Outlook 2010 and redirected My Documents folder will not connect using VPN with Verizon MiFi.

Do you have routes to the servers when you are connected by VPN? because VPN clients can be in another subnet, different from the servers, and not having access to the servers. Can you ping the file server where My docs is hosted or can you ping the exchange server when you are connected trough VPN?

I can ping both the exchange server and the file server that hosts the documents by LAN IP only. if I try to ping by name, it attempts to ping the public IP address and fails as that address is assigned to our SonicWALL pro 2040.  If I enter the UNC path to folders including the IP of the server, I can sometimes get to the folders but it is intermittent.  My MiFi is set up to give me a 192.168.88.xxx IP and the office is 192.168.1.xxx    My DNS server for my wireless connection is the IP of the MiFi  The DNS server for the VPN connection is the exchange server / RAS server.

here is the route with the VPN connected. I have replaced our public IP with xxx.  192.168.1.190 is the IP I get through the VPN assigned by RRAS.

===========================================================================
Interface List
0x1 ........................... MS TCP Loopback interface
0x2 ...00 25 64 44 e4 16 ...... Broadcom NetXtreme 57xx Gigabit Controller - Packet Scheduler Miniport
0x3 ...00 25 56 95 7a ed ...... Dell Wireless 1397 WLAN Mini-Card - Packet Scheduler Miniport
0x80005 ...00 53 45 00 00 00 ...... WAN (PPP/SLIP) Interface
===========================================================================
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0    192.168.1.190   192.168.1.190        1
          0.0.0.0          0.0.0.0     192.168.88.1    192.168.88.2        26
  xxx.xxx.xxx.xxx  255.255.255.255     192.168.88.1    192.168.88.2        25
        127.0.0.0        255.0.0.0        127.0.0.1       127.0.0.1        1
      169.254.0.0      255.255.0.0     192.168.88.2    192.168.88.2        20
    192.168.1.190  255.255.255.255        127.0.0.1       127.0.0.1        50
    192.168.1.255  255.255.255.255    192.168.1.190   192.168.1.190        50
     192.168.88.0    255.255.255.0     192.168.88.2    192.168.88.2        25
     192.168.88.2  255.255.255.255        127.0.0.1       127.0.0.1        25
   192.168.88.255  255.255.255.255     192.168.88.2    192.168.88.2        25
        224.0.0.0        240.0.0.0     192.168.88.2    192.168.88.2        25
        224.0.0.0        240.0.0.0    192.168.1.190   192.168.1.190        1
  255.255.255.255  255.255.255.255    192.168.1.190   192.168.1.190        1
  255.255.255.255  255.255.255.255     192.168.88.2               2        1
  255.255.255.255  255.255.255.255     192.168.88.2    192.168.88.2        1
Default Gateway:     192.168.1.190
===========================================================================
Persistent Routes:
  None

you get any strange log entries on the sonicwall when connectivity issues are occurring?

digitap: I will take a look, but this seems more to do with the MiFi than anything else. I can connect to other Wifi networks, and the VPN works fine.

You can ping by ip but not by name, so that explains why outlook is not working because outlook will try to reach exchange by name and not by ip. can you do a \\ip_of_server\folder to connect to the my documents folder when connected by vpn? if so then you have a DNS issue. Whats the DNS server that client is using when connected by VPN? The workaround/test can be you entering in the hosts file in c:\%windows folder%\system32\drivers\etc\hosts folder entries matching the names to the LAN ips. do a ipconfig \flushdns and try pinging by ip again

GreatVargas I tried that but when I put the full server.domain.net address in the host file then the VPN will not connect because it tries to connect to the LAN IP instead of the public IP. So I changed the VPN (recreated it manually) and used the public IP instead of the DNS name of the RRAS server (which is the same as the exchange server)  That works! Sync'd My Docs and connected/updated Outlook but now I cannot connect to Outlook Web Access when disconnected from the VPN as it is looking for the internal IP to a network it is not connected to. OWA address is this format https://server.domain.net/exchange.   This is so very close to the solution, I'm sure the final step is there somewhere.

hosts file was just a workaround but like you said it brings other problems. try and see what's the DNS server that vpn connecting is issuing and try and understand why this dns server cannot resolve the internal names of the servers.

I will check DNS results tonight or tomorrow and post my results. We are using OpenDNS in addition to our own DNS servers, so some settings there may be contributing.

I have had to back burner this issue for the time being.I've got the laptop that has the issue and the pres has the Vista one that works fine for now. I appreciate everyone's input, and I believe I can get the issue resolved with the info you gave me. Thanks again