diff --git a/lib/rspec/sorbet/doubles.rb b/lib/rspec/sorbet/doubles.rb
index 18c81c3..b2ff838 100644
--- a/lib/rspec/sorbet/doubles.rb
+++ b/lib/rspec/sorbet/doubles.rb
@@ -23,7 +23,7 @@ def allow_doubles!
       private
 
       INLINE_DOUBLE_REGEX =
-        /T.(?:let|cast): Expected type (?:T.(?<t_method>any|nilable|class_of)\()?(?<expected_types>[a-zA-Z0-9:: ,]*)(\))?, got (?:type .* with value )?#<(?<double_type>Instance|Class|Object)?Double([\(]|[ ])(?<doubled_type>[a-zA-Z0-9:: ,]*)(\))?/.freeze
+        /T.(?:let|cast): Expected type (?:T.(?<t_method>any|nilable|class_of)\()*(?<expected_types>[a-zA-Z0-9:: ,]*)(\))*, got (?:type .* with value )?#<(?<double_type>Instance|Class|Object)?Double([\(]|[ ])(?<doubled_type>[a-zA-Z0-9:: ,]*)(\))?/.freeze
 
 
       def handle_call_validation_error(signature, opts)
diff --git a/spec/lib/rspec/sorbet_spec.rb b/spec/lib/rspec/sorbet_spec.rb
index 53c323a..a32aeb2 100644
--- a/spec/lib/rspec/sorbet_spec.rb
+++ b/spec/lib/rspec/sorbet_spec.rb
@@ -171,11 +171,15 @@ def rectangular_class?(klass); end
           expect { T.let(class_double(Rectangle), Rectangle) }.to raise_error(TypeError)
           expect { T.let(Rectangle, T.class_of(Rectangle)) }.not_to raise_error
           expect { T.let(class_double(Rectangle), T.class_of(Rectangle)) }.to raise_error(TypeError)
+          expect { T.let(Rectangle, T.nilable(T.class_of(Rectangle))) }.not_to raise_error
+          expect { T.let(class_double(Rectangle), T.nilable(T.class_of(Rectangle))) }.to raise_error(TypeError)
           subject
           expect { T.let(Rectangle, Rectangle) }.to raise_error(TypeError)
           expect { T.let(class_double(Rectangle), Rectangle) }.to raise_error(TypeError)
           expect { T.let(Rectangle, T.class_of(Rectangle)) }.not_to raise_error
           expect { T.let(class_double(Rectangle), T.class_of(Rectangle)) }.not_to raise_error
+          expect { T.let(Rectangle, T.nilable(T.class_of(Rectangle))) }.not_to raise_error
+          expect { T.let(class_double(Rectangle), T.nilable(T.class_of(Rectangle))) }.not_to raise_error
         end
 
         specify 'method signatures' do