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How Hotmail Changed Microsoft (and Email) Forever (arstechnica.com) 84

Posted by BeauHD from the blast-from-the-past dept.
An anonymous reader quotes a report from Ars Technica: Twenty years ago this week, on December 29, 1997, Bill Gates bought Microsoft a $450 million late Christmas present: a Sunnyvale-based outfit called Hotmail. With the buy -- the largest all-cash Internet startup purchase of its day -- Microsoft plunged into the nascent world of Web-based email. Originally launched in 1996 by Jack Smith and Sabeer Bhatia as "HoTMaiL" (referencing HTML, the language of the World Wide Web), Hotmail was initially folded into Microsoft's MSN online service. Mistakes were made. Many dollars were spent. Branding was changed. Spam became legion. Many, many horrendous email signatures were spawned. But over the years that followed, Hotmail would set the course for all the Web-based email offerings that followed, launching the era of mass-consumer free email services. Along the way, Hotmail drove changes in Windows itself (particularly in what would become Windows Server) that would lay the groundwork for the operating system to make its push into the data center. And the email service would be Microsoft's first step toward what is now the Azure cloud.

Former Microsoft executive Marco DeMello, now CEO of mobile security firm PSafe Technology, was handed the job of managing the integration of Hotmail as the lead program manager for MSN -- Microsoft's own answer to America Online. In an interview with Ars, DeMello -- who would go on to be director of Windows security and product manager for Exchange before leaving Microsoft in 2006 -- recounted how, right after he was hired in October of 1996 to manage MSN, he was summoned to Redmond for a meeting with Bill Gates. "He gave me and my team the mission of basically finding or creating a system for free Web-based email for the whole world that Microsoft would offer," DeMello said.
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How Hotmail Changed Microsoft (and Email) Forever

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  • Beware of the Passive Voice (Score:5, Insightful)

    by 140Mandak262Jamuna ( 970587 ) on Friday December 29, 2017 @06:52PM (#55831469) Journal

    Mistakes were made. Many dollars were spent.

    The most powerful weapon in the hands of the spinmeister is the passive voice. You can make reasonable sounding statements, keep who did the mistakes and who spent the dollars out of focus, lull the listener into some kind of mental lethargy, ... and then bham! Whack them before they know what hit them.

    • The most powerful weapon in the hands of the spinmeister is the passive voice.

      This is one reason for the dominance of English in many fields. It provides so many opportunities for nuance, ambiguity, and evasion.

  • "How about spam, eggs, long signatures and spam? That don't have much spam init."

    • Comment removed based on user account deletion

      • I may be misremembering how advanced cyber-security was at the time. But how quickly would a brute-force SMTP attack be shut down back then? Would it be? Just sending to every combination of letters and numbers before the @ sign would be very quick when their servers were still fast and not overloaded.

  • hotmail serves a vital purpose (Score:3)

    by roc97007 ( 608802 ) on Friday December 29, 2017 @07:07PM (#55831531) Journal

    When ordering online requires an email address that the vendor can then spam the dickens out of, having some dummy hotmail spam collectors can be very useful.

    • Re:hotmail serves a vital purpose (Score:4, Informative)

      by JaredOfEuropa ( 526365 ) on Friday December 29, 2017 @07:43PM (#55831697) Journal
      Just get your own domain and create throwaway addresses that you rotate on a regular basis. As a bonus, you don't have to change your actual email address if you switch providers or if your online email service provider goes under. Been doing that since '97.

      • Bingo. Works like a charm for me too. Add to that a custom Haraka server with a black/white list and no more spam problem.

      • Same here, but it's also worth remembering Schneier's advice: if you sign up to netflix as netflix@example.com, there's a good chance that he can guess what email address you use for amazon! It's also good security if you use different email addresses for each service, because if one of them has poor security then whoever compromises them will try your username and password on a all of their services, and now they have two things that hopefully won't match.

    • When ordering online requires an email address that the vendor can then spam the dickens out of, having some dummy hotmail spam collectors can be very useful.

      I always preferred Rocketmail, but they were bought out by Yahoo and the service sucked afterward. Though I still use a hotmail address for all the sites I don't really care about.

  • I left hotmail after Microsoft bought it

  • Hotmail isn't email (Score:1, Interesting)

    by Anonymous Coward

    As long as Hotmail silently drops incoming, accepted mails without generating a bounce (blatantly ignoring SMTP RFC) it has absolutely nothing to do with email and should never be called that, the correct description is 'broken POS'. SMTP server admins should collectively blacklist them and move on into a better future.

    • Generating a bounce is just a way to allow spammers to know if they've found a valid address. I would agree that blocking IPs after X invalid email addresses across X minutes would be smarter - but it doesn't do much against a botnet either.

    • Our emails at least get a bounce message from Microsoft addresses, which I suppose is something :-)

      Earlier in the year, following WannaCry, we were getting a lot of bounces from UK government addresses as they tightened their filters. At the time, we were using the service providers webmail (1&1 as it happens), so everything went through their pool of SMTP servers. Not surprisingly, there are a lot of unsavory characters using these same servers, so blacklisting them wasn't unreasonable. The solution we

  • was hotmail in that period tween BBS and webmail was a thing, successfully transitioned beyond that, lasted longer than hotmail in the picture of history, but yea hotmail, where every spammer I ever ran across got sent to a "eatmyass@hotmail, suckadick@hotmail, gofuckyourself@hotmail, fuckyourmamma@hotmail" response

    hotmail was nothing special, in the sense that @aol.com was nothing special, unless you were 8 and completely clueless dumb fucks at the time

  • I was a hotmail user long before Microsoft bought it, gmail didn't exist back then.
    I kept using hotmail even after MS bought it, I really didn't give it much tought.

    Suddenly hotmail asked me to enter my cellphone number that they would verify with a message, and I could not log in without this verification.

    That's how I lost years worth of emails and why I will never use Microsoft services again.

    • Yeah, had a very similar experience - set up my hotmail pre-Microsoft, and used it as a principal destination address for about ten years (my work and ISP based addresses changed quite often back then, so it was good to have a stable point of contact). Nowadays I use gmail for the same purpose, but I was still getting the odd email sent to the hotmail address, usually from old work colleagues or mates wanting to get back in touch - all autoforwarded to gmail.
      Then earlier this year Microsoft decided that I n

    • I was a hotmail user long before Microsoft bought it, gmail didn't exist back then. I kept using hotmail even after MS bought it, I really didn't give it much tought. Suddenly hotmail asked me to enter my cellphone number that they would verify with a message, and I could not log in without this verification. That's how I lost years worth of emails and why I will never use Microsoft services again.

      They are going to ask me for what! Well I hope not, I may have to give up one of my burner accounts!

  • In the early years i was online (1996 - 2000 ) most web based email providers offered 25 MB of storage. Then google came and offered 2 GB with Gmail, which for me was the biggest leap i had seen. I mean companies used to charge for a 100MB plan. This has come at a privacy cost/penalty, though.

  • "He gave me and my team the mission of basically finding or creating a system for free Web-based email for the whole world that Microsoft would offer," DeMello said.

    Which sounds really impressive except 1) he got the idea from hotmail and other free services that already existed, this was obviously another "embrace, extend and extinguish" attempt and 2) the "whole world" meant people connected to the internet in 1996, not the billions we have today. The smartphone revolution wasn't even a fantasy in 1996 and even billy gates's wildest dream was only that we'd get as far as "a computer in every home" not one in every pocket.

  • I've had a hotmail account, since 1997. I use it for "junk mail". Anytime I have to log into any site with an email address...they get my hotmail address. Keeps the spam/junk out of my real email account.

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