Hotmail is more like HotFAIL
I've been doing a lot of database/website programming work for Sushu's family's Chinese school. It started as a volunteer project for Mozilla Service Week, but now that I know how their code works I have become sort of a go-to guy for further fixes.
The latest problem I've been tackling is that attachments couldn't be sent to Hotmail addresses. You could attach a file to an email and send it, and everyone who had a non-Hotmail address would get it fine, but people with a Hotmail address would get an unreadable email. The body and the attached file would both be screwed up.
I started researching Hotmail attachment bugs and discovered that Hotmail is even worse than I thought. One guy who did some informal experimentation, sending attachments to and from both Hotmail and non-Hotmail addresses, found that Hotmail was losing sixty to eighty percent of incoming and outgoing mails with attachments. These mails weren't going to spam folders or generating bounce messages - they were simply disappearing. I always thought Hotmail was bad, but I had no idea it was this bad.
I worked around Hotmail's bugs by having the email script detect any Hotmail addresses in a To: or CC: list and splitting them out into a separate email. Instead of trying to send them an attachment, it uploads the attachment file to a public directory on the server and sends the Hotmail users a link. It's a bit of a clunky workaround, which will require the attachment directory to be periodically purged so as not to consume the disk, but at least there's nothing Hotmail can do to screw it up.
To test this, I made myself a Hotmail account. When you sign up for one it demands your real name and location, which irked me. I didn't see any reason Microsoft needs to know that, so I told them I was Bartholemew Cubbins from Hyderabad, Pakistan.