Since I talked about the recent introduction of circles in Gmail, it seems only fair to point out that Hotmail also added a series of solid features to the web site. Officially announced a little more than a month ago, I saw the updates last week. Here are the main changes:
Keep important messages on top with flags
Flags (or stars) have always been used to mark up special messages, something that you would need to quickly find later or where you need to follow up. Traditionally they would have a dedicated folder or view; Hotmail brings the concept a step further, by having flagged messages pinned on top of the regular inbox, so you can’t miss them. It’s basically a scaled down version of Gmail’s priority inbox, without automatic learning or unread messages. Since these older messages can quickly hide newer ones, you can easily hide the section with a click on the separator or turn the feature off completely through the settings (‘Customizing Hotmail’ ► ‘Flagging’).
Instant actions
Desktop clients have always had an edge over webmail when it comes to speed and efficiency in performing common actions. If you look at Thunderbird, for example, you can quickly mark messages as read, star, delete or report as spam with one click. To make up some of the difference, web clients like Gmail have introduced keyboard shortcuts; later Hotmail followed, even offering several modes in the hope of attracting Gmail users. Now Hotmail has ‘instant actions’: while hovering over a message in the list, you will see a set of common actions – by default ‘flag’, ‘mark as read’ and ‘delete’. So, like in a desktop client, you have one-click-access to them. The list is configurable through the options (‘Customizing Hotmail’ ► ‘Instant actions’), including whether the action is always visible or only on hover. Unfortunately, instant actions don’t recognize multiple selections, they only act upon the current email; so as soon as you need to process more than a couple of messages it becomes more efficient to select them and use the top menu or a shortcut to perform the action. 
Organize messages with categories
Another major innovation in organization was the introduction of labels in Gmail; instead of moving messages around and assigning them to a single folder, you could tag them with several labels and use search to locate them. Later labels were added in Outlook 2007 as categories and now they are available in Hotmail as well. There are a number of built-in categories, like ‘Newsletters’ or ‘Social updates’, that are assigned automatically and contribute to the filters on top of the inbox, but you can also create your personal categories and that will immediately generate a new ‘quick view’ for it. To make Hotmail even more like a desktop client, you can enable the category column (‘Categories’ ► ‘Manage’) and set up instant actions to quickly add messages to certain frequently used categories. Personally I use them in Outlook all the time at work in connection with search folders, it feels much easier to organize and find messages, because they combine incoming and outgoing messages in a single view.
Schedule cleanup
Probably the single most innovative feature in the list, ‘schedule cleanup’ is an extension of ‘sweep’ allowing users to define rules for how long messages will remain in the inbox (from 3 to 60 days) and what happens to them after that time – they get deleted or moved to a folder. It’s the perfect solution for most newsletters because it keeps the inbox clean with very little user action; after all, these messages usually become obsolete after a couple of days and just end up unnecessarily filling up the inbox. I must admit I am guilty of similar email mismanagement, neglecting to clean up hundreds of messages about job postings that are no longer active. The Hotmail feature is powerful and easy to use, but not very flexible: you are limited to four time frames and the scheduled clean-up filters cannot be edited from settings, only deleted and recreated with other parameters. I simply wish Gmail would introduce something similar; it would be perfect along with the more fine-grained filter controls.
Easily navigate to older messages
I’m not sure if this control is new, but I noticed it recently and find it very useful: for navigating back through messages, there is a small ‘Go to’ link next to the arrows on the bottom of the message list. It opens a small calendar; click on a date and you will be taken to the messages from that day. Easy!
Even if some of the features have been done before, it’s good to see Hotmail adding them on a regular basis, at least when you compare this with the largely aesthetic updates in Yahoo! mail. I remain a happy Gmail user and from that perspective Hotmail seems to target regular, casual users; there are no conversations, a killer Gmail selling point and the POP3 support is limited – you can only download messages in the inbox, not the ones filed away in folders. But now, with a careful combination of categories and cleanup, that might not matter anymore!
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