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Why is using Hotmail for my business such a bad idea?


I’ve seen you rail against using Hotmail for “anything important”, and you
call out using it for business as a particularly bad idea. Why? What do you
have against Hotmail? Why should I incur yet another expense for my small
business if I can get email for free?

Because you want your email to get through, and because you want your
business to be taken seriously.

I don’t have anything against Hotmail, per se, or Microsoft for that matter.
Remember, I worked there for many years.

My issues with Hotmail and other free email services arose mostly out of my
experience here on Ask Leo!. Or, to put it
more correctly, the experience of thousands of people asking me questions.

Those experiences lead me to this conclusion: using Hotmail or any free
email service exclusively is bad for your business.

Let me explain why I hold that opinion that so strongly.

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It falls into two buckets: technical and perception.


I get more reports of problems with Hotmail than I do for any other mail
service. Mail that disappears, account access that’s lost, email that doesn’t
arrive, email that can’t be sent … these are all common issues that I see
every day.

Hotmail is not alone in this regard, but I do get the most email related to

So why do I lump all free email services into the same bucket as

Because they all share one common characteristic: there’s virtually no
customer service.

If you have a problem with Hotmail, or Yahoo mail, or Google mail or
whatever free email service you’re using, you have nowhere to turn. There may
be a customer service email address or web form, but from what I’ve heard and
experienced myself, it’s apparently only there for show. IF you get a
response at all, which is rare, it’s likely to take a long time and be a
“canned” response. If you need hands-on help to deal with your particular
situation, there’s nowhere to go.


Because you’re getting what you paid for. You paid nothing, and that’s what
you’re getting. The provider is under no obligation to do anything for you.
They’re well within their rights to ignore you completely, which is apparently
what most do.

At least if you pay someone for service you have some leverage. First of
all, these providers typically promise service, and if they don’t deliver, you
have the option of taking your business elsewhere.


OK, I’ll put this as bluntly as I can.

When I see a business using a free email account, particularly a Hotmail
account, I immediately think: “this business doesn’t care about email, or using
the internet to communicate with their customers.”

And that perception is not uncommon among internet-savvy

The perception might be wrong. I get that. The company may be
deeply devoted to their internet-using customers. But using a free email
account doesn’t say that. A free email account says “we’re not willing to take
the relatively small expense to make sure we have reliable email”.

And that’s a shame.

In my opinion, any business small or large, should have their own internet
domain, and handle their email using that domain. Most domain registrars make
that easy, and offer very competitively priced packages. And customer

“” will always look cheaper and less professional than

Not to mention that “” is more likely to have technical
problems without anyone to help you resolve them.

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21 comments on “Why is using Hotmail for my business such a bad idea?”

  1. Right on! Your perception section is exactly what I think of when I see a free email account associated with a business. It also always gives me a feeling of a fly by night operation. I’m far less likely to trust any company that lists their company email as a free email account, regardless of whether I would want to communicate over the Internet or not.

    It indicates to me that they don’t take their business seriously, not just they aren’t taking their online communications seriously.

  2. What I don’t understand are those companies that have their own domain, yet still use Hotmail, AOL, and Yahoo e-mail addresses.

    I’ve seen more than one business card with “” and “”

  3. I agree with Ken. If you’re connected you can have proper email addresses – usually 5 of them. The only thing I would suggest is that if you think you might change your ISP – which you probably will do sooner or later – use a service like which redirects your mail to your current mailbox. If you change your ISP just change the redirection address at bigfoot and life goes on as usual. Bigfoot is free but if you go over the free limit it’s only $10 per quarter. I wouldn’t be without it.

  4. You mentioned the extra expense of having email in a domain that you own.

    What hosting service that hosts a web site – even a one pager – does NOT supply email accounts with the basic package? Even the hosting services that are under $10 per month (and there are many) provide at least a few email addresses with the service. I have NEVER seen a hosting company that doesn’t.

    At, a free service for on-line merchants to help them protect against credit card fraud, we immediately reject any application that does not use an email within the domain being registered.

    And, on a personal level, I will not do business with anyone that has a web site and uses any of the free email services. It’s just totally unprofessional.

  5. Funny I have a slightly different perception. (or any other Hotmail/Windows Live International site) and look bad. means even worse, because they’ve paid for the priviledge of Hotmail’s poor service, but doesn’t look so bad (to me personally).

    Whilst I personally have had no trouble with any Hotmail or Windows Live server, and actually have not known many people who have trouble with those services, I do understand that this could be simply luck. Hotmail’s customer service is very often pathetically formal and don’t deal with the issue at hand. (They tell you their engineers are working on it… and they can’t tell you when it will be fixed)

    I have not heard of technial problems with GMail, and certainly means that the company is prepared to pay for a reliable email service.

  6. i ignore anything that pertains to business from a or
    too many thieves located in foreign countries use these accounts to scam millions of Americans every year and i don’t want to take chances.

  7. The perception thing is great. I think it is good advice not to have an anyone but the new live services are superior. In fact I no longer use my gmail acct because I prefer hotmail. On top of that there is email forwarding. Anyone remember that. I get all the emails AND i can change in hotmail the FROM to my email address. SO while I do agree about the perception, it is easily remedied.

  8. I agree with the point about perception. Once a business has registered their domain name, they could sign up for Google Apps for Business at no cost. This will give them professional looking email addresses for all of their employees with a great, easy-to-use webmail interface. Best of both worlds!

    While I’m reluctant to endorse relying on a free service for business related email, this is definitely an approach to consider particularly if you also include in your backup strategy a “what if we lose our Google account?” contingency.

    – Leo
  9. I agree wholeheartedly with everything above but I’m surprised no one has cautioned another, and equally important reason, for giving a wide berth to Hotmail and Yahoo! They are responsible, without doubt, for the vast majority of spam and, even worse, fraudulent activity via e-mail.

    I know several companies who filter out all mail originating from a Hotmail or Yahoo! account. I don’t go that far but scrutinise all such mail very carefully. I’ve also noticed, increasingly, e-mail originating from a bogus address but with a Hotmail or Yahoo! ReplyTo: address. Without exception, these are all engaged in some form of scam.

    Finally, a business using a free e-mail service, particularly Hotmail or Yahoo!, is not conveying a professional image.

  10. Bill Chubb is on my wavelength. Don’t blanket ignore/delete Hotmail/Yahoo! but check VERY carefully.
    Regarding Autoport’s comment (April 8) “…too many thieves located in foreign countries … scam millions of Americans every year and i don’t want to take chances.”
    You’re absolutely right not to take chances. But I think you’ll find that people in other countries take a very similar but subtly different view, viz. “Too many thieves located in America originate spam/scam emails to billions of the rest of the world.”

  11. Yup. I’ve been telling my writers who seem to insist on using Yahoo! email for queries this same thing for years! Some of them even have their own domains and websites for their writing but still insist on using free email accounts! (Strangely, though, I don’t seem to mind gmail accounts AS much. Shrug.)

  12. I agree with you Leo with one small caveat, Gmail. Gmail is very reliable in my opinion, much more so than other paid email providers. On top of that, you can have all of your mail and contacts wherever you are, and its searchable. Furthermore, you can integrate it with your domain name so that it looks professional.

    Thanks for the newsletters, I really enjoy them.

  13. In addition to earlier comments… think about the names themselves. “Hotmail” and “Yahoo!”. What do they conjure up in your mind! In my opinion these web-based e-mail services were never intended to be used for serious commercial purposes. They were fun services with fun names intended for domestic, or private, purposes. Anyone in business wanting to portray an impression of professionalism and to be taken seriously should give them a wide berth.

  14. When I see a hotmail or free account email address associated with business, it says to me: “This business has something to hide because these address are hard to trace.” I could be wrong.

  15. Hi Leo,

    You just forgot that Hotmail offers paid email service called Hotmail Plus ($19,95 per year). So thinking in that way:
    “When I see a business using a free email account, particularly a Hotmail account, I immediately think: “this business doesn’t care about email, or using the internet to communicate with their customers.”

    Is a little bit stereotypical thinking.

    From what I’m hearing, paid Hotmail doesn’t really get you much, particularly in the way of customer service, so no – a business is still sending a very poor message when they rely on a Hotmail email address.


  16. From free Hotmail I switched to MSN for $10/month. So far the support is doing what I need & escalates when needed. Downside is it’s still that low-rent hotmail address, but it’s an easy switch for hotmailers who need support. [p.s. thanks for answering my question, now I know you’re real, Santy Claus, owe you a latte.)

  17. A domain costs $35 or less per year. There are web hosting services that offer a free option for a generous amount of low-traffic volume which includes several email boxes. If that’s too much cost to add to your business, then your business is too frail and unstable to do business with mine.

  18. Hey Leo, I’ve read your article with interest. I use Windows Live Hotmail for my business.
    Of course, I have my business and personal domain name linked to hotmail using Windows Live Admin Center, so my e-mail addresses matches my domain names.
    I’ve never had issues of disappearing e-mails or e-mail that can’t be send. Once in a while a connection problem occurs, but that has always been resolved in a short moment.
    A few years ago, the hotmail spam filter caused some issues, due to blacklisted provider domains. That was a good thing, I think.
    Today, I seldom have a spam message in my inbox.
    In case of problems, you can always go to Never needed to do that because it just works fine.
    I have used multiple e-mail clients, using pop3, imap and http. No problem at all.
    Ok, I don’t use webmail (hotmail by using the website) to send e-mail, because that concatenates a footer to the e-mails.
    Recently, I even have ActiveSync pushing my (hot)mail to my phone.
    Some of my customers uses e-mail services that came with a hosting package. No, not a cheap package. I was hired to solve problems like ‘mailbox full’, ‘message to big’ and other malfunctioning.
    E-mail is a comodity and Microsoft serves it well. And it’s all free! Hurray!
    Oops, your article is from 2006, well maybe you’ve changed your opinion about hotmail (?)

    My opinion about Hotmail has not changed. If anything, the intervening years have only served to further convince me.

    You’re doing one thing right: you’re using your own email address (like telling people that and having it forwarded to your Hotmail account. If you must use Hotmail for business, that’s the way to do it. It also means you can switch to any other service at another time without changing your public email address.


  19. I’ve used several domain providers for my email. Frankly, I find Hotmail more reliable, and with more sophisticated spam technology. Perhaps in 2001 this article would have been more relevant, but not anymore. People don’t care what your email address is. They usually contact you through Facebook or Twitter now anyway.

    It’s 2011 and nothings changed. still portrays a negative image of your business, and I continue to hear of more problems with Hotmail than with any other mail service.


  20. I’m not the corporate business type. I’m rather more of the “everyday customer” with some tech experience (like many out there)..and when I see a free email account on a business card, it does strike me as less professional, less impressive, and that perhaps it’s not a highly successful business financially. While I also realize at the same time that it may not be an accurate impression-or matter at all if they are good at what they do (I’d still hire them if they had good references)- it does strike me that way initially all the same. It might be worth it for a business to encourage a good impression from the start (“there’s never a second chance at a first impression” as they say) rather having to work harder than necessary to get to that point.

  21. I meant to add also that a free email account has a less “established” feel to it (like someone working an idea to make some money rather than an established, solvent business people can rely upon). I think my boss pays only $10 a year for a domain and $3.50 a month for email with Not too bad, eh?


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