If it's understood the Lebesgue integral is being taken with respect to the Lebesgue measure, then if the Riemann integral is defined for a function (which is exactly when the set of points on which the function is discontinuous has Lebesgue measure $0$), it will agree with the Lebesgue integral wrt Lebesgue measure. So unless a particular measure is alluded to, you should use whichever integral you please when the Riemann exists (you could theoretically come up with a function where the Lebesgue is easier to calculate, though I couldn't name one off the top of my head), while noting that a "nice" function will typically have a Riemann integral; and use Lebesgue wrt Lebesgue measure when it exists. Note that when an author wants you to think Lebesgue, she may likely make explicit that integration is occurring over a set, e.g. $\int_{[a, b]}$ instead of $\int_{a}^{b}$.
When an author wants you to Lebesgue-integrate with respect to a measure that is not Lebesgue measure (often denoted λ), they will typically note the measure they want in the differential. The most common notation is $\int_{E} f \mathrm{d} \mu$, where $\mu$ is our measure, but you may also see $\int_{E} f(x) \mathrm{d} \mu$ or $\int_{E} f(x) \mathrm{d} \mu (x)$, depending on the author. In these cases though, it should be evident what measure you're (Lebesgue-)integrating wrt.