diff --git a/tsdb/head_append.go b/tsdb/head_append.go
index e271ff6c5e..d1f4d3035e 100644
--- a/tsdb/head_append.go
+++ b/tsdb/head_append.go
@@ -1282,12 +1282,6 @@ func (s *memSeries) appendPreprocessor(t int64, e chunkenc.Encoding, o chunkOpts
 		// There is no head chunk in this series yet, create the first chunk for the sample.
 		c = s.cutNewHeadChunk(t, e, o.chunkRange)
 		chunkCreated = true
-	} else if len(c.chunk.Bytes()) > maxBytesPerXORChunk {
-		if c.maxTime >= t {
-			return c, false, false
-		}
-		c = s.cutNewHeadChunk(t, e, o.chunkRange)
-		chunkCreated = true
 	}
 
 	// Out of order sample.
@@ -1295,6 +1289,12 @@ func (s *memSeries) appendPreprocessor(t int64, e chunkenc.Encoding, o chunkOpts
 		return c, false, chunkCreated
 	}
 
+	// Check the chunk size, unless we just created it and if the chunk is too large, cut a new one.
+	if !chunkCreated && len(c.chunk.Bytes()) > maxBytesPerXORChunk {
+		c = s.cutNewHeadChunk(t, e, o.chunkRange)
+		chunkCreated = true
+	}
+
 	if c.chunk.Encoding() != e {
 		// The chunk encoding expected by this append is different than the head chunk's
 		// encoding. So we cut a new chunk with the expected encoding.