Are Free Email Services Worth It?

This is a major update to what I consider one of my most important articles, dating all the way back to 2004 (with intermediate updates in 2010 and 2013).

My answer has changed from “mostly no” to “mostly yes”, with the following important caveats:

  • You must understand the costs.
  • You must understand the risks.
  • You must prepare for disaster.
  • You must take responsibility.

I’ll dive into each of these in detail, but before I do, I’ll share one concrete datapoint: all of my email is currently being processed via free email accounts. Clearly, I believe it can be done safely.

Read moreAre Free Email Services Worth It?

Gmail’s Confidential Mode Isn’t

Google recently rolled out a feature called “confidential mode”, which claims to prevent disclosure of an email message to anyone other than its intended recipient. The message can only be viewed by the person you send it to, and cannot be forwarded or copied.

Or can it?

What’s that old saying? Oh yeah: “If it can be seen, it can be copied.”

Let me show you how by sharing one of my so-called “confidential” messages.

Read moreGmail’s Confidential Mode Isn’t

What’s the Difference Between Hotmail.com, Msn.com, Live.com and Now Outlook.com?

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Is there no longer a hotmail.com? I am so confused. I sign into hotmail and it automatically sends me to outlook.com. It would not take my old password, so I had to change it. But, there is nothing in the account. How do you retrieve information that was in hotmail.com. This is crazy!!How can I get my messages from my old account or is this really something that has happened. Is there no longer a MSN hotmail.com? or is this a joke of some kind.

It’s no joke.

Microsoft continues a long history of confusing the heck out of us with the names they choose for their services, and then changing those names as they go along.

Outlook.com is what we once knew as Hotmail, which was also called “MSN Hotmail” and was also “Windows Live Hotmail”. That’s relatively easy, albeit confusing. But there’s more to it than that.

For the record: none of this involves losing any email. That’s something else entirely.

Read moreWhat’s the Difference Between Hotmail.com, Msn.com, Live.com and Now Outlook.com?

Enabling Google Two-Factor Authentication

A high percentage of the questions I’ve received over the years have related to account loss due to hacks or other compromises. Two-factor authentication is one of the best ways to prevent your account from being compromised, even if the hackers somehow get your password.

Exactly how it works and how to set it up isn’t always easily understood. On top of that, what I consider a critical step to maintaining your account access is often overlooked.

So, let’s set up two-factor authentication in your Google account.

Read moreEnabling Google Two-Factor Authentication

Can I Still Get a Hotmail Email Address?

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I don’t want an Outlook email address, I want Hotmail. Can I still get one?

Much to my surprise, the answer appears to be yes!

What with the demise of hotmail.com a few years ago – it was replaced by outlook.com – I was expecting the ability to create an email address on the hotmail.com domain to have disappeared as well.

I was wrong. At least as of this writing, you can still do it. I’ll show you how, and discuss a few other popular Microsoft-related email domains.

Read moreCan I Still Get a Hotmail Email Address?

My ISP Went Under; How Do I Recover My Email and Email Address?

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It looks like my ISP suddenly went out of business. As a result, my email address no longer works, and I can’t get to all the email that was accessible using the ISP’s web access. What can I do? 

Fortunately, your scenario isn’t all that common, but unfortunately, what you’re experiencing is. It happens any time someone changes their ISP or loses access to their free email account.

Thus, it’s an excellent opportunity to review some very important points I’ve mentioned before.

Read moreMy ISP Went Under; How Do I Recover My Email and Email Address?

How Not To Get Locked Out of Your Microsoft Account While Traveling

I’m writing this on the last day of a trip taken to the Netherlands to visit relatives. As planned, I decided to play a little with a couple of my Microsoft accounts (aka Hotmail or Outlook.com accounts) to see if I could duplicate what so many people seem to experience: getting locked out while travelling abroad.

I didn’t get locked out.

Why I didn’t run into problems is pretty simple: I was prepared. (Though I also think something else played a part for at least one of my accounts; more on that in a moment.) But I can see how a lack of preparation can end up with accounts inaccessible until you return home.

Let’s review exactly what I mean by “preparation”, and how you can avoid getting locked out of your Microsoft account when you hit the road. I’ll also touch on why Microsoft takes these additional security steps.

Read moreHow Not To Get Locked Out of Your Microsoft Account While Traveling

How Do Outlook and Outlook.com Relate?

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I use Outlook.com. Does that mean I don’t need Outlook? Are those just other names for the same thing? If not, how do they relate to each other?

The short answer is, they don’t. Not at all. They have only two things in common: they’re both related to email, and have the word “Outlook” in their names.

That’s pretty much where the similarity ends. It’s frustrating, because people often refer to “Outlook” when they mean “Outlook.com” … which is not actually related to “Outlook”.

Let’s define ’em, shall we?

Read moreHow Do Outlook and Outlook.com Relate?

4 Alternatives for Windows Live Mail and Outlook.com

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Is the attached really true and how can I keep all my emails in hotmail on my PC and work with those when I am off line? I also store all my emails on my PC in WLM as well as have many groups created for my bulk mail-outs.

That’s just one of several questions that arrived recently in response to Microsoft’s announcement that their Windows Live Mail 2012 desktop email program would no longer support Outlook.com-based email accounts, including email addresses at hotmail.com, outlook.com, msn.com, live.com, and more.

Naturally, this took a lot of people by surprise.

As it turns out, the dire warnings, while certainly significant, may not be entirely accurate. And, of course, the warnings fail to mention some very viable alternatives that don’t involve Microsoft.

Read more4 Alternatives for Windows Live Mail and Outlook.com

How do I close my Hotmail or Outlook.com account?

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I need to close my Hotmail account. I’m getting too much spam, and besides, I think it’s been hacked. I just want to close it and stop it from bothering anyone anymore. How do I do that?

I’d actually suggest that you seriously reconsider closing your account.

Closing your account will not stop spam that looks like it came from the account; hackers often fake the “From:” address whether or not the account exists.

Closing your account will not stop your contacts from “being bothered”; if they had even brief access to your contact list, the spammers have probably already made a copy.

Closing your account is not guaranteed to cause emails sent to it to bounce back to the sender; bounce messages are optional, and many services choose not to send them, to reduce spam.

Closing your account may not even be possible if it’s been hacked, and you don’t have access to it yourself.

All that being said, if you still want to close it, I’ll walk you through the steps; it’s not really that hard.

Read moreHow do I close my Hotmail or Outlook.com account?

I searched and found a Hotmail support number, but is it legit?

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I Googled Hotmail telephone contact US, and one of the sites that came up was {redacted}, the Phone number on the site is: {redacted}. I called the number on this site and was put by the first caller to someone he described as his supervisor who with my permission could access my computer to resolve the problem.

I followed the instructions from the guy and allowed him to access my computer, then he asked me to open one of my hotmail accounts, which I did. He then showed me on my computer a number of files which he informed me were persons trying to gain access to my hotmail account,  and said that this and other things needed be cleaned out so the laptop could function effectively again.

He indicated that they provide a technical service to Hotmail for its customers.

Is the site a safe one to go to?
Is there a telephone number to contact Hotmail?
Should I allow him to access my computer?
Should I allow him to clean out what he says needs cleaning out?
If not, now that he had access to my computer have I opened myself to any risk and is there something I could do to prevent him from accessing my computer again?

That’s actually an excerpt of a lengthier question I recently received from someone experiencing difficulty logging into their Hotmail / Outlook.com account while travelling overseas, a very common and often unsolveable problem.

His approach seems sound on the surface: search for a Hotmail support number, and see if the person at the other end can help.

Unfortunately, this path typically leads to even worse problems.

Read moreI searched and found a Hotmail support number, but is it legit?

How Do Gmail Labels Relate to Folders?

Google Mail, or Gmail to most, is a wildly popular free email service. It’s fast, easy to use, and sports one of the best spam filters around.

What most people don’t quite realize is that Gmail looks at the world a little differently than most. And in doing so, it leverages something else that Google has a strong track record in: search.

Gmail labels are aren’t what most people think they are. Normally, that’s not an issue, but when accessing Gmail using a desktop email program via IMAP, it can cause a lot of confusion.

Read moreHow Do Gmail Labels Relate to Folders?

How Do I Change My Gmail Password?

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I can’t figure out how to change my password on Google for my Gmail account.

I’ll show you.

However, I do have to point out that in order to change your password, you must be able to log in. I mean, if you can’t log in then you can’t prove that you’re the rightful owner of the account. If Google did allow you to change your password without logging in first, then anyone could change it, whether or not they were actually authorized to do so.

So, step 1: login to your Gmail account.

Read moreHow Do I Change My Gmail Password?

What for-pay email providers do you recommend?

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I get that you strongly recommend against using free email accounts for important stuff. But that, then, begs the question: which paid email providers with full features do you recommend?

A fair question. There are many approaches that I do recommend, depending on your specific situation.

I need to explain what I’m looking for, first. Then it’s just possible we’ll find that you already have what you need.

Read moreWhat for-pay email providers do you recommend?

I see lots of failed attempts to login to my account, should I do anything?

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Hi, Leo. I was changing my password tonight on Hotmail and went into a section I never noticed before called recent activity. I was shocked to see that in the past two weeks there were a ton of failed attempts from nearly every country on the map that had tried to login to my Hotmail account. Is this normal? Should I be scared? Should I close the account? I’ve had this account since 1997 so it has lots of information about me in different folders. Thanks.

Honestly, what you’re seeing doesn’t surprise me. I do have some suggestions on what you should do, but closing your account isn’t one of them.

Read moreI see lots of failed attempts to login to my account, should I do anything?

How Do I Copy Email from Outlook to Gmail?

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I would like to copy all folders in Outlook 2003 to my Gmail account as I’m going to change from XP to Windows 7 soon. I’ve not been able to do this so far although I’ve successfully copied Contacts. In view of the expiration date of XP being soon, this could be a very useful article for a lot of people. Could you please give step-by-step-instructions for how to do this?

There are a couple of possible confusions in this question. Copying existing email to Gmail can be a very useful thing. I’ve done it myself. But I want to make sure you know exactly what it means.

Read moreHow Do I Copy Email from Outlook to Gmail?

Why Do I Always Have to Sign Out Other Sessions in Gmail?

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Leo, I’ve got one computer and I’m the only one who uses it. I don’t have any kind of mobile device that I use with Gmail. I never accessed any of my accounts from any other computer or location. Before I shut my computer down, I always go to Internet Options and clear my cache and cookies. I check every box except the top and bottom ones and then I go to disk cleanup where I always check all the boxes and clean up everything. I change my passwords at least once a month on the websites. I use it every day and yet, at least once a week I have to close other sessions in Gmail when I click on the Details. I have a free account so of course it’s next to impossible to get an explanation from Google themselves. Should I be concerned or is this some kind of a glitch in email? This isn’t new; it’s been happening for some time.

It’s actually a pretty nifty feature in Gmail. Basically, it’s telling you where Gmail has seen your account being accessed from. Naturally, it’s a little scary to see things like 1, 2 or 3 other places, when you believe that you’ve logged in from exactly and only one. I’ll throw out a few ideas as to why that might be and what, if anything, you need to do.

Read moreWhy Do I Always Have to Sign Out Other Sessions in Gmail?

How can I get my lost Hotmail emails back?

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My old emails have disappeared from my Hotmail/Outlook.com account. I’ve logged into the account on a weekly basis so I know that isn’t the issue. I searched old emails and they’re just gone; anything past 2013 emails are gone which I need to have. What can be done? When I found out and panicked I searched links and saw a link without reading carefully about Hotmail help. It turned out that it was not Hotmail but a company called [company redacted]; they took over my computer remotely before I realized they were not directly associated with Microsoft. Are they legit? Do they do further damage?

Keeping anything critically important in only a free email account like Hotmail is unfortunately a recipe for disaster.

I want to go over how you might have been better prepared for this. I’ll touch on what you might do to get your email back (but to be honest, I’m not very hopeful) and I’ll talk about the service that you let access your machine.

Read moreHow can I get my lost Hotmail emails back?

Why Can’t I Set Yahoo! as My Default Mail Program?

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Hi, Leo. I’ve followed your instructions in the article, “How do I change the “mailto:” or default mail program?” The newer versions of Yahoo Instant Messenger don’t have a Yahoo! browser services option. I’ve also downloaded that Yahoo toolbar, but the mail plug-in is not available in newer versions. I’m using Windows 7 Professional, 64-bit.

It’s possible that you can no longer do what you’re doing with the latest round of changes to Yahoo Mail. I honestly haven’t looked at it  closely enough to say yes or no, but what you describe sounds exactly like what I would expect if that functionality were removed.

That means that we have to do things a little differently. The whole default mail program is all about a default mail program.

Read moreWhy Can’t I Set Yahoo! as My Default Mail Program?

How Do I Make a New Hotmail Account? Or Outlook.com Account?

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How do I make a new Hotmail account?

Hotmail was replaced with Outlook.com. You probably already know this; that’s where you now go to access your Hotmail email.

You can create your new new email account using Outlook.com – and maybe even make it a Hotmail.com email address.

But first, there’s a step that is apparently not quite as obvious to as many people as we might expect.

Read moreHow Do I Make a New Hotmail Account? Or Outlook.com Account?

What Are Outlook.com’s IMAP, POP3, and SMTP Settings?

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How do I use Hotmail or Outlook.com with my desktop email program? It wants something about POP3 and SMTP. What should I put in?

With the proliferation of devices running their own email programs, settings for POP3, SMTP, and now more frequently IMAP are a popular request for the various email services.

For a long time, Microsoft didn’t provide the ability to connect to a desktop email program, but they added it to Hotmail a few years ago. With the transition to Outlook.com as Hotmail’s replacement, that functionality remains.

Read moreWhat Are Outlook.com’s IMAP, POP3, and SMTP Settings?

How Do I Use and Clear Outlook.com Contacts and Auto-complete Suggestions?

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I am finding the new Outlook.com very annoying. How do I find my list of addresses and save a new one? When forwarding, I have to click through a whole load of addresses to get to the ones I want and then, delete the ones that I did not want. It wastes a lot of time.

Outlook.com is the online replacement for Hotmail. It’s unrelated to Microsoft’s Office Outlook  email program.

Outlook.com attempts to provide a clean, easy-to-use interface for managing not only your email, but your contacts, calendar, and (with the addition of SkyDrive) your data files as well.

Unfortunately, cleanliness or simplicity only goes so far. You’re not the only one who finds the displayed contacts and email addresses confusing when you compose a new email.

Let’s look at how it all works.

Read moreHow Do I Use and Clear Outlook.com Contacts and Auto-complete Suggestions?

How do I change my Hotmail or Outlook.com password?

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I cannot get to the Account Summary or Options page for my Hotmail account. I needed to change my password.

As Microsoft updates its mail offering, some of its features are moving or changing.

As I’ve mentioned before, if you have a Hotmail (or Outlook.com, as it’s now called) account, you should expect change. Change happens. Sometimes, it’s small and other times, it’s quite dramatic – such as how you change your password.

I’ll walk through the steps to change your password in the current (as of this writing) design.

Read moreHow do I change my Hotmail or Outlook.com password?

How Can I View Two Different Email Accounts at Once in a Browser?

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I’m using Windows 7 and I want to keep my two Yahoo email addresses open just like on my cell phone. But when I sign into the second Yahoo email, it signs me out of the first. Ideally, I want both to be open when I turn on the computer so I can view both at any time.

Surprisingly, this is a common desire. Many people have more than one email address these days. You can use a couple of approaches to do this.

Read moreHow Can I View Two Different Email Accounts at Once in a Browser?

How Do I Get Rid of Gmail Tabs?

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Gmail just turned on some kind of tabbed inbox feature. It’s randomly putting mail into different “categories.” How do I turn that off?

Full disclosure: that was me asking the question.

While I was out on a trip, Google enabled their new “tabbed” inbox. My first reaction?

How do I turn this thing off?

Read moreHow Do I Get Rid of Gmail Tabs?

How Do I Get a New Mail Notification for Yahoo! Mail?

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I’m unable to activate the new mail notification on my PC. I clicked on Control Panel and then Sound and Change. I’ve tried many times, but it just won’t work. I’m 82; I live alone; I’m dumb about PCs. Please advise on a simple way to alleviate this problem. Something was said about Messenger and I do have Yahoo Messenger, but still “no go.”

First, please don’t say that you’re dumb.

You’re not dumb about PCs. This is absolutely one of my pet peeves: in my opinion, it just doesn’t help to characterize yourself in derogatory terms like that when all that’s missing is just a little information.

As for your question, unfortunately, there’s no simple way to address that. Let me explain.

Read moreHow Do I Get a New Mail Notification for Yahoo! Mail?

Why do I keep getting a CAPTCHA?

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Hi, Leo. I’m really annoyed with those CAPTCHA things that Yahoo sometimes wants me to fill out before my email can be sent. Now, I realize that if I were to send an email addressed to many recipients that Yahoo might assume that I’m spamming, but if I’m just replying to an email from a friend, I really don’t think that this CAPTCHA is called for. I’ve contacted them several times about this, but to no avail.

Before I answer your question, I have to say that I’m not surprised in the least that you’re not getting a response. Yahoo is a free email service and they actually have very little (if any) customer support. It’s not something that I would ever expect them to change. Quite literally, you’re getting what you’re paying for in that regard.

As for your question, why do you keep getting a CAPTCHA?

Read moreWhy do I keep getting a CAPTCHA?

How do I automatically forward Hotmail in Outlook.com?

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I’m changing email accounts, but I don’t want to lose people who have my Hotmail address. How do I automatically forward Hotmail messages messages to my new account at a different provider?

The recent forced switch-over to the Outlook.com user interface left many long-time Hotmail users upset and dissatisfied. Many are considering leaving Outlook.com behind, except that this would mean abandoning their Hotmail.com email address.

Fortunately, it’s very easy to automatically forward Hotmail messages or any email that comes into your Outlook.com account to another email provider.

Read moreHow do I automatically forward Hotmail in Outlook.com?

What Does It Mean that Yahoo! Is Releasing Email Addresses?

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Yahoo! announced that they were releasing email addresses that hadn’t been used in a year. Does that mean I’m going to lose my Yahoo! email address? Why are they doing this anyway?

As long as you’ve logged in to your Yahoo! account recently, you don’t need to worry about losing your Yahoo! email address. If you’re not certain, go log into it now, and you can “reset the clock,” so to speak.

I’m somewhat surprised that Yahoo! felt the need to make an announcement at all. I’m also surprised that some people are upset by this plan.

It’s something that many providers have been doing all along.

And it’s something that you should understand, even if you’ve never touched a Yahoo! account.

Read moreWhat Does It Mean that Yahoo! Is Releasing Email Addresses?

How Do I Print an Email in Outlook.com (Formerly Hotmail)?

This is another of those “representative” questions that I get a lot; more than I would expect, to be honest.

But when you think about it, with all the changes that Hotmail users have been through in the last few years, it’s understandable that the latest change to Outlook.com would lead to a lot of confusion.

It turns out it’s not hard at all to print an email in Outlook.com. You just need to get used to looking in a new place for some additional options.

Let me show you. (Now with video!)

Read moreHow Do I Print an Email in Outlook.com (Formerly Hotmail)?

How do I open an .isc file in Outlook.com?

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So Hotmail changed its name to “Outlook”…fine. The problem that I’m having is that someone has sent me a “.isc” file which is apparently an Outlook-part of Office calendar. Is there some way to view this file with in Outlook (previously Hotmail)? It seems like if they are trying for a seamless integration, there would be. If they are just trying to annoy us,… well, that’s working.

So the naming is very, very unfortunate. I really cringed when they first announced Outlook.com.

The bottom line is that Outlook.com (formerly known as Hotmail) is not related to Outlook, the desktop email program that comes with Microsoft Office. It sounds like the .isc file needs the Office desktop program. It’s part of Outlook the program, not Outlook.com.

But wait … there may be something else going on here.

Read moreHow do I open an .isc file in Outlook.com?

Do Gmail preview images pose a security risk?

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My question is somewhat similar to what others have asked before, but this time, I explicitly want to talk about Gmail. As you 
know, some attachments show a thumbnail of its contents on the email footer. There are times that I receive legitimate emails by mistake, so I open the email to reply and notify about it. By doing that and by being able to see the 
preview thumbnail, am I putting my computer at risk of malware? I never download things that I’m not expecting, but I’m 
unsure if just having this “default preview” setting, I may actually be executing whatever there could be without really knowing it.

By now, it’s just good common sense to turn off images in your email viewer. That prevents spammers from using images embedded in a message to confirm that they’ve found a real email address where someone actually reads their email.

Attachments, on the other hand, are a little different. They typically make it to your inbox, and your security depends on your ability to distinguish between safe and unsafe attachments. By now, you should know only to open attachments that you know are safe.

Google occasionally includes preview images of your attachments. Because attachments can be dangerous and images are sometimes an invasion of privacy, is there an issue here?

Not really. In fact, it’s just the opposite. I’ll explain why.

Read moreDo Gmail preview images pose a security risk?

How Do I Find the IP Address of the Person Who Created a Gmail Account in My Name?

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How do I find the IP address of the person who created a Gmail account in my name? I tried the last ten IP address searches and it was all mine. How can I see the one where it was opened with?

This is a bit of a confusing question only because you seem to have access to the last ten IP addresses. That means you have access to the account created in your name.

If that’s true, then I’m afraid I don’t really know what caused this. If somebody created an account in your name, it would really depend on the steps that you took to go through and gain access to that account.

Read moreHow Do I Find the IP Address of the Person Who Created a Gmail Account in My Name?

Should I Be Worried about the “Open in Other Locations” Message from Gmail?

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When I go to my Gmail account, mainly to clear out existing email, I always click on or open the Details link in the lower right. Sometimes, I see a “Sign out of other sessions” link so I can click on this to supposedly sign out any other session. So my question is: why do I see this and what “paranoid rating” (for lack of a better word) do I give this? I use basically three options for checking my email. One is using Mailwasher Pro, the second is using Thunderbird, and the third is using Firefox and going to Gmail.

Let me start by explaining this feature. If you have a Gmail account and you log in, there’s a link in the lower right corner that either reads “The latest activity was # minutes ago” or “Open in # of other places” followed by a Details link.

When you click the link, Gmail opens an Activity Information window which displays what the access type was, what the IP address was, and the date of the access. For instance, if I was logged into Gmail and opened the Activity Information window, I’d see that I’m accessing it from my IP address, which is somewhere in the United States.

This is really neat feature – one that can ultimately protect your Gmail account from hackers.

Read moreShould I Be Worried about the “Open in Other Locations” Message from Gmail?

How do I keep my email address when I switch ISPs?

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I’m moving and my new home will have a new ISP. I’ve had my @att.net email address for years, but AT&T doesn’t serve my new location. My new ISP will be Comcast. How do I keep my @att.net email address? I really don’t want to have to change.

You’re probably going to have to change.

I’ll throw out one idea that might let you avoid it if your old ISP allows it, but a) most probably don’t and b) you’re not going to like it either.

Instead, I’ll describe what’s going on and what you should do to make this the first and last time that you need to change your email address.

Read moreHow do I keep my email address when I switch ISPs?

How do I change my Hotmail alternate email address?

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The email address I used for recovery is no longer valid. I can’t figure out how to change my alternate email address.

Your alternate email address is a critical bit of information that you’ll need if you ever lose your password, or if your account ever gets hacked.

It’s good of you to note that your current one is invalid – if you no longer have access to your alternate email address then it’s just as bad as, perhaps even worse than, not having set up an alternate email address at all.

I’ll show you how to change it.

Read moreHow do I change my Hotmail alternate email address?

How Do I Change My Hotmail Name or Address?

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My MSN Hotmail name is “something@hotmail.com”. I really don’t like the “something”. What I’d really like is to be “somethingelse@hotmail.com”. How do
I change it?

This is another one of those seemingly simple questions that I get several times every day.

What you’re asking for is not to change your name, but your email address. Unfortunately, your email address is how MSN Hotmail identifies you. A different email address means a completely different MSN Hotmail account.

Read moreHow Do I Change My Hotmail Name or Address?

How do I move my Outlook Express folders to my new machine?

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How do I move my Outlook Express folders to my new machine?

In particular, the person asking had just received a new Windows XP machine to replace her Windows 98 machine.

There are several approaches, naturally, but in a nutshell we’ll locate the folders on the old machine, copy them to the new machine, and then import them.

And then we’ll do something similar for the address book.

Read moreHow do I move my Outlook Express folders to my new machine?