Repository: trailofbits/algo

Issue #1629: macOS Catalina: Connection with wireguard works flawlessly and then intermittently retrying handshake and no route to host
Created: 2019-11-01T11:35:04Z
I didn't go with the a bug report because I do not believe this to be a bug with the actual configuration of Algo or Wireguard. The reason I come to this conclusion is because my setup for wireguard works perfectly on other devices (such as my Android phone). However, on my macbook pro it appears that something weird is happening, presumably related to routing, which causes my wireguard on-demand connection to intermittently "no route to host" about once everyday.
My symptoms or what happens
I generally find that it occurs after I play some sort of media like youtube or some sort of stream. Before I had algo, I had my own openvpn setup from the angristan script and it also worked fine and then would frequently no route to host after a while (but also wouldn't happen on my phone). I then moved away from openvpn thinking my configuration was broken or something and tried Algo with Wireguard. However, then the issue began reappearing. I had adjusted my tun-mtu thinking maybe that was the issue when I had openvpn but that still didn't prevent drop outs. I always appear to be connected to the internet and wireguard on my laptop will still say 'active' and airport still thinks it is connected. However, if I ping anything or traceroute there is no DNS resolution. I cannot ping ips on the internet, but I can ping my router.
This is the logs on wireguard when the drop out occurs
2019-10-31 17:13:41.399 [NET] peer(JC5l…vKik) - Sending keepalive packet
2019-10-31 17:15:12.056 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:15:12.056 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:17.366 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:15:17.366 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:22.598 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 3)
2019-10-31 17:15:22.598 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:27.332 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:15:27.851 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:15:27.851 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:32.972 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 3)
2019-10-31 17:15:32.973 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:38.307 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 4)
2019-10-31 17:15:38.307 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:42.618 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:15:43.383 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:15:43.383 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:48.396 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:15:48.396 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:53.434 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:15:53.434 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:15:57.982 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:15:58.532 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:15:58.533 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:03.857 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:16:03.857 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:08.932 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:13.222 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:16:13.989 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:16:13.989 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:19.222 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:16:19.223 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:24.318 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:16:24.318 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:28.656 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:16:29.522 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:16:29.522 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:34.599 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:39.603 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:39.627 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.755 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.770 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.776 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.846 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.876 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.898 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.930 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:39.947 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.006 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.269 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.376 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.414 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.428 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.504 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.577 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.608 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.631 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.850 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.879 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:40.950 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:41.264 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:41.374 [NET] peer(JC5l…vKik) - Failed to send data packet write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:41.417 [NET] peer(JC5l…vKik) - Awaiting keypair
2019-10-31 17:16:44.125 [NET] peer(JC5l…vKik) - Retrying handshake because we stopped hearing back after 15 seconds
2019-10-31 17:16:44.642 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:44.642 [NET] peer(JC5l…vKik) - Failed to send handshake initiation write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:49.712 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:49.713 [NET] peer(JC5l…vKik) - Failed to send handshake initiation write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:54.751 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:16:54.752 [NET] peer(JC5l…vKik) - Failed to send handshake initiation write udp4 0.0.0.0:52840->serverip:51820: sendto: no route to host
2019-10-31 17:16:59.952 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:16:59.952 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:17:05.071 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:17:10.374 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)

The weird thing is I can fix this problem immediately by turning airport on and off or forcefully deactivating the wireguard connection to reforce or try again; this leaves me to believe it has nothing to do with my actual server algovpn configuration. When this issue occurs I also try my phone which is also connected to the same Wireguard server and it will work flawlessly. These are the logs after I reactivate:
2019-10-31 17:28:15.589 [APP] startDeactivation: Tunnel: laptop-full
2019-10-31 17:28:15.592 [APP] Tunnel 'laptop-full' connection status changed to 'disconnecting'
2019-10-31 17:28:15.808 [NET] Network change detected with satisfied route and interface order [en0]
2019-10-31 17:28:15.808 [NET] Routine: receive incoming IPv6 - stopped
2019-10-31 17:28:15.808 [NET] Routine: receive incoming IPv4 - stopped
2019-10-31 17:28:15.808 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:28:15.808 [NET] Routine: receive incoming IPv4 - started
2019-10-31 17:28:15.808 [NET] Routine: receive incoming IPv6 - started
2019-10-31 17:28:15.809 [NET] UDP bind has been updated
2019-10-31 17:28:15.896 [NET] Stopping tunnel
2019-10-31 17:28:15.896 [NET] Device closing
2019-10-31 17:28:15.896 [NET] Routine: event worker - stopped
2019-10-31 17:28:20.856 [NET] peer(JC5l…vKik) - Handshake did not complete after 5 seconds, retrying (try 2)
2019-10-31 17:28:20.856 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:28:35.588 [APP] Tunnel 'laptop-full' connection status changed to 'disconnected'
2019-10-31 17:28:35.597 [APP] Tunnel 'laptop-full' connection status changed to 'connecting'
2019-10-31 17:28:35.717 [NET] App version: 0.0.20191012 (14); Go backend version: 0.0.20190909
2019-10-31 17:28:35.717 [NET] Starting tunnel from the OS directly, rather than the app
2019-10-31 17:28:35.794 [NET] Tunnel interface is utun2
2019-10-31 17:28:35.795 [NET] Attaching to interface
2019-10-31 17:28:35.795 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.795 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.795 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.795 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.795 [NET] Routine: TUN reader - started
2019-10-31 17:28:35.796 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.796 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.796 [NET] Routine: event worker - started
2019-10-31 17:28:35.796 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.796 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.797 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.797 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.798 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.798 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.798 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.798 [NET] Routine: encryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: decryption worker - started
2019-10-31 17:28:35.798 [NET] Routine: handshake worker - started
2019-10-31 17:28:35.798 [NET] UAPI: Updating private key
2019-10-31 17:28:35.798 [NET] UAPI: Removing all peers
2019-10-31 17:28:35.798 [NET] UAPI: Transition to peer configuration
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - UAPI: Created
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - UAPI: Updating preshared key
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - UAPI: Updating endpoint
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - UAPI: Updating persistent keepalive interval
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - UAPI: Removing all allowedips
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - UAPI: Adding allowedip
2019-10-31 17:28:35.799 [NET] Routine: receive incoming IPv6 - started
2019-10-31 17:28:35.799 [NET] Routine: receive incoming IPv4 - started
2019-10-31 17:28:35.799 [NET] UDP bind has been updated
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - Starting...
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - Routine: nonce worker - started
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - Routine: sequential receiver - started
2019-10-31 17:28:35.799 [NET] peer(JC5l…vKik) - Routine: sequential sender - started
2019-10-31 17:28:35.800 [NET] Device started
2019-10-31 17:28:35.801 [APP] Tunnel 'laptop-full' connection status changed to 'connected'
2019-10-31 17:28:36.074 [NET] peer(JC5l…vKik) - Sending handshake initiation
2019-10-31 17:28:36.075 [NET] peer(JC5l…vKik) - Awaiting keypair
2019-10-31 17:28:36.088 [NET] peer(JC5l…vKik) - Received handshake response
2019-10-31 17:28:36.088 [NET] peer(JC5l…vKik) - Obtained awaited keypair

Please let me know if there's anything else I should provide. When it happens again I can try do a netstat or whatever that may show the issue, but it's driving me crazy that it happened both on Openvpn and now Wireguard so it is clear something is clearly wrong with my network configuration on this computer. I'm thinking there also might be a connection between putting my laptop to sleep with on-demand vpn still on because the issue occurs always sometime after I close the lid and then resume use later; however, it may also be unrelated -- I have also disable power nap during sleep.

Duplicate issue #1643: Huge packet loss [>80%] pinging server
Created: 2019-11-24T01:23:27Z
My setup:
Server is running on EC2 t3.micro instance in the Bahrain AWS region.
Client is MacOS running wireguard official gui.
Issue:

Wg has in general been inconsistently very sluggish when deployed via Algo.
I say it's inconsistent as it works ok-ish sometimes�—poor initial webpage load times, but when things start loading, it chugs along. For example if I test speed on fast.com, it will stay at 0kbps and not load anything for maybe 30s and then when it finally does start loading, it pulls ~40-50mbps.
I have tested a commercial VPN provider who provides wireguard support and they work fine, so I don't believe it's ISP level DPI/throttling.
Pinging sites resulted in inconsistent packet-loss. Seemingly at random it would work fine, but most times I would get a timeout.

While digging deeper, I noticed that when pinging 10.19.49.1 from the wg client, I get huge packet loss. This may be the weak link where I'm losing packets. My internet connection is definitely not the issue. Why would I be having packet loss when pinging 10.19.49.1? Is it an issue with my EC2 networking? It surely can't be my wireguard client as then it wouldn't work with the commercial wg VPN provider.
Here is the ping results:
ping 10.19.49.1
PING 10.19.49.1 (10.19.49.1): 56 data bytes
Request timeout for icmp_seq 0
Request timeout for icmp_seq 1
64 bytes from 10.19.49.1: icmp_seq=2 ttl=64 time=15.560 ms
Request timeout for icmp_seq 3
Request timeout for icmp_seq 4
Request timeout for icmp_seq 5
Request timeout for icmp_seq 6
Request timeout for icmp_seq 7
Request timeout for icmp_seq 8
Request timeout for icmp_seq 9
Request timeout for icmp_seq 10
Request timeout for icmp_seq 11
Request timeout for icmp_seq 12
Request timeout for icmp_seq 13
64 bytes from 10.19.49.1: icmp_seq=14 ttl=64 time=19.007 ms
Request timeout for icmp_seq 15
64 bytes from 10.19.49.1: icmp_seq=16 ttl=64 time=16.106 ms
^C
--- 10.19.49.1 ping statistics ---
17 packets transmitted, 3 packets received, 82.4% packet loss
round-trip min/avg/max/stddev = 15.560/16.891/19.007/1.513 ms

Closing comment (2019-11-25T19:15:45Z): So what jumps out at me is about 13 seconds of repeated Failed to send data packet messages, despite attempts to activate and deactivate the tunnel:
2019-11-24 18:44:00.872541: [NET] peer(UpED…wfCw) - Received handshake response
2019-11-24 18:44:00.872882: [NET] peer(UpED…wfCw) - Sending keepalive packet
2019-11-24 18:45:57.026651: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.082005: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.091933: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.092089: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.138757: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.203670: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.269888: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.332078: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.399803: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.465415: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.533183: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:45:57.597919: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is down
2019-11-24 18:46:00.883135: [NET] peer(UpED…wfCw) - Sending handshake initiation
2019-11-24 18:46:02.869071: [NET] peer(UpED…wfCw) - Retrying handshake because we stopped hearing back after 15 seconds
2019-11-24 18:46:05.894437: [NET] peer(UpED…wfCw) - Sending handshake initiation
2019-11-24 18:46:08.262460: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: can't assign requested address
2019-11-24 18:46:08.263858: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: can't assign requested address
2019-11-24 18:46:08.264451: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: can't assign requested address
2019-11-24 18:46:08.287636: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.301510: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.301635: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.301777: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.301857: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.301936: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.303893: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.350050: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.373338: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.373455: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.377392: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.377515: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.412722: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.430741: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.435930: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.476672: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.528186: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.528408: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.543036: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.566236: [NET] Network change detected with unsatisfied route and interface order [en0, utun2]
2019-11-24 18:46:08.568455: [NET] Routine: receive incoming IPv4 - stopped
2019-11-24 18:46:08.568983: [NET] Routine: receive incoming IPv6 - stopped
2019-11-24 18:46:08.569269: [NET] Routine: receive incoming IPv4 - started
2019-11-24 18:46:08.569388: [NET] Routine: receive incoming IPv6 - started
2019-11-24 18:46:08.569546: [NET] UDP bind has been updated
2019-11-24 18:46:08.569643: [NET] peer(UpED…wfCw) - Sending keepalive packet
2019-11-24 18:46:08.569779: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.570667: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.570932: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.571150: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.571283: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.573068: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.573264: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.573421: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.573518: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.574256: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.574368: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.579276: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.579623: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.610430: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.676137: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: network is unreachable
2019-11-24 18:46:08.694881: [NET] Network change detected with unsatisfied route and interface order [utun2]
2019-11-24 18:46:08.696636: [NET] Routine: receive incoming IPv4 - stopped
2019-11-24 18:46:08.697084: [NET] Routine: receive incoming IPv6 - stopped
2019-11-24 18:46:08.697295: [NET] Routine: receive incoming IPv6 - started
2019-11-24 18:46:08.697385: [NET] Routine: receive incoming IPv4 - started
2019-11-24 18:46:08.697458: [NET] UDP bind has been updated
2019-11-24 18:46:08.697538: [NET] peer(UpED…wfCw) - Sending keepalive packet
2019-11-24 18:46:08.697608: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.738751: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.772542: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.775761: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.776360: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.805085: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.839347: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.868954: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.879272: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.928226: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.928362: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929034: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929128: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929269: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929412: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929500: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929581: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929653: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929725: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929793: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929862: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.929958: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930020: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930099: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930175: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930253: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930328: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930401: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.930810: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.931516: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:08.997849: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:09.001674: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:09.042560: [NET] Network change detected with unsatisfied route and interface order [utun2, en0]
2019-11-24 18:46:09.043250: [NET] Routine: receive incoming IPv4 - stopped
2019-11-24 18:46:09.043334: [NET] Routine: receive incoming IPv6 - stopped
2019-11-24 18:46:09.043631: [NET] Routine: receive incoming IPv6 - started
2019-11-24 18:46:09.043686: [NET] Routine: receive incoming IPv4 - started
2019-11-24 18:46:09.043878: [NET] UDP bind has been updated
2019-11-24 18:46:09.043946: [NET] peer(UpED…wfCw) - Sending keepalive packet
2019-11-24 18:46:09.044034: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:09.067688: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:09.077056: [NET] peer(UpED…wfCw) - Failed to send data packet write udp4 0.0.0.0:57616->15.185.65.36:51820: sendto: no route to host
2019-11-24 18:46:09.756173: [NET] Network change detected with satisfied route and interface order [en0, utun2]
2019-11-24 18:46:09.756358: [NET] Routine: receive incoming IPv4 - stopped
2019-11-24 18:46:09.757639: [NET] Routine: receive incoming IPv6 - stopped
2019-11-24 18:46:09.757825: [NET] Routine: receive incoming IPv6 - started
2019-11-24 18:46:09.757857: [NET] Routine: receive incoming IPv4 - started
2019-11-24 18:46:09.757954: [NET] UDP bind has been updated
2019-11-24 18:46:09.758630: [NET] peer(UpED…wfCw) - Sending keepalive packet
2019-11-24 18:46:09.832253: [NET] Interface set up
2019-11-24 18:46:10.224886: [NET] Network change detected with satisfied route and interface order [en0, utun2]
2019-11-24 18:46:10.227137: [NET] Routine: receive incoming IPv4 - stopped
2019-11-24 18:46:10.227614: [NET] Routine: receive incoming IPv6 - stopped
2019-11-24 18:46:10.227860: [NET] Routine: receive incoming IPv6 - started
2019-11-24 18:46:10.227943: [NET] Routine: receive incoming IPv4 - started
2019-11-24 18:46:10.228109: [NET] UDP bind has been updated
2019-11-24 18:46:10.228181: [NET] peer(UpED…wfCw) - Sending keepalive packet
2019-11-24 18:46:10.937350: [NET] peer(UpED…wfCw) - Sending handshake initiation
2019-11-24 18:46:12.542169: [NET] peer(UpED…wfCw) - Received handshake response

And then you were pretty error-free after that. Wonder if you can check your EC2 console logs in Cloudwatch for rejected packets during that time?
Also, these were the same errors reported in #1629, which according to most recent update by @Ezzahhh may not be a pure macOS 10.15 problem after all.