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Thanks Matt for your response. I do call ActivationRequest everytime our VPN app is started. I am following same as SimpleFirewall example from WWDC 2019 https://docs-assets.developer.apple.com/published/f74706e42c/FilteringNetworkTraffic.zip. Let me check whether it can be handled differently. Thanks

1293 default 2020-12-03 11:17:13.298505 -0500 Connect vtc Replacing extension com.weavernetworks.sdvn.Wire42.PacketTunnel version 4.2.0 with version 4.2.0 1294 default 2020-12-03 11:17:13.298615 -0500 sysextd attempting to realize properties with identifier com.weavernetworks.sdvn.Wire42.PacketTunnel 1295 default 2020-12-03 11:17:13.303921 -0500 sysextd Realizing target path: file:///Applications/Connect.app/Contents/Library/SystemExtensions/com.weavernetworks.sdvn.Wire42.PacketTunnel.systemextension/ 1296 default 2020-12-03 11:17:13.304131 -0500 sysextd Bundle class: UncachedBundle 1297 default 2020-12-03 11:17:13.315362 -0500 sysextd staging extension with identifier com.weavernetworks.sdvn.Wire42.PacketTunnel 1298 default 2020-12-03 11:17:13.318556 -0500 sysextd staging bundle from /Applications/Connect.app/Contents/Library/SystemExtensions/com.weavernetworks.sdvn.Wire42.PacketTunnel.systemextension to: /Library/SystemExtensions/.staging/A77F31CE-435B-4E24-9714-E5743DA97498/ com. weavernetworks.sdvn.Wire42.PacketTunnel.systemextension 1299 info 2020-12-03 11:17:13.342587 -0500 thermald 72/22/22 SFI:67/67/67/0/0/0 GPU:0/0/0/0 IO:0/0/0/0 1300 default 2020-12-03 11:17:13.360719 -0500 distnoted register name: NSSnappingPrefsDidChangeNotificationNameGlobal object: kCFNotificationAnyObject token: 380000003e pid: 4475 1301 default 2020-12-03 11:17:13.369913 -0500 sysextd Making activation decision for extension with teamID teamID("897HPDQQM3"), identifier com.weavernetworks.sdvn.Wire42.PacketTunnel 1302 default 2020-12-03 11:17:13.369915 -0500 sysextd No extension policy -- activation decision is UserOption 1303 default 2020-12-03 11:17:13.369919 -0500 sysextd validating extension with identifier com.weavernetworks.sdvn.Wire42.PacketTunnel 1304 info 2020-12-03 11:17:13.382958 -0500 syspolicyd looking up ticket: {length = 20, bytes = 0xc71b48e250f55c9df1a1f3f331f8431951ca8b94}, 2, 0 1305 info 2020-12-03 11:17:13.384175 -0500 syspolicyd completing lookup: {length = 20, bytes = 0xc71b48e250f55c9df1a1f3f331f8431951ca8b94}, 0 1306 info 2020-12-03 11:17:13.402132 -0500 sysextd Returning cdhash for local arch x8664 of extension com.weavernetworks.sdvn.Wire42.PacketTunnel 1307 default 2020-12-03 11:17:13.402256 -0500 sysextd waiting for external validation of extension with identifier com.weavernetworks.sdvn.Wire42.PacketTunnel 1308 default 2020-12-03 11:17:13.402395 -0500 nesessionmanager Validating system extension com.weavernetworks.sdvn.Wire42.PacketTunnel 1309 info 2020-12-03 11:17:13.421921 -0500 sysextd moving bundle to: /Library/SystemExtensions/A77F31CE-435B-4E24-9714-E5743DA97498/com.weavernetworks.sdvn.Wire42.PacketTunnel.systemextension 1310 default 2020-12-03 11:17:13.423835 -0500 sysextd Upgrading extension com.weavernetworks.sdvn.Wire42.PacketTunnel/teamID("897HPDQQM3") version 00240 (activatedenabled) to version 00240 1311 default 2020-12-03 11:17:13.424995 -0500 sysextd Starting upgrade of com.weavernetworks.sdvn.Wire42.PacketTunnel/teamID("897HPDQQM3") version 00240 1312 default 2020-12-03 11:17:13.425005 -0500 sysextd Notifying delegates about replacement of com.weavernetworks.sdvn.Wire42.PacketTunnel 1313 info 2020-12-03 11:17:13.425074 -0500 sysextd Returning cdhash for local arch x8664 of extension com.weavernetworks.sdvn.Wire42.PacketTunnel 1314 info 2020-12-03 11:17:13.425096 -0500 sysextd Returning cdhash for local arch x8664 of extension com.weavernetworks.sdvn.Wire42.PacketTunnel 1315 default 2020-12-03 11:17:13.425501 -0500 nesessionmanager Replacing system extension com.weavernetworks.sdvn.Wire42.PacketTunnel 4.2.0/00240 with extension com.weavernetworks.sdvn.Wire42.PacketTunnel 4.2.0/00240 1316 default 2020-12-03 11:17:13.425586 -0500 sysextd Starting disable of com.weavernetworks.sdvn.Wire42.PacketTunnel/teamID("897HPDQQM3") version 00240 for upgrade, state: activatedenabled 1317 default 2020-12-03 11:17:13.426706 -0500 sysextd clearing +x bit on executable in bundle file:///Library/SystemExtensions/360B2B64-3AF3-4D6B-8FDF-CD24C11A0D7E/com.weavernetworks.sdvn.Wire42.PacketTunnel.systemextension/ 1318 default 2020-12-03 11:17:13.427004 -0500 sysextd notifying categories that extension com.weavernetworks.sdvn.Wire42.PacketTunnel will terminate 1319 info 2020-12-03 11:17:13.427072 -0500 sysextd Returning cdhash for local arch x8664 of extension com.weavernetworks.sdvn.Wire42.PacketTunnel 1320 default 2020-12-03 11:17:13.427344 -0500 nesessionmanager System extension com.weavernetworks.sdvn.Wire42.PacketTunnel will be terminated

1 info 2020-12-03 11:17:07.114964 -0500 nesessionmanager NESMVPNSession[Primary Tunnel:Connect:966CA0C0-ADD2-4AD8-B179-A331B23C718F:(null)]: timed out while waiting for network configuration to change (pending flags = 0x2) 2 default 2020-12-03 11:17:07.115413 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel [Extension com.weavernetworks.sdvn.Wire42]: Calling stopTunnelWithReason because: Stop command received 3 info 2020-12-03 11:17:07.115415 -0500 nesessionmanager NESMVPNSession[Primary Tunnel:Connect:966CA0C0-ADD2-4AD8-B179-A331B23C718F:(null)]: Request to clear network agent from all interfaces 4 default 2020-12-03 11:17:07.115484 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel vtc Stop tunnel is getting called!!! 5 info 2020-12-03 11:17:07.115516 -0500 configd NetBIOS name (network configuration) = USER-MACBOOK 6 default 2020-12-03 11:17:07.115530 -0500 nesessionmanager nwnetworkagentremovefrominterface Successfully removed agent from "utun2" 7 info 2020-12-03 11:17:07.115571 -0500 nesessionmanager NESMVPNSession[Primary Tunnel:Connect:966CA0C0-ADD2-4AD8-B179-A331B23C718F:(null)]: Removed network agent from utun2 8 default 2020-12-03 11:17:07.115582 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel [C1 FAE1F1AF-2EF1-4825-97AF-B2D448C23F02 100.64.0.100:1234 udp] cancel 9 info 2020-12-03 11:17:07.115621 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel <comweavernetworkssdvnWire42PacketTunnel.PacketTunnelProvider: 0x7f7fd0d0deb0>: Stopping with reason 1 10 default 2020-12-03 11:17:07.115634 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel [Extension com.weavernetworks.sdvn.Wire42]: IPC detached 11 default 2020-12-03 11:17:07.115662 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel [C1 FAE1F1AF-2EF1-4825-97AF-B2D448C23F02 100.64.0.100:1234 udp] cancelled 12 [C1 75908BA5-85B7-47D5-B854-5C249EEF695F 192.168.1.18:57672<->100.64.0.100:1234] 13 Connected Path: satisfied (Path is satisfied), viable, interface: en0, scoped, ipv4, ipv6, dns 14 Duration: 82.844s, UDP @0.001s took 0.000s 15 bytes in/out: 0/0, packets in/out: 0/0, rtt: 0.000s, retransmitted bytes: 0, out-of-order bytes: 0 16 info 2020-12-03 11:17:07.115677 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel [Extension com.weavernetworks.sdvn.Wire42]: Calling stop completion handler with error (null) 17 info 2020-12-03 11:17:07.115725 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel nwendpointhandlercancel [C1 100.64.0.100:1234 ready socket-flow (satisfied (Path is satisfied), viable, interface: en0, scoped, ipv4, ipv6, dns)] 18 info 2020-12-03 11:17:07.115740 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel nwassociationscheduledeactivation <nwassociation 100.64.0.100:1234> will become dormant after 10 seconds of inactivity 19 default 2020-12-03 11:17:07.115746 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel nwflowdisconnected [C1 100.64.0.100:1234 cancelled socket-flow ((null))] Output protocol disconnected 20 default 2020-12-03 11:17:07.115756 -0500 com.weavernetworks.sdvn.Wire42.PacketTunnel nwconnectionreportstatewithhandleronnwqueue [C1] reporting state cancelled 21 default 2020-12-03 11:17:07.115885 -0500 nesessionmanager NESMVPNSession[Primary Tunnel:Connect:966CA0C0-ADD2-4AD8-B179-A331B23C718F:(null)] in state NESMVPNSessionStateStopping: plugin NEVPNTunnelPlugin(com.weavernetworks.sdvn.Wire42[inactive]) did detach from IPC 22 info 2020-12-03 11:17:07.115899 -0500 UserEventAgent File Handle Maintainer got a 2 action with token 703 23 info 2020-12-03 11:17:07.115906 -0500 UserEventAgent File Handle Maintainer got a 1 action with token 704 24 default 2020-12-03 11:17:07.115938 -0500 nesessionmanager NESMVPNSession[Primary Tunnel:Connect:966CA0C0-ADD2-4AD8-B179-A331B23C718F:(null)] in state NESMVPNSessionStateStopping: plugin NEVPNTunnelPlugin(com.weavernetworks.sdvn.Wire42[inactive]) disconnected with reason Plugin initiated 25 default 2020-12-03 11:17:07.115967 -0500 nesessionmanager NESMVPNSession[Primary Tunnel:Connect:966CA0C0-ADD2-4AD8-B179-A331B23C718F:(null)] in state NESMVPNSessionStateStopping: plugin disconnected, disposing all plugins 26 default 2020-12-03 11:17:07.116024 -0500 UserEventAgent Current file handles for com.apple.networkextension.file-descriptor-maintainer: ( 27 "Network Agent Registration socket (174) 966CA0C0-ADD2-4AD8-B179-A331B23C718F 9DC96782-8243-4C07-99E7-405986D6DAFF 1 (null) agent flags 0", 28 "Policy Session MasterSession socket (199)", 29 "Policy Session LowPrioritySession socket (200)" 30 )

Hi eskimo, Can you provide some steps what needs to be setup for NEMachServiceName in Info.plist. I suspect this is root cause of the failure. I have configured it to PacketTunnelProvider bundleid. Is that right?Error log:807: 0x32de3 default 22:03:27.842000-0400 nesessionmanager Signature check failed: code failed to satisfy specified code requirement(s)807: 0x32de3 error 22:03:27.842669-0400 nesessionmanager NEVPNTunnelPlugin(app bundleId[617]): Validation of the extension failed5374: 0x1dfac default 22:03:27.852216-0400 vmnet-bridge Dynamic store changed807: 0x32de3 default 22:03:27.852125-0400 nesessionmanager NESMVPNSession[Primary Tunnel:&lt;app&gt;:EA8AE281-C93C-4680-92CF-4E70068392EB:(null)] in state NESMVPNSessionStateStarting: plugin NEVPNTunnelPlugin(&lt;app bundleID&gt;[617]) started with PID 0 error (null)807: 0x32de3 default 22:03:27.854466-0400 nesessionmanager NESMVPNSession[Primary Tunnel:&lt;app&gt;:EA8AE281-C93C-4680-92CF-4E70068392EB:(null)]: Leaving state NESMVPNSessionStateStarting807: 0x32de3 default 22:03:27.854676-0400 nesessionmanager NESMVPNSession[Primary Tunnel:&lt;app&gt;:EA8AE281-C93C-4680-92CF-4E70068392EB:(null)]: Entering state NESMVPNSessionStateStopping, timeout 20 seconds180: 0x3a9 default 22:03:27.847522-0400 configd network changed807: 0x32de3 default 22:03:27.854935-0400 nesessionmanager &lt;NESMServer: 0x7fd0ead0c730&gt;: Request to uninstall session: NESMVPNSession[Primary Tunnel:Connect42:EA8AE281-C93C-4680-92CF-4E70068392EB:(null)]807: 0x32de3 default 22:03:27.855108-0400 nesessionmanager NESMVPNSession[Primary Tunnel:&lt;app&gt;:EA8AE281-C93C-4680-92CF-4E70068392EB:(null)]: status changed to disconnecting807: 0x32de3 default 22:03:27.855197-0400 nesessionmanager NESMVPNSession[Primary Tunnel:&lt;app&gt;:EA8AE281-C93C-4680-92CF-4E70068392EB:(null)]: Updated network agent (inactive, compulsory, not-user-activiated, not- kernel-activated)

Thanks eskimo for your response. Initially, I used Apple Development for bringing up. It worked fine. Later, I wanted to sign with Developer ID certificate for wider distribution. PacketTunnel.systemextension is failing with this error.I followed your Jan 14th response of this thread https://forums.developer.apple.com/thread/125508 to sign with Developer ID certificate. I dont get any error while signing or notarizing app with Apple.It throws error while trying to bring up app. Thanks.