The paper addresses the introduction of predictive maintenance for military ground equipment under field conditions through assisted diagnostics and remote expert collaboration. It proposes a “field-level PdM” process–data framework linking on-site evidence capture, standardized recording of maintenance events, and subsequent analytics, including remaining useful life (RUL) prognostics. The approach is examined via scenario-based pilot testing that evaluates time to fault identification, record quality, and robustness under degraded connectivity. Expected outcomes include reduced downtime, improved asset availability, and enhanced data readiness for PdM analyses. The discussion situates the approach within current initiatives of the Czech Armed Forces and highlights ergonomic and safety considerations associated with long-term use of hands-free devices. The study provides a basis for further operational and economic assessment.