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I'm migrating from hosted Exchange 2007 using Sherweb to using Office 365. Once I've set up the mailboxes and migrated all data to O365 (using MigrationWiz), how do I least painfully update workstations or instruct users to update workstations so their Outlook points at the O365 server and ideally doesn't have to download the entire mailbox again?

I'm guessing they could each either:

  1. delete their account and re-add it, or
  2. Account Settings > select Exchange account > Change > More Settings > Connection tab > Exchange Proxy Settings > modify the urls.

Option 1 is probably terrible as it'll require outlook to re-download their entire mailbox, but maybe that's required (e.g. if the id's of the mail items aren't preserved when migrating from one server to another)?

I have about a dozen users and their workstations aren't managed by Active Directory but I'm happy to run through a few steps with each of them. It's not the end of the world if it's a manual process and requires re-downloading the entire mailbox, but I'd love to avoid that if possible.

I have already performed the MigrationWiz migrations and updated the DNS records.

Most users now have Outlook from Office 365 installed, with a couple still on Outlook 2010.

This discussion suggests they need to add a new account and presumably delete the old one when it's no longer needed...

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  • Autodiscover...? – Mathias R. Jessen May 25 '13 at 21:57
  • Can you elaborate? I've updated the autodiscover CNAME, but this doesn't appear to update the server name or connectivity information for my Outlook profile. Do users need to create new profiles, etc. – Rory May 25 '13 at 22:06
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    I'm guessing you were forced to figure this out...but one way that works pretty well is to use config365.com I found that I didn't quite like the way it changed a few Outlook settings as well, but it is pretty seamless to run and work on user's workstations. – TheCleaner Oct 8 '13 at 1:46
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In a few cases you will end up re-creating profiles - I've not had a single migration yet where that was not the case so I always prepare for that.

If no one is using the old mail server any longer AND the original client configuration was setup by Autodiscover, it should be as simple as updating the AutoDiscover A record to point to O365 (which is part of the migration process). Clients that were manually configured will need a new profile created as they won't pickup the autodiscover changes. You may have to clear out Outlook cache as well.

You can check your autodiscover responses (as you mentioned you made the CNAME change) by using Exchange Connectivity Analyzer. https://testconnectivity.microsoft.com/ Be sure you don't have duplicate methods for Autodiscover in place. Also - if you have internal users and have not decommissioned your Exchange server than Outlook with pickup settings via SCP entries for Active Directory.

AutoDisocver does not always negate the need to recreate the profiles. I do a lot of "Hybrid" migration and find about 25% of users still need to have new profiles created to avoid issues. To minimize this we configure those accounts to only receive the minimum mail for offline access. After it's all working - we can increase the offline use gradually if needed. This is a good way to change user habits as well - as most don't need all their mail offline (and search is integrated so they can still find their mail).

Microsoft has a new tool for troubleshooting Outlook for O365. https://support.microsoft.com/en-us/kb/3073666 - this can be used by users to setup Outlook for O365 (It will create new profiles for those users).

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