The deployment of Large Language Models (LLMs) as assistants in electric grid operations promises to streamline compliance and decision-making but exposes new vulnerabilities to prompt-based adversarial attacks. This paper evaluates the risk of jailbreaking LLMs, i.e., circumventing safety alignments to produce outputs violating regulatory standards, assuming threats from authorized users, such as operators, who craft malicious prompts to elicit non-compliant guidance. Three state-of-the-art LLMs (OpenAI's GPT-4o mini, Google's Gemini 2.0 Flash-Lite, and Anthropic's Claude 3.5 Haiku) were tested against Baseline, BitBypass, and DeepInception jailbreaking methods across scenarios derived from nine NERC Reliability Standards (EOP, TOP, and CIP). In the initial broad experiment, the overall Attack Success Rate (ASR) was 33.1%, with DeepInception proving most effective at 63.17% ASR. Claude 3.5 Haiku exhibited complete resistance (0% ASR), while Gemini 2.0 Flash-Lite was most vulnerable (55.04% ASR) and GPT-4o mini moderately susceptible (44.34% ASR). A follow-up experiment refining malicious wording in Baseline and BitBypass attacks yielded a 30.6% ASR, confirming that subtle prompt adjustments can enhance simpler methods' efficacy.