sbs2003 to Office 365

I now there has been a lot written about moving users mailboxes from SBS2003 to O365, however there are a couple of questions that I can't seem to find answers to.

I found this article that steps though the migration process (I am sure there are other articles) - http://blogs.technet.com/b/canitpro/archive/2013/05/31/step-by-step-migration-of-exchange-2003-server-to-office-365.aspx

The above article references this site - Exchange Deployment Assistant  - (http://technet.microsoft.com/en-us/exdeploy2013/Checklist?state=2284-W-AAAAAAAAQAAAAAEAAAAAAA%7e%7e) - which allows for the migration of the mailboxes.  I am looking at doing a Cutover Migration.

 
What I am not sure about and would like answered is;
1)  Does the syncing continue after the initial sync, or do you have to manually run it again to bring in email that arrives between the time the initial sync was completed and MX replication has finished?

2) This article (which also covers the Cutover Migration) indicates, under next steps - Implement single sign-on,  which points to (http://community.office365.com/en-us/wikis/exchange/835.aspx)
In this article step 2 is  - Convert on-premises mailboxes to mail-enabled users.

I can't do Single Sign-On with FS.  Therefore do I need to do/is it advisable to do - this step.
I am looking at implementing Dirsync for password syncing.

3) Configuring Outlook.  
     We have a mixture of Outlook 2007/10 - Once we cut the MX records to O365 Outlook will need to be reconfigured - is it just a case of creating the autodiscover canme record?
If outlook does not pick up this autodiscover record, can Outlook be reconfigured manually without creating a new OST file?

I know there is a lot of information here, but I believe in providing everything I know and letting you determine if it is relevant.

You help is very much appreciated.
bmcollisAsked:
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Vasil Michev (MVP)Connect With a Mentor Commented:
1) yes
2) this has nothing to do with SSO, it is to prevent Outlook related issues after the migration mainly. With SBS 2003 I think you will be fine though, if Im not mistaken E2003 does not have SCP, so the autodiscover CNAME will be the first thing the client hits. You might still need to push some registry settings to prevent Outlook connecting to the on-prem mailbox.
3) The autodiscover CNAME is a must, Office 365 no longer supports manual Outlook config. It still can be done, but it's not as easy as before. Make sure you have all the needed Outlook updates, at minimum these:

•Outlook 2010 must be current to at least the April 2012 cumulative public update (KB2553248).
•Outlook 2007 must be current to at least the July 2012 cumulative public update (KB2596598)

Preferably, isntall these also:

¿Outlook 2010 Nov 2012 cumulative public update (KB2687623)
¿Outlook 2007 Nov 2012 cumulative public update (KB2687404)

2007 needs to be SP3, 2010 SP1.

You will need to create a new Outlook profile/add the new mailbox
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bmcollisAuthor Commented:
Thanks vasilcho for the quick response.

Your answer to 1 & 3 are great and the added info on the updates is really appreciated.  I will be adding a line item in my plan to confirm these updates.

In regard to 2.
Unsure what SCP is, but guessing as you refer to the autodiscover CNAME it has to do with Outlook autodiscovering where to connect to.
You indicate I might have to push out registry settings to prevent Outlook connecting to the on-prem mailbox.    If the mailboxes are converted to "mail-enabled users" would this not stop/prevent this from happening, as there would be no mailbox to connect to?

Thanks again for your quick response.
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Vasil Michev (MVP)Commented:
Yes, that's the idea. You convert them to avoid issues with the clients still connecting to the on-prem mailboxes. Take a look at this article for info on Autodiscover and the registry settings:

http://support.microsoft.com/kb/2212902
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bmcollisAuthor Commented:
Thanks for your very quick answers.
Look for additional questions as my project unfolds.
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