diff --git a/core/src/main/scala/kafka/log/Log.scala b/core/src/main/scala/kafka/log/Log.scala
index 2249b5eccbbe3..33a416ef3c5d9 100644
--- a/core/src/main/scala/kafka/log/Log.scala
+++ b/core/src/main/scala/kafka/log/Log.scala
@@ -1864,7 +1864,9 @@ class Log(@volatile private var _dir: File,
    */
   def deleteOldSegments(): Int = {
     if (config.delete) {
-      deleteRetentionMsBreachedSegments() + deleteRetentionSizeBreachedSegments() + deleteLogStartOffsetBreachedSegments()
+      deleteLogStartOffsetBreachedSegments() +
+        deleteRetentionSizeBreachedSegments() +
+        deleteRetentionMsBreachedSegments()
     } else {
       deleteLogStartOffsetBreachedSegments()
     }
diff --git a/core/src/test/scala/unit/kafka/log/LogTest.scala b/core/src/test/scala/unit/kafka/log/LogTest.scala
index 1a953c53d5d9b..9fdede45249f8 100755
--- a/core/src/test/scala/unit/kafka/log/LogTest.scala
+++ b/core/src/test/scala/unit/kafka/log/LogTest.scala
@@ -1515,6 +1515,27 @@ class LogTest {
       "expect a single producer state snapshot remaining")
   }
 
+  @Test
+  def testRetentionIdempotency(): Unit = {
+    val logConfig = LogTest.createLogConfig(segmentBytes = 2048 * 5, retentionBytes = -1, retentionMs = 900, fileDeleteDelayMs = 0)
+    val log = createLog(logDir, logConfig)
+
+    log.appendAsLeader(TestUtils.records(List(new SimpleRecord(mockTime.milliseconds() + 100, "a".getBytes))), leaderEpoch = 0)
+    log.roll()
+    log.appendAsLeader(TestUtils.records(List(new SimpleRecord(mockTime.milliseconds(), "b".getBytes))), leaderEpoch = 0)
+    log.roll()
+    log.appendAsLeader(TestUtils.records(List(new SimpleRecord(mockTime.milliseconds() + 100, "c".getBytes))), leaderEpoch = 0)
+
+    mockTime.sleep(901)
+
+    log.updateHighWatermark(log.logEndOffset)
+    log.maybeIncrementLogStartOffset(1L, ClientRecordDeletion)
+    assertEquals(2, log.deleteOldSegments(),
+      "Expecting two segment deletions as log start offset retention should unblock time based retention")
+    assertEquals(0, log.deleteOldSegments())
+  }
+
+
   @Test
   def testLogStartOffsetMovementDeletesSnapshots(): Unit = {
     val logConfig = LogTest.createLogConfig(segmentBytes = 2048 * 5, retentionBytes = -1, fileDeleteDelayMs = 0)