Short List of My Favorite Microsoft Outlook Add-ins

I enjoy installing new add-ins for Microsoft Outlook just to see how they were designed, whether companies might benefit from their use, and also to pick up ideas on additional potential improvements for Outlook. I'm often asked what add-ins I use or which ones I consider most valuable for other users. There are hundreds of add-ins for Outlook available with a wide range in price and usefulness.

I decided to compile a short list of the Outlook add-ins that I've found most beneficial to overall user experience with Outlook as a personal information manager (PIM) versus a basic email client. Others might have very different lists because we all use Outlook a little differently. I especially appreciate add-ins that help me improve my efficiency in Outlook and add-ins that can eliminate the need for other applications by integrating functionality into the Outlook interface.


With a name that's Inbox spelled backwards, Xobni has been around for several years now. It created a buzz from its debut by presenting data we already had access to, but in a different and more useful way. It works with Outlook 2003 and later, requiring Windows XP or later. Xobni tells us more about our communications with Outlook contacts than any other application had previously. Other applications come close, such as Gist [ Mailbox Intelligence: Understanding the Gist Communication Efficiency Tool], but Xobni is still the leader among applications that try to present your Inbox in a more organized manner.

Xobni maintains its own index of your mailbox, identifying metrics for your contacts, including, for example, what times of day they send messages to you. Xobni's reporting becomes more dependable when it has more history to work with. If you have a brand-new, empty mailbox on a Microsoft Exchange Server, it's going to take time before the output presented by Xobni can be used to identify accurate trends in messaging. Figure 1 shows the Xobni add-in in Outlook.

Figure 1: The Xobni add-in in Outlook

Xobni is probably my all-time favorite add-in for Outlook. Xobni Pro is the company's paid offering; it can connect information on contacts across Gmail, Outlook, and certain mobile devices (although not Windows Phone).


RedCritter for Outlook is a gateway to an array of developer-provided applications that integrate with and access Outlook. The company hosts an application gallery with a variety of third-party applications that integrate content with Outlook, including social media content. The applications are developed in Silverlight, and they can reference additional content based on the email message or contact you have highlighted in Outlook. Applications are installed and accessed through RedCritter's App Player within a pane in Outlook.

For example, if I highlight a message from a customer and the RedCritter Twitter application is chosen, that customer's Twitter feed is retrieved and displayed in RedCritter. The weather where contacts live can be shown if the Weather app is displayed in RedCritter. If the Office Docs application is shown in RedCritter, Microsoft Office applications referencing the contact you have highlighted in Outlook will be listed. One of the default apps that comes with RedCritter is the dual clock, which Figure 2 shows. This app shows the relative time difference between you and the sender of a message. Red Critter as a whole has the potential to make Outlook a true, comprehensive dashboard.

Figure 2: The RedCritter dual clock app

RedCritter depends on third-party developers for its application contributions, so this add-in platform, combined with various add-ins you install from the application gallery, can consume a lot of workstation resources-it all depends on the components you choose. This situation can pose particular problems when other comprehensive add-ins unrelated to RedCritter are competing for resources (such as Xobni).

To be sure, RedCritter still needs some work, but this add-in is the type that solidifies Outlook as much more than just email, but the Personal Information Manager. Mike Beatty, the CEO of RedCritter, advised me in December 2011 that the company is in a holding pattern in terms of further development of RedCritter for Outlook until Microsoft releases Silverlight for 64-bit systems.

Sperry Software Schedule Recurring Email

Sperry Software has developed a suite of add-ins for Outlook over the years. These products aren't free, but they can pay for themselves in productivity improvements. One product in the company's suite is the Schedule Recurring Email Add-In for Microsoft Outlook.

For companies or departments that need to send out recurring email messages, this add-in lets users easily schedule such messages within Outlook. An example of this might be an HR reminder to submit expense reports near month end, or perhaps a common message from IT advising users of their usual late-night maintenance window. Figure 3 shows the interface to manage scheduled messages, all in one place.

The Recurring Email add-in also lets you use attachments with scheduled messages. This feature is relevant when the recurring message doesn't change, but perhaps a document that you send with it might need to be updated. You can make changes to the attachment independent of the recurring message without changing the recurring message. Figure 3 shows the settings options for sending recurring messages, including making the message dependent on the presence of an attachment or attachments in a specified location.

Figure 3: Sperry Software's Schedule Recurring Email Add-In (click image for larger view)

Sperry Software makes several Outlook add-ins, and the Recurring Email add-in is one that can save time for those who schedule many messages in a business setting.

Adding Value and Solving Annoyances

Many other Outlook add-ins are available that provide significant value to users, and many other add-in providers, such as MAPILab and AbleBits, are solving little annoyances or apparent feature omissions in Outlook. Now and then, we review add-ins that we think readers might find useful, such as YouSendIt for big attachments or PocketKnife Peek for email security. Do you have any specific add-ins that you find vital in your daily use of Microsoft Outlook?

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