Retinal vein cannulation is a demanding procedure proposed to treat retinal vein occlusion by direct therapeutic agent delivery methods. Challenges in identifying the moment of venous puncture, achieving cannulation and maintaining cannulation during drug delivery currently limit the feasibility of the procedure. In this study, we respond to these problems with an assistive system combining a handheld micromanipulator, Micron, with a force-sensing microneedle. The integrated system senses the instant of vein puncture based on measured forces and the position of the needle tip. The system actively holds the cannulation device securely in the vein following cannulation and during drug delivery. Preliminary testing of the system in a dry phantom, stretched vinyl membranes, demonstrates a significant improvement in the total time the needle could be maintained stably inside of the vein. This was especially evident in smaller veins and is attributed to decreased movement of the positioned cannula following venous cannulation.