It’s not possible. The hurdles are detailed below. Skype SMS costs around 5c to 11c per message.
What is Skype?
Skype is a voice-over-IP phone, chat, video, and meeting application from Microsoft. Originally, it was an entirely proprietary VOIP application, but is now based around WebRTC and other technologies. It’s still an ongoing company, but less high profile as more competitors have entered the video meeting business.
How I got Skype Credit Cheaply
I used Bing Rewards to get points for doing searches on Bing. Then, those points were used to buy Skype Credit. Credit is used to make phone calls from Skype to the plain-old-telephone network, and to send messages to the SMS text system.
Skype SMS Feature
Skype can send SMS messages for around 5 cents for a short message, and 11 cents for a longer message. The feature is under the “Chat” icon’s menu.
Cannot Import Contacts into Skype
I wanted to do a mass SMS from Skype. My first hurdle was getting a CSV file of phone numbers imported into Skype. I was unable to do it.
Information About Sync with Skype on the Microsoft Site is Out of Date
Searches turned up instructions about how to sync Contacts with Skype, but they appeared to be out of date. I followed the instructions, and could not find a sync option.
Contacts Imported into Live/Outlook.com/Hotmail do not Sync With Skype
I imported my contact list into my Hotmail/Outlook.com email account, and hoped they would show up in Skype contact searches. No suck luck.
How to Mass SMS?
I just did a lot of copypasta to send the SMS messages. It wasn’t that bad. Each message cost 11 cents, and I used up some of my Skype credit.
If you have Skype credit, this is a good way to use it up.