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This is driving me crazy here. Our company has a hosted exchange server (which I have no access to). Right now, it seems to be working fine for everyone. Users can connect from both inside and outside our office networks, via both outlook and via OWA. However I have one remote user (working from home) that cannot access their exchange email at all. Outlook no longer connects and if I try to access OWA the request times out and I'm never even asked to log in. Thankfully I have access to this person's PC via teamviewer. As far as I know, nothing has changed on the PC or with their internet that would cause this.

Thus far I've set DNS to google and flushed it, I've turned off the firewall, reset the clock, added owa to the safe sites list, turned down the IE security level, and generally tried everything I can think of. Even more odd, I tried using a free proxy (hidemyass) and I get to the Authorization Required screen of OWA, but I can't successfully login as that user or as myself. Via the proxy I've tried every variation on domain\user name, but I can't login. Both logins work fine both here at the office and remotely from my home internet. The trouble PC in question has no problems connecting to any other websites as far as I can tell.

I've looked through their home router and everything remains at it's default. The exchange email server has ping disabled, but the IP that the trouble PC gets is the same I get from anywhere else. I'm not sure what else it could be, but I imagine that if I can get it to connect to OWA then outlook will work. Thanks

John
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    You're getting a paid-for hosted Exchange service from a provider - why aren't you engaging their support to help solve this? – mfinni Apr 24 '14 at 18:14
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    quick thoughts - there could be a routing problem between the remote user's ISP and the hosted Exchange server. It might not work through the proxy service if the proxy doesn't allow the type of authentication that OWA is asking for. – mfinni Apr 24 '14 at 18:16
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    Run a tracert to the Exchange server. It will fail at the Exchange server but you should be able to see the path pretty far toward the Exchange server (hopefully to the edge firewall or router on the Exchange side) which should highlight any routing problem that might exist. – joeqwerty Apr 25 '14 at 01:32
  • Can you have a look in this problem PC's host file too and see if there are any manual entries? – Brad Bouchard Apr 25 '14 at 05:07

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