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I have a few clients (notably only in the IS department) that aren't able to connect to Exchange 2010 with Outlook 2010 over our PPTP VPN connection, citing that Exchange is unavailable. This is true whether using an existing profile or attempting to create a new one. OWA functions fine and I can ping the mailserver by hostname, FQDN and IP address. There is a hosts file on all PCs and I have confirmed that they contain the exact same entries on the two PCs I'm testing this on.

It appears to be an issue with a few PCs as I have tested this with some other laptops and haven't had any issues.

I have double-checked the VPN configuration on my main PC (which, when connected to our guest wifi and VPNs in, will not connect to Exchange via Outlook) and on a test laptop (which will connect to Exchange in the same circumstances) but I'm not sure what other settings I should be looking at... Something in the way the Outlook client is configured?

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  • 1. What's in the Hosts file, exactly? 2. Why are you using the Hosts file to begin with? 3. Why aren't you using Outlook Anywhere? Or are you?
    – joeqwerty
    Nov 26, 2014 at 16:55
  • 1. Specifically in regards to this, a mapping of the IP address of the mailserver to its hostname and FQDN. 2. We always have... I've suggested eliminating them but that hasn't gained any traction. They don't seem to cause any issues. 3. I had some trouble configuring OA (it seemed to cause trouble for users in branch offices that are still on our LAN) so I believe it's disabled right now. No remote user doesn't VPN in, and if they can't for some reason then OWA is available, so I don't really see a need for OA.
    – NaOH
    Nov 26, 2014 at 17:00
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    I'm with @joeqwerty ...I'm surprised nobody has asked for their mobile phone to sync their email and necessitate Outlook Anywhere. But regardless, if the VPN works, I would test the autoconfiguration (right click the outlook icon holding CTRL in the taskbar) and see what errors you get.
    – TheCleaner
    Nov 26, 2014 at 17:07
  • ActiveSync works fine for all our mobile devices... As far as I'm aware iPhone and BB10 connectivity doesn't require OA. Results of the Autoconfiguration test are here: i.imgur.com/ojmlOzM.png I don't see any errors, but nothing should be configured as grape.domain.com... grape is the name of our Exchange server but not publicly... publicly it should be owa.domain.com. Where do I correct these entries (Availability Service URL, OOF URL, OAB URL)?
    – NaOH
    Nov 26, 2014 at 17:37

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