Why You Should Dump Outlook and Windows Live Mail

Category: Email

Are you still struggling with the limitations of Outlook, Outlook Express, or Windows Live Mail? Join the many email users who have dumped desktop email clients for the ease and convenience of web-based email. Here's my advice on why it's time to switch to webmail...

Survey Says... "Webmail is Better!"

In a 2010 poll conducted by Mashable.com, 70 per cent of voters preferred web-based Gmail over Microsoft Outlook. Voters' comments suggest the main advantage of Gmail is portability. Webmail lets you check send and receive email from your own computer desktop, or any computer in the world. Why stay chained to your desktop, when you can check email from your laptop, iPad, or mobile phone?

Gmail is my personal favorite among the webmail services, but the same benefits apply for any webmail service provider. Millions of people use Hotmail, Yahoo Mail and other webmail services to stay connected to their email inbox anywhere there is an Internet connection.

Webmail is maintenance-free for users, too. There is no need to download, install or update software, junk mail definition databases, or other app components. Webmail requires only a standard web browser, eliminating one more disk-hogging application program.
Why You Should Dump Outlook

Over time, email messages can consume a lot of disk space, but with webmail, messages remain on the provider's server. Messages are easily searched, archived, deleted, forwarded, etc., all without eating up your hard drive, processor power or bandwidth. That's especially important when dealing with messages that include large attached files.

Setup and Security is Simplified

There is very little to configure when setting up a webmail account compared to desktop email clients. You don't need to know the cryptic names of POP and SMTP servers. You don't have to select the type of connection to make, confusing security options, or what to do with mail after it is read. Just make up an email address and password, and you're all set. But you can still configure folders, message filing rules, custom spam filters, signatures and other personal touches.

Security is another reason to rely on webmail instead of a desktop email client. The spam filters and anti-malware software used by Web-based email servers are industrial-strength and kept up to date by dedicated IT pros. Encrypted HTTP connections to webmail ensure that no one can intercept your mail in transit. And if your laptop or smartphone gets lost or stolen, your email won't be on it for others to read.

One of the best reasons for switching to a webmail solution may not be obvious. How many times have you switched your ISP (internet service provider), and had to go through the hassle of getting a new email address, and then notifying all your contacts? With webmail, you can keep the same address even if you switch providers.

If you like, you can continue to receive mail at your old address, because webmail systems can easily retrieve that mail as well. You can even migrate email, contacts and calendar data from Microsoft Outlook to Gmail with a migration tool. I haven't researched it, but there may be similar tools to import into Hotmail and Yahoo.

You'll Have to Pry Outlook From My Cold, Dead Fingers!

There are some cases in which a desktop email client makes more sense than webmail. Users with multiple email addresses for work, personal mail, etc., may find it more convenient to route all mail to a desktop client. If you have to save a very large volume of email, storage limits imposed by webmail providers may hinder you. But Gmail, for example, provides a generous 7.5 GB of storage space.

Also, you may not be able to attach certain types of files to a webmail email message. For security reasons, Gmail does not accept files that are executable, i.e., .EXE., .COM, etc. Even if such files are archived in a ZIP file, Gmail will sniff them out and reject them.

And there's always the remote possibility that your webmail provider will mysteriously lose all your email, or erroneously lock you out of your account. I've been using GMail for over seven years, and I've never had an outage lasting more than a few minutes. Compare that to the number of people who've written to me saying they lost all their mail because their Outlook PST file got corrupted, and I'll choose webmail every time.

For most users, the advantages of webmail far outweigh its limitations. If your existing email service provider offers a webmail alternative, it might be worth a look. But you'll still be tied to your ISP, and it will probably lack the cutting edge features offered by Gmail, Hotmail and Yahoo. My advice: cut the desktop email cord and give webmail a try. You won't regret doing so.

What's YOUR favorite thing about webmail? Post your comment or question below?

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Most recent comments on "Why You Should Dump Outlook and Windows Live Mail"

(See all 26 comments for this article.)

Posted by:

14 May 2011

I took your idea a step further. I use hotmail, and have for years. I use "windows live mail" on my laptop and my desktop. It works great. I have both computers requiring a password to log on. Any changes I make with WLM is refelected (example; delete, move to another folder, etc) on the hotmail server. I of course can still, and do, log in with any computer anywhere at any time to check my hotmail account. I love WLM, would never consider accessing my email from my computers from a browser, just makes no sense to me. I could go on about how much easier it is to use, and the advantages, but I suggest you try it, you'll love. BTW, the only virus I have gotten was very recently with my rarly used gmail account, which I access thru a browser only???

Posted by:

14 May 2011

I had email accounts through Windows Live Mail, Gmail and Yahoo Mail. I love the web based emails one hundred times more than ISP based ones.

Web based email is easier to maintain. In the unlikely event that there is a problem, it is usually solved in a matter of minutes. Also, I like being able to check my email from public computers when I'm on the road, because I don't have a smartphone or laptop.

Posted by:

14 May 2011

All my email, even from my website is retrieved and stored in my gmail account. I love it.

Is there an ap that will upload to gmail my sent emails and inbox emails currently residing on my hard drive in Mozilla Thunderbird?

Posted by:

15 May 2011

I've been using web based email for 14 years. It's much easier than using an email client, and like your article states, there is no software maintenance. The only thing I've been concerned about is the lack of the ability to back up email with "free" yahoo mail. Gmail is a better choice for a free account- you can download to back-up as well as forward it to another account if you wish. I'm considering setting up my own domain name and just forward everything to a gmail account for even more control. Opinions?

Posted by:

16 May 2011

While there are good reasons to disallow the attaching of .exe files, sometimes there is a legitimate need. My colleague found a way around the .exe file attachment restriction with Gmail. My Visual Basic students sometimes needed to e-mail me their zipped project folders, which often contained an .exe of their project. We found that if you change the extension of the .zip file to something else, like .tmp, Gmail did not sniff around and actually let the attachment pass. Of course, you have to remind the recipient to change the extension back to .zip in order to unzip the folder.

Posted by:

David Permenter
21 May 2011

I have been using Gmail for about 6 years. First as my personal and later my business also. Recipients of my mails see my personal mails from my personal address and my business mails from my company domain. All my mail in one inbox, can't beat it! Also, gmail is adding new bells & whistles seemingly daily. Really fun, cool & useful stuff. How often does your Outlook get (or give) you a bonus gift or new feature? Lastly, and why I made the final business jump, every time I got a new laptop I would have to go through the tedious process of exporting and importing my pst files, something I never felt very comfortable with. It was never so easy for me. With gmail, never again! I rest my case...

Posted by:

Rich Miles
26 May 2011

You are confusing mail servers with mail clients. All of my mail servers are cloud-based (live domains, gmail, hotmail), but I still use Windows Live Mail (I prefer it over Outlook right now) to retrieve my mail on my laptop. If I am not at one of my computers I can still log into the web mail client and retrieve my mail that way.

I highly recommend moving to a cloud-based email account(s), but I only use the web based client as a client of last resort. This is true for my phones as well.

Posted by:

12 Oct 2011

I am an Outlook user and I do not like web-based mail at all. I have a Yahoo account, and a Hotmail account, but I rarely use them. I find them clunky and slow compared to Outlook. Navigating page by page is a pain!

If I am away from home and have access to the internet, I can get to my ISP's server to read my mail.

I am more confident regarding security and privacy when the mail resides on my computer, not somewhere in "the cloud" or on someone else's server. I take precautions that I do not trust to anyone else.

Posted by:

bud budnick
12 Oct 2011

I use Outlook 2010 with several Comcast and Yahoo email addys and have had no real problems with it....I can check all these accounts at one place at one time. I've been happy with Yahoo but Hotmail is horrible. I signed into Hotmail one day and found they had locked my account due to someone supposedly using it to spam. To get the account unlocked there was no person or email addy to contact....Hotmail actually tells you to go to a discussion group to find out how to get it unlocked! I can't imagine a more ridiculous response to a problem I didn't cause. Others I know simply find out one day that their Hotmail account had vanished....gone into la-la-land with no record of where it went or how to get it back...stay away from Hotmail! While Yahoo and other free email services provide very basic to and from email....nothing they offer even starts to cover the options available in Outlook

Posted by:

13 Oct 2011

I prefer to combine my web/desktop mail clients to obtain all the benefits of both systems.
I have multiple accounts including MSN, Yahoo & Gmail all set up to deliver (POP) mail to individual desktop Outlook express Identities which use my own ISP only for sending (SMTP) to get around the webmail attachment restrictions.

I find MSN the least reliable of the three, so use it as a throw-away service & have it set to forward all it's mail to another gmail account which then filters the junk prior to forwarding to my OE desktop.
I find that Gmail is the superior webmail service with excellent spam filtering.

I've remained with OE as unlike it's M$ replacements, OE allows me to setup & easily switch between multiple identities each configured differently & isolated from each other in the event of corruption.

Posted by:

16 Oct 2011

I have been a happy Outlook user for many years. I have multiple email addresses coming thru several websites of mine as well as my personal email addresses. Having them all come into Outlook where I can sort how I look at them, archive what I choose, and delete in batches, as well as sync my calendar and contacts, and receive the emails that are important on my smart phone. I've had a gmail account for several years which I'm now switching from to my yahoo account for the simple reason gmail suddenly has made it nearly impossible to get the email to actually come into Outlook any more. The turf wars between some of the major players really irritates me. I'm looking at 4g phone upgrade and not sure what my options are going to be on keeping my Outlook calendar and syncing easily with the phone.... A work in progress for sure.

Posted by:

19 Jun 2012

The main reason I keep Outlook is the CALENDAR. I can set reminders which SO help this person with 'old-timers'. And now I am struggling yet again with the 'starttls' error which won't let me send email. Arrrrrrrrrrrrggghhhh I dislike Microsoft because it makes it virtually impossible to use anything else because of conflicts.

Posted by:

Sandy Papavasiliou
08 Aug 2013

I couldn't control the SPAM emails (Vi*gra, etc) coming in through Window 7 Mail. My ISP email address and a hotmail one were routed through there. I gave up and made a gmail email which I now use exclusively. 3 days ago unwanted emails have appeared. Is there a setting that will block these?
Other than that, gmail has improved 200% and does everything you need.

Posted by:

Sandy Papavasiliou
08 Aug 2013

I forgot to mention that Gmail also has the calendar. Easy to handle and sends you email reminders if you set it up right.

Posted by:

03 Sep 2013

I use Outlook on my desktop at home for my ISP's webmail via Yahoo, because I can save what I want. Hotmail(Outlook.com) has many features not available in Yahoo mail--I can sweep all mail from one sender to a designated folder, I can block whole domains from placing mail in my inbox, it gets deleted before I see it, I only wish I could do the same in Yahoo, I have begun to get hundreds of spam messages in Yahoo that are now blocked in Microsoft's mail--which is down to 10 a week form hundreds. With two web based addresses, I cannot keep up with a third, so gmail is rarely used. I can't imagine the newsletters and spam in a third account that I don't have time to read.

Posted by:

04 Oct 2013

Whilst it's true that if most of your email accounts are from your ISP, setting up a desktop client such a WLM to send and receive them can be quite intimidating for some. But once you have successfully set them up, you can export all those email accounts to a folder, from where you can import them whenever you do a clean install (as long as you remember to back up your personal files to another partition before you do the install!) Same applies to your contacts folder AND all the emails you've saved in your Storage Folder:-)

And with a desktop client, one big plus is that you don't have to remember and enter your email address and password every time you want to check your emails :-) This is not a security risk, as long as you password protect your computer's user account and set it to require a password after a specified time of non-activity, in case you walk away, leaving it unattended.

And having multiple email addresses means you can use one for personal contacts, another for online shopping and another for registering new accounts on forums etc. Whereas if you only have one web-based email account such as Outlook (Hotmail) or gmail, you will use the same email address for everything.

But I do have to admit that if you leave your ISP, losing all the email aliases you had with them, would be a real pain:-( But seriously, how often do most people change their ISP's? I have never changed mine, as for many years mine has been the only fibre optic broadband service in the UK and I don't like broadband that comes via a phone line!

Posted by:

04 Oct 2013

I use both web and client. Web is useful because you can access from anywhere and any machine with a browser. Client is useful because I can have it encrypt and sign emails and I have local copies for those times without a connection. Also I can set up clients so that I get copies of emails my children (still young) send and I can hide the details of their account settings, they just start the email client (Thunderbird on Linux). (I get copies of received emails directly.)

I use GMail and have that suck up mails from other providers so I only need to go to one place.

Posted by:

avram malek
06 Oct 2013

I like YAHOO better than GMAIL and have been using YAHOO for 18 years, but still find that OUTLOOK has two vital features unavailable on WEBMAIL servers. OUTLOOK allows one to control the time that a message is sent, which allows multiple people in my office to process one message without the message going out when someone presses "send" by mistake. OUTLOOK also and allows one to add comments or tags to an item AFTER it is sent (or received). I have not seen such features on YAHOO or on GMAIL or on HOTMAIL.

Posted by:

23 Jan 2014

"You'll Have to Pry Outlook From My Cold, Dead Fingers! " - you can say that again! I liked its email but had to give it up because it was using too much of my computer's resources, so I switched to gmail, and still miss Outlook mail's Word formatting features. But what I really can't live without is the seamlessness of Outlook's Calendar, Tasks & reminders, and haven't found a cloud substitute. I've just been looking again on the Microsoft Community website forum and it says that Outlook.com has a a Tasks element in its Calendar, but the best it can do for Reminders is to send an email reminder, which is just plain clunky. I don't have a smart phone and don't want one, but I do have an ipad and a Chrome tablet. I want the functions right on my computer and tablet desktop. I just discovered GogTasks for Outlook; I'm going to look into that and see whether it might do what I want...has anyone here tried it?

Posted by:

27 Feb 2015

In my oppinion this article or guide or whatever you want to call it. A fat lie (either from knowlingly missleading people or through pure ignorance. Either way, people should not be lead astray to the scorge of the net by someone uncunning as you. Regarding choosing a mail.

And here is why;


2. A link to a REAL search enginge (might feel a litle hard in the begining..buuuut! You have not really searched for anything since you first sat down at www.altavista.com or webbcrawler..;) Takes a little while to realize that THIS is the Internet..without Google. As it were intended back in the days so i'm afraid you will have to learn how to think for yourself again. But don't worry, a little at a time..;P Is what i'm really saying! :P Here, no logging of IP or browsing habbit https://duckduckgo.com (can also find Onion pages if you connect to TOR!) Startpage.com is another "hybrid". They uses Googles result based on a "new profile". But there have been some speculations wheter or not they can call themselfs a search engine with Google, if only their results.. Well do as you will! Startpage.com does at least not log your IP. That much one can be fairly certain of! Or continue with that abnornmality that did not even spelled the mathematical term for a 1 and 100 zeros after; GOGOOL..(One might think that one of the partners that first made paypal a success whould know this, buuuuut no. Either way, a search engine they are not and have never been and will never become! THAT is a FACT! (Prove me wrong..)

3. Unless there is a protocol i have missed completely they all work at the same level don't they? The Web? No matter if you have a web based client or a client for web based mail, is it?

4. There is currently, as far as my knowledge goes, only one survivor (although not unharmed..but never broken!) that has NEVER been hacked. Nor gotten their diskless (hehe) system confiscated by the new SS.. And that is Https://countermail.com (You pay completely anonymous and they encrypt every mail with a 2046kb encryption..which is enough. Unless you got a passion for safety..;) Then the next two steps are your only chooice.

5. LEARN GPG4WIN! Here is a good way to start..https://www.youtube.com/watch?v=Y2U5RzWLEHI
*tip! Just open your usual media player what ever that may be. And copy the link in the "Stream video" bar.. Much safer!

6. TAILS or Total Amnesic Invisible Live Operatingsystem. Which is a Linux system built for anonymity. Complete with browser, every write, editing, sound, video players and alot of other VERY usefull software pre-installed. And easy to put on a disc (iso)! So no Linux experience needed. At all.. Download here: https://torproject.org OR direct to the "Tails section": https://tails.boum.org/ BUT! READ THE WARNINGS AND WHAT NOT TO DO! LIKE OPEN DOCUMENTS WHILE CONNECTED TO STAY SECURE.

Then you have tenminutemail which is exactly that. A mail that lasts for ten minutes then self destruct! (You can reset the timer as many times as you want though..). And Guerilla mail. Where you can make it permanent or let it self destruct in 20 minutes. Also there is a thing called Burn Note that self destructs after a set of seconds or minutes that you choose for the recipient. You can also choose to let them copy and keep the mail. Or let it selfdestruct as soon as the recipient closes down the webpage. (How secure this three services REALLY are is extremely hard to tell. Guerilla mail have been around for a while and so have some "burn note" services. But how legit (safe) they are. I cannot say. I have uses ten minute mail several times when regging some sh*t you already know u never going to buy. Like game trials, p**n sites..very handy for that! (Pun intended..LOL!)

That was my 2 cents. English is my third language so hope you can disregard my bad grammar.. =)

Take care! (And go offline as much as you go online.. Otherwise your not living in a real world most of the time. A virtuall world that, disregaring what you might think or belive, devides and alienate people. FACT! Just something to think about from someone that has been around since the dawn of the Internet.

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