diff --git a/pkg/ccl/streamingccl/streamingest/datadriven_test.go b/pkg/ccl/streamingccl/streamingest/datadriven_test.go
index 5290961a5ed6..fe816f6b074b 100644
--- a/pkg/ccl/streamingccl/streamingest/datadriven_test.go
+++ b/pkg/ccl/streamingccl/streamingest/datadriven_test.go
@@ -12,6 +12,7 @@ import (
 	"context"
 	gosql "database/sql"
 	"fmt"
+	"regexp"
 	"strconv"
 	"strings"
 	"testing"
@@ -163,7 +164,8 @@ func TestDataDriven(t *testing.T) {
 				}
 				var as string
 				d.ScanArgs(t, "as", &as)
-				output := ds.queryAs(t, as, d.Input)
+				output, err := ds.queryAs(ctx, t, as, d.Input)
+				require.NoError(t, err)
 				output = strings.TrimSpace(output)
 				values := strings.Split(output, "\n")
 				if len(values) != len(d.CmdArgs)-1 {
@@ -207,11 +209,18 @@ func TestDataDriven(t *testing.T) {
 
 			case "query-sql":
 				var as string
+				var regexError string
+				d.MaybeScanArgs(t, "regex-error", &regexError)
 				d.ScanArgs(t, "as", &as)
 				if d.HasArg("retry") {
-					ds.queryAsWithRetry(t, as, d.Input, d.Expected)
+					ds.queryAsWithRetry(ctx, t, as, d.Input, d.Expected, regexError)
+				}
+				output, err := ds.queryAs(ctx, t, as, d.Input)
+				if regexError != "" {
+					require.NoError(t, handleRegex(t, err, regexError))
+					return ""
 				}
-				return ds.queryAs(t, as, d.Input)
+				return output
 
 			case "compare-replication-results":
 				ds.replicationClusters.CompareResult(d.Input)
@@ -346,7 +355,7 @@ func TestDataDriven(t *testing.T) {
 FROM system.span_configurations
 WHERE start_key >= '\x%x' AND start_key <= '\x%x'
 ORDER BY start_key;`, startKey, endKey)
-				return ds.queryAsWithRetry(t, as, listQuery, d.Expected)
+				return ds.queryAsWithRetry(ctx, t, as, listQuery, d.Expected, "")
 
 			default:
 				t.Fatalf("unsupported instruction: %s", d.Cmd)
@@ -378,30 +387,43 @@ func (d *datadrivenTestState) cleanup(t *testing.T) {
 	}
 }
 
-func (d *datadrivenTestState) queryAs(t *testing.T, as, query string) string {
+func (d *datadrivenTestState) queryAs(
+	ctx context.Context, t *testing.T, as, query string,
+) (string, error) {
 	var rows *gosql.Rows
+	var err error
 	switch as {
 	case "source-system":
-		rows = d.replicationClusters.SrcSysSQL.Query(t, query)
+		rows, err = d.replicationClusters.SrcSysSQL.DB.QueryContext(ctx, query)
 	case "source-tenant":
-		rows = d.replicationClusters.SrcTenantSQL.Query(t, query)
+		rows, err = d.replicationClusters.SrcTenantSQL.DB.QueryContext(ctx, query)
 	case "destination-system":
-		rows = d.replicationClusters.DestSysSQL.Query(t, query)
+		rows, err = d.replicationClusters.DestSysSQL.DB.QueryContext(ctx, query)
 	case "destination-tenant":
-		rows = d.replicationClusters.DestTenantSQL.Query(t, query)
+		rows, err = d.replicationClusters.DestTenantSQL.DB.QueryContext(ctx, query)
 	default:
 		t.Fatalf("unsupported value to run SQL query as: %s", as)
 	}
 
+	if err != nil {
+		return "", err
+	}
 	output, err := sqlutils.RowsToDataDrivenOutput(rows)
 	require.NoError(t, err)
-	return output
+	return output, nil
 }
 
-func (d *datadrivenTestState) queryAsWithRetry(t *testing.T, as, query, expected string) string {
+func (d *datadrivenTestState) queryAsWithRetry(
+	ctx context.Context, t *testing.T, as, query, expected string, regexError string,
+) string {
 	var output string
+	var err error
 	testutils.SucceedsSoon(t, func() error {
-		output = d.queryAs(t, as, query)
+		output, err = d.queryAs(ctx, t, as, query)
+		if regexError != "" {
+			output = ""
+			return handleRegex(t, err, regexError)
+		}
 		if output != expected {
 			return errors.Newf("latest output: %s\n expected: %s", output, expected)
 		}
@@ -425,6 +447,19 @@ func (d *datadrivenTestState) execAs(t *testing.T, as, query string) {
 	}
 }
 
+func handleRegex(t *testing.T, err error, regexError string) error {
+	if err == nil {
+		return errors.Newf("expected non nil error to match %s", regexError)
+	}
+	matched, matchStringErr := regexp.MatchString(regexError, err.Error())
+	require.NoError(t, matchStringErr)
+	if matched {
+		return nil
+	} else {
+		return errors.Wrapf(err, "error does not match regex error %s", regexError)
+	}
+}
+
 func newDatadrivenTestState() datadrivenTestState {
 	return datadrivenTestState{
 		cleanupFns: make([]func() error, 0),
diff --git a/pkg/ccl/streamingccl/streamingest/testdata/jobs_post_cutover b/pkg/ccl/streamingccl/streamingest/testdata/jobs_post_cutover
new file mode 100644
index 000000000000..6d028a2a9e5f
--- /dev/null
+++ b/pkg/ccl/streamingccl/streamingest/testdata/jobs_post_cutover
@@ -0,0 +1,48 @@
+
+create-replication-clusters
+----
+
+start-replication-stream
+----
+
+exec-sql as=source-tenant
+SET CLUSTER SETTING jobs.debug.pausepoints = 'backup.after.write_first_checkpoint';
+----
+
+query-sql as=source-tenant regex-error=(backup.after.write_first_checkpoint)
+BACKUP INTO 'nodelocal://1/example-schedule';
+----
+
+let $backupID as=source-tenant
+WITH jobs AS (SHOW JOBS) SELECT job_id FROM jobs WHERE job_type='BACKUP';
+----
+
+query-sql retry as=source-tenant
+WITH jobs AS (SHOW JOBS) SELECT status FROM jobs WHERE job_id=$backupID;
+----
+paused
+
+let $ts as=source-system
+SELECT clock_timestamp()::timestamp::string
+----
+
+cutover ts=$ts
+----
+
+start-replicated-tenant
+----
+
+exec-sql as=destination-tenant
+SET CLUSTER SETTING jobs.debug.pausepoints = '';
+----
+
+exec-sql as=destination-tenant
+RESUME JOB $backupID
+----
+
+
+query-sql retry as=destination-tenant
+WITH jobs AS (SHOW JOBS) SELECT status FROM jobs WHERE job_id=$backupID;
+----
+failed
+