If a message is known to be too long to send to a chat or IM, and it's an HTML message, strip the HTML, re-encode, and try again. The chat part is particularly useful given the short maximum message length and the fact that purple_markup_linkify() will have linkified long links to being twice the number of characters. The IM part is not triggerred in my experience because MAXMSGLEN seems to be far above the number of characters allowed; perhaps it is a number of bytes, not characters?