Directly setting an object which contains an optional item defined with an interface doesn't bypass `Object is possibly 'null' or 'undefined'.`

TypeScript Version: 3.9.0-dev.20200305

Search Terms:

• object is possibly 'null' or 'undefined'

Code
https://github.com/mckaysalisbury/typescript-direct-set

// See the above repo for a little more self containment.
// Most notably `"strictNullChecks": true`
interface I {
  optional?: (I | null);
  required: number;
}

let workaround: I;
workaround = {
  optional: { required: 2 },
  required: 1
};

workaround.optional.required;  // This is where the error occurs

Expected behavior:
This code should properly compile without errors, even with "strictNullChecks": true
Actual behavior:
With "strictNullChecks": true, there is a possibly undefined error.

Playground Link:
Typescript Playground

Related Issues:

• https://github.com/microsoft/TypeScript/issues/35523
  Not that related
• https://github.com/microsoft/TypeScript/issues/36193
• https://github.com/microsoft/TypeScript/issues/35964

Reproduce the example in the linked TypeScript Playground with strictNullChecks enabled, then read the related issues for the existing discussion of this behavior. Determine whether the compiler should narrow the optional property after the direct object assignment; done means an agreed behavior and a regression test covering the example if a change is accepted.