The advancement of Pre-Trained Language Models (PTLMs) and Large Language Models (LLMs) has led to their widespread adoption across diverse applications. Despite their success, these models remain vulnerable to attacks that exploit their inherent weaknesses to bypass safety measures. Two primary inference-phase threats are token-level and prompt-level jailbreaks. Token-level attacks embed adversarial sequences that transfer well to black-box models like GPT but leave detectable patterns and rely on gradient-based token optimization, whereas prompt-level attacks use semantically structured inputs to elicit harmful responses yet depend on iterative feedback that can be unreliable. To address the complementary limitations of these methods, we propose two hybrid approaches that integrate token- and prompt-level techniques to enhance jailbreak effectiveness across diverse PTLMs. GCG + PAIR and the newly explored GCG + WordGame hybrids were evaluated across multiple Vicuna and Llama models. GCG + PAIR consistently raised attack-success rates over its constituent techniques on undefended models; for instance, on Llama-3, its Attack Success Rate (ASR) reached 91.6%, a substantial increase from PAIR's 58.4% baseline. Meanwhile, GCG + WordGame matched the raw performance of WordGame maintaining a high ASR of over 80% even under stricter evaluators like Mistral-Sorry-Bench. Crucially, both hybrids retained transferability and reliably pierced advanced defenses such as Gradient Cuff and JBShield, which fully blocked single-mode attacks. These findings expose previously unreported vulnerabilities in current safety stacks, highlight trade-offs between raw success and defensive robustness, and underscore the need for holistic safeguards against adaptive adversaries.