If the number input is ever less than Num1, you will NEVER again go through this code:
1 2 3 4 5 6 7
while (Input > Num1)
{
Tries++;
cout << "Try a smaller number." << endl;
cout << "Please enter a number: ";
cin >> Input;
}
So the very first time the user guesses a number smaller than the correct answer, your code will NEVER be able to handle them guessing a bigger number than the correct answer.
Put another way, once execution gets to line 24, how could it ever go back to line 17?