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Iphone 5 not syc with exchange 2003 on SBS Server

Posted on 2013-01-29
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Last Modified: 2013-01-30
I have an iphone 5 & Exchange 2003 sp2 running on a SBS server, I enter all the information under the exchange setup on the phone and it puts checks on all the settings.  But the mail, cal, contacts will not sync. I get this error "cannot get mail, the connection to the server failed" from the mail app.  I have a local ssl cert which was expired but i recreated it. Still nothing on the phone.

I can get to outlook owa but it does give me a error on the ssl cert.
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Question by:plakis
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21 Comments
 
LVL 8

Expert Comment

by:jbvernej
ID: 38832971
hello
you can do more diagnostics with the following link (it is a microsoft online tool):
Exchange Test Connectivity:
www.testexchangeconnectivity.com
and choose Activesync without Autodiscover

It will check your config activesync from outside and in the report you will see what it is wrong in your cert
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Author Comment

by:plakis
ID: 38832992
ExRCA is testing Exchange ActiveSync.
The Exchange ActiveSync test failed.
Test Steps
Attempting to resolve the host name eb-computing.dnsalias.com in DNS.
The host name resolved successfully.
Additional Details
Testing TCP port 443 on host eb-computing.dnsalias.com to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The SSL certificate failed one or more certificate validation checks.
Test Steps
ExRCA is attempting to obtain the SSL certificate from remote server eb-computing.dnsalias.com on port 443.
ExRCA successfully obtained the remote SSL certificate.
Additional Details
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Validating certificate trust for Windows Mobile devices.
Certificate trust validation failed.
Test Steps
ExRCA is attempting to build certificate chains for certificate CN=EB-Computing.dnsalias.com, CN=companyweb, CN=eb-sbs, CN=localhost, CN=eb-sbs.EB-Computing.local.
A certificate chain couldn't be constructed for the certificate.
 Tell me more about this issue and how to resolve it
Additional Details
The certificate chain didn't end in a trusted root. Root = CN=EB-Computing.dnsalias.com, CN=companyweb, CN=eb-sbs, CN=localhost, CN=eb-sbs.EB-Computing.local
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38833131
Please tick the Ignore Trust for SSL check box on the Activesync Test Screen (also make sure you use manual server settings) and re-run the test please.

Alan
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Author Comment

by:plakis
ID: 38833562
ExRCA is testing Exchange ActiveSync.
Exchange ActiveSync was tested successfully.
Test Steps
Attempting to resolve the host name eb-computing.dnsalias.com in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 69.119.200.8
Testing TCP port 443 on host eb-computing.dnsalias.com to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Test Steps
ExRCA is attempting to obtain the SSL certificate from remote server eb-computing.dnsalias.com on port 443.
ExRCA successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=EB-Computing.dnsalias.com, CN=companyweb, CN=eb-sbs, CN=localhost, CN=eb-sbs.EB-Computing.local, Issuer: CN=EB-Computing.dnsalias.com, CN=companyweb, CN=eb-sbs, CN=localhost, CN=eb-sbs.EB-Computing.local.
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name eb-computing.dnsalias.com was found in the Certificate Subject Common name.
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
Additional Details
The certificate is valid. NotBefore = 1/27/2013 5:31:10 PM, NotAfter = 1/27/2018 5:31:10 PM
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Accept/Require Client Certificates isn't configured.
Testing HTTP Authentication Methods for URL https://eb-computing.dnsalias.com/Microsoft-Server-ActiveSync/.
The HTTP authentication methods are correct.
Additional Details
ExRCA found all expected authentication methods and no disallowed methods. Methods found: Basic
An ActiveSync session is being attempted with the server.
Testing of an Exchange ActiveSync session completed successfully.
Test Steps
Attempting to send the OPTIONS command to the server.
The OPTIONS response was successfully received and is valid.
Additional Details
Headers received: MicrosoftOfficeWebServer: 5.0_Pub
Pragma: no-cache
Public: OPTIONS, POST
Allow: OPTIONS, POST
MS-Server-ActiveSync: 3.0.4215.0
MS-ASProtocolVersions: 1.0,2.0,2.1
MS-ASProtocolCommands: Sync,SendMail,SmartForward,SmartReply,GetAttachment,GetHierarchy,CreateCollection,DeleteCollection,MoveCollection,FolderSync,FolderCreate,FolderDelete,FolderUpdate,MoveItems,GetItemEstimate,MeetingResponse,Notify
Content-Length: 0
Date: Wed, 30 Jan 2013 01:13:41 GMT
Server: Microsoft-IIS/6.0
X-Powered-By: ASP.NET
Attempting the FolderSync command on the Exchange ActiveSync session.
The FolderSync command completed successfully.
Additional Details
Number of folders: 19
Attempting the initial sync to the Inbox folder. This initial sync won't return any data.
The Sync command completed successfully.
Additional Details
Status: 1
Attempting to test the GetItemEstimate command for the Inbox folder.
ExRCA successfully received the GetItemEstimate response from the server.
Additional Details
Estimate: 248 messages
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38833591
That looks like a Pass - is that correct?

If so - what details are you entering into what filed on the iPhone as it should be working.

Alan
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LVL 10

Expert Comment

by:cpmcomputers
ID: 38833824
Alan I saw this recently
Cause appeared to be that was SMIME was enabled
(The last option on the exchange account setup )
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Author Comment

by:plakis
ID: 38835171
The SMIME is not on.  it will not verify with it on.
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LVL 10

Expert Comment

by:cpmcomputers
ID: 38835195
Is the exchange account the only mail account on the phone ?
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LVL 10

Expert Comment

by:cpmcomputers
ID: 38835259
Your server settings look fine ??

Have you hard reset the phone ? ios6 apparently has a number of issues

Is this below a possibility ? If so sync from outside or turn wifi off

I will always get this error when I'm in the office and connected to our wireless network. I forget that it automatically connects to the wifi and cannot connect to our OWA from inside our office with the settings I use to access the exchange server outside of the office.
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38835267
Earlier comment:

"That looks like a Pass - is that correct?"

Please can you confirm if the test on the test site passed.

Thanks

Alan
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Author Comment

by:plakis
ID: 38835359
yes it passed
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38835578
Okay - so what settings are you entering into which field when setting up the iPhone?

If the test passes, the phone should sync, although sometimes that isn't always the case if the settings on the server are slightly adrift from what they should be.

The suggestion about WiFi is also one to check as it can fail to configure locally, but I don't see that being a problem with your FQDN.
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Author Comment

by:plakis
ID: 38836407
My email address Username@eb-computing.com
server =eb-computing.dnsalias.com
domain eb-computing
username = username
password= password
ssl is on.

also the exchange email is the only email on the phone.
and I tried it from outside the office and it still does not work.
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LVL 76

Accepted Solution

by:
Alan Hardisty earned 500 total points
ID: 38836782
Okay - time to get you to check your settings using my article:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_1798-Exchange-2003-Activesync-Connection-Problems-FAQ.html

Please have a run through and advise of any differences (before making any changes).

Thanks

Alan
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LVL 10

Expert Comment

by:cpmcomputers
ID: 38836877
Trust me and follow Alan's advice if anyone can sort this he can

(No pressure Alan:-).
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38836897
Thanks - no pressure here (yet)!
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LVL 10

Expert Comment

by:cpmcomputers
ID: 38837036
Cool :-)
(Thinking out loud) by all accounts there should  not be an issue here
Problem is therefore server side - re your article
Or
Dnsalias.com - dynamic Ip ?
Integrated authentication ?
Caching of expired certificate
Firmware /oS on this particular device  (lots to issues and (apparent fixes) for ios6 iPhone 5
Usual ,alter this ,stand on your head sort of stuff?
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38837625
The problem is quite likely to be server-side.  The dynamic IP shouldn't be a problem and the cert is fine as is the authentication according to the test site, so there may be a slight setting tweak needed.

Doubt it will be the iPhone - not come across one yet that can't sync to Exchange when the Exchange server is configured happily.

I've seen many a server that passes the test but fails to sync properly and it is usually a server-side setting that needs a minor adjustment.
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Author Comment

by:plakis
ID: 38837741
ok it was missing sp2.  I was mistaken when i said it was installed.
I installed it and it started working right away.
thanks for all your help.
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 38837743
Excellent - great news it is working and thanks for the points.

Alan
0
 
LVL 10

Expert Comment

by:cpmcomputers
ID: 38838012
Spent ages on this one

Next time
First - Check this link (did wonder to ask if Sp2 was actually installed - thought I would get a frowned look :-))

Then we will m
Move on

Cheers Alan (til next time )
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