The ancient world provides us with the unique possibility of uncovering and understanding how life, in all its facets, was like for ancient man. We can glimpse back in the past at man's more primitive morals, beliefs, politics, entertainment and everyday life and compare it to our own modern world. This is truly the gift of antiquity. However, this gift does not present itself in simple facts which we can simply take and accept as truths. Rather, it disguises its secrets and like a scrambled puzzle, provides us with bits and pieces of archaeological evidence to interpret and form our own big picture. Interpretation is therefore the only real tool we have to uncover this picture and consequently, results in a number of challenges. Thus in this paper, I shall highlight these challenges which the interpretation of ancient artefacts holds, with specific reference to Pompeii. My goal is to bring these problems to the consciousness of historians and arachnologist, so that it can be addressed. This critical approach is necessary if it is the hope of the modern world to know and understand what life was like in antiquity. As mentioned above, the focus of this essays will be on the rediscovery of Pompeii. In going about this, I shall firstly provide a short background on Pompeii, focusing on the cities demise. This will allow a better understanding as to why this ancient city is unique and thus why arachnologists are interested in its secrets. Thereafter, I shall look at the different types of materials or archaeological evidence found at Pompeii. Together with this, after addressing the type of material found, I shall discuss the possibilities which each individual piece of evidence holds towards rediscovering Pompeii. The following section of my paper will highlight and discuss various problems archaeologists and historians face regarding the interpretation of material evidence found. Followed by this I shall then discuss how these problems limits the possibility of interpretation.