OK. Stick with me here. It is going to take me a few to explain this. I am writing a small application in VB.NET. The ultimate task is to make a web browser, within a web browser. Basically, You open IE, FireFox, Safari, or whatever browser you like and go to the web application I am building. At the top of the web page, I have a tool bar, ...

This pattern might do what you need.  (?ms)(?<=^(TO|INFO)\s).*?(?=\s+^(?:INFO|GR)\s) It will only work reliably if there are no two other lines starting with TO, INFO or GR in the message body, i.e. after the first GR. It will return one or two matches, depending on the presence of the INFO part.  You will have to split those ...