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William Hilsum
Asked: 2015-05-13 07:09:32 +0800 CST

Migrating emails from Exchange (2010/SBS2011) to Office 365

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After spending several weeks and reading many different guides, I just have not been able to come up with a solution other than to use a third party tool and I would be greatful if someone can help me here.

I have a client with SBS 2011 that is constantly getting IP blacklisted (bad ISP, not spam!), and they have decided to move to Office 365 and get rid of local Exchange.

First things first, I followed a few guides and got Active Directory sync to work and confirmed changes are replicated.

I then set the users up with their Office 365 licenses.

After reading a lot of advice, it seems that cutover migration is the best path - however, I just couldn't select that option... After opening up a support case, I was told that cutover migration is not available after setting up dirsync, and I would have to disable it, delete synced users and then perform the migration... However, users will then be mastered on Azure AD and things like password sync won't work.

I said that syncing was essential and I was advised to instead remove the exchange licenses as a mailbox can't exist already and perform a Remote Move migration.

I spent a few days preparing the server, scheduling an upgrade (as I needed a higher service pack) and doing all the other essentials and after preparing the migration - a few users reported done (with a few on timeout errors...).

so, I don't really understand how this works or where the emails get migrated to as there is no license assigned, but, that is what the guides say... I then gave the user an office 365 license, however, when I tried to sign in as that user, I get the following:

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I raised a case with Microsoft again and I have just been speaking to someone for 2 hours where he stated that I shouldn't have done this migration and instead said that I should have done a Hybrid configuration followed by a move (he attempted to set this up, but, we failed as I need to get a public SSL cert for autodiscover).

Last year I moved a client to Gmail and the migration tool and AD sync had it all done so fast! I don't think what I want to do is so complicated and this just seems to be such a headache... Does anyone know what the correct migration path is and what I should actually be doing?

exchange-2010

1 Answers

  1. You need to start from scratch on Office 365 and perform a cutover migration following the detailed step-by-step instructions here.

    You will need to obtain a valid public SSL certificate and ensure that autodiscover and outlook anywhere (RPC over https) are correctly set up and working. You can test this at http://exrca.com.

    If you're unable to make this work (with the free support from MS), then you'll need to hire a consultant to do it for you / show you what to do.

    As specified in the instructions, you have to configure DirSync AFTER you have done the mailbox migration.

    The reason you have had problems is because you didn't read / follow the instructions provided by MS for a cutover migration:

    If you’ve activated and installed the Azure Active Directory Sync tool, you can’t run a cutover migration. If you’ve already installed the directory synchronization tool, but haven’t run the tool yet, you can deactivate directory synchronization in your Office 365 tenant and then run a cutover migration.

    The email migration service uses RPC over HTTP, or Outlook Anywhere, to connect to your on-premises Exchange server... ...Your Outlook Anywhere configuration must be configured with a certificate issued by a trusted certification authority (CA). It can't be configured with a self-signed certificate.

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