From your log (sanitized):
Thu Aug 30 10:19:58 2018 us=204586 SENT CONTROL [VPN - CA]: 'PUSH_REQUEST' (status=1)
Thu Aug 30 10:19:58 2018 us=289249 PUSH: Received control message: 'PUSH_REPLY,route 192.168.237.0 255.255.255.0,dhcp-option DOMAIN [redacted].com,dhcp-option DNS 192.168.237.5,dhcp-option DNS 192.168.237.10,route-gateway 10.8.0.1,topology subnet,ping 10,ping-restart 60,ifconfig 10.8.0.4 255.255.255.0,peer-id 2,cipher AES-256-GCM'
Thu Aug 30 10:19:58 2018 us=289249 OPTIONS IMPORT: timers and/or timeouts modified
Thu Aug 30 10:19:58 2018 us=289249 OPTIONS IMPORT: --ifconfig/up options modified
Thu Aug 30 10:19:58 2018 us=289249 OPTIONS IMPORT: route options modified
Thu Aug 30 10:19:58 2018 us=289249 OPTIONS IMPORT: route-related options modified
Thu Aug 30 10:19:58 2018 us=290291 OPTIONS IMPORT: --ip-win32 and/or --dhcp-option options modified
Thu Aug 30 10:19:58 2018 us=290291 OPTIONS IMPORT: peer-id set
Thu Aug 30 10:19:58 2018 us=290291 OPTIONS IMPORT: adjusting link_mtu to 1624
Thu Aug 30 10:19:58 2018 us=290291 OPTIONS IMPORT: data channel crypto options modified
Thu Aug 30 10:19:58 2018 us=290291 Data Channel: using negotiated cipher 'AES-256-GCM'
Thu Aug 30 10:19:58 2018 us=290291 Data Channel MTU parms [ L:1552 D:1450 EF:52 EB:406 ET:0 EL:3 ]
Thu Aug 30 10:19:58 2018 us=290291 Outgoing Data Channel: Cipher 'AES-256-GCM' initialized with 256 bit key
Thu Aug 30 10:19:58 2018 us=290291 Incoming Data Channel: Cipher 'AES-256-GCM' initialized with 256 bit key
Thu Aug 30 10:19:58 2018 us=290291 interactive service msg_channel=816
Thu Aug 30 10:19:58 2018 us=304261 ROUTE_GATEWAY 10.0.1.1/255.255.0.0 I=17 HWADDR=5c:ea:1d:60:56:1f
Thu Aug 30 10:19:58 2018 us=306258 open_tun
Thu Aug 30 10:19:58 2018 us=309237 TAP-WIN32 device [Ethernet 2] opened: \\.\Global\{D234EF63-6783-4CAA-B149-E86F4E399ACF}.tap
Thu Aug 30 10:19:58 2018 us=309237 TAP-Windows Driver Version 9.21
Thu Aug 30 10:19:58 2018 us=309237 TAP-Windows MTU=1500
Thu Aug 30 10:19:58 2018 us=314230 Set TAP-Windows TUN subnet mode network/local/netmask = 10.8.0.0/10.8.0.4/255.255.255.0 [SUCCEEDED]
Thu Aug 30 10:19:58 2018 us=314230 Notified TAP-Windows driver to set a DHCP IP/netmask of 10.8.0.4/255.255.255.0 on interface {D234EF63-6783-4CAA-B149-E86F4E399ACF} [DHCP-serv: 10.8.0.254, lease-time: 31536000]
Thu Aug 30 10:19:58 2018 us=314230 DHCP option string: 0f0e636f 6e73756c 74707373 2e636f6d 0608c0a8 ed05c0a8 ed0a
Thu Aug 30 10:19:58 2018 us=316175 Successful ARP Flush on interface [55] {D234EF63-6783-4CAA-B149-E86F4E399ACF}
Thu Aug 30 10:19:58 2018 us=327144 do_ifconfig, tt->did_ifconfig_ipv6_setup=0
Thu Aug 30 10:19:58 2018 us=327144 MANAGEMENT: >STATE:1535649598,ASSIGN_IP,,10.8.0.4,,,,
Thu Aug 30 10:20:03 2018 us=731777 TEST ROUTES: 1/1 succeeded len=1 ret=1 a=0 u/d=up
Thu Aug 30 10:20:03 2018 us=731777 MANAGEMENT: >STATE:1535649603,ADD_ROUTES,,,,,,
Thu Aug 30 10:20:03 2018 us=731777 C:\WINDOWS\system32\route.exe ADD 192.168.237.0 MASK 255.255.255.0 10.8.0.1
Thu Aug 30 10:20:03 2018 us=733775 Route addition via service succeeded
Thu Aug 30 10:20:03 2018 us=733775 Initialization Sequence Completed
Thu Aug 30 10:20:03 2018 us=733775 MANAGEMENT: >STATE:1535649603,CONNECTED,SUCCESS,10.8.0.4,#.#.#.#,1194,,
Thu Aug 30 10:21:27 2018 us=336202 [VPN - CA] Inactivity timeout (--ping-restart), restarting
Thu Aug 30 10:21:27 2018 us=337086 TCP/UDP: Closing socket
Thu Aug 30 10:21:27 2018 us=337086 SIGUSR1[soft,ping-restart] received, process restarting
Thu Aug 30 10:21:27 2018 us=337086 MANAGEMENT: >STATE:1535649687,RECONNECTING,ping-restart,,,,,
Thu Aug 30 10:21:27 2018 us=337086 Restart pause, 5 second(s)
Thu
No errors here ..
The only useful information in your server log:
12:01:49 pfSense openvpn[22915]: dsugg/#.#.#.#:60550 [dsugg] Inactivity timeout (--ping-restart), restarting
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_VER=2.4.4
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_PLAT=win
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_PROTO=2
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_NCP=2
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_LZ4=1
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_LZ4v2=1
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_LZO=1
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_COMP_STUB=1
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_COMP_STUBv2=1
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_TCPNL=1
Aug 23 12:02:47 pfSense openvpn[22915]: 75.150.234.154:55090 peer info: IV_GUI_VER=OpenVPN_GUI_11
Aug 23 12:02:47 pfSense openvpn: user 'dsugg' authenticated
Aug 23 12:02:47 pfSense openvpn[22915]: #.#.#.#:55090 [dsugg] Peer Connection Initiated with [AF_INET]75.150.234.154:55090
Aug 23 12:02:47 pfSense openvpn[22915]: dsugg/#.#.#.#:55090 MULTI_sva: pool returned IPv4=10.8.0.2, IPv6=(Not enabled)
Aug 23 12:23:09 pfSense openvpn[22915]: dsugg/#.#.#.#:55090 [dsugg] Inactivity timeout (--ping-restart), restarting
Aug 23 [/b]A
Inactivity timeout .. so --keepalive 's are not working ?
Your Server Config: