This example is too simplified to understand if it's worth adding an except clause or not. If all you're doing is pulling the text out of the file, why can't you just make a function for this? lines = fancyread("myfile.txt") #Returns "couldn't open", "couldn't close", etc. in case of errors The point of the with statement is that your want to do more sophisticated stuff with the file contents, but still want the file closed at the end. But if you're doing more sophisticated stuff, it's not clear that you'd suddenly want to have "can't close" substituted in for whatever it was you whipped up by processing the file contents. So, I think we need a better example before we can judge the merits of an except clause. There's also the question of what the except clause would apply to. There are three places where a "with" could throw an exception: with open("myfile") as f: #Could barf on opening f.read() #Could barf in processing #Could barf during clean up Which of the three spots will the except clause deal with? All of them? As it is, barfing in the middle is already given to the context manager to clean up (though the context manager could always throw its own error during its own clean up), so it would be weird to have any other custom clean up that went in addition to what the context manager is already doing. -- Carl