diff --git a/clients/shared/merge.go b/clients/shared/merge.go
index 7378173c8..e2442fa06 100644
--- a/clients/shared/merge.go
+++ b/clients/shared/merge.go
@@ -90,9 +90,14 @@ func Merge(ctx context.Context, dwh destination.DataWarehouse, tableData *optimi
 		for attempts := 0; attempts < backfillMaxRetries; attempts++ {
 			backfillErr = BackfillColumn(dwh, col, tableID)
 			if backfillErr == nil {
-				tableConfig.Columns().UpsertColumn(col.Name(), columns.UpsertColumnArg{
+				err = tableConfig.Columns().UpsertColumn(col.Name(), columns.UpsertColumnArg{
 					Backfilled: typing.ToPtr(true),
 				})
+
+				if err != nil {
+					return fmt.Errorf("failed to update column backfilled status: %w", err)
+				}
+
 				break
 			}
 
diff --git a/lib/typing/columns/columns.go b/lib/typing/columns/columns.go
index 779fdc839..792c45c9c 100644
--- a/lib/typing/columns/columns.go
+++ b/lib/typing/columns/columns.go
@@ -2,6 +2,7 @@ package columns
 
 import (
 	"errors"
+	"fmt"
 	"slices"
 	"strings"
 	"sync"
@@ -108,9 +109,9 @@ type UpsertColumnArg struct {
 
 // UpsertColumn - just a wrapper around UpdateColumn and AddColumn
 // If it doesn't find a column, it'll add one where the kind = Invalid.
-func (c *Columns) UpsertColumn(colName string, arg UpsertColumnArg) {
+func (c *Columns) UpsertColumn(colName string, arg UpsertColumnArg) error {
 	if colName == "" {
-		return
+		return fmt.Errorf("column name is empty")
 	}
 
 	if col, isOk := c.GetColumn(colName); isOk {
@@ -127,7 +128,7 @@ func (c *Columns) UpsertColumn(colName string, arg UpsertColumnArg) {
 		}
 
 		c.UpdateColumn(col)
-		return
+		return nil
 	}
 
 	col := Column{
@@ -148,6 +149,7 @@ func (c *Columns) UpsertColumn(colName string, arg UpsertColumnArg) {
 	}
 
 	c.AddColumn(col)
+	return nil
 }
 
 func (c *Columns) AddColumn(col Column) {
diff --git a/lib/typing/columns/columns_test.go b/lib/typing/columns/columns_test.go
index 7c283e09e..1b9ea82f3 100644
--- a/lib/typing/columns/columns_test.go
+++ b/lib/typing/columns/columns_test.go
@@ -194,25 +194,25 @@ func TestColumns_UpsertColumns(t *testing.T) {
 
 	// Now selectively update only a, b
 	for _, key := range []string{"a", "b"} {
-		cols.UpsertColumn(key, UpsertColumnArg{
+		assert.NoError(t, cols.UpsertColumn(key, UpsertColumnArg{
 			ToastCol: typing.ToPtr(true),
-		})
+		}))
 
 		// Now inspect.
 		col, _ := cols.GetColumn(key)
 		assert.True(t, col.ToastColumn)
 	}
 
-	cols.UpsertColumn("zzz", UpsertColumnArg{})
+	assert.NoError(t, cols.UpsertColumn("zzz", UpsertColumnArg{}))
 	zzzCol, _ := cols.GetColumn("zzz")
 	assert.False(t, zzzCol.ToastColumn)
 	assert.False(t, zzzCol.primaryKey)
 	assert.Equal(t, zzzCol.KindDetails, typing.Invalid)
 
-	cols.UpsertColumn("aaa", UpsertColumnArg{
+	assert.NoError(t, cols.UpsertColumn("aaa", UpsertColumnArg{
 		ToastCol:   typing.ToPtr(true),
 		PrimaryKey: typing.ToPtr(true),
-	})
+	}))
 	aaaCol, _ := cols.GetColumn("aaa")
 	assert.True(t, aaaCol.ToastColumn)
 	assert.True(t, aaaCol.primaryKey)
@@ -220,7 +220,7 @@ func TestColumns_UpsertColumns(t *testing.T) {
 
 	length := len(cols.columns)
 	for i := 0; i < 500; i++ {
-		cols.UpsertColumn("", UpsertColumnArg{})
+		assert.ErrorContains(t, cols.UpsertColumn("", UpsertColumnArg{}), "column name is empty")
 	}
 
 	assert.Equal(t, length, len(cols.columns))
diff --git a/models/event/event.go b/models/event/event.go
index 70a786df2..889bc2845 100644
--- a/models/event/event.go
+++ b/models/event/event.go
@@ -54,13 +54,17 @@ func ToMemoryEvent(event cdc.Event, pkMap map[string]any, tc kafkalib.TopicConfi
 	// Now iterate over pkMap and tag each column that is a primary key
 	if cols != nil {
 		for primaryKey := range pkMap {
-			cols.UpsertColumn(
+			err = cols.UpsertColumn(
 				// We need to escape the column name similar to have parity with event.GetColumns()
 				columns.EscapeName(primaryKey),
 				columns.UpsertColumnArg{
 					PrimaryKey: typing.ToPtr(true),
 				},
 			)
+
+			if err != nil {
+				return Event{}, fmt.Errorf("failed to upsert column: %w", err)
+			}
 		}
 	}
 
@@ -223,9 +227,13 @@ func (e *Event) Save(cfg config.Config, inMemDB *models.DatabaseData, tc kafkali
 		}
 
 		if toastedCol {
-			inMemoryColumns.UpsertColumn(newColName, columns.UpsertColumnArg{
+			err := inMemoryColumns.UpsertColumn(newColName, columns.UpsertColumnArg{
 				ToastCol: typing.ToPtr(true),
 			})
+
+			if err != nil {
+				return false, "", fmt.Errorf("failed to upsert column: %w", err)
+			}
 		} else {
 			retrievedColumn, isOk := inMemoryColumns.GetColumn(newColName)
 			if !isOk {