It's Not You!
In the past I have been contacted by followers having trouble uploading images to TypePad, and I had experienced the problem myself at one point. Back then, I created this article on fixing the problem - basically to first save the post as a Draft, then continue with your image uploading - and it worked.
Trouble Uploading Images?
However, yesterday a reader and long time customer contacted me saying the solution wasn't working and she just couldn't upload not matter what she tried - rebooting, clearing cache, saving as draft, trying and trying again and again. So then I told her to try and contact TypePad support.
The solution is to use a different web browser.
And I commonly tell people to use FireFox as Internet Explorer normally is the culprit like it was in this case. TypePad is not compatible with Internet Explorer 10 at the moment! Here is a link to their supported browsers: http://help.typepad.com/browsers_supported.html.
Thanks for visitng today and have a great weekend!