diff --git a/CHANGES.txt b/CHANGES.txt
index cae6a43c50..30203a0bb0 100644
--- a/CHANGES.txt
+++ b/CHANGES.txt
@@ -46,6 +46,7 @@ Merged from 5.0:
  * Use estimated compressed size for tables to check if there is enough free space for a compaction (CASSANDRA-21245)
  * Fix failing select on system_views.settings for non-string keys (CASSANDRA-21348)
 Merged from 4.0:
+ * Consider first token of SSTable when calculating SSTable intersection in LeveledScanner  (CASSANDRA-21369)
  * Remove inFlightEcho entry on ECHO_REQ failure (CASSANDRA-21428)
  * Validate snapshot names (CASSANDRA-21389)
 
diff --git a/src/java/org/apache/cassandra/db/compaction/LeveledCompactionStrategy.java b/src/java/org/apache/cassandra/db/compaction/LeveledCompactionStrategy.java
index a22f06e562..609052c047 100644
--- a/src/java/org/apache/cassandra/db/compaction/LeveledCompactionStrategy.java
+++ b/src/java/org/apache/cassandra/db/compaction/LeveledCompactionStrategy.java
@@ -405,7 +405,7 @@ public class LeveledCompactionStrategy extends AbstractCompactionStrategy
 
     // Lazily creates SSTableBoundedScanner for sstable that are assumed to be from the
     // same level (e.g. non overlapping) - see #4142
-    private static class LeveledScanner extends AbstractIterator<UnfilteredRowIterator> implements ISSTableScanner
+    protected static class LeveledScanner extends AbstractIterator<UnfilteredRowIterator> implements ISSTableScanner
     {
         private final TableMetadata metadata;
         private final Collection<Range<Token>> ranges;
@@ -465,8 +465,7 @@ public class LeveledCompactionStrategy extends AbstractCompactionStrategy
             {
                 for (SSTableReader sstable : sstables)
                 {
-                    Range<Token> sstableRange = new Range<>(sstable.getFirst().getToken(), sstable.getLast().getToken());
-                    if (range == null || sstableRange.intersects(range))
+                    if (range == null || range.intersects(sstable.getBounds()))
                         filtered.add(sstable);
                 }
             }
diff --git a/test/unit/org/apache/cassandra/db/compaction/LeveledCompactionStrategyTest.java b/test/unit/org/apache/cassandra/db/compaction/LeveledCompactionStrategyTest.java
index 954bc312c1..0aeab98f79 100644
--- a/test/unit/org/apache/cassandra/db/compaction/LeveledCompactionStrategyTest.java
+++ b/test/unit/org/apache/cassandra/db/compaction/LeveledCompactionStrategyTest.java
@@ -76,6 +76,7 @@ import org.apache.cassandra.utils.Pair;
 import org.apache.cassandra.utils.TimeUUID;
 
 import static java.util.Collections.singleton;
+import static org.apache.cassandra.schema.MockSchema.readerBounds;
 import static org.apache.cassandra.utils.TimeUUID.Generator.nextTimeUUID;
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.junit.Assert.assertEquals;
@@ -1061,6 +1062,32 @@ public class LeveledCompactionStrategyTest
         }
     }
 
+    @Test
+    public void testLevelScannerIntersection()
+    {
+        Collection<SSTableReader> sstable = Collections.singleton(MockSchema.sstableWithLevel(1, 10, 20, 1, cfs));
+
+        // SSTable range - [10, 20]
+        // range - (1, 9]
+        Range<Token> range = new Range<>(readerBounds(1).getToken(), readerBounds(9).getToken());
+        assertEquals(0, LeveledCompactionStrategy.LeveledScanner.intersecting(sstable, Collections.singleton(range)).size());
+
+        // SSTable range - [10, 20]
+        // range - (1, 10]
+        range = new Range<>(readerBounds(1).getToken(), readerBounds(10).getToken());
+        assertEquals(1, LeveledCompactionStrategy.LeveledScanner.intersecting(sstable, Collections.singleton(range)).size());
+
+        // SSTable range - [10, 20]
+        // range - (1, 15]
+        range = new Range<>(readerBounds(1).getToken(), readerBounds(15).getToken());
+        assertEquals(1, LeveledCompactionStrategy.LeveledScanner.intersecting(sstable, Collections.singleton(range)).size());
+
+        // SSTable range - [10, 20]
+        // range - (20, 25]
+        range = new Range<>(readerBounds(20).getToken(), readerBounds(25).getToken());
+        assertEquals(0, LeveledCompactionStrategy.LeveledScanner.intersecting(sstable, Collections.singleton(range)).size());
+    }
+
     private Pair<Set<SSTableReader>, Set<SSTableReader>> groupByLevel(Iterable<SSTableReader> sstables)
     {
         Set<SSTableReader> l1after = new HashSet<>();