Damages may be deemed insufficient when they cannot accurately compensate for the loss due to the unique value of the contract or when the harm is ongoing and incalculable. Additionally, damages are inadequate if they fail to provide a deterrent for future breaches or if there’s difficulty proving the extent of loss with certainty.
For example: A singer contracts exclusively with a venue for concerts, but the venue hosts another artist. Damages are hard to compute for loss of reputation and potential future gigs.