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I've got Outlook setup with POP *1 to download my Gmail. It works fine when I'm off VPN.
However when I'm on VPN it gives me an error when I try to send or receive:

Outlook cannot connect to your outgoing (SMTP) e­mail server.

I'm on a Windows 7 laptop with Office 2007. IE is the browser our company systems are compatible with, and the proxy is set via a script *2. I asked our Service Desk for help, and they say they do not support what I'm doing, but our customer is sending datafiles larger than Outlook will allow. Gmail works, and from testing I've done it seems the macros I've got in Outlook will work just fine.

Now if I can only get mail to download while I'm on VPN. Help, please?

(FYI -
*1 - When I tried IMAP first, it wasn't working - will try that again, but wonder if the problem with the proxy will be the same.
*2 - I saved a copy of the script to a local file, pointed the proxy there, and tried adding lines for ◦smtp.gmail.com and ◦pop.gmail.com, but it did not work.)

     Thanks,
          Frank

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What proxy are you using? One provided by your company? If not, are you able to reach it when connected directly to your company's network? –  Taegost Aug 9 '13 at 18:48
    
Thanks for the questions, @Taegost -- The proxy script is provided by my company. It's accessed via proxyconf.glb.ourdomain.net/proxy.pac. I saved a copy of proxy.pac to my computer, edited it, then told IE to look at D:\userdata\userid\My Documents\proxy2.pac. Didn't work. (Don't know anything about proxy scripts.) > able to reach it when connected directly to your company's network I actually work at a customer site. So to access my company's network, I start VPN. Work that way all day, every day. –  Frank Overman Aug 9 '13 at 18:52
    
Do you need ALL internet traffic to go through the vpn? You could disable the default gateway setting in de vpn setting so all your traffic goes directly to the internet except the traffic of your company internal network. (See setting "use default gateway on remote network") –  Rik Aug 9 '13 at 19:02
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1 Answer

Couple ideas to consider:

  • Set your VPN client to allow split tunneling.
  • Use a large file sending service (like SendBigFiles.com) instead of Gmail.
  • Hassle your company's IT for a way to deal with your work-related issue (getting files from customer) that they DO support.
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Thanks for your answer @techie007 - VPN client ... split tunneling: I'll look into it. Not sure how much control I have as a user. - large file sending service: I'll check this out as well. The customer distributes the data via a mailing list. It was working fine before the file got larger than our Outlook was configured for, and our IT can't (won't) change it. The Gmail works very well, just better if it to worked on VPN. - Hassle your company's IT: Not opposed to it, but looking to see if there's a way to lower the water before I have to consider raising the bridge. –  Frank Overman Aug 9 '13 at 19:12
    
Going to your IT (and perhaps your boss) explaining WHY to need larger limits (or an alternative method) is the best way to deal with this, otherwise you may be seen as trying to circumvent things. IT is there to help you so you can serve your customers - if they are presented as preventing customers form being helped, your boss won't be happy. ;) –  techie007 Aug 9 '13 at 19:16
    
How large are the files? If they are still growing it can be time to look at a different solution then e-mail. A sending service usually involves manually actions. Perhaps a ftp solution with scripts where everyone in the mailinglist can retreive the file or even a shared folder in something like dropbox/skydrive/google drive can be a better solution for the future. –  Rik Aug 9 '13 at 20:20
    
@Rik - The last files I'd gotten were 10 MB for some time. So I'm guessing they're maybe 11mb now. The customer uses an automated system, I've asked our guy to talk to their guy to see if they could zip the contents which would drop it down to a nice 1.5mb, but the answer is no. There is no flexibility in the output of their reporting system. It won't zip. All it will do is spit out the file to an email address. In a perfect world we'd fix the problem. In our world, we probably spend as much or more on bandaids! Thanks for the help techie007 and RIK! –  Frank Overman Aug 9 '13 at 20:48
    
For your information: the maximum size of a gmail message is 25mb. This is the sum of the message's text and the encoded attachment. So if your file is at about 17 to 20mb (un-encoded) you wil get in trouble. Even with gmail. Keep that in mind... –  Rik Aug 9 '13 at 22:09
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