Gents, sorry for the delay and thanks very much for the replies. Unfortunately, I don’t have control over the design or why the original developer used .INI which is why I specifically scoped my question to the RichTextbox and .INI files. Dilettante, as usual you are always extremely helpful in the most thoughtful and practical ways. I tried your solution but oddly enough it didn’t work out for me but really appreciated the strawman to test out. Sam, although familiar with the split array method as you proposed - I didn’t think I’d end up using that. But it did end up that way. I basically resolved by extracting the data from the RTB into an array and then in fact looping through the array replacing elements as needed. Thanks for all the input, all set gents!