Now my Debian box is showing the same symptoms. (hopefully that will be easier to diagnose)
Linux shark 4.9.0-12-amd64 #1 SMP Debian 4.9.210-1 (2020-01-20) x86_64 GNU/Linux
Client log
Mon Jun 8 15:02:09 2020 us=396945 OpenVPN 2.4.0 x86_64-pc-linux-gnu [SSL (OpenSSL)] [LZO] [LZ4] [EPOLL] [PKCS11] [MH/PKTINFO] [AEAD] built on Oct 14 2018
Mon Jun 8 15:02:09 2020 us=396953 library versions: OpenSSL 1.0.2u 20 Dec 2019, LZO 2.08
Mon Jun 8 15:02:09 2020 us=397267 WARNING: No server certificate verification method has been enabled. See http://openvpn.net/howto.html#mitm for more info.
Mon Jun 8 15:02:09 2020 us=397757 Control Channel MTU parms [ L:1621 D:1212 EF:38 EB:0 ET:0 EL:3 ]
Mon Jun 8 15:02:11 2020 us=354983 Data Channel MTU parms [ L:1621 D:1450 EF:121 EB:406 ET:0 EL:3 ]
Mon Jun 8 15:02:11 2020 us=355177 Local Options String (VER=V4): 'V4,dev-type tun,link-mtu 1601,tun-mtu 1500,proto UDPv4,cipher AES-256-CBC,auth SHA512,keysize 256,key-method 2,tls-client'
Mon Jun 8 15:02:11 2020 us=355232 Expected Remote Options String (VER=V4): 'V4,dev-type tun,link-mtu 1601,tun-mtu 1500,proto UDPv4,cipher AES-256-CBC,auth SHA512,keysize 256,key-method 2,tls-server'
Mon Jun 8 15:02:11 2020 us=356181 TCP/UDP: Preserving recently used remote address: [AF_INET]80.229.131.73:1194
Mon Jun 8 15:02:11 2020 us=356269 Socket Buffers: R=[212992->212992] S=[212992->212992]
Mon Jun 8 15:02:11 2020 us=356296 UDP link local: (not bound)
Mon Jun 8 15:02:11 2020 us=356322 UDP link remote: [AF_INET]80.229.131.73:1194
Mon Jun 8 15:02:11 2020 us=356350 NOTE: UID/GID downgrade will be delayed because of --client, --pull, or --up-delay
Mon Jun 8 15:03:11 2020 us=200776 [UNDEF] Inactivity timeout (--ping-restart), restarting
Mon Jun 8 15:03:11 2020 us=201012 TCP/UDP: Closing socket
Mon Jun 8 15:03:11 2020 us=201098 SIGUSR1[soft,ping-restart] received, process restarting
Mon Jun 8 15:03:11 2020 us=201169 Restart pause, 5 second(s)
Server log
Mon Jun 8 07:02:11 2020 us=535762 MULTI: multi_create_instance called
Mon Jun 8 07:02:11 2020 us=535887 101.118.29.231:36723 Re-using SSL/TLS context
Mon Jun 8 07:02:11 2020 us=535983 101.118.29.231:36723 Control Channel MTU parms [ L:1621 D:1212 EF:38 EB:0 ET:0 EL:3 ]
Mon Jun 8 07:02:11 2020 us=536005 101.118.29.231:36723 Data Channel MTU parms [ L:1621 D:1450 EF:121 EB:406 ET:0 EL:3 ]
Mon Jun 8 07:02:11 2020 us=536059 101.118.29.231:36723 Local Options String (VER=V4): 'V4,dev-type tun,link-mtu 1601,tun-mtu 1500,proto UDPv4,cipher AES-256-CBC,auth SHA512,keysize 256,key-method 2,tls-server'
Mon Jun 8 07:02:11 2020 us=536072 101.118.29.231:36723 Expected Remote Options String (VER=V4): 'V4,dev-type tun,link-mtu 1601,tun-mtu 1500,proto UDPv4,cipher AES-256-CBC,auth SHA512,keysize 256,key-method 2,tls-client'
Mon Jun 8 07:02:11 2020 us=536105 101.118.29.231:36723 TLS: Initial packet from [AF_INET]101.118.29.231:36723, sid=15946bcb f4a41b79
Mon Jun 8 07:02:21 2020 us=14167 101.118.29.231:40414 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Mon Jun 8 07:02:21 2020 us=14200 101.118.29.231:40414 TLS Error: TLS handshake failed
Mon Jun 8 07:02:21 2020 us=14307 101.118.29.231:40414 SIGUSR1[soft,tls-error] received, client-instance restarting
Mon Jun 8 07:03:11 2020 us=19990 101.118.29.231:36723 TLS Error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)
Mon Jun 8 07:03:11 2020 us=20044 101.118.29.231:36723 TLS Error: TLS handshake failed
Mon Jun 8 07:03:11 2020 us=20161 101.118.29.231:36723 SIGUSR1[soft,tls-error] received, client-instance restarting
Mon Jun 8 07:03:16 2020 us=382468 MULTI: multi_create_instance called
Mon Jun 8 07:03:16 2020 us=382587 101.118.29.231:41486 Re-using SSL/TLS context
Mon Jun 8 07:03:16 2020 us=382674 101.118.29.231:41486 Control Channel MTU parms [ L:1621 D:1212 EF:38 EB:0 ET:0 EL:3 ]
Mon Jun 8 07:03:16 2020 us=382697 101.118.29.231:41486 Data Channel MTU parms [ L:1621 D:1450 EF:121 EB:406 ET:0 EL:3 ]
Mon Jun 8 07:03:16 2020 us=382751 101.118.29.231:41486 Local Options String (VER=V4): 'V4,dev-type tun,link-mtu 1601,tun-mtu 1500,proto UDPv4,cipher AES-256-CBC,auth SHA512,keysize 256,key-method 2,tls-server'
Mon Jun 8 07:03:16 2020 us=382764 101.118.29.231:41486 Expected Remote Options String (VER=V4): 'V4,dev-type tun,link-mtu 1601,tun-mtu 1500,proto UDPv4,cipher AES-256-CBC,auth SHA512,keysize 256,key-method 2,tls-client'
Mon Jun 8 07:03:16 2020 us=382796 101.118.29.231:41486 TLS: Initial packet from [AF_INET]101.118.29.231:41486, sid=069f7d46 6db7456b
I did update this today via apt
Upgrade: ca-certificates:amd64 (20161130+nmu1+deb9u1, 20200601~deb9u1)
Other than that 3 hours ago it worked... now it does not.
Could something have expired? (grasping at straws)