Thank you for the example. I do mostly the same thing and as a Safari user there is no way to place the caret in "the right spot". What I found working (but I still have to test on other browsers and make my mind if it is really worth the hack) is to place a dummy marker with [contenteditable="false"] at the beginning and the end of the inline elements (the one on the end has to be skipped to avoid getting stuck in a limbo inside the parent element). This way the result is similar to the one in Bike, with the caret that stops on both sides of the element. Let's see if this thing goes somewhere...