Random users getting "no connection" with shared calendars

We recently made changes to autodiscover and a new SSL cert. Although this issue has been happening before hand. It seems to be random users. Outlook 2013 and 2010. OWA works great
The olkdisc.log from an affected user shows errors:
4692 0xDDECFB5C
05/01/14 10:46:10 AUTODISCOVER GET SETTINGS END
4692 0xDDECFB5C
05/01/14 10:46:10 -----------------------------
964 0xDDECFB6C
05/01/14 10:46:10 +++++++++++++++++++++++++++++++
964 0xDDECFB6C
05/01/14 10:46:10 AUTODISCOVER GET SETTINGS BEGIN
964 0xDDECFB6C
05/01/14 10:46:10  [email protected]
964 0xDDECFB7C
05/01/14 10:46:10 Attempting URL https://mail.domain.com/autodiscover/autodiscover.xml found through SCP
964 0xDDECFB7C
05/01/14 10:46:10 Autodiscover to https://mail.domain.com/autodiscover/autodiscover.xml starting
964 0xDDECFB7C
05/01/14 10:46:10 AutoDiscover doing Pre-Auth with saved data.
964 0xDDECFB7C
05/01/14 10:46:10 AutoDiscover PRE-AUTH pcreds->dwAuthScheme:
964 0xDDECFB7C
05/01/14 10:46:10  <NONE>
964 0xDDECFB7C
05/01/14 10:46:10 GetLastError=12007; httpStatus=0.
964 0xDDECFB7C
05/01/14 10:46:10 Autodiscover to https://mail.domain.com/autodiscover/autodiscover.xml Failed (0x800C8203)
964 0xDDECFB7C
05/01/14 10:46:10 Autodiscover to https://domain.com/autodiscover/autodiscover.xml starting
964 0xDDECFB7C
05/01/14 10:46:10 AutoDiscover doing Pre-Auth with saved data.
964 0xDDECFB7C
05/01/14 10:46:10 AutoDiscover PRE-AUTH pcreds->dwAuthScheme:
964 0xDDECFB7C
05/01/14 10:46:10  <NONE>
964 0xDDECFF52
05/01/14 10:46:11 Autodiscover to https://domain.com/autodiscover/autodiscover.xml Failed (0x80070006)
964 0xDDECFF52
05/01/14 10:46:11 Autodiscover to https://autodiscover.domain.com/autodiscover/autodiscover.xml starting
964 0xDDECFF52
05/01/14 10:46:11 Autodiscover to https://autodiscover.domain.com/autodiscover/autodiscover.xml Failed (0x80040113)
964 0xDDECFF52
05/01/14 10:46:11 Local autodiscover for domain.com starting
964 0xDDECFF52
05/01/14 10:46:11 Local autodiscover for domain.com Failed (0x8004010F)

thank you for the reply. here is the response I get:
Name                           : RAMAIL
AutoDiscoverServiceInternalUri : https://mail.domain.com/autodiscover/autodiscover.xml
When I visit the url this is what I get: I will try the rebuild next
This XML file does not appear to have any style information associated with it. The document tree is shown below.
<Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">
<Response>
<Error Time="05:30:03.4595514" Id="3427233440">
<ErrorCode>600</ErrorCode>
<Message>Invalid Request</Message>
<DebugData/>
</Error>
</Response>
</Autodiscover>
That is expected. 
Can you create a new Outlook profile automatically? 
Unless you have full mailbox access and have auto-mapped those shared mailboxes, autodiscovery doesnt come into play here.
Twitter!: Please Note: My Posts are provided “AS IS” without warranty of any kind, either expressed or implied.

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    2009-05-21 12:12:46+1000 [-] [caldav-8009] [AMP,client] Provisioning file: (groups) projects
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    2009-05-21 12:12:46+1000 [-] [caldav-8010] [AMP,client] "Directory service <SudoDirectoryService '/Search': FilePath('/etc/caldavd/sudoers.plist')> has no GUID; generating service GUID from realm name."
    2009-05-21 12:12:46+1000 [-] [caldav-8010] [AMP,client] PROPFIND / HTTP/1.1
    2009-05-21 12:13:22+1000 [-] [caldav-8009] [AMP,client] Unauthenticated users not enabled with the 'calendar' SACL
    2009-05-21 12:13:22+1000 [-] [caldav-8009] [AMP,client] Provisioning file: (users) john
    2009-05-21 12:13:22+1000 [-] [caldav-8009] [AMP,client] PROPFIND /principals/groups/projects/ HTTP/1.1
    2009-05-21 12:14:29+1000 [-] [caldav-8009] [AMP,client] Unauthenticated users not enabled with the 'calendar' SACL
    2009-05-21 12:14:29+1000 [-] [caldav-8010] [AMP,client] GET /principals/groups/projects/ HTTP/1.1
    2009-05-21 12:14:29+1000 [-] [caldav-8010] [AMP,client] Initializing database /Library/CalendarServer/Documents/principals/.db.calendaruserproxy

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