Windows 7 Forums
Welcome to Windows 7 Forums. Our forum is dedicated to helping you find support and solutions for any problems regarding your Windows 7 PC be it Dell, HP, Acer, Asus or a custom build. We also provide an extensive Windows 7 tutorial section that covers a wide range of tips and tricks.


Windows 7: Outlook 2010 unable to send mail when connected to VPN

3 Weeks Ago   #1
dmcmillen

Windows 7 Home Premium 64bit
 
 
Outlook 2010 unable to send mail when connected to VPN

Win 7, 64 desktop, AMD 8350 8-core, 16gb, Linksys EA8300 router, Arris SB6190 cable modem, xfinity hi-speed int

I am running IPVanish (latest version) & Outlook 2010. Outgoing smtp server is smtp.office365.com and outgoing server is configured as 587, TLS. Outgoing server requires authentification/use same settings as incoming mail server.

IPVanish with L2TP, OpenVPN Port 443.

This seems to be a common problem that I see in the forums all the time and affects multiple versions of Outlook (and other mail providers, as well) and multiple VPN providers. Right now my only solution is to disconnect VPN before sending mail.

Here are the things I have tried:
  • Tried different VPN protocols/ports
  • Tried logging on in Outlook specifying username and pw
  • Tried logging on in Outlook using SPA (didn't expect that to work)
  • Tried logging onto incoming mail server before sending mail
  • Tried adding 127.0.0.1 smtp.office365.com to hosts file

What I would like to do now is to add a route to force using the regular network instead of the VPN network for smtp.office365.com. The problem is that MS uses multiple ip addresses; I'm sure there are farms of servers. Here is the ip resolution from ipaddress.com:



When I ping smtp.office365.com it returns an ip (either vp4 or ip6) which is different. See ping here:



I'm pretty much at a loss at this point as what to do. route print or netstat -r are not helping me but I am a bit out of my element here so I would appreciate any help. Disconnecting VPN before sending mail isn't the end of the world, just a bit of a pain, especially if I forget and come back hours later to see unsent mail.


My System SpecsSystem Spec
.
Reply

 Outlook 2010 unable to send mail when connected to VPN




Thread Tools




Similar help and support threads
Thread Forum
I want Outlook 2010 to only send mail
I have been looking everywhere and can't find a way to setup Outlook 2010 to only send emails and not receive any. I have a cloud RDS server and I'm running a program that uses Outlook to send emails, but the problem is that i don't have a lot of space on the server so I would like to stop outlook...
Microsoft Office
Outlook 2010 won't send - straight to outlook
When I'm at work outlook 2010 will send e-mails without any problems. When I go home after work and try to send an e-mail, they go straight to the outbox folder. They won't send until I'm back at work the following day. I don't understand. Any help will be appreciated. Thanks
Microsoft Office
Outlook Connector (Outlook 2010) Won't send/receive
Hi, I've just started using Outlook 2010 instead of WLM 2010, because it is getting too slow and really bugging me. I'm able to send/receive mail from a web account (from a website I administrate), my Gmail and ONE windows live account, but my main email (the second windows live account) just...
Browsers & Mail
Outlook 2010: Unable to import mail from WLM
First, I tried to get Outlook 2010 to see my .dbx folders from Outlook Express, it wouldn't. I then migrated my OE mail to WLM. I then tried to both export my mail to Outlook 2010 and Import from Outlook 2010. When importing, Outlook only saw the welcome mail message but didnt see anything...
Microsoft Office
Outlook won't send (neither will WL Mail)
Outlook, Office 2010 x64 I was able to send last weekend, but this weekend I could not (send/receive error is all Outlook says) The email is still sitting in my Outbox. WL Mail won't send because it doesn't recognize the address I am sending to (not in the contacts, with no option to add new...
Microsoft Office


Our Sites

Site Links

About Us

Find Us

Windows 7 Forums is an independent web site and has not been authorized, sponsored, or otherwise approved by Microsoft Corporation. "Windows 7" and related materials are trademarks of Microsoft Corp.

Designer Media Ltd

All times are GMT -5. The time now is 12:58.
Twitter Facebook