diff --git a/frappe/email/doctype/email_queue/email_queue.py b/frappe/email/doctype/email_queue/email_queue.py
index 095471c82f..edccabc174 100644
--- a/frappe/email/doctype/email_queue/email_queue.py
+++ b/frappe/email/doctype/email_queue/email_queue.py
@@ -8,12 +8,14 @@ from frappe import _
 from frappe.model.document import Document
 from frappe.email.queue import send_one
 from frappe.limits import get_limits
+from frappe.utils import now_datetime
+
 
 class EmailQueue(Document):
 	def set_recipients(self, recipients):
 		self.set("recipients", [])
 		for r in recipients:
-			self.append("recipients", {"recipient":r})
+			self.append("recipients", {"recipient":r, "status":"Not Sent"})
 
 	def on_trash(self):
 		self.prevent_email_queue_delete()
@@ -37,6 +39,9 @@ def retry_sending(name):
 		doc.status = "Not Sent"
 		doc.save(ignore_permissions=True)
 
+	frappe.db.sql("""update `tabEmail Queue Recipient` set status='Not Sent', modified=%s where parent=%s""",
+		(now_datetime(), name))
+
 @frappe.whitelist()
 def send_now(name):
 	send_one(name, now=True)