I take a lot of pride in my work. I spend a large portion of every year in various kinds of training so that I may continue to be at the top of my field. Over the years I have spent thousands of dollars on training materials and hardware to test different systems.

All of this allows me to show up knowing that I can fix almost any computer problem. Typically the only exceptions to that are things that are simply out of my hands. If the reason that you can't get to the internet turns out to be that your isp is in the middle of a service outage, there is obviously nothing I can do about that. But mostly, if it is broken, I can fix it.

However, when it comes to Windows Live Hotmail, chronic problems on Hotmail's side are the rule instead of the exception. Windows Live Hotmail suffers from numerous problems, some of them are long-term and ongoing, but most of them are temporary or intermittent. I am not the only person seeing this. When I visit a client with a Hotmail problem they either start out by telling me that they have already paid someone else to look at it but were told the problem is with Hotmail's service and can't be fixed, or I hear back from customers that after I was there they had someone else out to look at the problem and again were told that the problem was not on their computer, but instead with Hotmail's system.

It goes against my sense of ethics to charge my customers for problems that I can't fix. Since most Hotmail problems are on Hotmail's side, it will not be something that I can fix. I see two options. The first option is to implement a policy that I will charge on all Hotmail service calls whether I am able to resolve the problem or not. Not only does this go against my personal ethics, it also leaves me with dissatisfied customers which is something I make every effort to avoid. The second option is to simply stop supporting Hotmail. At this time that is exactly my plan.

The following are some examples of recent but ongoing issues with Hotmail.

1. Hotmail fails to deliver up to 81% of all emails with attachments. Independent testing shows that when an email with an attachment is sent from one Hotmail account to another it will be delivered only 26% of the time. Attachment email from a Hotmail account to an external email address will be delivered 23% to 33% of the time, and from an external address to Hotmail 34% to 41% will be delivered. The real problem here is that the emails that aren't delivered simply vanish. No notice is returned to the sender that the email is undeliverable for any reason. The email does not arrive in the recipient's mailbox or junk mail folder. Just gone. These numbers are staggering. There is no legitimate reason for mail to simply disappear, and I know no other provider that would accept it happening with this many messages. This information came from http://hubpages.com/hub/Hotmail_Fails_To_Deliver_Up_To_81_Of_All_Attachment_Emails [4].
2. Windows Live Hotmail does not allow you to check your email from an email client using the POP or IMAP protocols. These are the standard protocols defined for email and supported by almost every other webmail provider including my preffered webmail service, Gmail. Up until recently, if you wished to use an email client to check your mail instead of the going to the Hotmail website your only choices were Outlook Express and Outlook. They would allow you to setup an http connection to access your Hotmail account. HTTP is much more a one-way communication protocol than POP or IMAP and using it for email means a much greater risk that messages won't be received correctly. The careful reader will note that I said that this was the case up until recently. This has changed. When Microsoft launched Windows Live Hotmail they ceased putting advertisments at the bottom of messages sent using Hotmail. Since this is a free email service the only revenue it generates is from the ads that you see when you visit the Hotmail site to check your mail. As a result, they no longer want you to be able to use an external mail client and bypass those ads. New Hotmail accounts cannot use Outlook express to check their mail and support for Outlook Express is being phased out for existing accounts, according to this knowledgebase article [5] from Microsoft. Now if you want to access your Hotmail account using an email client your choices are to upgrade to Windows Live Plus which is a paid service or use Microsoft Outlook 2003 or Microsoft Outlook 2007. In case you're curious, the retail price for Microsoft Outlook 2007 is around $90 USD.
3. Hotmail's antispam measures catch numerous legitimate emails as well. It is possible to meet all of the technical standards that Microsoft has set [6] for email sent to Hotmail accounts, and for your mail server to not have a history of sending spam or be on any blacklists, and still have your mail rejected by Hotmail's antispam filter. Microsoft support offers no solutions to this other than to suggest that enrolling in their fee-based, third-party accreditation service, Sender Score Certified, at a price tag or $1400 USD, might solve the problem. This problem is leading many organizations to stop accepting users or customers with Hotmail accounts. These two Google searches will give you an idea of how big this problem is. Search1 [7] Search2 [8]
4. Hotmail imposes strict caps on the number of Hotmail recipients any one message can go to. Microsoft says this limit is 250 recipients from one sender in one day, but many reports show this limit to be as low as 10 recipients for any one message. RFC2821 [9], one of the standards that all mail servers are supposed to follow, does not allow for the rejection of messages with fewer than 100 recipients. http://www.theregister.co.uk/2007/10/09/limits_on_hotmail/ [10]

I know it's a real pain to change your email address, but my personal recommendation if you are using Hotmail would be to find a new email account. My personal favorite free webmail provider is Gmail [11]. If you prefer to keep your Hotmail account then I will leave you with this article [12] which includes a number of tips on how to deal with various problems you might encounter.