diff --git a/lib/sorbet-coerce/converter.rb b/lib/sorbet-coerce/converter.rb
index 2fd90f9..cd2a8a2 100644
--- a/lib/sorbet-coerce/converter.rb
+++ b/lib/sorbet-coerce/converter.rb
@@ -59,28 +59,7 @@ def _convert(value, type, raise_coercion_error, coerce_empty_to_nil)
     elsif type.is_a?(T::Types::Simple)
       _convert(value, type.raw_type, raise_coercion_error, coerce_empty_to_nil)
     elsif type.is_a?(T::Types::Union)
-      true_idx = T.let(nil, T.nilable(Integer))
-      false_idx = T.let(nil, T.nilable(Integer))
-      nil_idx = T.let(nil, T.nilable(Integer))
-
-      type.types.each_with_index do |t, i|
-        nil_idx = i if t.is_a?(T::Types::Simple) && t.raw_type == NilClass
-        true_idx = i if t.is_a?(T::Types::Simple) && t.raw_type == TrueClass
-        false_idx = i if t.is_a?(T::Types::Simple) && t.raw_type == FalseClass
-      end
-
-      return value unless (
-        (!true_idx.nil? && !false_idx.nil? && !nil_idx.nil?) || # T.nilable(T::Boolean)
-        (type.types.length == 2 && (
-          !nil_idx.nil? || (!true_idx.nil? && !false_idx.nil?) # T.nilable || T::Boolean
-        ))
-      )
-
-      if !true_idx.nil? && !false_idx.nil?
-        _convert_simple(value, T::Boolean, raise_coercion_error, coerce_empty_to_nil)
-      else
-        _convert(value, type.types[nil_idx == 0 ? 1 : 0], raise_coercion_error, coerce_empty_to_nil)
-      end
+      _convert_union(value, type, raise_coercion_error, coerce_empty_to_nil)
     elsif type.is_a?(T::Types::TypedHash)
       return {} if _nil_like?(value, type, coerce_empty_to_nil)
 
@@ -117,6 +96,25 @@ def _convert(value, type, raise_coercion_error, coerce_empty_to_nil)
     end
   end
 
+  def _convert_union(value, type, raise_coercion_error, coerce_empty_to_nil)
+    type.types.each do |t|
+      # Always raise coercion error so that we can handle it here
+      if t.is_a?(T::Types::Simple) && (t.raw_type == NilClass || t.raw_type == TrueClass || t.raw_type == FalseClass)
+        return _convert_simple(value, T::Boolean, true, coerce_empty_to_nil)
+      end
+
+      return _convert(value, t, true, coerce_empty_to_nil)
+    rescue TypeCoerce::CoercionError, TypeCoerce::ShapeError
+      # Keep trying to coerce
+    end
+
+    if raise_coercion_error
+      raise TypeCoerce::CoercionError.new(value, type)
+    else
+      value
+    end
+  end
+
   def _convert_enum(value, type, raise_coercion_error, coerce_empty_to_nil)
     if raise_coercion_error
       type.deserialize(value)
diff --git a/spec/coerce_spec.rb b/spec/coerce_spec.rb
index ed90d62..e6a124b 100644
--- a/spec/coerce_spec.rb
+++ b/spec/coerce_spec.rb
@@ -71,13 +71,13 @@ class UnsupportedCustomType
       # Does not respond to new
     end
 
-    class WithSupportedUnion < T::Struct
+    class WithNilableUnion < T::Struct
       const :nilable, T.nilable(String)
       const :nilable_boolean, T.nilable(T::Boolean)
     end
 
-    class WithUnsupportedUnion < T::Struct
-      const :union, T.any(String, Integer)
+    class WithComplexUnion < T::Struct
+      const :union, T.any(WithNilableUnion, Integer, String)
     end
 
     class WithFixedArray < T::Struct
@@ -217,9 +217,9 @@ class Param2 < T::Struct
   end
 
   context 'when given union types' do
-    context 'supported union types' do
+    context 'nilable types' do
       it 'coerces correctly' do
-        coerced = TypeCoerce[WithSupportedUnion].new.from({
+        coerced = TypeCoerce[WithNilableUnion].new.from({
           nilable: 2,
           nilable_boolean: 'true'
         })
@@ -228,16 +228,20 @@ class Param2 < T::Struct
       end
     end
 
-    context 'unsupported union types' do
-      it 'keeps the values as-is' do
-        coerced = TypeCoerce[WithUnsupportedUnion].new.from({union: 'a'})
+    context 'when give complex union types' do
+      it 'nested types' do
+        coerced = TypeCoerce[WithComplexUnion].new.from({union: 'a'})
         expect(coerced.union).to eq('a')
 
-        coerced = TypeCoerce[WithUnsupportedUnion].new.from({union: 2})
+        coerced = TypeCoerce[WithComplexUnion].new.from({union: 2})
         expect(coerced.union).to eq(2)
 
+        coerced = TypeCoerce[WithComplexUnion].new.from({union: { nilable: "Test", nilable_boolean: nil } })
+        expect(coerced.union.nilable).to eq("Test")
+        expect(coerced.union.nilable_boolean).to eq(nil)
+
         expect do
-          TypeCoerce[WithUnsupportedUnion].new.from({union: nil})
+          TypeCoerce[WithComplexUnion].new.from({union: nil})
         end.to raise_error(TypeError)
       end
     end