Criticised over the years for its lack of community focus -- even though the site is community run and led by thousands of volunteers and contributors -- its current problem is with its complex machinery of templates, editing and strict editorial guidance.
Scrambling to make the editorial process simpler and easier for the general population to engage with, speaking to the Associated Press, Wales described some of the setbacks that Wikipedia has to deal with to evolve.
With over 3 million entries, the site's articles are subject to daily pranks, misinformation and mass defacing of articles.
Wales spoke of contributors leaving as one of the main issues. "We are not replenishing our ranks".
At 90,000 active contributors by March, the goal is to attain another 5,000 by next June.
Speaking about its contributor base, the typical profile appears to be a "26-year-old geeky male", while others leave as there is a short supply of further articles to add.
But as the fifth most visited site on the web, and nearly a decade old, it is struggling to maintain its community effort with so many contributors are leaving.
Wales acknowledges the issues with Wikipedia from a founders' perspective, yet others who actively engage with the site see other barriers.
Speaking to ZDNet's senior technology editor, Jason Perlow, for which has his own Wikipedia entry, resonated similar feelings earlier with me on the phone in regards to Wikipedia's fundamental issues.
"Wikipedia appears to have a strange undefined organisational structure, or lack thereof. It seems to be run by some Mad Max-like community stuck in the middle of the desert. Contributors have to submit to many editors that follow meticulously baroque editorial guidelines, which are imposed in an inconsistent fashion."
He went on to explain that the site in its very essence is user unfriendly. Media uploads can be one of the major setbacks to new Wikipedians, partly for the complex licenses on offer and the lack of understanding around which images can be used for which purpose.
Perlow described how not only is the wiki-syntax old and outdated, along with the further complexity of the site's features and editorial processes, the community spirit could be the site's fatal flaw.
"Wikpedia is not a community conducive to creating content. The site is open to abuse. The number of times I have had to edit my own Wikipedia page because of some blatant libel, I lose count. The site is probably edited by 14-year-olds."
For users who have something they want to say or write, seem to need to be part of a niche crowd -- difficult to get in to from the word go; while others with their own entries are deterred due to the abusive edits they often have to endure.