dynamicType of optional chaining not the same as assignment

TLDR;

The playground sidebar/column will dynamically resolve expressions in the playground, be it values assigned to variables (mutables/immutables) or just "free-floating" non-assigned values.

Your first example applies dynamicType to a value, which will resolve to the type of that specific value (true.dynamicType: Bool.Type).

Your second example, on the other hand, applies dynamicType to a variable (an immutable, but I'll use variable here to differ from value), which must have a concrete type, and hence will resolve to a type that can hold any kind of wrapped values (true or false) as well as nil (here, nil is, specifically, Optional<Bool.Type>.None), no matter what value the variable actually holds. Hence, the dynamicType will resolve to Optional<Bool.Type>.Type in your second example.

Details

The value displayed in the playground sidebar/column generally follows the following display rules:

• For an assignment expression, the value shown in the sidebar is the value assigned, e.g.

  var a = 4 // shows '4'
  a = 2     // shows '2'
  let b: () = (a = 3)
            /* shows '()': the _value_ assigned to 'b', which is the _result_
               of the assignment 'a = 3', to which a _side effect_ is that 'a'
               is assigned the value '3'. */
  

• For an expression that contains no assignment, the value shown in the sidebar is generally the result of the expression, e.g.

  true          // shows 'true'
  1 > 3         // shows 'false'
  let c = 3
  c             // shows '3'
  c.dynamicType // shows 'Int.Type'
  

In your first example (lines 2-3), we have no assignment, and the playground will dynamically resolve the value(/result) of the expression prior to resolving the dynamicType of that value. Since we're dealing with optionals, the value is either simply the value of the wrapped type (in this case, true), or the value is a type specific .None. Even if the playground shows e.g. the result of let a: Int? = nil as just nil in the sidebar, the value shown is in fact not the same .None (nil) as for say let b: String = nil

• For let a: Int? = nil, the value of a is in fact Optional<Int.Type>.None,
• whereas for let b: String? = nil, the value of b is Optional<String.Type>.None

With this in mind, it's natural that the resolved dynamicType of a non-nil value will be the concrete wrapped type (in your example, Bool.Type is naturally the type of true), whereas the resolved dynamicType of a nil value will include both the general optional and the wrapped type information.

struct Foo {
    let bar: Bool = true
}

var foo: Foo? = Foo()

/* .Some<T> case (non-nil) */
foo?.bar             // true <-- _expression_ resolves to (results in) the _value_ 'true'
foo?.bar.dynamicType // Bool.Type <-- dynamic type of the _result of expression_
true.dynamicType     // Bool.Type <-- compare with this

/* .None case (nil) */
foo = nil
foo?.bar.dynamicType // nil <-- _expression_ resolves to the _value_ 'Optional<Foo.Type>.None'
Optional<Foo.Type>.None.dynamicType
                     // Optional<Foo.Type>.Type <-- compare with this

Now, if you assign the values to a variable, naturally the variable must have a concrete type. Since the value we assign at runtime can be either .None or .Some<T>, the type of the variable must be one that can hold values of both these cases, hence, Optional<T.Type> (disregarding of whether the variable holds nil or a non-nil value). This is the case which you've shown in your second example: the dynamicType of the variable (here, immutable, but using variable to differ from value) isOk is the type that can hold both .None and .Some<T>, no matter what the actual value of the variable is, and hence dynamicType resolves to this type; Optional<Bool.Type>.Type.

Wrapping expressions in parantheses escapes the runtime introspection of the Swift Playground?

Interestingly, if an expression is wrapped in parantheses prior to applying .dynamicType, then the playground sidebar resolves .dynamicType of the wrapped expression as the type of the expression, as if its actual value was unknown. E.g., (...) in (...).dynamicType is treated as a variable with a concrete type rather than a runtime-resolved value.

/* .Some case (non-nil) */
foo?.bar               // true
(foo?.bar).dynamicType /* Optional<Bool>.Type <-- as if (...) 
                          is a _variable_ of unknown value         */

/* .None case (nil) */
foo = nil
(foo?.bar).dynamicType /* Optional<Bool>.Type <-- as if (...) 
                          is a _variable_ of unknown value         */

We can further note that any lone expression wrapped in parantheses in the playground will not resolve to anything at all (in the sidebar). It's as if we escape the sidebar:s runtime introspection if wrapping expressions in parantheses (which would explain why the dynamicType of expressions wrapped in parantheses will resolve as if the playground cannot make use runtime information of these expressions)

var a = 4 // shows '4'
(a = 2)   // shows nothing; can't expand or get details in sidebar

Tbh, I cannot explain why this is, and will categorize it as a peculiarity of the Swift playground.