Exactly as we ask others how many languages they can speak, the ultimate goal that the majority of people wish to accomplish when they attempt learning a foreign/second language is the ability to speak that language fluently, and accurately. This desire for improving in the skill of speaking seems to have turned into a need, as well, in the recent years, owing to the globalization of English language, and its significance in the international communications, education, and trade. Meanwhile, it is fair enough to claim not all learners improve in their speaking at the same pace. Better put, given similar pedagogical quality, learners with different personality variables (e.g. risk-taking, reflectiveness, expressiveness, etc.) are prone to progress in speaking proficiency at different rates. Aiming at using technology as a setting for improving speaking proficiency, this study focused on two basic learner variables – introversion and extroversion – to compare its impacts on introvert and extrovert learners. To draw this comparison, 85 intermediate learners from 4 private English institutes in Tehran were selected on a random basis, and a Cambridge PET test was used to homogenize their general English proficiency, which reduced the population to 64. A 57-item version of Eysenck Personality Inventory was also used to diagnose the introversion and extroversion of the population, based on which 56 learners – 28 introvert and 28 extroverts – made it to the study. They were exposed to 51 hours of speaking practice via SKYPETM software, participating in a wide variety of pair and group discussions on diverse topics. After administration of the speaking section of the PET test again, as the post-test, and analyzing the results through Independent Samples T-Test, the introvert learners reported a higher rate of progress in their speaking proficiency that the extrovert learners. This proved that introvert learners could gain noticeable benefits in their oral production in the virtual instructional and interactional settings