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

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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How Google is slowly losing me as a client to Microsoft

It all began when Google decided to axe their Reader service (switch reason #1). Google Reader is was regarded as the single go-to solution for an RSS aggregator.  It was The Little Google Service That Could, and everything it did, it did well.  An API used by countless of 3rd party services and mobile apps, fast, clean, integration with other services like Pocket, sharing to social media, etc.

Since I used Reader multiple times a day, and there initially wasn’t an awesome alternative around that had the same to offer, I was really displeased.  Especially since, in my view, together with Gmail, it was one of the irreplaceable cornerstones of Google’s application landscape.  Why are they discontinuing it ?  I’m pretty sure it has to do with money somewhere (as in not-generating-a-fortune money).  Removing iGoogle ?  That I understand.

Ever since this news was published, I have switched over to Feedly.  As long as Reader is still alive, they sync with it, and once it dies, they (promise to) switch over to a proprietary system called Normandy.  I’m cool with that, because Feedly has filled the Reader gap to the best extent of all the alternatives.

Then there is also the fact that I switched from an Android smartphone to a Windows Phone one in December 2012.  I changed partly because I simply wanted to try something fresh.  After having used Windows Phone 8 for a couple of weeks, I realised I wouldn’t want to go back to an Android experience (on a phone).  I still have an Android tablet to tinker around with, but I am of the opinion that WP8 is the superior smartphone platform today.

I use the Google services on my Windows Phone, most prominently Gmail, Google Calendar, Google Contacts, and to a lesser extent Google Drive.  I never really cared for SkyDrive, until I moved my pictures to it as a cause of switch reason #2: Picasaweb.

Picasaweb, the online photo album service of Google, I was always reasonably happy with.  I found it a bit unintuitive at times with the coupling to the Picasa desktop application with regards to online synchronization, but it offered good features and storage space.  But then Google decided to hide Picasa(web) in the background and annoyingly push for integration in Google+.  In fact, I think that annoyed me the most.  Yes, you could go back to the classic Picasaweb view, but I am sure it too will be axed in favor of Google pushing their social network down our throats. I don’t want my photo albums on a social network, only a selection of separate pictures.

So I gave SkyDrive a try, also because I though it would be handy to move my Dropbox files there, and end up with one integrated system for pictures, documents and files that are automatically synced, easily shared, and provide a good online interface to share photo albums.  As an extra, SkyDrive currently has roughly the same pricing as Google had until about a year ago: around $5/yr for 20 GB.  Switch reason #3: storage pricing.  Granted, my Google storage subscription plan is kept as an early adopter, but if I want to expand it, or I miss a payment, pricing will become $10/month for about the same. SkyDrive is unquestionably the cheapest at the moment.

In conclusion: so far I switched RSS reader, online file storage and online photos to Microsoft.  The integration on their mobile platform, interweaved with social media content, is awesome.  Google’s integration used to be awesome, but at least for me, it’s dwindling at a rapid speed (especially photos).  I still use Google Drive, but that I could also switch very easily to SkyDrive. YouTube I don’t care for much (Vimeo is a good alternative), and I already switched search engines long ago to DuckDuckGo.

Remains: mail, contacts and calendar.  The most difficult triplets to switch.  I have a huge history kept in Gmail, and my calendar and contacts are meticulously maintained.  An import of all my mails from Gmail to Outlook.com has already been completed, but for the moment Gmail is still ahead in terms of speed and options.  Labels I can map to Outlook categories, but that manual task is beyond my situation.  The fact that many logins are linked to my Google account helps them a bit as well.

But it won’t take much anti-user decisions on Google’s part to make me also switch those last remaining services over.  And why wouldn’t I, aside from the hassle ?  It would mean an even leaner integration on my phone, desktop and possible future Windows tablet.

I kind of just ‘had it’ with them, to be brutally honest, and I’m not alone.  It has actually come to a point where I trust the old Micro$oft more than Google.  Who knew ?

Update

Oh, I even forgot to mention what irritates me the most about the current Google policy.  The fact that they deliberately ignore the Windows Phone customers.  There are official Google apps on every platform (Apple and even Blackberry), but they obstinately refrain from releasing Windows Phone apps for Gmail, YouTube, Maps, Drive, etc…  I guess they are afraid of something.  This is nothing more than blocking a promising player in the mobile market.  And that is exactly the kind of egotistic behaviour that ticks me off, and drives me further away from them.  Remember your own slogan, Google: “Don’t be evil”.

 

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

Moving webmail from Gmail to Outlook.com
Moving address book from Google Contacts to Microsoft People
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