Github user jayapalu commented on the issue: https://github.com/apache/cloudstack/pull/872 I have created two VPCs and configured the s2s vpn from UI. My tunnels are coming up without manually restarting the ipsec in this branch. s2s_customer_gateway: +----+--------------------------------------+------+---------------+-----------------+------------+-------------------+------------+--------------+--------------+-----+-------------+-----------+------------+---------+ | id | uuid | name | gateway_ip | guest_cidr_list | ipsec_psk | ike_policy | esp_policy | ike_lifetime | esp_lifetime | dpd | force_encap | domain_id | account_id | removed | +----+--------------------------------------+------+---------------+-----------------+------------+-------------------+------------+--------------+--------------+-----+-------------+-----------+------------+---------+ | 7 | 9cff8e2a-2848-46fc-80ef-7dcc47bfd4e4 | cg1 | 10.147.46.102 | 10.1.0.0/16 | 1234567890 | 3des-md5;modp1024 | 3des-md5 | 86400 | 3600 | 0 | 0 | 1 | 2 | NULL | | 8 | 60bd9e15-0a18-4334-ab98-ff56b0f839a5 | cg2 | 10.147.46.103 | 10.2.0.0/16 | 1234567890 | 3des-md5;modp1024 | 3des-md5 | 86400 | 3600 | 1 | 0 | 1 | 2 | NULL | +----+--------------------------------------+------+---------------+-----------------+------------+-------------------+------------+--------------+--------------+-----+-------------+-----------+------------+---------+ 2 rows in set (0.00 sec) ipsec status Security Associations (1 up, 0 connecting): vpn-10.147.46.102[17]: ESTABLISHED 10 minutes ago, 10.147.46.103[10.147.46.103]...10.147.46.102[10.147.46.102] vpn-10.147.46.102{21}: INSTALLED, TUNNEL, ESP SPIs: c562e87d_i c6a45be4_o vpn-10.147.46.102{21}: 10.2.0.0/16 === 10.1.0.0/16
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