One embodiment of the present invention provides a system and method for appending server-side glossary definitions to transient Web content in a networked computing environment. A glossary database stores a glossary, which includes a plurality of structured records. Each structured record is keyed by a unique identifier derived from a key word and contains a definition associated with the key word. A parser receives Web content, which includes text in transit to a Web client, and parses the text into one or more tokens corresponding to one such key word. A comparator module matches the tokens against each unique identifier in the glossary and retrieves each structured record containing a matching unique identifier. A constructor inserts a hyperlink in place of the text corresponding to each matched token and references the definition contained in the retrieved structured record for the matching unique identifier.