As noted in the introduction to this project, consistent collection of documentary materials ceased in 1989, but librarians and the Middletown Historical Society did save souvenirs of seminal moments in the succeeding decades. One such moment: the 150th anniversary of the Middletown Library. Just as in the 100th anniversary, a short history of the library was created, adding 50 more years of storied community service. However, unlike in previous anniversaries, the library stood on the precipice of some monumental changes, both to its own function and to the information landscape of the entire world; In 1998 the digital era was beginning in earnest, and the library contended not only with a need for updated computer facilities, but also with the need to expand once more. In 20 short years, demand had grown so much that the "new" building was filled once again, and its interior space was proving inadequate for the programming put on by the library. For the above reasons, the library was poised to make some sweeping changes in the upcoming years.

Just after the 150th anniversary festivities, new DIrector Robert Balliot was appointed to lead the MPL through a large computerization project. During the 150th,  Balliot's predecessor, Cynthia Logan, also announced that the library would be pursuing funding for a series of renovations to facilitate ease of access and use of patrons. Among these changes were a new meeting room in the building, a new reading room, an expanded children's section, and increased shelving to hold the ever-increasing collection. Balliot added internet connected computers to the list as part of his mandated initiative. These changes were able to be accomplished in part with grants and donations pursued by the library, but the full scope of the updates could not be realized without a more significant investment. An investment that would have to be sought from the town.

In early 2011 the town began to formally investigate the prospects of redeveloping the land off Coddington and West Main, where the Middletown Public Library currently sits. The flooding of 2010 reinforced the need for a purpose built facility to house the library, and a number of proposals sprang up in the succeeding years. Most of these proposals hinged around offering some portion of the land for private development to fund the municipal complex that would occupy the rest, allowing the plan to be executed at little cost to Middletown Taxpayers. Though these proposals were put forward with varying levels of support from the library and received well generally, to date none of them have materialized.