diff --git a/s3-extensions/src/main/java/io/druid/storage/s3/S3Utils.java b/s3-extensions/src/main/java/io/druid/storage/s3/S3Utils.java
index 0dfa685d3bd7..598153ec778a 100644
--- a/s3-extensions/src/main/java/io/druid/storage/s3/S3Utils.java
+++ b/s3-extensions/src/main/java/io/druid/storage/s3/S3Utils.java
@@ -58,7 +58,7 @@ public static void closeStreamsQuietly(S3Object s3Obj)
   public static <T> T retryS3Operation(Callable<T> f) throws IOException, S3ServiceException, InterruptedException
   {
     int nTry = 0;
-    final int maxTries = 3;
+    final int maxTries = 10;
     while (true) {
       try {
         nTry++;
@@ -89,13 +89,10 @@ public static <T> T retryS3Operation(Callable<T> f) throws IOException, S3Servic
   private static void awaitNextRetry(Exception e, int nTry) throws InterruptedException
   {
     final long baseSleepMillis = 1000;
-    final double fuzziness = 0.2;
-    final long sleepMillis = Math.max(
-        baseSleepMillis,
-        (long) (baseSleepMillis * Math.pow(2, nTry) *
-                (1 + new Random().nextGaussian() * fuzziness))
-    );
-    log.info(e, "S3 fail on try %d, retrying in %,dms.", nTry, sleepMillis);
+    final long maxSleepMillis = 60000;
+    final double fuzzyMultiplier = Math.min(Math.max(1 + 0.2 * new Random().nextGaussian(), 0), 2);
+    final long sleepMillis = (long) (Math.min(maxSleepMillis, baseSleepMillis * Math.pow(2, nTry)) * fuzzyMultiplier);
+    log.warn("S3 fail on try %d, retrying in %,dms.", nTry, sleepMillis);
     Thread.sleep(sleepMillis);
   }
 
diff --git a/server/src/main/java/io/druid/segment/realtime/plumber/RealtimePlumberSchool.java b/server/src/main/java/io/druid/segment/realtime/plumber/RealtimePlumberSchool.java
index 74893edbf020..35abfcaf866a 100644
--- a/server/src/main/java/io/druid/segment/realtime/plumber/RealtimePlumberSchool.java
+++ b/server/src/main/java/io/druid/segment/realtime/plumber/RealtimePlumberSchool.java
@@ -98,6 +98,8 @@ public class RealtimePlumberSchool implements PlumberSchool
   private final IndexGranularity segmentGranularity;
   private final Object handoffCondition = new Object();
 
+  private volatile boolean shuttingDown = false;
+
   @JacksonInject
   @NotNull
   private volatile ServiceEmitter emitter;
@@ -410,14 +412,16 @@ public void doRun()
                   log.makeAlert(e, "Failed to persist merged index[%s]", schema.getDataSource())
                      .addData("interval", interval)
                      .emit();
+                  if (shuttingDown) {
+                    // We're trying to shut down, and this segment failed to push. Let's just get rid of it.
+                    abandonSegment(truncatedTime, sink);
+                  }
                 }
 
                 if (mergedFile != null) {
                   try {
-                    if (mergedFile != null) {
-                      log.info("Deleting Index File[%s]", mergedFile);
-                      FileUtils.deleteDirectory(mergedFile);
-                    }
+                    log.info("Deleting Index File[%s]", mergedFile);
+                    FileUtils.deleteDirectory(mergedFile);
                   }
                   catch (IOException e) {
                     log.warn(e, "Error deleting directory[%s]", mergedFile);
@@ -433,6 +437,8 @@ public void finishJob()
       {
         log.info("Shutting down...");
 
+        shuttingDown = true;
+
         for (final Map.Entry<Long, Sink> entry : sinks.entrySet()) {
           persistAndMerge(entry.getKey(), entry.getValue());
         }
@@ -613,26 +619,7 @@ public ServerView.CallbackAction segmentAdded(DruidServer server, DataSegment se
                       final String sinkVersion = sink.getSegment().getVersion();
                       if (segmentVersion.compareTo(sinkVersion) >= 0) {
                         log.info("Segment version[%s] >= sink version[%s]", segmentVersion, sinkVersion);
-                        try {
-                          segmentAnnouncer.unannounceSegment(sink.getSegment());
-                          FileUtils.deleteDirectory(computePersistDir(schema, sink.getInterval()));
-                          log.info("Removing sinkKey %d for segment %s", sinkKey, sink.getSegment().getIdentifier());
-                          sinks.remove(sinkKey);
-                          sinkTimeline.remove(
-                              sink.getInterval(),
-                              sink.getVersion(),
-                              new SingleElementPartitionChunk<Sink>(sink)
-                          );
-
-                          synchronized (handoffCondition) {
-                            handoffCondition.notifyAll();
-                          }
-                        }
-                        catch (IOException e) {
-                          log.makeAlert(e, "Unable to delete old segment for dataSource[%s].", schema.getDataSource())
-                             .addData("interval", sink.getInterval())
-                             .emit();
-                        }
+                        abandonSegment(sinkKey, sink);
                       }
                     }
                   }
@@ -706,6 +693,31 @@ public ScheduledExecutors.Signal doCall()
                 }
             );
       }
+
+      /**
+       * Unannounces a given sink and removes all local references to it.
+       */
+      private void abandonSegment(final long truncatedTime, final Sink sink) {
+        try {
+          segmentAnnouncer.unannounceSegment(sink.getSegment());
+          FileUtils.deleteDirectory(computePersistDir(schema, sink.getInterval()));
+          log.info("Removing sinkKey %d for segment %s", truncatedTime, sink.getSegment().getIdentifier());
+          sinks.remove(truncatedTime);
+          sinkTimeline.remove(
+              sink.getInterval(),
+              sink.getVersion(),
+              new SingleElementPartitionChunk<>(sink)
+          );
+          synchronized (handoffCondition) {
+            handoffCondition.notifyAll();
+          }
+        }
+        catch (IOException e) {
+          log.makeAlert(e, "Unable to abandon old segment for dataSource[%s]", schema.getDataSource())
+             .addData("interval", sink.getInterval())
+             .emit();
+        }
+      }
     };
   }