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Switching webmail from Google’s Gmail to Microsoft’s Outlook.com

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Update:

Over at the Microsoft blog was announced a new tool that makes all of the above obsolete.  You can now make use of this built-in Outlook.com feature to import all your e-mail, contacts, folder structure and read/unread mail status.  Easy peasy !

outlook_cover_640x360

As the (probably) final post in the series about switching online services from Google to Microsoft, this post describes what for many will be the most difficult migration / switch-over.  It sure was for me, as I have a very big e-mail archive that is meticulously organised with labels.

But I now had switched over my other services, so consistency demanded I did the same for my webmail.  Besides, I truly loved the minimal, modern UI of Outlook.com so much, I was even prepared to take some of the cons with it.

Personal cons of Outlook.com:

  • Message filtering.  It is by far one of my biggest gripes with MS’s webmail.  It’s just too limited, as you cannot specify multiple filters per filter field.  In Gmail, you can put ‘OR’ between e-mail addresses to filter a whole list of senders for example.  Also, you are unable to assign more than one action to a filter, like applying a category (which is Gmail’s label, btw) AND moving the message to a different folder.
  • Advanced searching.  There’s no search criterium available to search within categories.  Since I don’t organise on folders, but on categories (allowing to tag a message more than once, instead of making a copy), this annoys me a lot.

Well, that’s it really, for me 🙂  Nothing that can’t be fixed in a humble update.
YMMV (Your Mileage May Vary).

So how would you go about switching webmail accounts ?

To begin with, or even if you just want to try out Outlook.com, without giving up any part of Gmail, you can configure Gmail to forward any incoming message to your new Outlook.com account.  There’s an option to keep forwarded messages, which effectively gives you a mirrored inbox; one on Google’s interpretation of webmail, one on Microsoft’s vision.  This is an excellent way to compare the two services side-by-side, should you be in doubt.  As a word of advice, it might be a good idea to run this forwarded mode for a couple of days or weeks, in order for you to really get to grips with the new webmail interface.  It will take time to notice certain stuff (like message filtering, contact integration, etc.).  Another bonus is that you now have a free backup of any new e-mail 🙂

forwarding

Next, the big move.  I assume you want to migrate your old e-mail messages, and rightly so.  There is more than one way to accomplish this, or at least, there used to be.  You might have heard of a service called TrueSwitch, which promises to move all of your e-mails, contacts and agenda entries from Gmail to Outlook.com.  I actually used this, because it provided the only way to retain any labelling: it created a folder for each label, so I could then place all messages in a folder under a category, and next archive those messages in a big ‘Archive’ folder.  Only drawback was that it apparently took only the first label (alphabetically?).  Oh, and it had troubles with foreign characters, like ‘è’.

But that option is now gone since a couple of weeks, as the service has shut down.

That leaves you with the other option: manual import/export.  It’s not as bad as it sounds, though, and as you will find loads of tutorials online for this, I won’t go into details.  The bottom line is: for the moment, Outlook.com does not support the IMAP protocol, so you can’t use just any desktop e-mail client (like Thunderbird) to set this up.  The best option is to use the Outlook desktop software which does support EAS (Exchange Active Sync).  There, you configure both your Gmail (using IMAP) and your Outlook.com (using EAS) inboxes.  Sync them completely (remember to check all folders, also ‘sent’).  Once your e-mail is downloaded, you can simply drag & drop your Gmail messages in the desired Outlook folders, and the e-mail client will sync everything on the go.  Once it’s done, you don’t have to use the client anymore if you don’t want to.

There is actually a third option, but that is only worth considering if either you don’t want to put in a lot of effort in the migration, or you only need a dump of your Gmail messages, without organisation.  Outlook.com, like the other webmail services, offers you the ability to download messages from another account via POP.  You could configure your Gmail account here, and Outlook.com would start downloading Gmail e-mails to your inbox.  Best is to set up a filter for these messages as to not flood your inbox (when I tried this, I let the downloaded messages land in a separate ‘@gmail’ folder).  Take note that this will take a very long time (possibly several weeks, depending on the size of your Gmail inbox), and you don’t really have any control or progress indication available, so the risk is there that you miss out on some messages.  Like I said, only an option if you don’t care that much about your e-mail archive.

pop

It’s clear that the biggest hurdle – at least for me it was – is the organisation of your messages, as Gmail uses the label system only (no folders).  You should think through how important this is for you with regards to finding ancient mail.  Keyword search obviously will still work, but I have noticed that Outlook.com uses a ‘wider’ search.  You will find more, but it’s also more difficult if your keywords are generic.  So it actually might go either way for you in deciding you need your historical Gmail labels.

Finally, if you decide you like what Microsoft has cooked up, you can either delete your Google account (which is very straightforward), or play on the safe side, and simply put it in sleep mode.  That is, don’t use it anymore, and activate a permanent auto-reply (aka OutOfOffice).  Make sure to check the option ‘send reply only to people in your address book’; you don’t want to acknowledge spambots of your valid e-mail address.  This way, you inform your contacts that you now use an “[at] outlook.com” address, without having to send out a huge spam mail yourself.

OoO

I already talked about migrating your contacts, and for now I still use Google’s Calendar.  Microsoft’s Calendar just simply isn’t up to Google’s level at the moment, and together with personal limitations (sharing of my wife’s personal and work calendar), this prevents me from switching just yet.  However, I’m sure Microsoft will address this, and once they do I am able to wave goodbye to that as well, truly unifying my online services once more…

Read my other posts about my online services switch from Google to Microsoft:

Moving address book from Google Contacts to Microsoft People
Moving photo albums from Picasaweb / Google+ Photos to SkyDrive
Switching personal cloud service from Google Drive to SkyDrive
Moving file hosting service from Dropbox to SkyDrive
How Google is slowly losing me as a client to Microsoft
Switching search engines from Google to DuckDuckGo

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Author: pleinolijf

father | volleyballer | software engineer

7 thoughts on “Switching webmail from Google’s Gmail to Microsoft’s Outlook.com

  1. Pingback: Moving address book from Google Contacts to Microsoft People | Room of a pleinolijf

  2. Pingback: Moving photo albums from Picasaweb / Google+ Photos to SkyDrive | Room of a pleinolijf

  3. Pingback: Switching personal cloud service from Google Drive to SkyDrive | Room of a pleinolijf

  4. Pingback: How Google is slowly losing me as a client to Microsoft | Room of a pleinolijf

  5. Pingback: Moving file hosting service from Dropbox to SkyDrive | Room of a pleinolijf

  6. Pingback: Switching Search Engine from Google to Duck Duck Go | Room of a pleinolijf

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    Like

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