Friend, you are correct with your example. Read Tax man's post as he is right on the money. Another point to add, once you've filed the initial paperwork, the extension is also required to be filed BEFORE your 90 days are up or you have to start all over again. They do make it difficult, but knowing how to play the game before you start certainly makes the waiting more bearable. Also, I am unsure about the cost of an extension once the initial 144 paperwork has been filed. I also believe it was mentioned by someone earlier (Herbalife?)that the company will be covering the cost of the opinion letter from the attorney. Keep in mind as tam man said...not all brokers handle rule 144 shares, and the costs/time frame may vary widely amongst them.