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Google Apps to Windows Live Domains

Migrating from Google Apps to Windows Live Domains

It's been a month since we had a smooth transition from Google Apps to Windows Live Domains for our email/app needs. The documents / resources we had to refer for the same weren't much comprehensive, so we had to find our own workarounds.

We had to make a hard choice of forfeiting our beloved Google Apps (a) Google Custom Domains account to find a lighter on cost (free) alternative for our emailing needs and primarily being Linux users offered us more problems to solve as the alternative we found suitable is from Microsoft.

We had been using the following resources on our old Google Apps account:

  • Email - Gmail, with advanced Filters & Labels
  • Calendar
  • Documents [Drive]
  • Chat [GTalk]
  • Google+
  • Hangout
  • Google Sites
  • Groups (email lists)

I'll try to cover up the migration methods we followed to get these moved onto the new Microsoft account.

We were most interested in migrating our Email with internal mailing lists & Documents [Drive] to the new account. Others can just be setup from the scratch - eg: GTalk alternative - MSN.. and our top priority was a friction-free migration without any downtime.

Signup for new Microsoft Account & Create User Accounts

First things first - we went onto signup for a new Microsoft Windows Live domain account ( & haven't done the domain mappings at this point of time. Also, created our user accounts to allow migration of data.

We did not have too many accounts to be migrated & hence manually creating accounts one by one was a viable option. You may have to find your workaround if you have too many accounts to migrate.

Email Migration

We were bit concerned about privacy of data & hence we decided to migrate the email data ourselves, and not rely on 3rd party providers who could fully automate the migration process, when given our account credentials [for a premium].

There was one officially recommended solution to migrate from Gmail to Hotmail - -- but that doesn't seem to work for migration to windows live custom domains, at the time of this writing. Another issue with using trueswitch is that the accounts we have to transfer from & transfer to will look the same ( ->, as we're just migrating our existing accounts.. which surely the trueswitch system wouldn't be able to handle with ease.

We also sought for any software tools that we could run on our desktop or on a Linux server to transfer our emails. Though we couldn't find any aptly suitable tool, the Microsoft Outlook desktop app looked close to what we need. We could simply connect both accounts on the Outlook app, select all emails & simply drag-drop onto new account.. neat! We know that IMAP allows server-to-server direct email transfer, so enabled IMAP on our old accounts. Though Microsoft uses a different variant of IMAP, we believed that our emails will be transferred directly to the new account without having to be downloaded on the local desktop. But, we came to know that emails are downloaded locally & then uploaded to new account. Our bulky inboxes doesn't make this a viable option without downtime.

Finally, we had to settle down with adding the old account in the email interface of new account [add POP account option], by logging into each of the new accounts. We didn't rely much on the POP protocol for an error-free complete transfer of emails, but we had no choice but to settle for this. It looked like our Sent email history & Chat history weren't transfer, and we have to compromise on that as well.

After all old emails are transferred, we removed the POP account added on the Microsoft Live account & made the DNS changes required to redirect emails to the new Microsoft inbox. We created an email forwarding rule to forward emails from old Google Apps accounts to new account, to not miss out on emails received before the migration is complete. Perhaps removing the POP account after about 1/2 weeks after the DNS change is done can also do the job.

Email Features Migration (Filters, Label, Archive, etc.,)

  • We had minimal filters support on the new account & we have no choice but to live with that
  • Folders & Categories came as rescue for Labels, but it's not as comprehensive as Gmail's
  • We certainly miss the "Archive" button to keep the Inbox clean.. But, we're quite happy with FLAG feature as alternative to keep important Inbox emails on top of the Junk.
  • Our email's timestamps were shown wrongly & it turns out to be that, Microsoft wasn't smart enough to set our correct timezone based on the location of signup. Visiting & updating timezone {once for each user} fixed the issue, however.

Calendar Migration

We didn't had too many Calendar items to migrate, except for few recurring reminders. So we were just happy to re-create our Calendar items. Also - I believe there will be a way to export & import calendar items.

Documents Migration

We were surprised with the availability of Google Drive alternative in the form of Skydrive and though it doesn't look / work as great as Google Docs, it just gets the job done.

We simply downloaded all documents from Google Drive using the Export option & then added them onto Skydrive, shared them among the team.

Chat Migration

Though chat support is provided within the interface of {we upgraded our Hotmail/live accounts to the newer}, we didn't find it very useful in real-time due to lack of Desktop Notifications support & it won't show list of currently logged in contacts unless clicked on the compose Chat Message box.. which is annoying as well.

We were looking for a decent Linux Desktop client, that can support Group Chat, file transfers.. and after many iterations, we settled with -- which is a very good native Linux client. We're very happy with it's notification system, group chat & it's sleek intuitive UI.

Still there's a problem here: the interface don't have a way to turn off CHAT & MSN can't login simultaneously in both web & desktop. The fix was simple: creating an /etc/hosts entry as: "" did the trick.

Update: Skype integration with Microsoft MSN eliminates the above-mentioned overhead and we've got Skype as Chat / Hangout alternative for our accounts!

Google+, Google Sites Migration

We're out of luck, there seems to be no alternative solutions.. But, we're okay with leaving out these feature on the new account & have it as an account that gives primary importance to email.

Hangout Migration

Though we don't have an alternative at this time, we're sure that the upcoming MSN-Skype integration will solve our Group-Call migration problem & serve as a decent Hangout alternative.

Internal Email List / Google Groups Migration

We extensively used the Google Groups as an internal mailing list to communicate with team members. It's a surprise that Windows Live domains doesn't support mailing lists out of the box. We had to sneak out with an alternative. We came up with a solution that relies on an external mailing list provider [on a different domain name] & have a forwarding account on the primary domain name.

Our old Google Groups account is still active & will always be active, though not much activity will take place. We activated the domain on our account and our old {group-id} will now be ready to listen at {group-id} & keep doing it's usual email forwarding business.

We then created a new account on the Windows Live domains: {group-id} and have it forwarded to the {group-id} address.

We were confronted with two major issues with the above method:

  1. Only the emails that aren't detected as SPAM will be forwarded: Microsoft's SPAM filter cannot be turned off & we could miss out legitimate emails {infact we missed out few important emails}.. To fix this - we removed the usual Forwarding Address method to forward emails & instead created a new filter, that will forward to the group-id of google-groups, if sender's address contains "@".
  2. We have to login to our FORWARDING accounts on the Microsoft account once in a while, to avoid that account being deleted: We just setup a few reminders to login to the forwarding accounts once in a while & are quite happy to just do the process manually.

That's pretty much the amount of work we carried on to get us transferred from Google Apps to Microsoft Live, with no downtime. Do let us know by comments if you find this useful / if you have a better solution to suggest.


Zakyn (not verified)

Fri, 11/30/2012 - 04:11

Hi I am currently going through the same migration and is wondering when you mentioned using Outlook Desktop as a conduit to migrate the email accounts.Wouldn't having the same domain create issues using IMAP?Is this your flow1) downloaded the email for all users using Google IMAP2) Switch MX records over to Live Custom Domains3) Sync via IMAP/Exchange for all users?Am i missing anything or you have a different method?Appreciate the help

Hi Zakyn,Outlook Desktop app won't have any issues connecting to same accounts - one from Microsoft & another from Google. Just that you have to choose different protocol for that.The method we ended up was something different:

  1. Create accounts at Microsoft
  2. Add the old gmail accounts as POP accounts & start pulling data
  3. Keep using the old account & once you think all email transferred, make the DNS change and start using the new account.

This doesn't seem to work anymore. Microsoft new accounts start pulling, and after about 50 to 100 emails, google stops authentication. I wonder if the discovered people making the switch this way, and put a stop to it.

I believe Skydrive groups won't allow us to create the group email as {group} We had many of our group-email contacts given out & can't change them. So, we had to use email forwarding to achieve mailing-list feature.Hope this clarifies.

Loki (not verified)

Thu, 12/20/2012 - 17:36

Hello!I'm thankful for your post, it was enlightening.One question though : did you used to use the "" trick to register to various sites ? If so, does Windows Live Domains provide that same functionality ?Second question : can you still use the android "Gmail" application though you use Windows Live mail services ?Third and last question : did you say that you didn't migrate your mails with the same name ? ( -> ; instead of keeping the same one)Thank you again.Cheers.

Thanks; Please find my responses below:

One question though : did you used to use the "" trick to register to various sites ? If so, does Windows Live Domains provide that same functionality ?

I'm not sure I understood the first question well.. If you meant - how I re-created Google Sites on Windows Live, we retained the Google Sites services as it is.

Second question : can you still use the android "Gmail" application though you use Windows Live mail services ?

No, we will have to use the Email app, which is available by default. Need to use "Microsoft Exchange" account with as the host.

Third and last question : did you say that you didn't migrate your mails with the same name ? ( -> ; instead of keeping the same one)

We used the same names on the new account. eg: ->

So you cannot create forwarding emails without creating individual accounts for each?  This seems shortsighted by Microsoft.  What if we want a single email address to forward to multiple accounts that are not under the same domain.  Creating a mailbox for these accounts that are subject to deletion if you don't "login" to them is a pain.  I cannot migrate until Microsoft fixes this issue (however, it's been like this for 6 years from the research I've done... doubt they will fix it). 

Loki (not verified)

Tue, 01/01/2013 - 19:01

Thank you for your answers.
My first question was about the functionality Google Apps provide that allows you to add "+anything" before the "@" in your email address and yet still recieve the message. That allows you to see what sites sells your info to spammers or spam you the more and create filters to fit any spamming situation.

For instance, when I created an account on, let's say,' forum, I used the address ""
I was wondering in question 1, if WL Domains provides that.

Thank you, and happy new year.

Hi Loki, thanks & happy new year.

I never knew such functionality exist in the email address naming for spam filtering. I just tried creating a new email account with + in the name, it didn't allow me to do so. May be WL domains don't have that functionality, but i'm not too sure about it.

Loki (not verified)

Wed, 01/02/2013 - 17:07

Oh it's not creating a new account, it's registering on a website with a "+" email, and yet recieve it on your inbox. ^^
sending a random email to one of your existing accounts with "+whatever" and see whether you recieve it should let us know =)

It looks like that is not possible with Microsoft account - I tried sending an email to "", but it was rejected with the following messages:

Delivery to the following recipient failed permanently:

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 550 550 Requested action not taken: mailbox unavailable (state 13).

Rodrigo Balest (not verified)

Thu, 03/14/2013 - 18:05

Thanks for the post Vannia.

We got an issue trying to import accounts. While configuring the pop settings in hotmail -, it says that I should choose an e-mail address that is not my own Outlook address.

The Gmail and Outlook addresses is the same.

Do you got any suggestions?

Hi, in that case, you could use the domain alias (which is provided by gmail). So - instead of adding an account:, you will have to use in the (same account but a different name that outlook would accept).

(make sure that this domain alias is activated here:…)

Vinod Tulsiani (not verified)

Mon, 04/01/2013 - 09:17

Thanks for posting your experience, I am curios to know how many emails can you send in a day and how many recipients are allowed in single email WL. Is it identical to Google Apps ? One of my customer blocked for a day for sending too many emails.

Hi, we've never reached daily email limits (and the number of emails / day varies with a rough average of 20). I believe most user's email requirements will be accommodated. Using an account as SMTP gateway (may be) can exceed the limits.

Microsoft have their own "App" now that imports automatically from Gmail:

It won't do Contacts though. So stop the import (top right in outlook) after Mail gets to 100% and just Export/Import contacts manually (took 10 seconds)

If you get a "Internal Error, fail to retrieve auth token" error (after importing) when sending from Outlook, then you need to go into Gmail settings and revoke Microsoft's access to Gmail and then follow these instructions from the last post…