diff --git a/compaction_test.go b/compaction_test.go
index c6af69f041..bc251df464 100644
--- a/compaction_test.go
+++ b/compaction_test.go
@@ -2240,7 +2240,10 @@ func TestCompactFlushQueuedMemTable(t *testing.T) {
 		}
 	}
 
-	require.NoError(t, d.Compact([]byte("a"), []byte("a")))
+	require.NoError(t, d.Compact([]byte("a"), []byte("a\x00")))
+	d.mu.Lock()
+	require.Equal(t, 1, len(d.mu.mem.queue))
+	d.mu.Unlock()
 	require.NoError(t, d.Close())
 }
 
@@ -2260,13 +2263,21 @@ func TestCompactFlushQueuedLargeBatch(t *testing.T) {
 	// queued but not automatically flushed.
 	d.mu.Lock()
 	d.largeBatchThreshold = d.opts.MemTableSize / 8
+	require.Equal(t, 1, len(d.mu.mem.queue))
 	d.mu.Unlock()
 
 	// Set a record with a large value. This will be transformed into a large
 	// batch and placed in the flushable queue.
 	require.NoError(t, d.Set([]byte("a"), bytes.Repeat([]byte("v"), d.largeBatchThreshold), nil))
+	d.mu.Lock()
+	require.Greater(t, len(d.mu.mem.queue), 1)
+	d.mu.Unlock()
+
+	require.NoError(t, d.Compact([]byte("a"), []byte("a\x00")))
+	d.mu.Lock()
+	require.Equal(t, 1, len(d.mu.mem.queue))
+	d.mu.Unlock()
 
-	require.NoError(t, d.Compact([]byte("a"), []byte("a")))
 	require.NoError(t, d.Close())
 }
 
@@ -2354,3 +2365,14 @@ func TestAdjustGrandparentOverlapBytesForFlush(t *testing.T) {
 		})
 	}
 }
+
+func TestCompactionInvalidBounds(t *testing.T) {
+	db, err := Open("", &Options{
+		FS: vfs.NewMem(),
+	})
+	require.NoError(t, err)
+	defer db.Close()
+	require.NoError(t, db.Compact([]byte("a"), []byte("b")))
+	require.Error(t, db.Compact([]byte("a"), []byte("a")))
+	require.Error(t, db.Compact([]byte("b"), []byte("a")))
+}
diff --git a/db.go b/db.go
index 4f1ed2f888..0679644831 100644
--- a/db.go
+++ b/db.go
@@ -935,7 +935,10 @@ func (d *DB) Compact(
 	if d.opts.ReadOnly {
 		return ErrReadOnly
 	}
-
+	if d.cmp(start, end) >= 0 {
+		return errors.Errorf("Compact start %s is not less than end %s",
+			d.opts.Comparer.FormatKey(start), d.opts.Comparer.FormatKey(end))
+	}
 	iStart := base.MakeInternalKey(start, InternalKeySeqNumMax, InternalKeyKindMax)
 	iEnd := base.MakeInternalKey(end, 0, 0)
 	meta := []*fileMetadata{{Smallest: iStart, Largest: iEnd}}
diff --git a/error_test.go b/error_test.go
index 6b5eb4d9ff..47411449dc 100644
--- a/error_test.go
+++ b/error_test.go
@@ -121,7 +121,7 @@ func TestErrors(t *testing.T) {
 		if err := d.Flush(); err != nil {
 			return err
 		}
-		if err := d.Compact(nil, nil); err != nil {
+		if err := d.Compact(nil, []byte("\xff")); err != nil {
 			return err
 		}
 
diff --git a/open_test.go b/open_test.go
index b060bb7773..d18605e971 100644
--- a/open_test.go
+++ b/open_test.go
@@ -313,7 +313,7 @@ func TestOpenReadOnly(t *testing.T) {
 		require.NoError(t, err)
 
 		// Verify various write operations fail in read-only mode.
-		require.EqualValues(t, ErrReadOnly, d.Compact(nil, nil))
+		require.EqualValues(t, ErrReadOnly, d.Compact(nil, []byte("\xff")))
 		require.EqualValues(t, ErrReadOnly, d.Flush())
 		require.EqualValues(t, ErrReadOnly, func() error { _, err := d.AsyncFlush(); return err }())
 
@@ -672,7 +672,7 @@ func TestOpenWALReplayReadOnlySeqNums(t *testing.T) {
 	// written to the MANIFEST. This produces a MANIFEST where the `logSeqNum`
 	// is greater than the sequence numbers contained in the
 	// `minUnflushedLogNum` log file
-	require.NoError(t, d.Compact([]byte("a"), []byte("a")))
+	require.NoError(t, d.Compact([]byte("a"), []byte("a\x00")))
 
 	// While the MANIFEST is still in this state, copy all the files in the
 	// database to a new directory.
diff --git a/range_del_test.go b/range_del_test.go
index 228846fb67..a60fa3ebcb 100644
--- a/range_del_test.go
+++ b/range_del_test.go
@@ -203,7 +203,7 @@ func TestRangeDelCompactionTruncation(t *testing.T) {
 	require.NoError(t, d.DeleteRange([]byte("a"), []byte("d"), nil))
 
 	// Compact to produce the L1 tables.
-	require.NoError(t, d.Compact([]byte("c"), []byte("c")))
+	require.NoError(t, d.Compact([]byte("c"), []byte("c\x00")))
 	expectLSM(`
 1:
   000008:[a#3,RANGEDEL-b#72057594037927935,RANGEDEL]
@@ -211,7 +211,7 @@ func TestRangeDelCompactionTruncation(t *testing.T) {
 `)
 
 	// Compact again to move one of the tables to L2.
-	require.NoError(t, d.Compact([]byte("c"), []byte("c")))
+	require.NoError(t, d.Compact([]byte("c"), []byte("c\x00")))
 	expectLSM(`
 1:
   000008:[a#3,RANGEDEL-b#72057594037927935,RANGEDEL]
@@ -260,7 +260,7 @@ func TestRangeDelCompactionTruncation(t *testing.T) {
 	// containing "c" will be compacted again with the L2 table creating two
 	// tables in L2. Lastly, the L2 table containing "c" will be compacted
 	// creating the L3 table.
-	require.NoError(t, d.Compact([]byte("c"), []byte("c")))
+	require.NoError(t, d.Compact([]byte("c"), []byte("c\x00")))
 	expectLSM(`
 1:
   000012:[a#3,RANGEDEL-b#72057594037927935,RANGEDEL]
@@ -329,7 +329,7 @@ func TestRangeDelCompactionTruncation2(t *testing.T) {
 	require.NoError(t, d.DeleteRange([]byte("a"), []byte("d"), nil))
 
 	// Compact to produce the L1 tables.
-	require.NoError(t, d.Compact([]byte("b"), []byte("b")))
+	require.NoError(t, d.Compact([]byte("b"), []byte("b\x00")))
 	expectLSM(`
 6:
   000008:[a#3,RANGEDEL-b#2,SET]
@@ -337,7 +337,7 @@ func TestRangeDelCompactionTruncation2(t *testing.T) {
 `)
 
 	require.NoError(t, d.Set([]byte("c"), bytes.Repeat([]byte("d"), 100), nil))
-	require.NoError(t, d.Compact([]byte("c"), []byte("c")))
+	require.NoError(t, d.Compact([]byte("c"), []byte("c\x00")))
 	expectLSM(`
 6:
   000012:[a#3,RANGEDEL-b#2,SET]
@@ -404,7 +404,7 @@ func TestRangeDelCompactionTruncation3(t *testing.T) {
 
 	// Compact a few times to move the tables down to L3.
 	for i := 0; i < 3; i++ {
-		require.NoError(t, d.Compact([]byte("b"), []byte("b")))
+		require.NoError(t, d.Compact([]byte("b"), []byte("b\x00")))
 	}
 	expectLSM(`
 3:
@@ -414,7 +414,7 @@ func TestRangeDelCompactionTruncation3(t *testing.T) {
 
 	require.NoError(t, d.Set([]byte("c"), bytes.Repeat([]byte("d"), 100), nil))
 
-	require.NoError(t, d.Compact([]byte("c"), []byte("c")))
+	require.NoError(t, d.Compact([]byte("c"), []byte("c\x00")))
 	expectLSM(`
 4:
   000020:[a#3,RANGEDEL-b#2,SET]
@@ -422,7 +422,7 @@ func TestRangeDelCompactionTruncation3(t *testing.T) {
   000022:[c#4,SET-d#72057594037927935,RANGEDEL]
 `)
 
-	require.NoError(t, d.Compact([]byte("c"), []byte("c")))
+	require.NoError(t, d.Compact([]byte("c"), []byte("c\x00")))
 	expectLSM(`
 5:
   000023:[a#3,RANGEDEL-b#2,SET]
@@ -434,7 +434,7 @@ func TestRangeDelCompactionTruncation3(t *testing.T) {
 		t.Fatalf("expected not found, but found %v", err)
 	}
 
-	require.NoError(t, d.Compact([]byte("a"), []byte("a")))
+	require.NoError(t, d.Compact([]byte("a"), []byte("a\x00")))
 	expectLSM(`
 5:
   000025:[c#4,SET-d#72057594037927935,RANGEDEL]