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Office 365  Testing and Migration

Barney Evans
Barney Evans asked
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Last Modified: 2018-03-14
Hi All,

I am getting ready to make the switch from my on premise Exchange server (Exchange 2003 Std.) to Office 365 for my office. I have 25 users across two email domains for the two companies in my office. They are using Outlook 2007 to access the exchange server. We are a much smaller organization than we were when the Exchange server was implemented in 2003.

I would like to do some testing on a couple of email accounts (including my email account) before I do a full migration. I need to test ease of migration, and day to day use of the hosted exchange. My users will not be happy if I don't know this inside and out before I move them to an new and unfamiliar email setup.

I've done a lot of research and find it a bit confusing. Can anyone with some experience in this migration give me some guidance?

Thank you!
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Most Valuable Expert 2015
Distinguished Expert 2019

Commented:
First of all, Outlook 2007 is a no-go. If you dont have the option to update to more recent version, use OWA and the mobile apps instead. Because of the outdated Exchange version, I'd also suggest to just create few mailboxes directly in O365 and work with them for a while.

In general the staged migration method (https://support.office.com/en-us/article/Perform-a-staged-migration-of-email-to-Office-365-83bc0b69-de47-4cc4-a57d-47e478e4894e?ui=en-US&rs=en-US&ad=US) allows you to move few mailboxes only, however if you want to test the full experience, I would imagine you also want to have the domain verified in O365 and mail flow configured, thus the commitment is larger.

We should be able to help with any confusion, don't be afraid to ask.
AmitIT Architect
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Distinguished Expert 2017

Commented:
In your case cut-over migration will be the best option. As your user base is below 2000.However, you need to plan well for cut-over migration and also update your user in advance. Check this KB
https://support.office.com/en-us/article/Cutover-migration-to-Office-365-9496e93c-1e59-41a8-9bb3-6e8df0cd81b4
Barney EvansIT System Administrator

Author

Commented:
Vasil, I am using Outlook 2010 on my system and will be updating my users Office software to the latest as part of our 365 subscriptions.

I would really like to do a full test before migration. Main issues are ease of setup on the users workstation and spam filtering. We are currently on a Vircom Modus Gate setup with 7 years of user whitelists.
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Most Valuable Expert 2015
Distinguished Expert 2019

Commented:
Again, depends on what you mean by full test. For example, if you want to test mailflow you will have to change the MX. Instead you can simply use a subdomain, verify it in O365, configure mail flow and so on. You can do some sort of forwarding so that users receive messages in both the on-prem and the cloud mailbox, and then see how EOP deals in comparison with your current hygiene solution.
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Barney EvansIT System Administrator

Author

Commented:
I think my main question would be, is there a method so I can move a couple of users to Office 365 and have those accounts depend exclusively on Office 365 while all other email is still delivered to my on premise Exchange server? I could then do my testing, and move the rest when the testing is finished.

This would give me an opportunity to get familiar with the all the aspects, develop training and be able to intelligently answer my users questions.