Well, I don't actually ever give bad news on the back of a chart reading, because I don't use astrology to predict good or bad news, so there's no bad news to give.
Having said that, if someone says that they have recently been experiencing difficult feelings, and I see that the transit(s) and/or progression(s) that seem to be relevant have some way to go before they fade, then I guess this is bad news. But then its the job of the astrologer, IMO, to encourage the native to see that phase of life as an opportunity as well as a difficult time.
The other thought that comes to mind is that certain natal aspects need very careful handling. As an example take Moon and Neptune in close, challenging aspect. I've seen this aspect in the charts of women who would dearly like to become mothers, but for whim things just haven't fallen into place. Careful handling of this aspect, IMO, involves not sharing with the native one of the traditional interpretations which associates this aspect with the denial of maternity. But I would normally talk about the Neptunian period of limbo which can be experienced with regard to motherhood, and how that period can be used creatively. Whether the period of limbo lasts a week or the rest of the native's lifetime, they hopefully have a more positive view of it. I wouldn't normally mention adoption, because this might come across as a suggestion that biological children would never come along. But I might mention the Moon Neptune propensity to be a 'mother to the world' - not just one's own children.
So in short, I would avoid making negative predictions, but would also try not to shy away from the difficult implications of the aspect.
I don't know if this in any way answers your question, Moog. Did you have a particular piece of bad news in mind in your original post.