One or more devices, systems, methods, and storage mediums for detecting and guiding optical connection(s) using one or more imaging modalities are provided herein. Examples of applications include imaging, evaluating and diagnosing biological objects, such as, but not limited to, for Gastro-intestinal, cardio and/or ophthalmic applications, and being obtained via one or more optical instruments, such as, but not limited to, optical probes, catheters, capsules and needles (e.g., a biopsy needle). Devices, systems, methods, and storage mediums may include or involve a method, such as, but not limited to, for guiding and/or determining status of engagement and/or disengagement of one or more optical connections. A device, system, method, or storage medium may detect, monitor, and/or guide a probe/catheter to minimize, reduce, and/or avoid engagement and disengagement failures and to have a robust means of determining status of probe/catheter engagement to an apparatus or system.