Optical network automation is a critical enabler of modern communication networks, enhancing efficiency, reliability, and scalability to meet escalating demands for highspeed, high-capacity data transmission. By automating tasks such as routing, spectral assignment, failure management, and resource optimization, automation minimizes operational costs while improving network performance. However, widespread adoption faces significant challenges, including organizational resistance, fragmented multi-vendor environments, and the need for high-quality training data in machine learning (ML) models. Physical impairments, financial constraints, regulatory compliance, vendor lock-in, and high computational demands for realtime operations further complicate implementation. Emerging technologies like digital twins and large language models (LLMs) offer promising solutions for network automation, predictive maintenance, and intelligent decision-making. However, LLMs face notable limitations, including a lack of understanding of signal degradation, fiber attenuation, and other physical network behaviors. Additionally, they struggle with persistent memory retention, causal inference, and multi-step planning, impacting their ability to diagnose network failures and optimize long-term performance. Digital twins help mitigate these constraints by providing real-time, dynamic simulations of the physical network, enabling LLMs to assimilate real-world conditions, improve reasoning, and enhance predictive analytics. Furthermore, advances in elastic optical networks (EONs), flexible grid systems, and federated learning support dynamic routing, real-time Quality of Transmission (QoT) evaluation, and predictive failure management while preserving data confidentiality. The synergy between digital twins, LLMs, and edge AI enables continuous monitoring, proactive reconfiguration, and autonomous network control, paving the way for self-optimizing, resilient next-generation optical networks. This paper explores both technical and non-technical challenges to automation, emphasizing how digital twins and LLMs can overcome energy constraints, interoperability issues, workforce reskilling challenges, and regulatory complexities. By addressing these barriers, these technologies promise a shift toward highly efficient, scalable, and sustainable optical networks, capable of meeting the growing demands of an increasingly datadriven world.