diff --git a/cmd/internal/batch_writer.go b/cmd/internal/batch_writer.go
index ad8bcee..f35d9ca 100644
--- a/cmd/internal/batch_writer.go
+++ b/cmd/internal/batch_writer.go
@@ -9,6 +9,9 @@ import (
 	"time"
 )
 
+const MaxObjectsInBatch int = 19000
+const MaxBatchRequestSize int = 20 * 1024 * 1024
+
 type BatchWriter interface {
 	Flush(stream *Stream) error
 	Send(record *Record, stream *Stream) error
@@ -48,50 +51,45 @@ func (h *httpBatchWriter) Flush(stream *Stream) error {
 		return nil
 	}
 
-	h.logger.Info(fmt.Sprintf("flushing [%v] messages for stream %q", len(h.messages), stream.Name))
+	batches := getBatchMessages(h.messages, stream, MaxObjectsInBatch, MaxBatchRequestSize)
+	h.logger.Info(fmt.Sprintf("flushing [%v] messages for stream %q in [%v] batches", len(h.messages), stream.Name, len(batches)))
+	for _, batch := range batches {
 
-	batch := ImportBatch{
-		Table:       stream.Name,
-		Schema:      stream.Schema,
-		Messages:    h.messages,
-		PrimaryKeys: stream.KeyProperties,
-	}
+		b, err := json.Marshal(batch)
+		if err != nil {
+			return err
+		}
 
-	b, err := json.Marshal(batch)
-	if err != nil {
-		return err
-	}
+		stitch, err := retryablehttp.NewRequest("POST", h.apiURL+"/v2/import/batch", bytes.NewBuffer(b))
+		if err != nil {
+			return err
+		}
+		stitch.Header.Set("Content-Type", "application/json")
+		stitch.Header.Set("Authorization", "Bearer "+h.apiToken)
 
-	stitch, err := retryablehttp.NewRequest("POST", h.apiURL+"/v2/import/batch", bytes.NewBuffer(b))
-	if err != nil {
-		return err
-	}
-	stitch.Header.Set("Content-Type", "application/json")
-	stitch.Header.Set("Authorization", "Bearer "+h.apiToken)
+		stitchResponse, err := h.client.Do(stitch)
+		if err != nil {
+			return err
+		}
 
-	stitchResponse, err := h.client.Do(stitch)
-	if err != nil {
-		return err
-	}
+		defer stitchResponse.Body.Close()
 
-	defer stitchResponse.Body.Close()
+		if stitchResponse.StatusCode > 203 {
+			body, err := ioutil.ReadAll(stitchResponse.Body)
+			if err != nil {
+				return err
+			}
+			return fmt.Errorf("server request failed with %s", body)
+		}
 
-	if stitchResponse.StatusCode > 203 {
-		body, err := ioutil.ReadAll(stitchResponse.Body)
-		if err != nil {
+		var resp BatchResponse
+		decoder := json.NewDecoder(stitchResponse.Body)
+		if err := decoder.Decode(&resp); err != nil {
 			return err
 		}
-		return fmt.Errorf("server request failed with %s", body)
-	}
 
-	var resp BatchResponse
-	decoder := json.NewDecoder(stitchResponse.Body)
-	if err := decoder.Decode(&resp); err != nil {
-		return err
+		h.logger.Info(fmt.Sprintf("Server response status : %q, message : %q", resp.Status, resp.Message))
 	}
-
-	h.logger.Info(fmt.Sprintf("Server response status : %q, message : %q", resp.Status, resp.Message))
-
 	h.messages = h.messages[:0]
 
 	return nil
@@ -106,6 +104,46 @@ func (h *httpBatchWriter) Send(record *Record, stream *Stream) error {
 	return nil
 }
 
+// getBatchMessages accepts a list of import messages
+// and returns a slice of ImportBatch that can be safely uploaded.
+// The rules are:
+// 1. There cannot be more than 20,000 records in the request.
+// 2. The size of the serialized JSON cannot be more than 20 MB.
+func getBatchMessages(messages []ImportMessage, stream *Stream, maxObjectsInBatch int, maxBatchSerializedSize int) []ImportBatch {
+	var batches []ImportBatch
+	allocated := 0
+	unallocated := len(messages)
+
+	for unallocated > 0 {
+		batch := ImportBatch{
+			Table:       stream.Name,
+			Schema:      stream.Schema,
+			Messages:    messages[allocated:],
+			PrimaryKeys: stream.KeyProperties,
+		}
+
+		// reduce the size of the batch until it is an acceptable size.
+		for batch.SizeOf() > maxBatchSerializedSize || len(batch.Messages) > maxObjectsInBatch {
+			// keep halving the number of messages until the batch is an acceptable size.
+			batch.Messages = batch.Messages[0:(len(batch.Messages) / 2)]
+		}
+
+		allocated += len(batch.Messages)
+		unallocated -= len(batch.Messages)
+		batches = append(batches, batch)
+	}
+
+	return batches
+}
+
+func (imb *ImportBatch) SizeOf() int {
+	b, err := json.Marshal(imb)
+	if err != nil {
+		return 0
+	}
+	return len(b)
+}
+
 func createImportMessage(record *Record) ImportMessage {
 	now := time.Now()
 	return ImportMessage{
diff --git a/cmd/internal/batch_writer_test.go b/cmd/internal/batch_writer_test.go
new file mode 100644
index 0000000..c89aa67
--- /dev/null
+++ b/cmd/internal/batch_writer_test.go
@@ -0,0 +1,31 @@
+package internal
+
+import (
+	"github.com/stretchr/testify/assert"
+	"testing"
+)
+
+func TestCanSplitIntoBatches(t *testing.T) {
+	var messages []ImportMessage
+
+	n := 1
+	for n <= 20 {
+		messages = append(messages, ImportMessage{
+			Action: "upsert",
+		})
+
+		n++
+	}
+
+	stream := &Stream{}
+
+	batches := getBatchMessages(messages, stream, 1, 100*1024*1024)
+	assert.Equal(t, len(messages), len(batches))
+	totalMessages := 0
+	for _, batch := range batches {
+		assert.Equal(t, 1, len(batch.Messages))
+		totalMessages += len(batch.Messages)
+	}
+
+	assert.Equal(t, len(messages), totalMessages)
+}