Office 365 migrate for Outlook 2011

[ryway09]

Hey,
I been at this all day and I hope some of you have had luck here. I am trying to work out a smooth transition from an on prem exchange server migration to Office 365. I know all about the fun of only being able to use Applescirpt with outlook for mac, but I can't seem to wrap my head around I need to do here.

I considered removing the existing outlook account and adding the new one in, but I don't see how I can script this and my google powers are failing me. The end goal would be to keep the Signature and rules intact if at all possible.

Please Help... I summon the Benevolent spirit that is TalkingMoose.

Thanks
Ryan

[BrentSlater]

In my previous role all I did was change the server address in the current Outlook account.

It may have been different for me as we were using a Hybrid environment and weren't moving everyone over in one go.

The other gotcha was that the username was the full email address of the user

[bpavlov]

If you already have Outlook 2011 installed then it really is as simple as changing the server address. Work with whoever is doing the migration to test it out. I can't speak to technically about it because I didn't handle the Exchange part of the migration, but there was a server redirect that took place that simply prompted the end-user about a web server address change. Once the end user allows the web re-direct, they will continue to get emails as if nothing ever changed. But I believe something needed to occur that allowed the on-prem server to re-direct that migrated user.

Another component to consider is that Office 2011 requires a subscription service with 365. I'm not sure if you have a volume license in which case it may not matter, but if you don't then prepare to tell users how to sign in with their 365 subscription. I hope that the email address is the same as username@company.com because otherwise prepare to have end users put in incorrect "email addresses" when prompted to subscribe. In my experience we had first.lastname@company.com which was different than username@company.com. The latter is what Microsoft needed to authenticate. We also had problems with free lancers who would come and go. Apparently 365 does not like reusing the same username or perhaps its a UID. Not sure what it was, but it definitely created issues if you removed a 365 account a few months ago and tried to create a new 365 account using the same account.

Also prepare to see weird issues with how Outlook 2011 sometimes behaves when it comes to email. Essentially all your end-users will be spread across hundreds of email servers. And if Microsoft decides to make changes (and they will) then you will start seeing some users get affected and others not as it rolls out to all 365 customers. You will open support cases with Microsoft. They will ask you for logs, but because the issue is so sporadic and comes and goes it becomes virtually impossible to catch the issue as it happens. But your users will know because they will get weird prompts asking them to authenticate multiple times. Or to re-direct their web server address even though it's correct. Or Outlook will look like its connected but it just stops downloading email while OWA works fine.

Honestly, it felt like there were more quirks with Exchange Online than Exchange on-prem. Of all companies I expected to get it right, I figured it'd be Microsoft. Like most email services it works great on the web, but it says nothing about the experience in an email client. Nothing has really come close to Exchange or ActiveSync when it comes to email clients. So how can they have so many problems with it? Perhaps some of the problems I experienced were organizational-based. Now I got to deal with another beast in Google Apps. Not even going to try to use the built in OS X apps after all the issues I've heard of. Anyways, I think I've digressed enough. Good luck with your roll out.

[ryway09]

Awesome,

Thanks for the advice? Has anyone actually managed to script some of this?

[talkingmoose · Accepted solution]

Just now seeing this and I agree with the folks here that changing the server address of the existing account may work just fine for you. It will, however, probably nuke all cached messages and force a re-download of messages. There's really no way to avoid that.

AppleScript syntax would be something like:

tell application "Microsoft Outlook"
    set server of exchange account 1 to "https://outlook.office365.com/"
end tell

A one-liner shell script version of this would be:

osascript -e "tell applications "Microsoft Outlook" to set server of exchange account 1 to "https://outlook.office365.com/""

What's the best way to implement this?

You can't send this command silently to Outlook since it's AppleScript. If Outlook isn't open and running, either script will activate Outlook. I suggest using Self Service to let folks transition themselves. Add the command to a policy, create a button and display a message at the end explaining what users can expect.

[pbetancourth]

Not sure if this helps, but in my organization, we had it set to simply redirect from the exchange server it originally pointed to the the new outlook.office365.com server address. Users simply logged in and got a prompt to accept a redirects, and once they accepted, everything worked without a hitch. We actually had less issues transitioning on the Mac end than on the Windows end.