Hotmail: Stuck in the ’90s?

A married couple, friends of mine, are having relationship troubles. You know the old story: she’s on Hotmail, he’s on Gmail, and they can’t see or share their respective calendars. A problem as old as time. 😉

I figured the solution was simple: move her away from Hotmail, to Gmail, and they’d live happily ever after sharing their Gmail calendars. Why Gmail? I think Google’s Web-based email and calendar system is superior to Hotmail, though I confess I’m not as familiar with Microsoft’s offerings as I used to be (I don’t do Web-based email). I created a Gmail account for her, logged into her Hotmail account, and tried to set up a simple forward that would shunt all her Hotmail email into her new Gmail account until everyone started to use her new Gmail address. I didn’t count on huge road-block that seems right out of 1998:

WHAT? Hotmail’s email forwarding will only forward to other Microsoft email accounts? What’s the point then? That’s something I’d expect from the 1998 “We want to rule the world” Microsoft, not the newer “We want to work with the world, as long as we can make money doing it” Microsoft. Having a limitation like this is just a slap in the face to a Hotmail customer – sure, she’s trying to leave Hotmail, but there’s no reason to make the exit an ugly one. If Microsoft offered a real forwarding option, it would leave the door open to coming back. I haven’t thought very highly of Hotmail over the years (mostly because people using the service never seem to get my email), but this really drops the service down a few notches in my eyes.

Does anyone have any suggestions? I find it incredibly hard to believe that what I want to do is really this hard. I’ve done a bit of research and found a few desktop-PC programs that act as email re-directors, but that’s not a good solution. Possibly something Web-based? I thought Hotmail would have an option to function as a POP3 account, so I could use Gmail to pull her email in, but they don’t offer that either. It’s no wonder Gmail is so popular, Hotmail is really unimpressive.

23 thoughts on “Hotmail: Stuck in the ’90s?”

  1. I forward my Hotmail to Outlook where I work and it works perfectly. Are you using newer Hotmail Live mail (free version) or still the old Hotmail? If not that may make a difference but it’s a simple upgrade.

  2. Something’s wrong. I *just* set up my hotmail account to forward to gmail, and it was very straightforward to do (once I dug through and found the option).

  5. The upgrade information should be on the Hotmail web page (PC size version). It’s been out for a few months. Unfortunately I’m at work now and I cannot access Hotmail from here (that’s why I forward) otherwise I’d take a look at the Hotmail home page.

  6. Ok, so I went to the Hotmail home page, and have wasted a good 15 minutes trying to figure out the upgrade process – and I’ve struck out. All my Google searches have also been for nought – I keep finding stuff about upgrading a 2 MB Hotmail account to a 250 MB Live Mail account.

  7. Hmm, I am using the newer UI. If I remember correctly, there was an upgrade link somewhere inside the preferences page. But this was some time ago, so YMMV. I thought Microsoft was going to transition everyone…?

  11. Ok, when I follow that link and log in with the Passport account I just end up at the Inbox. It does say I have 5 GB of storage, which I think means I have the “new” Hotmail, right? So I guess the question becomes, why are you so sure that this should work? 😉 I’m using the newer UI as well…does your UI not look like this below?

  12. If I remember, on the far right side there is an options list and somewhere in there is the forward mail settings.

  13. That’s the right page, hopefully it works. I was using PIE last night and the UI page was a blur but now I can see it (using Netfront).

  14. Buzzard,
    Sorry man, it’s still not working – as the screen shot above shows, it still has the same limitations on the forward. I can’t explain this, but it seems like Janak and you must have a different type of account than my friend does. Does the UI for your forwarding look like the screenshot above? Janak?

  16. Microsoft has done some weird things in the past with hotmail accounts. This may be one of them. I know for a fact that they grandfather account options down to clients (such as the ability to access your Hotmail via Outlook). At one point, anybody registering a new account from that particular day forwards (or who hadn’t used it as of yet), were unable to access their hotmail accounts via Outlook.

    Now, that’s not to say that it is still the case, but it wouldn’t surprise me in the least if this was something that “newer” accounts aren’t able to do… Just my $0.02 anyway.

  17. Cold Flame,
    Thanks for the comments. Yeah, something truly bizarre is going on here. I ended up using Izymail (http://v3.izymail.com) as a solution, though it kind of sucks at the free level because it only forwards the email every 60 minutes…but it’s better than nothing, which is what Hotmail is offering me right now.

  18. I was just looking through GMail and found this:

    http://mail.google.com/support/bin/static.py?page=switchguide.html&switch=1

    Might be something to do. Their suggestion for switching from hotmail.com is to change your “reply-to” address and also change your signature in hotmail… plus some other useful tips such as how to export your address book from hotmail too.

    I feel your pain though, Jason, they sure don’t make it easy to move away from them! I keep a hotmail account though it is rarely used anymore; it’s used more for my Passport than anything else, but a few friends still use it. Just for the record, I am also unable to forward to my hotmail account to gmail for the same reason you have reported, so it’s not just you. And my hotmail account is, oh, ~10 years old now…

  20. Did you try ignoring the Hotmail words and just enter an address that didn’t agree with their list just to see if it works? It seems odd that some people would be offered one method and others something different, I don’t know how they would keep track of it.

  21. Buzzard,
    You bet I tried that – the screen shot in my blog post is what it comes back with when I tried. I’ve tried both an @gmail.com and an @jasondunn.com email address, and neither worked. I’ve sinced used the Izymail system and have “solved” this problem. Way too much hassle though…! 🙁

  22. I give up then. The other difference on your screen shot is that it states that forwarded email is deleted. I was given an option and chose to not delete until I could verify that everything was being forwarded (it is). I just started forwarding on 11/16/07.

    Looks like Cold Flame is correct, strange happenings at Hotmail.

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