diff --git a/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitor.java b/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitor.java
index 825e774..78ae1cf 100644
--- a/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitor.java
+++ b/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitor.java
@@ -20,6 +20,7 @@
 import java.io.IOException;
 import java.nio.file.FileVisitResult;
 import java.nio.file.Files;
+import java.nio.file.NoSuchFileException;
 import java.nio.file.Path;
 import java.nio.file.SimpleFileVisitor;
 import java.nio.file.attribute.BasicFileAttributes;
@@ -75,6 +76,18 @@
         return FileVisitResult.CONTINUE;
     }
 
+    @Override
+    public FileVisitResult visitFileFailed(Path file, IOException ioException) throws IOException {
+        // LOG4J2-2677: Appenders may rollover and purge in parallel. SimpleVisitor rethrows exceptions from
+        // failed attempts to load file attributes.
+        if (ioException instanceof NoSuchFileException) {
+            LOGGER.info("File {} could not be accessed, it has likely already been deleted", file, ioException);
+            return FileVisitResult.CONTINUE;
+        } else {
+            return super.visitFileFailed(file, ioException);
+        }
+    }
+
     /**
      * Deletes the specified file.
      * 
diff --git a/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitor.java b/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitor.java
index 7bf76b6..0b9f1ca 100644
--- a/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitor.java
+++ b/log4j-core/src/main/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitor.java
@@ -17,8 +17,12 @@
 
 package org.apache.logging.log4j.core.appender.rolling.action;
 
+import org.apache.logging.log4j.Logger;
+import org.apache.logging.log4j.status.StatusLogger;
+
 import java.io.IOException;
 import java.nio.file.FileVisitResult;
+import java.nio.file.NoSuchFileException;
 import java.nio.file.Path;
 import java.nio.file.SimpleFileVisitor;
 import java.nio.file.attribute.BasicFileAttributes;
@@ -32,6 +36,7 @@
  */
 public class SortingVisitor extends SimpleFileVisitor<Path> {
 
+    private static final Logger LOGGER = StatusLogger.getLogger();
     private final PathSorter sorter;
     private final List<PathWithAttributes> collected = new ArrayList<>();
 
@@ -50,6 +55,18 @@
         collected.add(new PathWithAttributes(path, attrs));
         return FileVisitResult.CONTINUE;
     }
+
+    @Override
+    public FileVisitResult visitFileFailed(Path file, IOException ioException) throws IOException {
+        // LOG4J2-2677: Appenders may rollover and purge in parallel. SimpleVisitor rethrows exceptions from
+        // failed attempts to load file attributes.
+        if (ioException instanceof NoSuchFileException) {
+            LOGGER.info("File {} could not be accessed, it has likely already been deleted", file, ioException);
+            return FileVisitResult.CONTINUE;
+        } else {
+            return super.visitFileFailed(file, ioException);
+        }
+    }
     
     public List<PathWithAttributes> getSortedPaths() {
         Collections.sort(collected, sorter);
diff --git a/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitorTest.java b/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitorTest.java
index 7258c23..ed472ad 100644
--- a/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitorTest.java
+++ b/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/DeletingVisitorTest.java
@@ -18,11 +18,14 @@
 package org.apache.logging.log4j.core.appender.rolling.action;
 
 import java.io.IOException;
+import java.nio.file.FileVisitResult;
+import java.nio.file.NoSuchFileException;
 import java.nio.file.Path;
 import java.nio.file.Paths;
 import java.nio.file.attribute.BasicFileAttributes;
 import java.util.ArrayList;
 import java.util.Arrays;
+import java.util.Collections;
 import java.util.List;
 
 import org.junit.Test;
@@ -132,4 +135,26 @@
         final Path child = Paths.get("/a/b/c/relative");
         visitor.visitFile(child, null);
     }
+
+    @Test
+    public void testNoSuchFileFailure() throws IOException {
+        final DeletingVisitorHelper visitor =
+                new DeletingVisitorHelper(Paths.get("/a/b/c"), Collections.emptyList(), true);
+        assertEquals(
+                FileVisitResult.CONTINUE,
+                visitor.visitFileFailed(Paths.get("doesNotExist"), new NoSuchFileException("doesNotExist")));
+    }
+
+    @Test
+    public void testIOException() {
+        final DeletingVisitorHelper visitor =
+                new DeletingVisitorHelper(Paths.get("/a/b/c"), Collections.emptyList(), true);
+        IOException exception = new IOException();
+        try {
+            visitor.visitFileFailed(Paths.get("doesNotExist"), exception);
+            fail();
+        } catch (IOException e) {
+            assertSame(exception, e);
+        }
+    }
 }
diff --git a/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitorTest.java b/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitorTest.java
index dd32a0c..06ee1ce 100644
--- a/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitorTest.java
+++ b/log4j-core/src/test/java/org/apache/logging/log4j/core/appender/rolling/action/SortingVisitorTest.java
@@ -17,9 +17,13 @@
 
 package org.apache.logging.log4j.core.appender.rolling.action;
 
+import java.io.IOException;
 import java.nio.file.FileVisitOption;
+import java.nio.file.FileVisitResult;
 import java.nio.file.Files;
+import java.nio.file.NoSuchFileException;
 import java.nio.file.Path;
+import java.nio.file.Paths;
 import java.nio.file.attribute.FileAttribute;
 import java.nio.file.attribute.FileTime;
 import java.util.Collections;
@@ -91,4 +95,24 @@
         assertEquals("2nd; sorted=" + found, bbb, found.get(1).getPath());
         assertEquals("3rd: most recent sorted; list=" + found, ccc, found.get(2).getPath());
     }
+
+    @Test
+    public void testNoSuchFileFailure() throws IOException {
+        SortingVisitor visitor = new SortingVisitor(new PathSortByModificationTime(false));
+        assertEquals(
+                FileVisitResult.CONTINUE,
+                visitor.visitFileFailed(Paths.get("doesNotExist"), new NoSuchFileException("doesNotExist")));
+    }
+
+    @Test
+    public void testIOException() {
+        SortingVisitor visitor = new SortingVisitor(new PathSortByModificationTime(false));
+        IOException exception = new IOException();
+        try {
+            visitor.visitFileFailed(Paths.get("doesNotExist"), exception);
+            fail();
+        } catch (IOException e) {
+            assertSame(exception, e);
+        }
+    }
 }
diff --git a/src/changes/changes.xml b/src/changes/changes.xml
index f4ad3a5..bcb403b 100644
--- a/src/changes/changes.xml
+++ b/src/changes/changes.xml
@@ -169,6 +169,9 @@
       <action issue="LOG4J2-2415" dev="ckozak" type="fix" due-to="Andrey Turbanov">
         Fix lock contention in the classloader using new versions of slf4j without EventData on slf4j logger creation.
       </action>
+      <action issue="LOG4J2-2677" dev="ckozak" type="fix">
+        Rollover handles parallel file deletion gracefully.
+      </action>
     </release>
     <release version="2.13.0" date="2019-12-11" description="GA Release 2.13.0">
       <action issue="LOG4J2-2058" dev="rgoers" type="fix">