There are a number of helpful tools exposed on this.utils primarily consisting of the exports from jest-matcher-utils.

The most useful ones are matcherHint, printExpected and printReceived to format the error messages nicely. For example, take a look at the implementation for the toBe matcher:

const diff = require('jest-diff');
expect.extend({
  toBe(received, expected) {
    const options = {
      comment: 'Object.is equality',
      isNot: this.isNot,
      promise: this.promise,
    };

    const pass = Object.is(received, expected);

    const message = pass
      ? () =>
          this.utils.matcherHint('toBe', undefined, undefined, options) +
          '\n\n' +
          `Expected: not ${this.utils.printExpected(expected)}\n` +
          `Received: ${this.utils.printReceived(received)}`
      : () => {
          const diffString = diff(expected, received, {
            expand: this.expand,
          });
          return (
            this.utils.matcherHint('toBe', undefined, undefined, options) +
            '\n\n' +
            (diffString && diffString.includes('- Expect')
              ? `Difference:\n\n${diffString}`
              : `Expected: ${this.utils.printExpected(expected)}\n` +
                `Received: ${this.utils.printReceived(received)}`)
          );
        };

    return {actual: received, message, pass};
  },
});

This will print something like this:

  expect(received).toBe(expected)

    Expected value to be (using Object.is):
      "banana"
    Received:
      "apple"

When an assertion fails, the error message should give as much signal as necessary to the user so they can resolve their issue quickly. You should craft a precise failure message to make sure users of your custom assertions have a good developer experience.