Moving from Gmail (back) to Hotmail

I had been happily using Gmail for several years. It became more valuable when I got my Android phone, a phone built on Google software and integrated with all things Google including mail, contacts, calendar, etc. But …


Recently, I started seeing the “Loading” message stuck at the top of my Gmail page for way too long. It would be there when I’d switch between my work and personal accounts. It would be there when I switched between folders, view contacts and view my calendar. Sometimes I’d just give up and refresh the page. Many times that wouldn’t make a difference.

It finally drove me to look at my options. And there were really only two.

Yahoo Mail – My mom has been on Yahoo Mail and I’ve been logging into her account periodically to help her with it. It was my first web-mail service and I used it for a long time. But I’m not liking the direction this service has been going. The functionality is presented in detached convoluted pieces. I’ll pass.

Hotmail – I was had been using Hotmail (aka Windows Live) just before I went to Gmail. When Microsoft started rolling out its upgraded web services and the Windows Phone 7 got rave reviews, I got excited at the prospect of having a digital ecosystem entwined with the Windows operating system on my computers. But I was really disappointed when SkyDrive and Mesh fell far short of something useful. I’d been teased by MS before and this was no different.

But a lot has changed over the past two years. SkyDrive has been combined with Office Web Apps and Mesh functionality has been merged into SkyDrive. Unfortunately, the User-interface is cartoonish.


I remembered how happy I was to discover Gmail’s Priority Inbox because it meant my phone wasn’t going to annoy me for every little thing that was emailed to me. Instead only emails that I designated as worthy were making it into my Priority Inbox. The rest were simply in the Inbox, still top-of-mind but not getting urgent treatment. But that wasn’t enough to make me tolerate the perpetual “Loading” situation.

So imagine my surprise when I figured out (not easy with the lack of useful guidance from Microsoft) that a great set of functionality is hidden in Hotmail’s “Sweep” menu. When faced with features offered under a “Sweep” label, you would assume they provide unilateral “sweeping,” changing or moving of entire folder contents. Not so! The most wonderful  tool is available under “Sweep- Move all from …”

From the Hotmail inbox (or any folder) select a group of emails (e.g. unimportant emails) and then select “Sweep – Move all from …” from the pull-down menu.


You will be presented with the above. I have created a folder labeled, “Not urgent,” that is a sub-folder of my Inbox. I now use “Sweep – Move all from …” to identify all mail I get that I don’t need to deal with right away and move it and (see the check box above?) all future email from the sender into this folder before it gets into my Inbox. This accomplishes the same benefit of Gmail’s Priority Inbox quite simply.

The folks at Microsoft have recently introduced the “Outlook” implementation of the Hotmail web-mail service. It’s pretty much all the same functionality in a different, simpler and less cartoony wrapper. That’s a bonus.


I was using Google Apps for my work email, having redirected that email to my Google Apps account. With Hotmail, I was able to much more easily go to and set everything up to enable redirecting email to my Hotmail account.

But what about all the contacts and emails I’m leaving behind on Gmail?

I set up all my email accounts, the new Hotmail ones and my previous Gmail ones, in the Windows Live Mail program (WLM). This program runs on my computer and is part of the free Windows Essentials package. Once I added all my accounts and they had completed downloading to WLM, I selected all emails in the Gmail inbox and dragged them to the corresponding Hotmail inbox in WLM.


There were thousands of emails so that process took a lot of time. I did the same for my Sent boxes. When it was all done, every email I had received or sent via Gmail was accessible to me in my Hotmail accounts.

Contacts were much simpler to move. Actually, they were simply being linked to from their location in Gmail. Hotmail allows you to connect to several services (e.g. Gmail and LinkedIn) so that your contacts in these other services will appear in your Hotmail Contacts lists. In many cases this means your information for someone is automatically updated when they change it on these other services. That’s pretty sweet.

So, Hotmail is where I am now and that is how I got here. SkyDrive just got a significant upgrade and I’m finally coming to realize the incredible freedom it provides. That will probably be my next post here.

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