Revamped Hotmail has a nice feature list, might be missing the point

Microsoft recently released a major refresh of its Hotmail webmail service as part of their recent push towards the cloud. I've just recently signed up for a new Hotmail account, and email is the kind of app that you really need to use for a while to evaluate. As such, I don't yet have a fully formed opinion, but a comparison of the new Hotmail and Gmail on Lifehacker.com seems consistent with some of my early impressions.

The features
There's no question that the new Hotmail offers some interesting features. Probably the most eye-popping is allowing 10GB of attachments using Windows SkyDrive (though no individual file can exceed 50MB). It also seems to do a nice job of displaying embedded content (pictures, videos, etc), and has a prominently placed search widget to include online content when composing emails. They've finally added threaded conversations (that can be disabled if desired). And while it doesn't seem to be as flexible as the filter and search tools in products like Gmail, the Sweep functionality in Hotmail looks to provide easy ways to process and organize mail. Finally, while we weren't that impressed with Microsoft Office Web Apps, Hotmail is supposed to integrate very nicely with them to allow editing of attached documents.

The problems
Like I said at the beginning, I haven't used Hotmail for too long, and I'm a huge Gmail proponent (and almost certainly biased). I've also been using it in Chrome on Linux and a Mac, which is definitely not the environment that Microsoft is likely imagining. That said, my overall user experience with Hotmail has been pretty weak. There are a number of decisions that either get in the way while trying to be helpful or just make for plain old bad UI.

The main culprit of getting in the way by trying to help out comes after you send an email. Once clicking send, you end up on a new dedicated page confirming that your mail was sent, and asking if you want to add the recipients as contacts. At various times, I was asked if I wanted to mark a contact as "safe" add them to "my contacts" or add them to "my network." I don't really know what the differences are between those three, but I find it hard to believe that this level of detail is needed. Regardless, I definitely don't need a new page whenever I send an email. This kind of interaction is exactly the reason people didn't like Clippy (Microsoft Office's "helpful" animated paper clip), but Microsoft doesn't seem to be learning from past mistakes.

In another "feature" reminiscent of prior Microsoft annoyances, when receiving an email from a contact that hasn't previously been marked as "safe," Hotmail will hide images and attachments (as many others do), but will also inactivate links. When you click on a link, you get a popup asking if you want to enable links, graphics, and attachments prior to opening the link. I understand that plenty of security risks arrive through links, but this seems like overkill and gets annoying very quickly. Hotmail also thought that an email from Netflix telling me what DVD they were shipping was a security risk, requiring two additional clicks to see the content. This really seems like Vista's much-maligned user-account-control (UAC) all over again.

There are also a number of decisions that really just make for bad UI in my opinion throughout the software. My inbox didn't auto-refresh so I had to actively poll to be notified about new emails. At one point, I clicked on a large button saying "Activate Autoreply" which launched a new tab with another copy of my inbox, and no indication of how to set up an autoreply (I still haven't found an option for that anywhere). The Help menu has two options "help" and "support." I have no idea what the difference between them is supposed to, but they either need to be combined or need new names.

Obviously, most of these things are small details, but they add up to make for a pretty disappointing user experience. We talk a lot on this blog about how software should feel good to use, and Hotmail just doesn't from my experience. I'm going to keep trying things out for a while, but so far this seems like another miss from Microsoft trying to move into the cloud.