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This is based on having several years worth of data already existing in Outlook 2007, but I will touch on the web interface briefly.

Google 

I was prompted to download the google apps sync tool which was less than 1MB and installed on my pc. During the setup it asked me if I wanted to migrate all my old email, contacts, calendar,tasks to GMail. I clicked yes, a new profile was created in Outlook, preserving all my data in outlook and after about 20 minutes, i reopened outlook to discover all my emails, data etc. in a new profile called ”myname@mbsnet.co.uk - Google Apps”. As a check I opened my existing PST file in my “normal” profile and all data was intact – useful if I need to roll back. I setup my server to forward email to the test domain created, as per the detailed instructions, did a test and email started flowing into Outlook. Simple!

Microsoft 365

The 365 setup was somewhat different, again I felt still “in the dark”. During the initial setup, outlook was “automatically updated” but I was given a link to a page with step by step instructions to manually create an exchange mailbox in Outlook (which was empty of course except a couple of welcome emails from Microsoft). I guess I would need to manually import my years of email, calendar and contact data into the exchange mailbox. After Outlook hung twice whilst trying to import my 1.2GB PST file I gave up!!

WINNER GOOGLE

Webmail

Both cloud apps are designed to be web based, so it is not surprising they have fully featured online email clients. Microsoft has Outlook Web Access which is like Outlook 2010 in a web browser – useful if you are used to working with Outlook. Google has GMail – the interface many of us who have free GMail accounts are familiar with. The concept of labels in GMail is somewhat different to Microsoft’s folders, but in the web interface it works very well and the search facility is extremely fast. The labels in GMail are represented correctly as folders in Outlook and you can customise which ones to be visible – a neat feature.

NO REAL WINNER