The 1st Circuit upheld Massachusetts's may-issue regime. The plaintiffs will petition SCOTUS for cert. Petition is due on April 1, 2019.

After Wrenn v. DC, where the DC Circuit ruled that may-issue is unconstitutional, there's now a circuit split on this issue. That increases the chances that SCOTUS will grant cert. Between this case and Rogers v. Grewal there are two cert petitions in Q1-Q2 2019 for carry cases. It's quite possible the justices will grant cert on one.

Update May 7, 2019: the case is now Gould v. Lipson instead of Gould v. Morgan.

Update June 11, 2019: there have been no updates since the case was distributed for the June 6 conference. The case is very possibly being held pending the result of New York State Rifle & Pistol Association v. City of New York. If that's what's happening, then once the ruling on that case comes out (in spring 2020), the justices will either decide on cert in this case or kick this case back down to the lower court to be re-decided in accordance with whatever the ruling in NYSRPA v. City of New York is.