I'll append my log files. First one is from the client, second from the server.
It's splitted into three parts:
1: 1st connection
2: disconnecting for 2nd connection
3: 2nd connection
Sun Oct 23 14:10:46 2016 OpenVPN 2.3.12 x86_64-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [IPv6] built on Aug 23 2016
Sun Oct 23 14:10:46 2016 Windows version 6.1 (Windows 7) 64bit
Sun Oct 23 14:10:46 2016 library versions: OpenSSL 1.0.1t 3 May 2016, LZO 2.09
Sun Oct 23 14:10:46 2016 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:25340
Sun Oct 23 14:10:46 2016 Need hold release from management interface, waiting...
Sun Oct 23 14:10:47 2016 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:25340
Sun Oct 23 14:10:47 2016 MANAGEMENT: CMD 'state on'
Sun Oct 23 14:10:47 2016 MANAGEMENT: CMD 'log all on'
Sun Oct 23 14:10:47 2016 MANAGEMENT: CMD 'hold off'
Sun Oct 23 14:10:47 2016 MANAGEMENT: CMD 'hold release'
Sun Oct 23 14:10:47 2016 MANAGEMENT: CMD 'proxy NONE '
Sun Oct 23 14:10:48 2016 Control Channel Authentication: using 'ta.key' as a OpenVPN static key file
Sun Oct 23 14:10:48 2016 Outgoing Control Channel Authentication: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:10:48 2016 Incoming Control Channel Authentication: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:10:48 2016 Socket Buffers: R=[8192->8192] S=[8192->8192]
Sun Oct 23 14:10:48 2016 MANAGEMENT: >STATE:1477224648,RESOLVE,,,
Sun Oct 23 14:10:48 2016 UDPv4 link local: [undef]
Sun Oct 23 14:10:48 2016 UDPv4 link remote: [AF_INET][my internet vpn server ip]:[server port]
Sun Oct 23 14:10:48 2016 MANAGEMENT: >STATE:1477224648,WAIT,,,
Sun Oct 23 14:10:48 2016 MANAGEMENT: >STATE:1477224648,AUTH,,,
Sun Oct 23 14:10:48 2016 TLS: Initial packet from [AF_INET][my internet vpn server ip]:[server port], sid=x x
Sun Oct 23 14:10:49 2016 VERIFY OK: depth=1, C=[...]
Sun Oct 23 14:10:49 2016 VERIFY OK: nsCertType=SERVER
Sun Oct 23 14:10:49 2016 VERIFY OK: depth=0, C=[...]
Sun Oct 23 14:10:51 2016 Data Channel Encrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:10:51 2016 Data Channel Encrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:10:51 2016 Data Channel Decrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:10:51 2016 Data Channel Decrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:10:51 2016 Control Channel: TLSv1.2, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 4096 bit RSA
Sun Oct 23 14:10:51 2016 [vpnserver] Peer Connection Initiated with [AF_INET][my internet vpn server ip]:[server port]
Sun Oct 23 14:10:53 2016 MANAGEMENT: >STATE:1477224653,GET_CONFIG,,,
Sun Oct 23 14:10:55 2016 SENT CONTROL [vpnserver]: 'PUSH_REQUEST' (status=1)
Sun Oct 23 14:10:55 2016 PUSH: Received control message: 'PUSH_REPLY,route 192.168.0.0 255.255.255.255,ping 10,ping-restart 120'
Sun Oct 23 14:10:55 2016 OPTIONS IMPORT: timers and/or timeouts modified
Sun Oct 23 14:10:55 2016 OPTIONS IMPORT: route options modified
Sun Oct 23 14:10:55 2016 ROUTE_GATEWAY [local internet gateway]/255.255.255.255 I=22 HWADDR=00:00:00:00:00:00
Sun Oct 23 14:10:55 2016 open_tun, tt->ipv6=0
Sun Oct 23 14:10:55 2016 TAP-WIN32 device [OpenVPN] opened: \\.\Global\{21BA3A38-868B-4248-B432-C395CA272A4E}.tap
Sun Oct 23 14:10:55 2016 TAP-Windows Driver Version 9.21
Sun Oct 23 14:10:55 2016 NOTE: FlushIpNetTable failed on interface [14] {21BA3A38-868B-4248-B432-C395CA272A4E} (status=1168) : Element nicht gefunden.
Sun Oct 23 14:10:57 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:10:57 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:10:59 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:10:59 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:01 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:01 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:03 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:03 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:04 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:04 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:05 2016 TEST ROUTES: 2/2 succeeded len=1 ret=1 a=0 u/d=up
Sun Oct 23 14:11:05 2016 C:\Windows\system32\route.exe ADD [my internet vpn server ip] MASK 255.255.255.255 [local internet gateway]
Sun Oct 23 14:11:05 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:05 2016 C:\Windows\system32\route.exe ADD 0.0.0.0 MASK 128.0.0.0 [vpn gateway]
Sun Oct 23 14:11:05 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:05 2016 C:\Windows\system32\route.exe ADD 128.0.0.0 MASK 128.0.0.0 [vpn gateway]
Sun Oct 23 14:11:05 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:05 2016 MANAGEMENT: >STATE:1477224665,ADD_ROUTES,,,
Sun Oct 23 14:11:05 2016 C:\Windows\system32\route.exe ADD 192.168.0.0 MASK 255.255.255.255 [vpn gateway]
Sun Oct 23 14:11:05 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:05 2016 Initialization Sequence Completed
Sun Oct 23 14:11:05 2016 MANAGEMENT: >STATE:1477224665,CONNECTED,SUCCESS,,[my internet vpn server ip]
Now the disconnect, deleting routes:
Sun Oct 23 14:11:41 2016 MANAGEMENT: CMD 'signal SIGHUP'
Sun Oct 23 14:11:41 2016 C:\Windows\system32\route.exe DELETE 192.168.0.0 MASK 255.255.255.255 [vpn gateway]
Sun Oct 23 14:11:41 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:41 2016 C:\Windows\system32\route.exe DELETE [my internet vpn server ip] MASK 255.255.255.255 [local internet gateway]
Sun Oct 23 14:11:41 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:41 2016 C:\Windows\system32\route.exe DELETE 0.0.0.0 MASK 128.0.0.0 [vpn gateway]
Sun Oct 23 14:11:41 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:41 2016 C:\Windows\system32\route.exe DELETE 128.0.0.0 MASK 128.0.0.0 [vpn gateway]
Sun Oct 23 14:11:41 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:41 2016 Closing TUN/TAP interface
Sun Oct 23 14:11:41 2016 SIGHUP[hard,] received, process restarting
Sun Oct 23 14:11:41 2016 MANAGEMENT: >STATE:1477224701,RECONNECTING,SIGHUP,,
Now the 2nd connection attempt:
Sun Oct 23 14:11:41 2016 OpenVPN 2.3.12 x86_64-w64-mingw32 [SSL (OpenSSL)] [LZO] [PKCS11] [IPv6] built on Aug 23 2016
Sun Oct 23 14:11:41 2016 Windows version 6.1 (Windows 7) 64bit
Sun Oct 23 14:11:41 2016 library versions: OpenSSL 1.0.1t 3 May 2016, LZO 2.09
Sun Oct 23 14:11:41 2016 Restart pause, 2 second(s)
Sun Oct 23 14:11:43 2016 MANAGEMENT: CMD 'proxy NONE '
Sun Oct 23 14:11:44 2016 Control Channel Authentication: using 'ta.key' as a OpenVPN static key file
Sun Oct 23 14:11:44 2016 Outgoing Control Channel Authentication: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:11:44 2016 Incoming Control Channel Authentication: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:11:44 2016 Socket Buffers: R=[8192->8192] S=[8192->8192]
Sun Oct 23 14:11:44 2016 MANAGEMENT: >STATE:1477224704,RESOLVE,,,
Sun Oct 23 14:11:45 2016 UDPv4 link local: [undef]
Sun Oct 23 14:11:45 2016 UDPv4 link remote: [AF_INET][my internet vpn server ip]:[port]
Sun Oct 23 14:11:45 2016 MANAGEMENT: >STATE:1477224705,WAIT,,,
Sun Oct 23 14:11:45 2016 MANAGEMENT: >STATE:1477224705,AUTH,,,
Sun Oct 23 14:11:45 2016 TLS: Initial packet from [AF_INET][my internet vpn server ip]:[port], sid=f6d9648e e8cefbec
Sun Oct 23 14:11:45 2016 VERIFY OK: depth=1, C=[...]
Sun Oct 23 14:11:45 2016 VERIFY OK: nsCertType=SERVER
Sun Oct 23 14:11:45 2016 VERIFY OK: depth=0, C=[...]
Sun Oct 23 14:11:46 2016 Data Channel Encrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:11:46 2016 Data Channel Encrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:11:46 2016 Data Channel Decrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:11:46 2016 Data Channel Decrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:11:46 2016 Control Channel: TLSv1.2, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 4096 bit RSA
Sun Oct 23 14:11:46 2016 [vpnserver] Peer Connection Initiated with [AF_INET][my internet vpn server ip]:[port]
Sun Oct 23 14:11:47 2016 MANAGEMENT: >STATE:1477224707,GET_CONFIG,,,
Sun Oct 23 14:11:48 2016 SENT CONTROL [vpnserver]: 'PUSH_REQUEST' (status=1)
Sun Oct 23 14:11:48 2016 PUSH: Received control message: 'PUSH_REPLY,route 192.168.0.0 255.255.255.255,ping 10,ping-restart 120'
Sun Oct 23 14:11:48 2016 OPTIONS IMPORT: timers and/or timeouts modified
Sun Oct 23 14:11:48 2016 OPTIONS IMPORT: route options modified
Sun Oct 23 14:11:48 2016 ROUTE_GATEWAY [local internet gateway]/255.255.255.255 I=22 HWADDR=00:00:00:00:00:00
Sun Oct 23 14:11:48 2016 open_tun, tt->ipv6=0
Sun Oct 23 14:11:48 2016 TAP-WIN32 device [OpenVPN] opened: \\.\Global\{21BA3A38-868B-4248-B432-C395CA272A4E}.tap
Sun Oct 23 14:11:48 2016 TAP-Windows Driver Version 9.21
Sun Oct 23 14:11:48 2016 NOTE: FlushIpNetTable failed on interface [14] {21BA3A38-868B-4248-B432-C395CA272A4E} (status=1168) : Element nicht gefunden.
Sun Oct 23 14:11:50 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:50 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:52 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:52 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:53 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:53 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:54 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:54 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:55 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:55 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:56 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:56 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:57 2016 TEST ROUTES: 0/2 succeeded len=1 ret=0 a=0 u/d=up
Sun Oct 23 14:11:57 2016 Route: Waiting for TUN/TAP interface to come up...
Sun Oct 23 14:11:58 2016 TEST ROUTES: 2/2 succeeded len=1 ret=1 a=0 u/d=up
Sun Oct 23 14:11:58 2016 C:\Windows\system32\route.exe ADD [my internet vpn server ip] MASK 255.255.255.255 [local internet gateway]
Sun Oct 23 14:11:58 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:58 2016 C:\Windows\system32\route.exe ADD 0.0.0.0 MASK 128.0.0.0 [vpn gateway]
Sun Oct 23 14:11:58 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:58 2016 C:\Windows\system32\route.exe ADD 128.0.0.0 MASK 128.0.0.0 [vpn gateway]
Sun Oct 23 14:11:58 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:58 2016 MANAGEMENT: >STATE:1477224718,ADD_ROUTES,,,
Sun Oct 23 14:11:58 2016 C:\Windows\system32\route.exe ADD 192.168.0.0 MASK 255.255.255.255 [vpn gateway]
Sun Oct 23 14:11:58 2016 env_block: add PATH=C:\Windows\System32;C:\Windows;C:\Windows\System32\Wbem
Sun Oct 23 14:11:58 2016 Initialization Sequence Completed
Sun Oct 23 14:11:58 2016 MANAGEMENT: >STATE:1477224718,CONNECTED,SUCCESS,,[my internet vpn server ip]
And here comes the server:
1st connection:
Sun Oct 23 14:11:10 2016 client ip:23117 TLS: Initial packet from [AF_INET]client ip:23117, sid=x x
Sun Oct 23 14:11:12 2016 client ip:23117 VERIFY OK: depth=1, C=[...]
Sun Oct 23 14:11:12 2016 client ip:23117 VERIFY OK: depth=0, C=[...]
Sun Oct 23 14:11:12 2016 client ip:23117 Data Channel Encrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:11:12 2016 client ip:23117 Data Channel Encrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:11:12 2016 client ip:23117 Data Channel Decrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:11:12 2016 client ip:23117 Data Channel Decrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:11:12 2016 client ip:23117 Control Channel: TLSv1.2, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 4096 bit RSA
Sun Oct 23 14:11:12 2016 client ip:23117 [vpnclient] Peer Connection Initiated with [AF_INET]client ip:23117
Sun Oct 23 14:11:12 2016 vpnclient/client ip:23117 MULTI: no dynamic or static remote --ifconfig address is available for vpnclient/client ip:23117
Sun Oct 23 14:11:16 2016 vpnclient/client ip:23117 PUSH: Received control message: 'PUSH_REQUEST'
Sun Oct 23 14:11:16 2016 vpnclient/client ip:23117 send_push_reply(): safe_cap=940
Sun Oct 23 14:11:16 2016 vpnclient/client ip:23117 SENT CONTROL [vpnclient]: 'PUSH_REPLY,route 192.168.0.0 255.255.255.255,ping 10,ping-restart 120' (status=1)
Sun Oct 23 14:11:26 2016 vpnclient/client ip:23117 MULTI: Learn: [mac address] -> vpnclient/client ip:23117
Sun Oct 23 14:11:29 2016 vpnclient/client ip:23117 MULTI: Learn: [mac address] -> vpnclient/client ip:23117
2nd connection:
Sun Oct 23 14:12:06 2016 client ip:25796 TLS: Initial packet from [AF_INET]client ip:25796, sid=x x
Sun Oct 23 14:12:07 2016 client ip:25796 VERIFY OK: depth=1, C=[...]
Sun Oct 23 14:12:07 2016 client ip:25796 VERIFY OK: depth=0, C=[...]
Sun Oct 23 14:12:07 2016 client ip:25796 Data Channel Encrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:12:07 2016 client ip:25796 Data Channel Encrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:12:07 2016 client ip:25796 Data Channel Decrypt: Cipher 'AES-256-OFB' initialized with 256 bit key
Sun Oct 23 14:12:07 2016 client ip:25796 Data Channel Decrypt: Using 512 bit message hash 'SHA512' for HMAC authentication
Sun Oct 23 14:12:07 2016 client ip:25796 Control Channel: TLSv1.2, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 4096 bit RSA
Sun Oct 23 14:12:07 2016 client ip:25796 [vpnclient] Peer Connection Initiated with [AF_INET]client ip:25796
Sun Oct 23 14:12:07 2016 MULTI: new connection by client 'vpnclient' will cause previous active sessions by this client to be dropped. Remember to use the --duplicate-cn option if you want multiple clients using the same certificate or username to concurrently connect.
Sun Oct 23 14:12:07 2016 MULTI: no dynamic or static remote --ifconfig address is available for vpnclient/client ip:25796
Sun Oct 23 14:12:09 2016 vpnclient/client ip:25796 PUSH: Received control message: 'PUSH_REQUEST'
Sun Oct 23 14:12:09 2016 vpnclient/client ip:25796 send_push_reply(): safe_cap=940
Sun Oct 23 14:12:09 2016 vpnclient/client ip:25796 SENT CONTROL [vpnclient]: 'PUSH_REPLY,route 192.168.0.0 255.255.255.255,ping 10,ping-restart 120' (status=1)
Sun Oct 23 14:12:09 2016 vpnclient/client ip:25796 MULTI: Learn: [mac address] -> vpnclient/client ip:25796
Sun Oct 23 14:12:20 2016 vpnclient/client ip:25796 MULTI: Learn: [mac address] -> vpnclient/client ip:25796
Except the hint of multiple connections from one client, I can't spot any differences between the two connection attempts.