diff --git a/include/bluetooth/conn.h b/include/bluetooth/conn.h
index b9ba626c21a779..1ab90c3a0f3f08 100644
--- a/include/bluetooth/conn.h
+++ b/include/bluetooth/conn.h
@@ -303,7 +303,7 @@ typedef enum __packed {
  *
  *  This function may return error if required level of security is not possible
  *  to achieve due to local or remote device limitation (e.g., input output
- *  capabilities).
+ *  capabilities), or if the maximum number of paired devices has been reached.
  *
  *  @param conn Connection object.
  *  @param sec Requested security level.
diff --git a/subsys/bluetooth/host/smp.c b/subsys/bluetooth/host/smp.c
index b9601dacea552f..baee012e4f6c81 100644
--- a/subsys/bluetooth/host/smp.c
+++ b/subsys/bluetooth/host/smp.c
@@ -2422,6 +2422,13 @@ int bt_smp_send_security_req(struct bt_conn *conn)
 		return -EINVAL;
 	}
 
+	if (!conn->le.keys) {
+		conn->le.keys = bt_keys_get_addr(conn->id, &conn->le.dst);
+		if (!conn->le.keys) {
+			return -ENOMEM;
+		}
+	}
+
 	if (smp_init(smp) != 0) {
 		return -ENOBUFS;
 	}
@@ -2457,6 +2464,13 @@ static u8_t smp_pairing_req(struct bt_smp *smp, struct net_buf *buf)
 		return BT_SMP_ERR_ENC_KEY_SIZE;
 	}
 
+	if (!conn->le.keys) {
+		conn->le.keys = bt_keys_get_addr(conn->id, &conn->le.dst);
+		if (!conn->le.keys) {
+			return BT_SMP_ERR_UNSPECIFIED;
+		}
+	}
+
 	/* If we already sent a security request then the SMP context
 	 * is already initialized.
 	 */
@@ -2601,6 +2615,13 @@ int bt_smp_send_pairing_req(struct bt_conn *conn)
 		return -EINVAL;
 	}
 
+	if (!conn->le.keys) {
+		conn->le.keys = bt_keys_get_addr(conn->id, &conn->le.dst);
+		if (!conn->le.keys) {
+			return -ENOMEM;
+		}
+	}
+
 	if (smp_init(smp)) {
 		return -ENOBUFS;
 	}