Evaluating an If condition to yield True/False

You need to use === (or SameQ) instead of == (or Equal) to test the condition. This is because === always returns True or False, whereas == can remain unevaluated. For example:

a === b
(* False *)

a == b
(* a == b *)

The fact that == remains unevaluated is why it is useful in Solve, Reduce and related functions, where you can write an expression such as a x^2 + b x + c == 0.

Now, == does evaluate in cases such as comparisons between numeric quantities and strings or when the objects being compared are identical. For example:

1 == 1
(* True *)

"abc" == "def"
(* False *)

2 == "a"
(* False *)

a == a
(* True *)

However, make note of the fact that comparison between machine numbers and exact numbers can give different results for == and ===:

1 === 1.
(* False *)

1 == 1.
(* True *)

This is because SameQ tests if the two expressions are exactly the same, down to the representation (which they're not), whereas for Equal (see link to docs above):

Approximate numbers with machine precision or higher are considered equal if they differ in at most their last seven binary digits (roughly their last two decimal digits).

Generally speaking the function you need is TrueQ:

TrueQ[expr] yields True if expr is True, and yields False otherwise.

Example:

TrueQ[ x == Automatic ]

False

Alternatively you can use SameQ (===) but this changes the meaning of the comparison from mathematical to structural. Frequently you want to match based on numeric rather than structural equivalence:

If[TrueQ[# == 0], "match", "fail"] & /@
   {0, 0., E^(I Pi/4) - (-1)^(1/4), 1, symbol}

{"match", "match", "match", "fail", "fail"}