loop repeats without prompting the user again?

Well you need to clear the error state before accepting new input. Call cin.clear() then cin.ignore() before trying to read input again.

I would do something like.

cout << "Enter a number: "; cin >> number; while(cin.fail()) { cin.clear(); cin.ignore(1000, '\n'); //some large number of character will stop at new line cout << "Bad Number Try Again: "; cin >> number; } 

First, cin.fail() is not going to adequately check if your answer is a natural number or not with the type set to int (could also be negative).

Second, your boolean isValidAnswer is really checking if it's is an invalid answer.

Third (and most importantly), as another answer suggests, you should put in cin.clear() to clear the failure state, and then followed by cin.ignore(), which will remove the failed string from cin.

Fourth, cin will only check if an int exists somewhere in the string. You'll need to perform your own string comparison to determine if the entire input is a int (see answer below, based on this answer).

Updated:

#include <iostream> #include <string> #include <cstdlib> using namespace std; bool isNum(string line) { char* p; strtol(line.c_str(), &p, 10); return *p == 0; } int main() { int userAnswer; string input; bool isInvalidAnswer = true; cout << 5 << " * " << 5 << " = "; while (isInvalidAnswer) { if (!(cin >> input) || !isNum(input)) { cout << "Answer is not a number! Please try again:\n"; cin.clear(); cin.ignore(); } else { userAnswer = atoi(input.c_str()); if (userAnswer < 0) { //user input is not an integer cout << "Answer is not a natural number! Please try again:\n"; } else { isInvalidAnswer = false; } } } cout << "Question answered!\n"; return 0; }