The Massachusetts inspector general is raising concerns about the Steamship Authority’s planned new reservation system, nearly a year after releasing a report that called out the ferry line for mismanagement of a now-shelved website.
In a letter to the Steamship last month, inspector general Jeffrey Shapiro called out delays in the multi-million dollar ticketing system, which is still in development and has been pushed back due to struggles with the different types of bookings that drivers can make aboard the ferries.
He noted that the Steamship’s treasurer and the chief operating officer appear to be expending a significant amount of time on guiding the new system, despite having full-time senior administrative duties in other departments. Mr. Shapiro also inquired into the cost of the system and how it would be incorporated into the website the Steamship spent millions on before putting it on pause.
“The OIG is pleased that SSA management and the SSA board are acknowledging and addressing the delays in the reservation system project, instead of downplaying them as they did with the website project, and that the SSA management and board are willing to review the project to determine the best course going forward,” Mr. Shapiro wrote in his Oct. 6 letter.
“However, the project management issues highlighted above suggest significant hurdles remain,” he continued.

The new reservation system is a major priority for the Steamship Authority, which hired an Italian firm with experience in ferry systems last year to build it. Though there were initial estimates that the system could be implemented in 2026, the Steamship has postponed its launch to next year.
Last week, Steamship general manager Alex Kryska said the boat line was looking into getting an outside assessment of the reservation system rollout plan to see if it is plausible. Officials said they wanted to avoid issues that other ferry services, such as the Caledonian MacBrayne ferries in Scotland, have run into with similar booking systems.
The inspector general’s letter, which also asked for updates on several of the recommendations highlighted in the inspector general’s 2025 report on the website, came up at the Steamship’s advisory port council meeting on Tuesday.
Mr. Kryska said that the ferry line has not yet responded, but he was in the process of writing to Mr. Shapiro.
“I’ve been working on that myself, and trying to get insight from others who were here before I was, so that I can provide a clear and complete response to him,” Mr. Kryska said.
“I do respect the [inspector general] and the report that he provided, and his continued guidance,” he said.
The 2025 inspector general’s report, released last December, tore into Steamship leadership for a lack of oversight into the new website that cost the ferry line millions of dollars. The inspector called the situation a “cascade of failures” and made 15 different recommendations for staff, the board and state officials.
Steamship staff are in the process of interviewing candidates for their first staff project manager, addressing the inspector general’s concern about other managers being pulled away from their main duties.
“The project manager is a long time coming. We’re excited about getting that position filled sooner rather than later,” Mr. Kryska said.
Ted Gavin, the Vineyard’s representative on the Steamship board, was pleased that the inspector general was keeping a watchful eye on the ferry line and noted the Steamship’s progress on many of the issues raised in the 2025 report.
“I was glad to see it,” he said of the letter. “I want to know everything the OIG knows. Sunlight is the greatest disinfectant.”
Mr. Gavin had previously questioned assigning the new reservation system to current employees, and had raised the potential of delaying the project to ensure that it is working properly when it goes live.
He also agreed with the inspector general’s call for policies and procedures to ensure major projects cross the finish line.
“I agree wholeheartedly with standardizing management practices and capital planning,” Mr. Gavin said.
The inspector general has asked for a breakdown of the cost for the new reservation system, and any extra money spent on keeping the old one going during the delays.
The Steamship has spent a little more than $2 million on the reservation system, and has not gone over the $5.5 million allocated for the project, according to Mr. Gavin.
The inspector general also urged the Steamship Authority to keep the board up to date on work from the previous, abandoned website project, and wondered if that earlier work would be integrated into the new reservation system.
“Both the ultimate value of the initial website project’s work and the current cost of the reservation system project are unclear, and the latter’s delays are cause for concern,” Mr. Shapiro wrote.
Mr. Gavin said he understood the concern, but that the website would be launched in conjunction with the new reservation system. Islanders who attended a budget hearing in Vineyard Haven last week also got a first glimpse of the site, which cost more than $4 million before it was paused.
The Steamship was working to ensure that the reservation system project didn’t snowball into a similar situation as the website, according to Mr. Gavin.
“Over my dead body,” he said after being asked about that prospect.

The inspector general’s letter did have some praise for the Steamship, citing progress on some of the recommendations in the 2025 report and a change in attitude at the ferry line.
“While the SSA’s recent ferry cancellations due to lapsed inspections were troubling, the swift response to address the problem as well as the assurance of a full, public review of the underlying issues that led to the failures shows meaningful change from past practices, starting with a more responsive tone from the top,” Mr. Shapiro wrote.
Mr. Kryska plans to see the inspector general in person next month.
“He is going to be coming to Falmouth, I believe the second of December, to do a community listening session, and I will be there,” he said.
Louisa Hufstader contributed to this article.
