diff --git a/extensions-core/s3-extensions/src/main/java/org/apache/druid/storage/s3/S3Utils.java b/extensions-core/s3-extensions/src/main/java/org/apache/druid/storage/s3/S3Utils.java
index 087d6684c7f..0948f46096b 100644
--- a/extensions-core/s3-extensions/src/main/java/org/apache/druid/storage/s3/S3Utils.java
+++ b/extensions-core/s3-extensions/src/main/java/org/apache/druid/storage/s3/S3Utils.java
@@ -73,6 +73,10 @@ public class S3Utils
       if (e == null) {
         return false;
       } else if (e instanceof IOException) {
+        if (e.getCause() != null) {
+          // Recurse with the underlying cause to see if it's retriable.
+          return apply(e.getCause());
+        }
         return true;
       } else if (e instanceof SdkClientException
                  && e.getMessage().contains("Data read has a different length than the expected")) {
diff --git a/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3DataSegmentPullerTest.java b/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3DataSegmentPullerTest.java
index 4577d5ba980..55773f0f2a1 100644
--- a/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3DataSegmentPullerTest.java
+++ b/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3DataSegmentPullerTest.java
@@ -131,7 +131,7 @@ public class S3DataSegmentPullerTest
   }
 
   @Test
-  public void testGZUncompressRetries() throws IOException, SegmentLoadingException
+  public void testGZUncompressOn4xxError() throws IOException
   {
     final String bucket = "bucket";
     final String keyPrefix = "prefix/dir/0";
@@ -165,6 +165,65 @@ public class S3DataSegmentPullerTest
     AmazonS3Exception exception = new AmazonS3Exception("S3DataSegmentPullerTest");
     exception.setErrorCode("NoSuchKey");
     exception.setStatusCode(404);
+    EasyMock.expect(s3Client.doesObjectExist(EasyMock.eq(object0.getBucketName()), EasyMock.eq(object0.getKey())))
+            .andReturn(true)
+            .once();
+    EasyMock.expect(s3Client.getObject(EasyMock.eq(bucket), EasyMock.eq(object0.getKey())))
+            .andThrow(exception)
+            .once();
+    S3DataSegmentPuller puller = new S3DataSegmentPuller(s3Client);
+
+    EasyMock.replay(s3Client);
+    Assert.assertThrows(
+        SegmentLoadingException.class,
+        () -> puller.getSegmentFiles(
+            new CloudObjectLocation(
+                bucket,
+                object0.getKey()
+            ), tmpDir
+        )
+    );
+    EasyMock.verify(s3Client);
+
+    File expected = new File(tmpDir, "renames-0");
+    Assert.assertFalse(expected.exists());
+  }
+
+  @Test
+  public void testGZUncompressOn5xxError() throws IOException, SegmentLoadingException
+  {
+    final String bucket = "bucket";
+    final String keyPrefix = "prefix/dir/0";
+    final ServerSideEncryptingAmazonS3 s3Client = EasyMock.createStrictMock(ServerSideEncryptingAmazonS3.class);
+    final byte[] value = bucket.getBytes(StandardCharsets.UTF_8);
+
+    final File tmpFile = temporaryFolder.newFile("gzTest.gz");
+
+    try (OutputStream outputStream = new GZIPOutputStream(new FileOutputStream(tmpFile))) {
+      outputStream.write(value);
+    }
+
+    S3Object object0 = new S3Object();
+
+    object0.setBucketName(bucket);
+    object0.setKey(keyPrefix + "/renames-0.gz");
+    object0.getObjectMetadata().setLastModified(new Date(0));
+    object0.setObjectContent(new FileInputStream(tmpFile));
+
+    final S3ObjectSummary objectSummary = new S3ObjectSummary();
+    objectSummary.setBucketName(bucket);
+    objectSummary.setKey(keyPrefix + "/renames-0.gz");
+    objectSummary.setLastModified(new Date(0));
+
+    final ListObjectsV2Result listObjectsResult = new ListObjectsV2Result();
+    listObjectsResult.setKeyCount(1);
+    listObjectsResult.getObjectSummaries().add(objectSummary);
+
+    File tmpDir = temporaryFolder.newFolder("gzTestDir");
+
+    AmazonS3Exception exception = new AmazonS3Exception("S3DataSegmentPullerTest");
+    exception.setErrorCode("Slow Down");
+    exception.setStatusCode(503);
     EasyMock.expect(s3Client.doesObjectExist(EasyMock.eq(object0.getBucketName()), EasyMock.eq(object0.getKey())))
             .andReturn(true)
             .once();
diff --git a/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3UtilsTest.java b/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3UtilsTest.java
new file mode 100644
index 00000000000..6667d78a8c6
--- /dev/null
+++ b/extensions-core/s3-extensions/src/test/java/org/apache/druid/storage/s3/S3UtilsTest.java
@@ -0,0 +1,111 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+
+package org.apache.druid.storage.s3;
+
+import com.amazonaws.services.s3.model.AmazonS3Exception;
+import org.junit.Assert;
+import org.junit.Test;
+
+import java.io.IOException;
+import java.util.concurrent.atomic.AtomicInteger;
+
+public class S3UtilsTest
+{
+  @Test
+  public void testRetryWithIOExceptions()
+  {
+    final int maxRetries = 3;
+    final AtomicInteger count = new AtomicInteger();
+    Assert.assertThrows(
+        IOException.class,
+        () -> S3Utils.retryS3Operation(
+            () -> {
+              count.incrementAndGet();
+              throw new IOException("hmm");
+            },
+            maxRetries
+        ));
+    Assert.assertEquals(maxRetries, count.get());
+  }
+
+  @Test
+  public void testRetryWith4XXErrors()
+  {
+    final AtomicInteger count = new AtomicInteger();
+    Assert.assertThrows(
+        IOException.class,
+        () -> S3Utils.retryS3Operation(
+            () -> {
+              if (count.incrementAndGet() >= 2) {
+                return "hey";
+              } else {
+                AmazonS3Exception s3Exception = new AmazonS3Exception("a 403 s3 exception");
+                s3Exception.setStatusCode(403);
+                throw new IOException(s3Exception);
+              }
+            },
+            3
+        ));
+    Assert.assertEquals(1, count.get());
+  }
+
+  @Test
+  public void testRetryWith5XXErrorsNotExceedingMaxRetries() throws Exception
+  {
+    final int maxRetries = 3;
+    final AtomicInteger count = new AtomicInteger();
+    S3Utils.retryS3Operation(
+        () -> {
+          if (count.incrementAndGet() >= maxRetries) {
+            return "hey";
+          } else {
+            AmazonS3Exception s3Exception = new AmazonS3Exception("a 5xx s3 exception");
+            s3Exception.setStatusCode(500);
+            throw new IOException(s3Exception);
+          }
+        },
+        maxRetries
+    );
+    Assert.assertEquals(maxRetries, count.get());
+  }
+
+  @Test
+  public void testRetryWith5XXErrorsExceedingMaxRetries()
+  {
+    final int maxRetries = 3;
+    final AtomicInteger count = new AtomicInteger();
+    Assert.assertThrows(
+        IOException.class,
+        () -> S3Utils.retryS3Operation(
+            () -> {
+              if (count.incrementAndGet() > maxRetries) {
+                return "hey";
+              } else {
+                AmazonS3Exception s3Exception = new AmazonS3Exception("a 5xx s3 exception");
+                s3Exception.setStatusCode(500);
+                throw new IOException(s3Exception);
+              }
+            },
+            maxRetries
+        )
+    );
+    Assert.assertEquals(maxRetries, count.get());
+  }
+}