Disclosed is a portable automatic electronic drop administration device and method of operation thereof. The device comprises a microcontroller communicatively coupled to at least an accelerometer and an electromechanical assembly to administer one or more drops of a liquid, semi-liquid or gaseous substance from any flexible container held within. The device detects whether it is in a suitable orientation before automatically self actuating the electromechanical assembly to administer one or more drops. It can be used in a variety of settings including self administration of eye drops, dispensing condiments or precise metering of liquid medications. Additionally, the device may contain sensors and wireless components to track usage and event data that may be communicated to a physician or other healthcare provider remotely.