diff --git a/tests/ast/test_pre_parser.py b/tests/ast/test_pre_parser.py
index 5427532c16..c10fa999b3 100644
--- a/tests/ast/test_pre_parser.py
+++ b/tests/ast/test_pre_parser.py
@@ -132,7 +132,7 @@ def test_prerelease_invalid_version_pragma(file_version, mock_version):
     #pragma optimize codesize
     #pragma evm-version shanghai
     """,
-        Settings(evm_version="shanghai", optimize=OptimizationLevel.GAS),
+        Settings(evm_version="shanghai", optimize=OptimizationLevel.CODESIZE),
     ),
     (
         """
@@ -160,6 +160,7 @@ def test_prerelease_invalid_version_pragma(file_version, mock_version):
 
 
 @pytest.mark.parametrize("code, expected_pragmas", pragma_examples)
-def parse_pragmas(code, expected_pragmas):
+def test_parse_pragmas(code, expected_pragmas, mock_version):
+    mock_version("0.3.10")
     pragmas, _, _ = pre_parse(code)
     assert pragmas == expected_pragmas
diff --git a/vyper/compiler/__init__.py b/vyper/compiler/__init__.py
index 0b3c0d8191..6f6e0d41ea 100644
--- a/vyper/compiler/__init__.py
+++ b/vyper/compiler/__init__.py
@@ -120,17 +120,18 @@ def compile_codes(
         # make IR output the same between runs
         codegen.reset_names()
 
-        with anchor_evm_version(settings.evm_version):
-            compiler_data = CompilerData(
-                source_code,
-                contract_name,
-                interfaces,
-                source_id,
-                settings,
-                storage_layout_override,
-                show_gas_estimates,
-                no_bytecode_metadata,
-            )
+        compiler_data = CompilerData(
+            source_code,
+            contract_name,
+            interfaces,
+            source_id,
+            settings,
+            storage_layout_override,
+            show_gas_estimates,
+            no_bytecode_metadata,
+        )
+        _ = compiler_data._generate_ast
+        with anchor_evm_version(compiler_data.settings.evm_version):
             for output_format in output_formats[contract_name]:
                 if output_format not in OUTPUT_FORMATS:
                     raise ValueError(f"Unsupported format type {repr(output_format)}")
diff --git a/vyper/compiler/phases.py b/vyper/compiler/phases.py
index a1c7342320..a480435167 100644
--- a/vyper/compiler/phases.py
+++ b/vyper/compiler/phases.py
@@ -91,6 +91,7 @@ def __init__(
     @cached_property
     def _generate_ast(self):
         settings, ast = generate_ast(self.source_code, self.source_id, self.contract_name)
+
         # validate the compiler settings
         # XXX: this is a bit ugly, clean up later
         if settings.evm_version is not None: