Skype chat within Outlook for Web

Outlook web access has been around for many years. Now you can use Skype chat within Outlook – on any browser… another nice integration feature for Office 365. Of course, we are talking about Skype for Business (SFB) here.

The practical benefit is, if you find that someone is online and you need quick response, chat with that person rather than sending an email. That is called “Instant Messaging”.

The Need

If you need to chat with someone in your organization, but you don’t have SFB app on your mobile, you do not have any other device, you are using someone else’s laptop (or an internet kiosk)… think about it. May be such situations have arisen before, but you did not know we can chat using any browser with an internet connection.

How to use Skype chat within Outlook for web

Login to Outlook on the browser using your Office 365 id. Notice the Skype icon on the top menu bar. Clicking the icon opens a chat window (pane).

How to use Skype chat within Outlook for web

That’s it. Now you can chat with your colleagues. If you have federation established with external organizations, you can include them as well in the chat.

Emoticons (not Emoji yet)

You get regular Skype emoticons by clicking on the blue smiley.


The yellow smiley is for providing feedback to Microsoft. The bell is to enable or deactivate chat notifications. It is a good idea to keep it enabled.

The not-so-obvious benefit

The obvious benefit is that you get Skype on web along with Outlook on web. But there is another benefit.

Most of us are used to sending email to each other – even one line emails:

You: “Should I close the deal at 4% discount?”
Boss: “Go ahead”

Why do we need such emails? Because we want legal proof of the conversation. Even though the boss is sitting next to you, we prefer to “put it on email”.

What many of us do not know that Skype for Business chat is also archived on the server – just like emails. Therefore, in case of disputes, SFB chat can also be used as evidence – just like emails.

You are about to send a mail to someone, but the presence icon shows that the person is available (green color), then why not get an instant response by chatting with the person? Is that not faster and smarter?

We eliminate one mail trail also in the process – helping both parties.


Try it out next time you are about to send a short mail to someone.


6 thoughts on “Skype chat within Outlook for Web”

  1. Great Post. As Paul Thorrot says SFB and Skype personal for desktop is getting old real fast. Microsoft needs to fix the desktop all version very quickly. It is buggy and many users who came from the old MSN messenger do not like the new interface and the constant ads. Our organisation have and will be slowly shifting away from Skype to other IM such as whatsapp web and mobile as well as wechat web and mobile. Both of these offer a much better UI type intergration with one drive and other services. SKYPE is on the way out their user numbers are declining. They should have bought whatsapp. Major problem is Skype is not tied to a unique number but rather Multiple email addresses. Skype file transfer is also extremely poor. Unsuitable for business use.

    1. Hi. Appreciate your feedback. Here is my response.
      I am NOT talking about personal chat applications (including Skype) here. This post is about Skype for Business and Outlook for web integration in the context of Office 365. SFB has no ads. WhatsApp and other peer to peer chats should not be compared with SFB because these do not provide all the business features. SFB provides automatic archival of chat on server side. The transcripts are available for eDiscovery as well (along with OneDrive, SharePoint and Exchange content). Skype for Business, as the name suggests, is designed for business use. It supports secure federation with other organizations for this purpose. File transfer is discouraged in corporate context because it creates multiple copies of the same document. As we are communicating with people from within the organization, it is recommended that we store the file in OneDrive, SharePoint site or a Group and send the link using SFB. In a corporate context, the corporate email id can be the ONLY true identifier of a user as phone number can remain the same even after the person leaves the organization.

    1. Comments on WordPress are scanned for spam. If the JetPack algorithm thinks that a particular item is a spam, it requires approval.

  2. Hi thanks

    Understand your point.

    Part of of Office 365 for business include SFB, but you must also agree with the rest of Windows world that the application stinks, for example we are a international organisation with many of our users using other methods for secure communications. The notion that file attatchments are no longer needed is not reality. International business organIzations and branch to branch still send attatchments, and nothing one can do about that. One drive cannot even Attatch excel files larger than a certain size and must be downloaded to open on the native app.

    Communications with , partners , suppliers and fellow colleagues alike find business gets done faster if we go to where our customer resides., and not many of them live on Skype anymore. Last I checked SFB doesn’t allow you to add users from outside the organIzation, it seems too rigid and only certain business that need strict compliance will use it successfully, Read the Skype FB Forums and see all the frustrations. Webapps like slack with IM are a much better alternative. Skype so far seems to be a dreary Waste of time-that so far seems a useless add on to the office for business package. Of course this is one IT managers rant against Skype and Microsofts poor support for it. It was once captain of communication but has been neglected by Redmond for far too long

    1. Hi
      Thank you for posting detailed comments. I agree that SFB is not meeting expectations of IT professionals globally.
      I would not call it a “Rant”, it is a disappointment due to under-delivered expectations (something very rare in Office platform).

      However, as an experienced IT person, you will also agree that the actual usage of this tool is dismally low. Poor usage is NOT due to the problems highlighted above. I am trying to address the underutilization issue in my blog.

      Most users don’t use it either because they simply do not know about it or because they don’t want to change their behavior. The first problem can be solved with better communication and internal marketing. The second problem is where more effort is needed. “What is in it for me?” is not clear. So people do not use it. That is what I was trying to highlight in this post. Another very powerful feature is ubiquitous presence of Presence! I will write about it soon.

      Dr Nitin

Comments? Suggestions? Wish list?