This thesis assesses the situation and potential success in legal practice of one major invention in the maritime industry, namely, the electronic bill of lading by taking into consideration developments of the relevant regulatory frameworks through time by some few important institutions involved including CMI (Comité Maritime International), Bolero (Bills of Lading Electronic Registry Organisation) and UNCITRAL (United Nations Commission on International Trade Law). The thesis focuses on analysing effectiveness of the legal attempts of these actors in supporting the electronic bill to be accepted as fully legally enforceable as in the paper-based case. In doing so, emphasis is placed on the question of how fundamental legal requirements of the traditional bill can also be met by this paperless replacement. The thesis argues that the trendy bill concerned shall be regarded as the electronic equivalent of the paper bill since, based on some of the recent guidelines and provisions offered, it certainly satisfies such traditional requirements. That is, the electronic bill of lading is, too, a legal document that can be signed and capable of performing all basic traditional functions which include being a receipt for the goods, being evidence of terms in a contract of carriage and, more sophisticatedly, being a negotiable document of title. The thesis points out that the CMI model fails to stay attractive for long as it is associated with a number of problems, while the Bolero system that follows, though imperfect, appears to be a better alternative for the contracting parties wishing to use the bill of lading in electronic form. UNCITRAL not only provides essential legal guidelines like Model Laws on Electronic Commerce and on Electronic Signatures, but also is developing Draft Convention on the Carriage of Goods [Wholly or Partly] [By Sea] purporting in part to build a thorough framework governing and help promoting the use of the electronic bill of lading. This great prospect expected by many to be a dream legal solution for the electronic bill has, however, some room for improvement as suggested in the thesis.