Mac VPN consistently doesn't connect 1st time, 2nd time, 3rd time...

I connect remotely to an office network via the built-in VPN function in Mac using PPTP using a simple username and password.

Every time I try and connect, the VPN status remains 'Connecting...' for ages until it eventually times out with the message:

"Your connection failed. Try reconnecting. If the problem continues, verify your settings and contact your Administrator."

I know the connection settings are correct, because I do eventually manage to connect if I keep trying and the connection then remains connected for the duration I remain connected without any issues or dropouts.

I have since started using the command to terminate the pppd daemon, otherwise I have to wait for the timeout each time before I can try reconnecting.

sudo killall pppd

The system.log simply shows this when it can't connect:

Jul 31 13:53:39 PHILMAC.local configd[17]: SCNC: start, triggered by SystemUIServer, type PPTP, status 0

Jul 31 13:53:39 PHILMAC.local pppd[45053]: pppd 2.4.2 (Apple version 596.13) started by phil, uid 501

Jul 31 13:53:39 PHILMAC.local pppd[45053]: PPTP connecting to server 'vpn.********.com' (**.***.209.41)...

And this when it does manage to connect:

Jul 31 13:57:02 PHILMAC.local configd[17]: SCNC: start, triggered by SystemUIServer, type PPTP, status 0

Jul 31 13:57:02 PHILMAC.local pppd[45139]: pppd 2.4.2 (Apple version 596.13) started by phil, uid 501

Jul 31 13:57:02 PHILMAC.local pppd[45139]: PPTP connecting to server 'vpn.*******.com' (**.***.209.42)...

Jul 31 13:57:02 PHILMAC.local pppd[45139]: PPTP connection established.

Jul 31 13:57:02 PHILMAC.local pppd[45139]: Connect: ppp0 <--> socket[34:17]

Jul 31 13:57:03 PHILMAC.local pppd[45139]: MPPE 128-bit stateless compression enabled

Jul 31 13:57:04 PHILMAC.local pppd[45139]: local IP address ***.1.61.7

Jul 31 13:57:04 PHILMAC.local pppd[45139]: remote IP address ***.1.61.1

Jul 31 13:57:04 PHILMAC.local pppd[45139]: primary DNS address ***.1.50.2

Jul 31 13:57:04 PHILMAC.local pppd[45139]: secondary DNS address ***.1.50.4

Jul 31 13:57:04 PHILMAC.local pppd[45139]: pptp_wait_input: Address added. previous interface setting (name: en1, address: 192.168.0.192), current interface setting (name: ppp0, family: PPP, address: ***.1.61.7, subnet: 255.255.0.0, destination: ***.1.61.1).

Jul 31 13:57:04 PHILMAC.local configd[17]: network changed: v4(en1:192.168.0.192) DNS* Proxy SMB

Jul 31 13:57:04 PHILMAC.local configd[17]: network changed: v4(en1:192.168.0.192, ppp0+:***.1.61.7) DNS* Proxy SMB

Jul 31 13:57:04 PHILMAC.local Spotify[5544]: Reachability Flag Status: -- ------- networkStatusForFlags

Jul 31 13:57:09 PHILMAC.local Spotify[5544]: Reachability Flag Status: -R ------- networkStatusForFlags

**** Obscured hostnames & IP addresses

I don't have any complicated settings in the VPN connection itself:

• Automatic IP address
• Automatic Encryption (128 but or 40 bit)
• Configure IPv4: Using PPP
• Confgure IPv6: Off (doesn't seem to make any difference if I change this)

I'm at a loss as to know where to look to try and diagnose why this is happening. In the past I've always been able to connect first time without experiencing this issue. Not sure what has changed, perhaps something in a software update.

Can anyone point me in the right direction to find out why this is happening? It's becoming quite frustrating to have to fire up terminal each time it doesn't connect to have to kill the job and try and again.

thanks