From Gmail to Hotmail: An Update

Earlier this month,I wrote about my decision to migrate my consolidated personal email accounts from Gmail to Hotmail, which I use along side Exchange-based solutions at work and with Office 365. Since then, I've gotten a lot of interesting feedback from readers and, perhaps not coincidentally, have seen some interesting moves from both Google and Microsoft in the web email space. But the big news, perhaps, is that this transition has gone a lot more smoothly than I'd imagined. Using Hotmail isn't just doable, it's actually really nice. So even though I'm only a few weeks in, it's time for an update.
First, if you haven't done so, please do take the time to read my previous article, What I Use: Hotmail and Exchange for Email as well as the relevant email consolidation articles cited within. I spent much of last year examining the different ways in which one can consolidate email accounts through a central "master" account, and what I've found is that it's better to forward email from what I think of as the sub-accounts (that is, your "non-master" email accounts; the "other" email accounts) than it is to collect email from sub-accounts using your master account. If that doesn't make sense to you, check out Email Consolidation: How To Forward Email To Other Accounts for the details.
Here's what I'm doing. 
I had previously configured all of my personal/secondary email accounts to forward to Gmail. And aside from my Hotmail account, they are all still doing so. The advantage of forwarding (vs. what I call "collecting") is that it's immediate. When an email comes in to another account, it's forwarded immediately. With collecting, things aren't immediate. 
I have several accounts forwarding to Gmail. These include two secondary Hotmail accounts, one with a custom domain, a secondary Gmail account with a custom domain, a Yahoo account, a MobileMe/iCloud account, a personal account on its own system, and so on. When I was using Gmail as my primary email account, I had configured it to send mail as all of these accounts. So I could start a new email and then choose the account from which to send it. But the truth is, I almost never needed to do this.
When switching to Hotmail, I first stopped forwarding the mail from Hotmail to Gmail, of course. Then, I configured Gmail to forward all of the mail received there to Hotmail, and to archive that mail so it didn't just sit in the Gmail inbox. This is configured in Mail Settings, Forwarding and IMAP in Gmail.


Since all of my other (secondary) email is still being forwarded to Gmail, it is, in turn, automatically forwarded to Hotmail now, thanks to Gmail's own forwarding. I could have reconfigured every secondary account to forward instead to Hotmail, but why bother? It works fine as is.
Once Gmail was set up to forward all of its mail, the effect was instant. As mail comes in, it's forwarded automatically and never hits the Gmail inbox (since its archived). This means email delivery to Hotmail is effectively instant, or at least appears to be, no matter where the email is delivered originally. 
OK, so email is coming into Hotmail. Check. The next step is configuring Hotmail properly. And there are a few things I did here to make Microsoft's webmail service work a bit more to my liking. Most of these settings can be found in Hotmail Options, which certainly presents a lot of information, but it's worth stepping through each to make sure everything's the way you like.


For me, there are a few critical options. First, in Sending/receiving email from other accounts, you can configure Hotmail to send mail as if it were another email account. Here, I configured Hotmail to be able to send mail as if it were Gmail, simply because so much of my personal email still goes through Gmail. That may change over time, I'd imagine, but being able to send mail as if from Gmail is currently useful to me.
In the past, I had described Gmail as "more efficient" than Hotmail, and while there were a few reasons for that description, Microsoft has been kind enough to eliminate one of the big ones. Now, you can navigate to Sent Message Confirmations in Hotmail Options and choose "Skip the sent message confirmation page and go directly to the inbox." This means you'll no longer be asked--every single time you send an email reply--if you'd like to add the recipient to your contact list. This is huge for me because I answer a lot of listener and reader emails and don't ever want to add those people to my contact list.
You might also want to take a look at the Keyboard Shortcuts area. If you're coming from another popular service--currently Yahoo! Mail or Gmail--Hotmail can be configured to use the keyboard shortcuts that work in those services. And I actually did configure this for Gmail originally. But since the other two accounts I'm currently using--Exchange 2010 and Exchange Online in Office 365--all use the same native keyboard shortcuts as does Hotmail, I've since decided to learn these and have configured Hotmail for "Hotmail and Outlook Web Access (OWA)." I'm getting the hang of it.
Hotmail also includes ways to import Google-based contacts and calendars, which makes the Hotmail migration all the easier. 
To import your Gmail contacts into Hotmail, navigate to Hotmail Options, Customizing Your Contacts, Importing Contacts. Gmail is one of the supported services, so just pick that and step through the wizard.
To import your Google Calendar-based calendars, first export your Google Calendar via Calendar Settings, Calendars, Export Calendars. This will create a ZIP file that contains an ICS file for each of your calendars. Extract each of the calendars to your Windows desktop or whatever. Then, in Hotmail, navigate to Hotmail Calendar and click Subscribe. Select "Import from an ICS file" and then choose one of the ICS files you extracted. (You must do one at a time.) Give the calendar a name, choose a color, and click Import Calendar. Done!
Since doing all this a few weeks back, I've been using Hotmail regularly and have really grown to like it. In fact, I've pinned Hotmail via Internet Explorer to my Windows taskbar (this works in Windows 8 and 7) and added my work related-email and Office 365 in other tabs, so each time I open Hotmail I get all my email in one window, much as would be the case with a native application. 

This pinned web app even provides new email notifications, though only for Hotmail:

Coincidentally, both Microsoft and Google have made some webmail-related moves in the past week that relate to my own conversion from Gmail to Hotmail.

First, Microsoft has posted its own post about this kind of migration. Called Turn over a new leaf and switch from Gmail to Hotmail in 3 easy steps, this post describes why you might want to make such a change--Hotmail and Facebook integration, easier sharing of photos via email, Office integration, and Hotmail's excellent graymail capabilities--before going on to explain how to make the switch. And this post highlights something I've not described: How to import your old Gmail messages into Hotmail. So if this is a need, be sure to check out the Microsoft post.

Meanwhile, Google this week fixed two issues with Gmail and Google Calendar with regards to Windows Phone. This undercuts a few of the advantages of using Hotmail with Windows Phone, which was a consideration for me in making this migration since I do use Windows Phone. And while i wrote about this a bit yesterday in my own post, Google Now Supports Multiple Calendars on Windows Phone 7.5, it's worth reiterating what these changes are here.

First, as suggested by my blog post title, Google now explicitly supports multiple Google Calendar-based calendars on Windows Phone 7.5, which is great because you previously had to know a workaround to get this to work. Second, Google is now supporting the Gmail "send as" feature I describe above on Windows Phone, meaning that you can configure your Gmail account on Windows Phone and then send mail as if from other email accounts too. That's pretty slick.

In fact, it's so slick you may be wondering why you can't do that with Hotmail. It's a fair enough question, but there is a workaround. And I coincidentally wrote about this very topic just last week in Windows Phone 7.5: Linked Inbox for Email Consolidation. The trick is to set up each email account in Windows Phone and then use the Linked Inbox feature to have a single, integrated email client that can send mail from each account.

In any event, my move from Gmail to Hotmail has gone so well I'm a bit surprised. Further surprising is that I had this notion in the back of my head that I'd one day move this centralized account over to Office 365, but after struggling through the custom domain process and a few other issues I'll be writing about in the coming weeks, I'm now not so sure. Hotmail is free, supports custom domains, and works well. It integrates nicely with the products and services I use everyday like Windows Phone, Xbox 360, SkyDrive, and Office, and even has some interesting features--SkyDrive-based email "attachments", graymail parsing, and so on--that other services can't match.

This is all very strange to me because there's a perception out there, especially among the technocrati, that Hotmail is somehow old fashioned or passé and that no one in the know would ever use this service. That's nuts. Overall, Hotmail works just as well as Gmail does, and once you factor in all the integration benefits, it's almost no contest. There's nothing wrong with Gmail, mind you, but only someone who's not really used Hotmail would criticize it. This service works very well. And I'm happy to stick with it.