Do you need to send another Chapter 93A demand letter?

In consumer actions for unfair trade practices, the Massachusetts statute requires a presuit demand letter before asserting the claim.  But what if you have sent a presuit demand letter, further shenanigans ensue and you want to amend your complaint to add more claims?  In a decision last year from the Massachusetts Superior Court, Business Litigation Session (Salinger, J.), the court held that the plaintiff did not need to send a second letter.  Deutsche v. Privilege Underwriters Reciprocal Exchange.  That’s a good, rational outcome.

But I would typically err on the side of caution and send the second letter.  In my experience, courts can be quite unpredictable in whether they will insist on a specific letter addressing the specific conduct at issue.  Some courts can be quite lenient. Others can be startlingly picayune.  It is not a lot of work to send a second (or third . . .) demand letter and the fewer outs you give the defendant, the better.