5c258d94699fd7c41448152a43346808e4fe0412..3e857f481c67fc709ea642dc20b63f680b17785a 100644
--- a/core/src/main/java/hudson/Util.java
+++ b/core/src/main/java/hudson/Util.java
@@ -75,6 +75,7 @@ import java.time.temporal.ChronoUnit;
 import java.util.*;
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.atomic.AtomicBoolean;
+import java.util.function.Predicate;
 import java.util.logging.Level;
 import java.util.logging.LogRecord;
 import java.util.logging.Logger;
@@ -241,7 +242,18 @@ public class Util {
      *      if the operation fails.
      */
     public static void deleteContentsRecursive(@Nonnull File file) throws IOException {
-        newPathRemover().forceRemoveDirectoryContents(fileToPath(file));
+        deleteContentsRecursive(fileToPath(file), path -> true);
+    }
+
+    /**
+     * Deletes the given directory contents (but not the directory itself) recursively using a filter.
+     * @param path a directory to delete
+     * @param pathFilter a predicate that when evaluated to true will delete that path; when false, will ignore that path
+     * @throws IOException if the operation fails
+     */
+    @Restricted(NoExternalUse.class)
+    public static void deleteContentsRecursive(@Nonnull Path path, @Nonnull Predicate<Path> pathFilter) throws IOException {
+        newPathRemover(pathFilter).forceRemoveDirectoryContents(path);
     }
 
     /**
@@ -252,7 +264,7 @@ public class Util {
      * @throws IOException if it exists but could not be successfully deleted
      */
     public static void deleteFile(@Nonnull File f) throws IOException {
-        newPathRemover().forceRemoveFile(fileToPath(f));
+        newPathRemover(path -> true).forceRemoveFile(fileToPath(f));
     }
 
     /**
@@ -264,7 +276,18 @@ public class Util {
      * if the operation fails.
      */
     public static void deleteRecursive(@Nonnull File dir) throws IOException {
-        newPathRemover().forceRemoveRecursive(fileToPath(dir));
+        deleteRecursive(fileToPath(dir), path -> true);
+    }
+
+    /**
+     * Deletes the given directory and contents recursively using a filter.
+     * @param dir a directory to delete
+     * @param pathFilter a predicate that when evaluated to true will delete that path; when false, will ignore that path
+     * @throws IOException if the operation fails
+     */
+    @Restricted(NoExternalUse.class)
+    public static void deleteRecursive(@Nonnull Path dir, @Nonnull Predicate<Path> pathFilter) throws IOException {
+        newPathRemover(pathFilter).forceRemoveRecursive(dir);
     }
 
     /*
@@ -1560,8 +1583,8 @@ public class Util {
     @Restricted(value = NoExternalUse.class)
     static boolean GC_AFTER_FAILED_DELETE = SystemProperties.getBoolean(Util.class.getName() + ".performGCOnFailedDelete");
 
-    private static PathRemover newPathRemover() {
-        return PathRemover.newRobustRemover(DELETION_MAX - 1, GC_AFTER_FAILED_DELETE, WAIT_BETWEEN_DELETION_RETRIES);
+    private static PathRemover newPathRemover(@Nonnull Predicate<Path> pathFilter) {
+        return PathRemover.newFilteredRobustRemover(pathFilter, DELETION_MAX - 1, GC_AFTER_FAILED_DELETE, WAIT_BETWEEN_DELETION_RETRIES);
     }
 
     /**
diff --git a/core/src/main/java/jenkins/util/io/PathRemover.java b/core/src/main/java/jenkins/util/io/PathRemover.java
index 747439927768022f8a102e1db7d456d11179f454..789c9b4d795d4a8377a51e915f9edfee0c83c17a 100644
--- a/core/src/main/java/jenkins/util/io/PathRemover.java
+++ b/core/src/main/java/jenkins/util/io/PathRemover.java
@@ -42,6 +42,7 @@ import java.util.ArrayList;
 import java.util.List;
 import java.util.Optional;
 import java.util.Set;
+import java.util.function.Predicate;
 import java.util.stream.Collectors;
 import java.util.stream.Stream;
 
@@ -49,21 +50,23 @@ import java.util.stream.Stream;
 public class PathRemover {
 
     public static PathRemover newSimpleRemover() {
-        return new PathRemover(ignored -> false);
+        return new PathRemover(ignored -> false, ignored -> true);
     }
 
     public static PathRemover newRemoverWithStrategy(@Nonnull RetryStrategy retryStrategy) {
-        return new PathRemover(retryStrategy);
+        return new PathRemover(retryStrategy, ignored -> true);
     }
 
-    public static PathRemover newRobustRemover(int maxRetries, boolean gcAfterFailedRemove, long waitBetweenRetries) {
-        return new PathRemover(new PausingGCRetryStrategy(maxRetries < 1 ? 1 : maxRetries, gcAfterFailedRemove, waitBetweenRetries));
+    public static PathRemover newFilteredRobustRemover(@Nonnull Predicate<Path> pathFilter, int maxRetries, boolean gcAfterFailedRemove, long waitBetweenRetries) {
+        return new PathRemover(new PausingGCRetryStrategy(maxRetries < 1 ? 1 : maxRetries, gcAfterFailedRemove, waitBetweenRetries), pathFilter);
     }
 
     private final RetryStrategy retryStrategy;
+    private final Predicate<Path> pathFilter;
 
-    private PathRemover(@Nonnull RetryStrategy retryStrategy) {
+    private PathRemover(@Nonnull RetryStrategy retryStrategy, @Nonnull Predicate<Path> pathFilter) {
         this.retryStrategy = retryStrategy;
+        this.pathFilter = pathFilter;
     }
 
     public void forceRemoveFile(@Nonnull Path path) throws IOException {
@@ -186,7 +189,7 @@ public class PathRemover {
         }
     }
     
-    private static Optional<IOException> tryRemoveFile(@Nonnull Path path) {
+    private Optional<IOException> tryRemoveFile(@Nonnull Path path) {
         try {
             removeOrMakeRemovableThenRemove(path.normalize());
             return Optional.empty();
@@ -195,7 +198,7 @@ public class PathRemover {
         }
     }
 
-    private static List<IOException> tryRemoveRecursive(@Nonnull Path path) {
+    private List<IOException> tryRemoveRecursive(@Nonnull Path path) {
         Path normalized = path.normalize();
         List<IOException> accumulatedErrors = Util.isSymlink(normalized) ? new ArrayList<>() :
                 tryRemoveDirectoryContents(normalized);
@@ -203,7 +206,7 @@ public class PathRemover {
         return accumulatedErrors;
     }
 
-    private static List<IOException> tryRemoveDirectoryContents(@Nonnull Path path) {
+    private List<IOException> tryRemoveDirectoryContents(@Nonnull Path path) {
         Path normalized = path.normalize();
         List<IOException> accumulatedErrors = new ArrayList<>();
         if (!Files.isDirectory(normalized)) return accumulatedErrors;
@@ -217,7 +220,8 @@ public class PathRemover {
         return accumulatedErrors;
     }
 
-    private static void removeOrMakeRemovableThenRemove(@Nonnull Path path) throws IOException {
+    private void removeOrMakeRemovableThenRemove(@Nonnull Path path) throws IOException {
+        if (!pathFilter.test(path)) return;
         try {
             Files.deleteIfExists(path);
         } catch (IOException e) {
@@ -256,9 +260,9 @@ public class PathRemover {
          $ rm x
          rm: x not removed: Permission denied
          */
-        Path parent = path.getParent().normalize();
-        if (parent != null && !Files.isWritable(parent)) {
-            makeWritable(parent);
+        Optional<Path> maybeParent = Optional.ofNullable(path.getParent()).map(Path::normalize).filter(p -> !Files.isWritable(p));
+        if (maybeParent.isPresent()) {
+            makeWritable(maybeParent.get());
         }
     }
 
diff --git a/core/src/test/java/jenkins/util/io/PathRemoverTest.java b/core/src/test/java/jenkins/util/io/PathRemoverTest.java
index 747775531dae900509365ff01ca04078fc1573f8..fbfdd45a56aae7e046e0ea2851352e475b5dff16 100644
--- a/core/src/test/java/jenkins/util/io/PathRemoverTest.java
+++ b/core/src/test/java/jenkins/util/io/PathRemoverTest.java
@@ -91,6 +91,7 @@ public class PathRemoverTest {
         given(path.toString()).willReturn(filename);
         given(path.toFile()).willReturn(file);
         given(path.getFileSystem()).willReturn(fs);
+        given(path.normalize()).willReturn(path);
         given(fs.provider()).willReturn(fsProvider);
         given(fsProvider.deleteIfExists(path)).willThrow(new FileSystemException(filename));
         given(fsProvider.readAttributes(path, BasicFileAttributes.class)).willReturn(attributes);