You can SMS message people using Skype though it ends up costing money per text message so I rarely use the feature. To be able to SMS message contacts or call contacts in your Skype contact list you used to have to synchronize these contacts via Outlook but now you can also enter “Phone Number” only contacts in Skype. If the number is not entered properly in the Outlook contact then Skype will tell you that it does not recognise the number and require you to dial it manually or you could fix the number to allow for one click dialing of this contact or for you to be able to SMS message this Skype contact. The error is shown in the below image at the bottom of the Skype window.
Outlook contacts not showing up in Skype has been a problem bugging me for a couple weeks but I have not had the time to look into it until tonight. I figured that it might be a bug or something with Skype since I recently upgraded however I was incorrect. For some reason when I turned on “Show Outlook Contacts” in Skype only two of my contacts were showing up. Luckily this was the case or it would have taken a lot longer to figure out.
The issue is that in my Skype setup (not sure if it is this way for all configurations) the numbers require a +1 to be in front of the area code. So for instance if you have a contact and the number is 502-123-1234 it will not show up in Skype unless you add a plus one for the number to show as +1502-123-1234. Below I describe a couple tips to convert all of your numbers a bit easier. There is probably a VB script out there that will do this easier but it was much easier to convert all of your Outlook contact numbers as I discuss below than manually editing each one.