Variational regularization is commonly used to solve linear inverse problems, and involves augmenting a data fidelity by a regularizer. The regularizer is used to promote a priori information, and is weighted by a regularization parameter. Selection of an appropriate regularization parameter is critical, with various choices leading to very different reconstructions. Existing strategies such as the discrepancy principle and L-curve can be used to determine a suitable parameter value, but in recent years a supervised machine learning approach called bilevel learning has been employed. Bilevel learning is a powerful framework to determine optimal parameters, and involves solving a nested optimisation problem. While previous strategies enjoy various theoretical results, the well-posedness of bilevel learning in this setting is still a developing field. One necessary property is positivity of the determined regularization parameter. In this work, we provide a new condition that better characterises positivity of optimal regularization parameters than the existing theory. Numerical results verify and explore this new condition for both small and large dimensional problems.