Upfront full disclosure: I am not a Hotmail user. However, Hotmail users who also take advantage of Microsoft Outlook might want to grab the Microsoft Office Outlook Connector. This tool allows you to access and control your Hotmail data directly from Outlook 2003/2007:

With Microsoft Office Outlook Connector, you can use Microsoft Office Outlook 2003 or Microsoft Office Outlook 2007 to access and manage your Microsoft Windows Live Hotmail or Microsoft Office Live Mail accounts, including e-mail messages, contacts and calendars for free!

This goes above and beyond the capabilities of POP and IMAP as you are able to control your contacts and calendar, which can be extremely useful.

So if you are a user of both, give this tool a try.

Situation: You’re up in the wee hours of the morning (around 1 or 2am) and find this oh-so cool YouTube video that you want to e-mail to your friends.

However if you send off the link at that time of the night everybody knows when you sent it. You are basically admitting to all “Yes, I was up at two in the morning doing stupid stuff on my computer.” Oh, the ridicule. Oh, the shame. Continued

Situation: You have a Gmail account and want to switch over to a Hotmail account - or - you want to do the exact reverse and switch from Hotmail to Gmail - and you want to keep all your existing mail.

This article will show you in detail how to do this - and you will be able to import all your existing mail with timestamps, sent mail and so on.

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Modern day home computing is not as it once was. Not-so long ago it used to be that in order to bring the most potential out of your computer box you had to use proprietary software.

Any app that runs solely on a specific operating system is proprietary. And yes there’s still lots of this stuff out there.

For the past few years I have been slowly transitioning the stuff I do on the web to being as cloud-based as possible. You’ve heard the term "cloud computing" so much that it probably makes you sick to hear it at this point - but you have to do it if you expect to make smooth transitions in the future from computer to computer.

If you don’t start transitioning now it will be very painful and stressful to get it done later.

A plain English description

"OS-less" means to be able to do what you do on a computer without the need for any specific operating system.

Using myself as an example, here’s a few things I do:

For my photos I made the decision to push those all to Flickr. It’s web-based. I can access it on any computer using any OS.

For my e-mail I decided to switch over to Hotmail (or to be more specific, Windows Live Admin Center). Previous to that I used self-hosted IMAP and before that plain ol’ POP. I can get to my mail from anywhere on any computer using any OS in any web browser - and it’s all there. It’s backed up and readily accessible.

For important documents that I need to hang on to (and even the not-so important ones), I push those over to Google Docs. This acts as my backup that is just as accessible as my mail is. Once again it’s accessible on any computer/OS.

Are you still in the stone age?

If you’re still using apps that are OS-proprietary and local to your computer only, you run the risk of losing all the data you have without warning. Let’s say for the moment you’re really good at backing things up routinely. What if your hard drive fails and the backup doesn’t work? What then? You basically curse and swear, then realize you lost it all and start from zero.

Nobody wants that to happen.

And what happens when you buy a new computer? Do you really want to go thru the process of reinstalling all your apps all over again, configuring them and wasting hours of time when all you want to do is just get going?

Of course you don’t.

Is it possible to go completely OS-less?

Not at present. However you can move over a significant chunk of what you do to cloud territory now. The more you move out there, the better.

Get your docs, photos and e-mail out in the cloud

No matter how much of an old fuddy-duddy you are (as in the type who positively refuses to try anything different), bear in mind the transition is stupidly easy to do for docs, photos and mail.

Docs

Google Docs is still your best bet. Get an account and upload them. Don’t worry, they’re all private uploads unless you specifically enable a share-out option (which is off by default).

Photos

If you use Flickr, get Windows Live Photo Gallery (Windows), Flickr Desktop Organizer (Linux) or Flickr Uploadr (Windows, Mac). Get a Flickr account and start uploading.

If you use Picasa, the Picasa client is well known to be super-awesome and super-easy to use. Works in Windows, Mac or Linux. Uploads stuff easily. It’s a no-brainer.

E-Mail

This is the one people fear the most - especially those who use POP and are under the impression it would be absolutely impossible to move hundreds, thousands or even tens of thousands of mails to another account.

Your two best bets are Gmail and Hotmail - and yes you can move all your mail over to either.

The short version of how to do it:

All modern e-mail clients support multiple e-mail accounts.

With Gmail, you can set up the new account alongside the old POP account in Outlook Express, Outlook, Windows Live Mail, Mozilla Thunderbird, Apple Mail or any number of other clients that support IMAP.

With Hotmail, you use the Windows Live Mail client. It will easily import all your old mail from Outlook or Outlook Express. Then you set up your Hotmail account alongside your POP account.

No matter which method you choose, once you have the multiple accounts set up you just drag and drop the mail from the old to the new. All the timestamps are saved and nothing is lost. Everything is moved over including the sent mail, attachments and so on. Furthermore the mail is instantly accessible on the web as well as in the client at that point via hotmail.com or gmail.com depending on which you chose.

Once done you no longer have to rely on your computer to send, retrieve and store your mail. All of it is in the cloud, backed up and accessible at any time. You can also still use the mail client if you feel like it. You can get to your mail either way when you push it to the cloud.

The long version of how to do it:

I go into grotesque detail on how to do this and it would take way too long to explain here - so watch for another article on it soon!

I am telling you now - start transitioning to the cloud

Said honestly, don’t put this off. You’ve got your docs, you’ve got your mail and if you take photos, those are most likely local to your computer box as well. Push this stuff out to the cloud (that being the internet).

You can continue (obviously) to perform local backups, but when (not if) the time comes that you get a new computer, the painful process of moving everything over will be so much less painful when you realize you can just open up a browser and get to everything - instantly.

Yes it’s true that there will be things you simply can’t push to the cloud (yet), but for the stuff you can get out there - do it.

Do it if for no other reason to have a secondary or tertiary free backup. The price is nice and all it costs is a small amount of your time.

There’s a reason I used the odd-cased HoTMaiL in the title because that’s the way it was originally written out. You’ll notice the capital letters are HTML. Hotmail was spelled that way many moons ago to really drive home the fact it was HTML (meaning web) based mail.

Microsoft this week decided to roll out the new-and-improved interface across the rest (if not all) of Windows Live Mail accounts, and this obviously includes Hotmail.

Some people like it while others don’t like or outright hate it. You can put me in the camp of people that genuinely do like it because it goes back to the way Hotmail used to be - simple and fast.

The single largest complaint I’ve seen about the new Windows Live Mail interface is that people say it’s "boring" and that the previous interface was "just fine".

Not true.

The previous interface was no less "boring" than the new one and was so chock full of bloat that it made it a chore to use. While it’s true there are some things I miss (the "check mail" button and several icons are gone), the speed more than makes up for it. I don’t remember Hotmail being this fast since the early 2000s.

E-Mail is not supposed to be "exciting" to use. You want exciting and a super-cool animated in-your-face interface? Go play a video game; stay out of my e-mail.

Microsoft is now the first of the big three (Hotmail, Yahoo! Mail, Gmail) to roll out a single interface and stick to it. Yahoo! Mail allows for a "Classic Mode" and Gmail an "Older version" option. The reason? Because the current-generation interfaces are too bloated. Microsoft was doing the same thing with their own "classic mode" as well - but with the new interface that is no longer the case.

Since using the new interface with Hotmail I can honestly that yes, this is truly new and improved. You can read things easier, it loads faster, the learning curve is minimal and most of all - it acts like a cloud-based app is supposed to act like.

Google and Yahoo! are officially going to have to start playing catch-up at this point.

Some of you out there who use Hotmail might have seen this today:

(click image for full size)

The reason I say some is because this is a gradual roll-out of the updated Windows Live Hotmail service. If you use this e-mail, you will see this upgrade possibly today, tomorrow, next week, etc. But it will eventually happen.

The bad sense of humor comes from the ² at the bottom of the above splash page, which states:

We’ve designed Windows Live Hotmail storage to grow with you, but at a reasonable pace. That means you should have plenty of storage unless you suddenly want to store the planet Jupiter on Hotmail, in which case we’ll send you a nice e-mail asking you to please not try to store planets on Windows Live Hotmail (although gradual storage of moons and asteroids is ok).

"..gradual storage of moons and asteroids"?

Um.. yeah. Thanks, Microsoft.

Anyway, the new interface is notably better. All of it can be seen in this screen shot:

(click image for full size)

Here’s what has changed:

1. Easier management of recipients

Each recipient in To, Cc or Bcc is now surrounded by a border with a small X so it’s easy to add/remove people from a mail. Very nice.

2. Ability to change from Rich Text/HTML/Plain Text at whim.

I am VERY happy this is now here, particularly with the plain text option. In addition, plain text now looks like plain text with the use of a monospaced font.

3. Less icons

Icons were removed to speed up the interface. I don’t like this because they were nice to have.

4. Arrows removed from Junk/Deleted, "Empty" link now present

There used to be a small "swish" arrow next to Junk and Deleted to empty those folders but those are gone now. Instead, when you click on those folders there’s an "Empty" button above the e-mail list. I’m not sure if I like this or not.

5. Ability to set priority on e-mail when composing

The red exclamation point icon means "high", the blue down arrow means "low".

And we’ve still got no way to filter by priority when searching/listing mail.

You can set it and send it, but can’t filter/sort by it.

Ugh.

6. Ability to select themes

This is a crappy feature because there are less color options. I use the Silver theme in the old Hotmail. In the new Hotmail you’ve got 8 crappy theme choices. No customization whatsoever other than what MS gives you.

Bleah.

~ ~ ~

This is about all I could spot for the time being unless there were other things I missed.

Overall, yes - it is faster and better. Even though the themes suck, the plain text option with monospaced font more than makes up for it because that’s a function I’ve been wanting in Hotmail for a really long time.

GMX is "Global Mail Exchange", found at www.gmx.com. This is a free e-mail service chock full of features and goodies that, said honestly, surprised me at how good it is.

A few of the features:

• Ability to choose an address ending in gmx.com, gmx.us or gmx.co.uk.
• Can import mail over from several popular e-mail services including Hotmail, Yahoo! Mail, Gmail, AOL Mail and a ton of others.
• You can add up to 10 additional GMX mail accounts right from within your primary account, all with separate e-mail signatures.
• Has autoresponder and forwarder capability.
• Has the ability to delete mail on a schedule. You can create a custom folder and instruct GMX to "Delete mails after [this] many days". Very, very trick.
• Full right-clickability inside the interface.
• 5GB storage

When I say I was surprised at how good this mail is, I meant it. Absolutely none of the other webmail providers have everything GMX has.

Check this out:

Above: When I right-click an e-mail, look at how many commands are assigned to literal keyboard shortcuts (that work). In addition, look at all the options I have. I can blacklist/whitelist/filter/spam/move all from just this menu.

You’re probably saying to yourself "Wow, looks just like an e-mail client". You’re right, it does - and GMX does it right.

Above: In the options panel you get way more control compared to the other guys…

GMX is really fast and has tons of good names still available, but what surprises me more than anything else is how GMX was literally able to produce a truly kick-ass webmail that obliterates everyone else in the functionality department.

This is the first webmail I’ve seen besides Yahoo! Mail that truly feels like a local e-mail client - with the speed of one.

In addition to that, it’s stupidly easy to use.

You seriously need to check out GMX. Even if you don’t want another e-mail account, get one anyway and try it.

I signed up two of them.

Thanks for the tip, Drew!

If you use Hotmail there are several ways to check your mail.

1. Physically login to mail.live.com or hotmail.com and check manually.
2. Use the Windows Live Mail e-mail client. Minimize when not in use and you’ll see a system tray notification when new mails arrive (identical to the way Outlook Express worked).
3. Use the Windows Live Messenger and watch for a notification. Unfortunately you have to have that software open (meaning not minimized) just to see if there’s any new mail or not. For example, if a mail was sent to you 30 minutes ago and you weren’t at your computer, you didn’t see the "toaster" pop-up notification, so you have to physically open the client just to see if mail is there.

Is there a better way to do this?

Yes.

You can use aMSN as a Hotmail notifier (much like the Gmail notifier).

What aMSN does (aside from being a Windows Live/MSN alternative messenger):

When aMSN checks your mail and you have a new message, it puts a nice small envelope icon in the system tray - with a sound notification and a toaster pop-up. When you click the envelope, it opens up your browser (even if it’s Firefox or Opera), logs in to Hotmail and goes straight to the message.

When you read the message, the envelope goes away unless there’s more new mail.

Aside from using the Windows Live Mail client, this is the fastest, easiest and most useful way to check your Hotmail account for new mail.

"But I don’t use Windows Live messaging…"

If you don’t feel like using it, just set yourself to "Appear Offline" mode. Done deal. It still checks the mail which is what counts.

In both Hotmail and Yahoo! Mail (but not Gmail) there is the option of using a "Blocked sender" list.

In Hotmail: Options Panel / Safe and blocked senders

In Yahoo! Mail: Options Panel / Block addresses

What is a Blocked list? It’s a friendly term for a blacklist.

More than likely you were already aware of this feature but there are more than a few that don’t truly understand how this feature works.

If you add an e-mail address to your blacklist…

Will e-mails received from that address go to your "Trash" folder? No.

Will e-mails received from that address go to your "Spam" folder? No.

What happens is that upon receive the e-mail is deleted and you never see it, period. It will be absolutely nowhere in your e-mail no matter where you look - and that’s the whole point.

Will the person you blacklist ever be aware of this?

No. The mail sent will still be received by the server, but will be deleted instantly upon arrival and never get to your inbox (or anywhere else in your e-mail).

In instant messaging, when you block someone they are aware of it because there are many ways to check someone’s online status via profile pages. When you block someone on IM, that someone just checks your profile page, sees you’re online and knows he’s been blocked at that point.

This isn’t the case with e-mail. When you blacklist someone, that someone can send mails until his fingers fall off and it doesn’t matter because you’ll never receive them. Ever. And there’s no way the person on the blacklist will ever know he’s been blacklisted by you (not unless you tell him).

Gmail doesn’t have this feature?

No. The closest equivalent is to set up a filter. You can enable the filter so that "If a mail is received from [this e-mail address], delete it." The problem is that it goes straight to the "Trash" to where you could still go in there and view it if you wanted to (temptation rises…)

Is blacklisting a spam prevention feature?

No. Spam filters and blacklists are two separate things. You have complete control over your blacklist whereas with spam filters this is controlled by the mail provider itself.

Blacklisting ensures that once you add an address (or several or just block out a whole range), you will absolutely never receive mails from it ever again.

This is written for the benefit of those who use the Hotmail webmail service. If your e-mail address ends in @msn.com, @live.com or @hotmail.com or you use Windows Live Domains, this applies to you.

POP-based Hotmail is not available in the free version at the time of this writing and I’ll say that right up front. You need to flip over $19.95 a year to get that feature currently. Yes, this turns off a lot of people (considering Gmail offers the same ability for free) but if you want the POP you gotta do it.

So let’s say you go ahead and do that. What are the server names you need to use to get to the goods?

This is what they are:

POP3 incoming server: pop3.live.com
Secure required: Yes
Port: 995

SMTP outgoing server: smtp.live.com
Secure required: No
Port: 25

How to login: Use your Windows Live ID (i.e. your e-mail address) and your existing mail password.

Will POP access ever be available in the free version?

Microsoft has said they "have plans" to do so. So watch for it. For now, you have to pay for POP if you use Hotmail.

For users of Windows Live Hotmail you may have noticed that for some (but not all) forwarded e-mails and newsletters that contain images show these images as nothing but little gray boxes.

In particular, this gray box:

http://gfx1.hotmail.com/mail/w3/pr01/ltr/i_safe.gif

This is a relatively new issue that seems to have sprouted up with Hotmail. There is no issue otherwise with it.

Is this a setting you can turn off?

No.

Why can’t I just click "Show content?"

In this specific issue the yellow bar at the top which prompts you to click "Show content" isn’t there so you’re forced to deal with it.

Is there a workaround?

Not in the web-based version. However you can alternatively use the Windows Live Mail client to access your Hotmail and it will show all inline images for forwarded e-mails and newsletters (when you tell it to by allowing it to show content).

Why does this happen in the first place?

Unknown, but were I to hazard a guess it would be that Hotmail’s safety filters are working a little too well.

Just when I thought I knew everything about Live from Microsoft, here comes another: www.WindowsLive.com. Is this the same at www.live.com? NO. It’s different. And I don’t mean different in a better or worse way. Just different.

First I’ll say that this is one of the few (if not only) web sites Microsoft has done that’s actually easy to figure out. You can consider this a "site map" of sorts for actual Live products including Hotmail, Mail (i.e. Windows Live Mail), SkyDrive and so on.

If you were confused - as everyone was/is - as to what Live is all about, this site at least puts things into better perspective and gives a general direction of where Microsoft is headed internet-wise.

Microsoft, believe it or not, "does internet" better than most and they’ve got the experience to back it up. For example, Hotmail predates Yahoo Mail. In fact it’s a challenge to find any e-mail service that’s still under the same ownership that’s been in operation on the internet for 12+ years.

Live’s competition is not Apple (especially considering they’ve been stumbling in the internet department). Rather, the competition is other internet companies.

Microsoft still has a way to go with Live. Although they’ve got some good stuff going on, there’s still a bit of clutter left to clean up. They can start with the naming conventions. Is it Hotmail? Windows Hotmail? Windows Live Hotmail? Live Hotmail? Live Mail? No one knows.

But at least WindowsLive.com helps you to figure that out.

For those who were bummed out (including me) that the "full version" of Hotmail didn’t work with Firefox 3, it appears that it’s now a-okay and working great. I logged in this morning and noticed no warning messages or anything like that.

In addition, the operation is smooth. Very nice. The operation of full-version Hotmail in FF3 is way faster than it is in IE 7.

If you use Hotmail and Firefox but don’t like the Windows Live Mail client for whatever reason, full-version web-based Hotmail will suit you nicely.

This tutorial will instruct you how to do one of the following (depending on which e-mail you like best):

• POP to Hotmail (including Sent Mail and folders)
• POP to Gmail (including Sent Mail and folders)

It’s easy enough to move everything in the inbox to a Hotmail or Gmail account. But what’s more important is your sent mail and mail you have stored in separate folders. There are many instances where you will need to get access to this, and without the ability to move everything, the move simply isn’t worth it. Continued

Most of you out there already pay for e-mail and probably aren’t even aware of it. If you are the primary account holder for your internet service (meaning the service is in your name and you pay each bill as it comes due), your ISP does include e-mail service. E-Mail is part of the package so yes, you do pay for it.

What is the single largest difference between using a free webmail account from a provider (such as Yahoo, Microsoft or Google) and your included from-ISP e-mail? The difference is that your ISP has an obligation to keep the e-mail service running whereas the free providers do not. Continued

In this small mini-series of videos I explain how to use the Windows Live Mail client that includes setting up with POP, IMAP, Gmail and of course Windows Live accounts like MSN, Hotmail and so on.

This is video 2 of 5. The other parts will be posted soon.

Name an e-mail service - any e-mail service - that offers both a web interface and a mail client, by the same company, that syncs mail, address book, calendar, instant messenger, and allows you to connect it directly to your domain…

…all for free.

As you can tell from the title of this article, Microsoft and its Live Services is the only one.

For those that say “Hey! Google does all that!” Not quite - they don’t have a true-blue mail client, and this is important. More on that in a moment. Continued