diff --git a/src/jetstream/datastore/20240818042100_RetryEndpointCACert.go b/src/jetstream/datastore/20240818042100_RetryEndpointCACert.go
new file mode 100644
index 000000000..cbf5fad6b
--- /dev/null
+++ b/src/jetstream/datastore/20240818042100_RetryEndpointCACert.go
@@ -0,0 +1,50 @@
+package datastore
+
+import (
+	"database/sql"
+	"log"
+
+	"github.com/pressly/goose"
+)
+
+func init() {
+	goose.AddMigration(Up20240818042100, nil)
+}
+
+func CheckIfMigrationExists(db *sql.Tx, migration string, args ...interface{}) (bool, error) {
+	query := "SELECT 1 FROM goose_db_version WHERE version_id = $1 LIMIT 1"
+	var exists bool
+	err := db.QueryRow(query, migration).Scan(&exists)
+	if err != nil && err != sql.ErrNoRows {
+		return false, err
+	}
+	return err != sql.ErrNoRows, nil
+}
+
+func Up20240818042100(txn *sql.Tx) error {
+	// When upgrading from 4.4.x, the migration 20201201163100 was not applied because 20210201110000 was already present.
+	exists, err := CheckIfMigrationExists(txn, "20201201163100")
+	if err != nil {
+		return err
+	}
+
+	if !exists {
+		log.Printf("Migration 20201201163100 has not been applied. Adding missing entries.")
+		createCertColumn := "ALTER TABLE cnsis ADD ca_cert TEXT"
+		_, err := txn.Exec(createCertColumn)
+		if err != nil {
+			return err
+		}
+
+		createEnableColumn := "ALTER TABLE tokens ADD enabled BOOLEAN NOT NULL DEFAULT TRUE"
+		_, err = txn.Exec(createEnableColumn)
+		if err != nil {
+			return err
+		}
+	} else {
+		// Migration has already been applied
+		log.Printf("Migration 20201201163100 has been applied.")
+		return nil
+	}
+	return nil
+}