The error doesn't need to be extremely specific or point to the actual root cause.

In your example,

- "Error while serving file" would be a bad error message,

- "Failed to read file 'foo/bar.html'" would be acceptable, and

- "Failed to read file 'foo/bar.html' due to EIO: Underlying device error (disk failure, I/O bus error). Please check the disk integrity." would be perfect (assuming the http server has access to the underlying error produced by the read operation).