diff --git a/go.mod b/go.mod
index 492f2096a..d92ccf3ad 100644
--- a/go.mod
+++ b/go.mod
@@ -12,7 +12,7 @@ require (
 	github.com/goccy/go-json v0.10.0
 	github.com/goccy/go-yaml v1.9.5
 	github.com/goccy/go-zetasql v0.5.5
-	github.com/goccy/go-zetasqlite v0.19.0
+	github.com/goccy/go-zetasqlite v0.19.1
 	github.com/google/go-cmp v0.5.9
 	github.com/googleapis/gax-go/v2 v2.11.0
 	github.com/gorilla/mux v1.8.0
@@ -75,11 +75,11 @@ require (
 	go.opencensus.io v0.24.0 // indirect
 	go.uber.org/atomic v1.7.0 // indirect
 	go.uber.org/multierr v1.6.0 // indirect
-	golang.org/x/crypto v0.16.0 // indirect
+	golang.org/x/crypto v0.21.0 // indirect
 	golang.org/x/mod v0.10.0 // indirect
-	golang.org/x/net v0.19.0 // indirect
+	golang.org/x/net v0.21.0 // indirect
 	golang.org/x/oauth2 v0.11.0 // indirect
-	golang.org/x/sys v0.15.0 // indirect
+	golang.org/x/sys v0.18.0 // indirect
 	golang.org/x/text v0.14.0 // indirect
 	golang.org/x/tools v0.9.1 // indirect
 	golang.org/x/xerrors v0.0.0-20220907171357-04be3eba64a2 // indirect
diff --git a/go.sum b/go.sum
index b5e3e93b4..327d1dcc3 100644
--- a/go.sum
+++ b/go.sum
@@ -94,8 +94,8 @@ github.com/goccy/go-yaml v1.9.5 h1:Eh/+3uk9kLxG4koCX6lRMAPS1OaMSAi+FJcya0INdB0=
 github.com/goccy/go-yaml v1.9.5/go.mod h1:U/jl18uSupI5rdI2jmuCswEA2htH9eXfferR3KfscvA=
 github.com/goccy/go-zetasql v0.5.5 h1:3JpXt3p2533rnZMu09upCcI7YJ2KfjKgdo2Lu0xo+fU=
 github.com/goccy/go-zetasql v0.5.5/go.mod h1:xvvooX2RG404vnbdFZuAM8bTFksYwVUlqeIUrUNuo40=
-github.com/goccy/go-zetasqlite v0.19.0 h1:pvWFw/QThPP5a3UMkgirIsb9/5tlfUq25DggFfhI86o=
-github.com/goccy/go-zetasqlite v0.19.0/go.mod h1:ThavIQcmI6a/sVTpvJtj+idUui32gwbnXe1jeb7pISY=
+github.com/goccy/go-zetasqlite v0.19.1 h1:yebtcyHgSNnNywan6FbI93uxJ6GXDpVMoqTlfT/Bdm4=
+github.com/goccy/go-zetasqlite v0.19.1/go.mod h1:ThavIQcmI6a/sVTpvJtj+idUui32gwbnXe1jeb7pISY=
 github.com/golang/glog v0.0.0-20160126235308-23def4e6c14b/go.mod h1:SBH7ygxi8pfUlaOkMMuAQtPIUF8ecWP5IEl/CR7VP2Q=
 github.com/golang/groupcache v0.0.0-20200121045136-8c9f03a8e57e/go.mod h1:cIg4eruTrX1D+g88fzRXU5OdNfaM+9IcxsU14FzY7Hc=
 github.com/golang/groupcache v0.0.0-20210331224755-41bb18bfe9da h1:oI5xCqsCo564l8iNU+DwB5epxmsaqB+rhGL0m5jtYqE=
@@ -250,8 +250,8 @@ golang.org/x/crypto v0.0.0-20200622213623-75b288015ac9/go.mod h1:LzIPMQfyMNhhGPh
 golang.org/x/crypto v0.0.0-20210921155107-089bfa567519/go.mod h1:GvvjBRRGRdwPK5ydBHafDWAxML/pGHZbMvKqRZ5+Abc=
 golang.org/x/crypto v0.0.0-20211215153901-e495a2d5b3d3/go.mod h1:IxCIyHEi3zRg3s0A5j5BB6A9Jmi73HwBIUl50j+osU4=
 golang.org/x/crypto v0.0.0-20220314234659-1baeb1ce4c0b/go.mod h1:IxCIyHEi3zRg3s0A5j5BB6A9Jmi73HwBIUl50j+osU4=
-golang.org/x/crypto v0.16.0 h1:mMMrFzRSCF0GvB7Ne27XVtVAaXLrPmgPC7/v0tkwHaY=
-golang.org/x/crypto v0.16.0/go.mod h1:gCAAfMLgwOJRpTjQ2zCCt2OcSfYMTeZVSRtQlPC7Nq4=
+golang.org/x/crypto v0.21.0 h1:X31++rzVUdKhX5sWmSOFZxx8UW/ldWx55cbf08iNAMA=
+golang.org/x/crypto v0.21.0/go.mod h1:0BP7YvVV9gBbVKyeTG0Gyn+gZm94bibOW5BjDEYAOMs=
 golang.org/x/exp v0.0.0-20190121172915-509febef88a4/go.mod h1:CJ0aWSM057203Lf6IL+f9T1iT9GByDxfZKAQTCR3kQA=
 golang.org/x/exp v0.0.0-20220827204233-334a2380cb91 h1:tnebWN09GYg9OLPss1KXj8txwZc6X6uMr6VFdcGNbHw=
 golang.org/x/exp v0.0.0-20220827204233-334a2380cb91/go.mod h1:cyybsKvd6eL0RnXn6p/Grxp8F5bW7iYuBgsNCOHpMYE=
@@ -278,8 +278,8 @@ golang.org/x/net v0.0.0-20210226172049-e18ecbb05110/go.mod h1:m0MpNAwzfU5UDzcl9v
 golang.org/x/net v0.0.0-20210405180319-a5a99cb37ef4/go.mod h1:p54w0d4576C0XHj96bSt6lcn1PtDYWL6XObtHCRCNQM=
 golang.org/x/net v0.0.0-20211112202133-69e39bad7dc2/go.mod h1:9nx3DQGgdP8bBQD5qxJ1jj9UTztislL4KSBs9R2vV5Y=
 golang.org/x/net v0.0.0-20220722155237-a158d28d115b/go.mod h1:XRhObCWvk6IyKnWLug+ECip1KBveYUHfp+8e9klMJ9c=
-golang.org/x/net v0.19.0 h1:zTwKpTd2XuCqf8huc7Fo2iSy+4RHPd10s4KzeTnVr1c=
-golang.org/x/net v0.19.0/go.mod h1:CfAk/cbD4CthTvqiEl8NpboMuiuOYsAr/7NOjZJtv1U=
+golang.org/x/net v0.21.0 h1:AQyQV4dYCvJ7vGmJyKki9+PBdyvhkSd8EIx/qb0AYv4=
+golang.org/x/net v0.21.0/go.mod h1:bIjVDfnllIU7BJ2DNgfnXvpSvtn8VRwhlsaeUTyUS44=
 golang.org/x/oauth2 v0.0.0-20180821212333-d2e6202438be/go.mod h1:N/0e6XlmueqKjAGxoOufVs8QHGRruUQn6yWY3a++T0U=
 golang.org/x/oauth2 v0.0.0-20200107190931-bf48bf16ab8d/go.mod h1:gOpvHmFTYa4IltrdGE7lF6nIHvwfUNPOp7c8zoXwtLw=
 golang.org/x/oauth2 v0.11.0 h1:vPL4xzxBM4niKCW6g9whtaWVXTJf1U5e4aZxxFx/gbU=
@@ -314,8 +314,8 @@ golang.org/x/sys v0.0.0-20220520151302-bc2c85ada10a/go.mod h1:oPkhp1MJrh7nUepCBc
 golang.org/x/sys v0.0.0-20220715151400-c0bba94af5f8/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.0.0-20220722155257-8c9f86f7a55f/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.0.0-20220811171246-fbc7d0a398ab/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
-golang.org/x/sys v0.15.0 h1:h48lPFYpsTvQJZF4EKyI4aLHaev3CxivZmv7yZig9pc=
-golang.org/x/sys v0.15.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
+golang.org/x/sys v0.18.0 h1:DBdB3niSjOA/O0blCZBqDefyWNYveAYMNF1Wum0DYQ4=
+golang.org/x/sys v0.18.0/go.mod h1:/VUhepiaJMQUp4+oa/7Zr1D23ma6VTLIYjOOTFZPUcA=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
 golang.org/x/term v0.0.0-20210927222741-03fcf44c2211/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
diff --git a/internal/contentdata/repository.go b/internal/contentdata/repository.go
index f737f949b..7be8c3bc7 100644
--- a/internal/contentdata/repository.go
+++ b/internal/contentdata/repository.go
@@ -5,7 +5,6 @@ import (
 	"database/sql"
 	"fmt"
 	"reflect"
-	"sort"
 	"strings"
 
 	"github.com/goccy/go-zetasqlite"
@@ -371,34 +370,58 @@ func (r *Repository) AddTableData(ctx context.Context, tx *connection.Tx, projec
 		_ = tx.MetadataRepoMode()
 	}()
 
-	var columns []string
+	var columns []*types.Column
 	for _, col := range table.Columns {
-		columns = append(columns, col.Name)
-	}
-	sort.Strings(columns)
-	rows := make([]string, 0, len(table.Data))
-	values := make([]interface{}, 0, len(table.Data)*len(columns))
-	for _, data := range table.Data {
-		placeholders := make([]string, 0, len(data))
-		for _, col := range columns {
-			values = append(values, data[col])
-			placeholders = append(placeholders, "?")
-		}
-		rows = append(rows, fmt.Sprintf("(%s)", strings.Join(placeholders, ",")))
+		columns = append(columns, col)
 	}
+
+	placeholders := make([]string, 0, len(columns))
 	columnsWithEscape := make([]string, 0, len(columns))
 	for _, col := range columns {
-		columnsWithEscape = append(columnsWithEscape, fmt.Sprintf("`%s`", col))
+		placeholders = append(placeholders, "?")
+		columnsWithEscape = append(columnsWithEscape, fmt.Sprintf("`%s`", col.Name))
 	}
+
 	query := fmt.Sprintf(
-		"INSERT `%s` (%s) VALUES %s",
+		"INSERT `%s` (%s) VALUES (%s)",
 		r.tablePath(projectID, datasetID, table.ID),
 		strings.Join(columnsWithEscape, ","),
-		strings.Join(rows, ","),
+		strings.Join(placeholders, ","),
 	)
-	if _, err := tx.Tx().ExecContext(ctx, query, values...); err != nil {
+
+	stmt, err := tx.Tx().PrepareContext(ctx, query)
+	if err != nil {
 		return err
 	}
+
+	for _, data := range table.Data {
+		values := make([]interface{}, 0, len(table.Columns))
+
+		for _, column := range columns {
+			if value, found := data[column.Name]; found {
+				isTimestampColumn := column.Type == types.TIMESTAMP
+				inputString, isInputString := value.(string)
+
+				if isInputString && isTimestampColumn {
+					parsedTimestamp, err := zetasqlite.TimeFromTimestampValue(inputString)
+					// If we could parse the timestamp, use it when inserting, otherwise fallback to the supplied value
+					if err == nil {
+						values = append(values, parsedTimestamp)
+						continue
+					}
+				}
+
+				values = append(values, value)
+			} else {
+				values = append(values, nil)
+			}
+		}
+
+		if _, err := stmt.ExecContext(ctx, values...); err != nil {
+			return err
+		}
+	}
+
 	return nil
 }
 
diff --git a/internal/types/types.go b/internal/types/types.go
index 471442920..ba8bef6cc 100644
--- a/internal/types/types.go
+++ b/internal/types/types.go
@@ -192,7 +192,7 @@ func Format(schema *bigqueryv2.TableSchema, rows []*TableRow, useInt64Timestamp
 	for _, row := range rows {
 		cells := make([]*TableCell, 0, len(row.F))
 		for colIdx, cell := range row.F {
-			if schema.Fields[colIdx].Type == "TIMESTAMP" {
+			if schema.Fields[colIdx].Type == "TIMESTAMP" && cell.V != nil {
 				t, _ := zetasqlite.TimeFromTimestampValue(cell.V.(string))
 				microsec := t.UnixNano() / int64(time.Microsecond)
 				cells = append(cells, &TableCell{