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Outlook Anywhere will not connect.

All PC's in one office stopped connecting to hosted Exchange on Monday 18th.  We believe we have eliminated the hosting provider, the ISP, and the local network/firewall, leaving the physical pc's as suspect.  All PC's are Windows 7 Pro with Office 2010 Pro.  (M3 is the customer.)

The problem manifests as "Loading Profile" and goes no further.  When setting up a new Outlook profile, 'an encrypted connection could not be established...", then try un-encrypted, no help, manual settings do not work either.

This is a workgroup environment, so no group policy in play.

Actions taken...
My laptop with hosted Exchange (different provider) connects fine on M3’s network.
A new Windows profile and new Outlook profile is not successful on any of M3’s pc’s on M3’s network.
Charter changed the IP block for M3 Resources.  New static address (block of 5 statics)  No help.
Created a new Windows profile and new Outlook profile on a pc iat a remote location on a Windstream network and successfully connected.
Created a new Windows profile and new Outlook profile on my laptop on M3’s network and successfully connected.
These actions seem to eliminate the Exchange provider, Charter, and the local M3 network, leaving the pc’s as suspect.
Malware/rootkit scans reveal nothing.
Uninstall/reinstall Office, to a new Windows profile, no help.
Autodiscover passes the test at https://testconnectivity.microsoft.com/

Any help/guidance much appreciated as we are stumped.  Our next step is to restore a pc backup prior to patch Tuesday, then maybe look at reimaging the entire environment.
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Mike Wood
Asked:
Mike Wood
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1 Solution
 
Simon Butler (Sembee)ConsultantCommented:
I am not aware of a bad update causing connecting problems with hosted Exchange in the last set. Usually if an update causes problems then it causes a lot of noise, and there has been nothing.

It would be highly unusual for all machines in a site to stop connecting. I would be looking for something common to them all that could cause it. Primary is third party software - particularly AV software.
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Mike WoodAuthor Commented:
I agree about the updates - There is no noise and all my other hosted Exchange customers are fine after updates.

They are only using MS Security Essentials (we only picked this customer up yesterday so have not yet corrected that).

Just for a reality check, the bus. owner took his laptop to another physical location/network and tried - no joy same results.

Customer has double checked with their IT person no changes made, no new software, etc...  their mail has been working fine until Monday

We have engaged the hosting provider Fusemail, the ISP Charter.  No help.  We believe we have eliminated the lan and router/firewall (Sonicwall) because MY personal laptop connects to both my hosted Exchange and theirs while connected to their lan.  Just can't get any of THEIR pc's or laptops to connect, despite new Windows profiles, new Outlook profiles.

The one rub is I configured my hosted Exchange (Sherweb) in a new Windows profile and Outlook profile on the customer's laptop and it connected and downloaded mail.  If it were some generic problem affecting Outlook Anywhere you would think my Exchange wouldn't connect on their pc's either.

Another thought...  They were using the ISP dns settings, I changed that to 8.8.8.8/8.8.4.4 on the sonicwall while troubleshooting but did not help.

Thanks so much for responding.
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Mike WoodAuthor Commented:
BTW...  small office, 6 pc's/laptops, one Dell switch, one Dell Sonicwall very basic config, one Dell Poweredge t420 for QB and some file storage.  Customer has Shadow Protect for backups.
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pgm554Commented:
Does OWA work?
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Mike WoodAuthor Commented:
yes that is what they are using currently in the meantime
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MdlinnettCommented:
Is your laptop getting it's IP address the same way as the clients?  If not your laptop test doesn't necessarily prove anything.

Have you checked all DNS records required by using something like MXToolbox.com?

IPCONFIG /FlushDNS on each Client?

Check the hosts file on each Client.

Sounds like the outgoing IT may have left you a nasty present.
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pgm554Commented:
Have  you tried creating a new user on the Exchange box?

How are you attempting to connect to the Exchange box?
Manual or automatic?
If your Outlook Anywhere autodiscover is correctly configured ,you should not have to do a manual setup.
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Mike WoodAuthor Commented:
Thanks for all the input really appreciate it.

Is your laptop getting it's IP address the same way as the clients?  If not your laptop test doesn't necessarily prove anything. Yes I am connecting via ethernet onto their lan with dhcp and dns supplied same as the client pc's.

Have you checked all DNS records required by using something like MXToolbox.com?  Yes.  We first checked the customer static ip for blacklisting, none present from mxtoolbox.  The hosting provider lists three mx records for the same IP (odd).  The SMTP test reveals a slow connection time of 6 to 8 seconds on average (also odd).  Also no 'postmaster' or 'abuse' addresses (checked dnsinspect dot com)

Have not flushed dns cache we can certainly try that.

Have not inspected the hosts file will also do that.

The 'other' IT guy is not hostile according to the business owner, he actually has a real day job and has done this 'on the side' so to speak.  I asked the owner the same question and he assured me that is not the case.

We have not requested a new Exchange account from the hosting provider for testing that is also an excellent suggestion.

We are using Outlook 2010 (Office 2010 Pro) using Outlook Anywhere protocols.  Automatic configuration works fine on another pc using existing credentials for an existing mailbox.  We did try manual to no avail.  Also I agree...  Autodiscover is working when we create a new profile on a different pc not the ones in the office...  I had mentioned earlier that I can use the owner's credentials here at my office on a lab machine and also on my personal laptop, and automatic configuration works like a snap.  When we try to setup a new profile on one of the pc's in the office, we get 'an encrypted connection could not be established.'  But that behavior is not confined to the office lan - the business owner took his laptop home with him today and tried to open Outlook - same results.

I keep coming back to some anomaly on the pc's at that business.  Update...  this afternoon, the outgoing IT restored a pc backup from the 13th and Outlook exhibits same behavior.   That is odd because the problem did not manifest until Monday 18th.

Is it wise or unwise to reveal the customer's email domain here?  I'm new here sorry for the ignorant question.
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Mike WoodAuthor Commented:
Again thanks so much for the interest, one more point to clarify/reiterate...  sitting in the customer conference room, connected via ethernet, ip supplied by dhcp on their lan, on my personal laptop I can create a new Windows account, log in, then open Outlook and complete the wizard using the owner's email address and password (automatic configuration) and it immediately connects and loads the owner's mail.  That same step on one of the office pc's fails.  HOWEVER, I create a new Windows account on one of THEIR pc's, open Outlook and use MY email address and password (Sherweb hosted Exchange), it works.   So my email works on their pc's but their email does not.  Can't grasp that.

So grateful for all the suggestions.
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MdlinnettCommented:
Does Ping work via autodiscover.domain.com? How about via IP?

Repeat it from your PC, how do the results vary? When pinging by name, do you get the same IP returned from both computers?

Work up the OSI layers with your troubleshooting.  95% of networking problems are DNS related.
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Mike WoodAuthor Commented:
Thanks Md I cannot check that from the customer lan until tomorrow (US Central time),

From here at my office...  Pinging autodiscover.domain.com record works.  I can also ping the ip address that autodiscover.domain.com resolves to.

I can say for sure that neither ping nor tracert works to the mx records ip.  The hosting provider advised on the phone they intentionally have that blocked.

I have overlooked checking the local pc ipv4 properties to be sure they are set to dhcp and not static.  Need to check that, need to check for an altered host file, flushdns, and check autodiscover resolution, also could IE proxy settings if affected by malware cause autodiscover to not connect?  Thanks Md you got my wheels spinning.
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MdlinnettCommented:
No problem Mike :) here to help!  Fresh eyes are always good.

IE Proxy settings could play a part if affected by Malware, but a restoration of a computer was performed which still failed remember...
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Mike WoodAuthor Commented:
Yep... and that restore was from the 13th, and the problem did not manifest until Monday the 18th.  

On that subject, I assume the .ost in that restored image was now invalid and Outlook would force creation of a new profile.  I was not there when the other IT performed the restore.
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MdlinnettCommented:
I think the OST would just re sync any data it was missing, no profile rebuild would be required. It would just grab any changes from the cloud.
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Mike WoodAuthor Commented:
The host file had an entry for autodiscover.domain.com set to the loopback address.  Customer states the hosting provider put this in about 18 months ago to get around a certificate error???  Not sure about all that, but removing the offending entry, reboot, create new Outlook profiles, and mail is flowing again.
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Mike WoodAuthor Commented:
Md with those initials I guess they call you the doctor.  Thanks for the interest.
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MdlinnettCommented:
LOL thanks Mike, glad you've got it sorted!
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Mike WoodAuthor Commented:
Appreciate the help.  Thanks again.
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