diff --git a/vyper/ast/annotation.py b/vyper/ast/annotation.py
index 90baaab59d..e21f3ae5a2 100644
--- a/vyper/ast/annotation.py
+++ b/vyper/ast/annotation.py
@@ -85,8 +85,9 @@ def _visit_docstring(self, node):
         return node
 
     def visit_Module(self, node):
-        node.path = self._module_path
         node.name = self._module_name
+        node.path = self._module_path
+        node.source_id = self._source_id
         return self._visit_docstring(node)
 
     def visit_FunctionDef(self, node):
diff --git a/vyper/ast/nodes.py b/vyper/ast/nodes.py
index 2497928035..604ccd36e9 100644
--- a/vyper/ast/nodes.py
+++ b/vyper/ast/nodes.py
@@ -589,7 +589,8 @@ def __contains__(self, obj):
 
 
 class Module(TopLevel):
-    __slots__ = ()
+    # metadata
+    __slots__ = ("path", "source_id")
 
     def replace_in_tree(self, old_node: VyperNode, new_node: VyperNode) -> None:
         """
diff --git a/vyper/exceptions.py b/vyper/exceptions.py
index 3bde20356e..2d9073e90c 100644
--- a/vyper/exceptions.py
+++ b/vyper/exceptions.py
@@ -229,6 +229,10 @@ class CallViolation(VyperException):
     """Illegal function call."""
 
 
+class ImportCycle(VyperException):
+    """An import cycle"""
+
+
 class ImmutableViolation(VyperException):
     """Modifying an immutable variable, constant, or definition."""
 
diff --git a/vyper/semantics/analysis/base.py b/vyper/semantics/analysis/base.py
index 6d1d50d688..c39342384b 100644
--- a/vyper/semantics/analysis/base.py
+++ b/vyper/semantics/analysis/base.py
@@ -1,11 +1,13 @@
+import contextlib
 import enum
-from dataclasses import dataclass
+from dataclasses import dataclass, field
 from typing import Any, Dict, List, Optional
 
 from vyper import ast as vy_ast
 from vyper.exceptions import (
     CompilerPanic,
     ImmutableViolation,
+    ImportCycle,
     StateAccessViolation,
     VyperInternalException,
 )
@@ -145,6 +147,37 @@ def __repr__(self):
         return f"<CodeOffset: {self.offset}>"
 
 
+@dataclass
+class ImportGraph:
+    _graph: dict[vy_ast.Module, list[vy_ast.Module]] = field(default_factory=dict)
+
+    # the current path in the import graph traversal
+    _path: list[vy_ast.Module] = field(default_factory=list)
+
+    def push_path(self, module_ast: vy_ast.Module):
+        if module_ast in self._path:
+            raise ImportCycle(
+                msg=" imports ".join(f'"{t.name}" (located at {t.path})' for t in self._path)
+            )
+
+        if len(self._path) > 0:
+            parent = self._graph.setdefault(self._path[-1], [])
+            parent.append(module_ast)
+
+        self._path.append(module_ast)
+
+    def pop_path(self, expected: vy_ast.Module):
+        assert expected == self._path.pop()
+
+    @contextlib.contextmanager
+    def enter_path(self, module_ast: vy_ast.Module):
+        self.push_path(module_ast)
+        try:
+            yield
+        finally:
+            self.pop_path(module_ast)
+
+
 # base class for things that are the "result" of analysis
 class AnalysisResult:
     pass
diff --git a/vyper/semantics/analysis/module.py b/vyper/semantics/analysis/module.py
index edfb6bde8d..8999084373 100644
--- a/vyper/semantics/analysis/module.py
+++ b/vyper/semantics/analysis/module.py
@@ -1,3 +1,4 @@
+import contextlib
 import os
 from pathlib import Path, PurePath
 from typing import Any
@@ -18,7 +19,7 @@
     VariableDeclarationException,
     VyperException,
 )
-from vyper.semantics.analysis.base import ModuleInfo, VarInfo
+from vyper.semantics.analysis.base import ImportGraph, ModuleInfo, VarInfo
 from vyper.semantics.analysis.common import VyperNodeVisitorBase
 from vyper.semantics.analysis.local import validate_functions
 from vyper.semantics.analysis.utils import (
@@ -34,7 +35,13 @@
 from vyper.semantics.types.utils import type_from_annotation
 
 
-def validate_semantics(module_ast: vy_ast.Module, input_bundle: InputBundle):
+def validate_semantics(module_ast, input_bundle):
+    return validate_semantics_r(module_ast, input_bundle, ImportGraph())
+
+
+def validate_semantics_r(
+    module_ast: vy_ast.Module, input_bundle: InputBundle, import_graph: ImportGraph
+):
     """
     Analyze a Vyper module AST node, add all module-level objects to the
     namespace, type-check/validate semantics and annotate with type and analysis info
@@ -42,9 +49,8 @@ def validate_semantics(module_ast: vy_ast.Module, input_bundle: InputBundle):
     # validate semantics and annotate AST with type/semantics information
     namespace = get_namespace()
 
-    with namespace.enter_scope():
-        namespace = get_namespace()
-        analyzer = ModuleAnalyzer(module_ast, input_bundle, namespace)
+    with namespace.enter_scope(), import_graph.enter_path(module_ast):
+        analyzer = ModuleAnalyzer(module_ast, input_bundle, namespace, import_graph)
         analyzer.analyze()
 
         vy_ast.expansion.expand_annotated_ast(module_ast)
@@ -85,14 +91,32 @@ def _find_cyclic_call(fn_t: ContractFunctionT, path: list = None):
 class ModuleAnalyzer(VyperNodeVisitorBase):
     scope_name = "module"
 
+    # class object
+    _ast_of: dict[int, vy_ast.Module] = {}
+
     def __init__(
-        self, module_node: vy_ast.Module, input_bundle: InputBundle, namespace: Namespace
+        self,
+        module_node: vy_ast.Module,
+        input_bundle: InputBundle,
+        namespace: Namespace,
+        import_graph: ImportGraph,
     ) -> None:
         self.ast = module_node
         self.input_bundle = input_bundle
         self.namespace = namespace
+        self._import_graph = import_graph
+
+        self.module_t = None
 
     def analyze(self) -> ModuleT:
+        # generate a `ModuleT` from the top-level node
+        # note: also validates unique method ids
+        if "type" in self.ast._metadata:
+            assert isinstance(self.ast._metadata["type"], ModuleT)
+            # we don't need to analyse again, skip out
+            self.module_t = self.ast._metadata["type"]
+            return self.module_t
+
         module_nodes = self.ast.body.copy()
         while module_nodes:
             count = len(module_nodes)
@@ -113,8 +137,6 @@ def analyze(self) -> ModuleT:
             if count == len(module_nodes):
                 err_list.raise_if_not_empty()
 
-        # generate a `ModuleT` from the top-level node
-        # note: also validates unique method ids
         self.module_t = ModuleT(self.ast)
         self.ast._metadata["type"] = self.module_t
 
@@ -157,6 +179,15 @@ def analyze_call_graph(self):
 
             _compute_reachable_set(fn_t)
 
+    @classmethod
+    def _ast_from_file(cls, file: FileInput, alias: str):
+        if file.source_id not in cls._ast_of:
+            cls._ast_of[file.source_id] = vy_ast.parse_to_ast(
+                file.source_code, module_path=str(file.path), module_name=alias
+            )
+
+        return cls._ast_of[file.source_id]
+
     def visit_ImplementsDecl(self, node):
         type_ = type_from_annotation(node.annotation)
         if not isinstance(type_, InterfaceT):
@@ -355,12 +386,13 @@ def _load_import(self, node: vy_ast.VyperNode, level: int, module_str: str, alia
             file = self.input_bundle.load_file(path_vy)
             assert isinstance(file, FileInput)  # mypy hint
 
-            # TODO share work if same file is imported
-            module_ast = vy_ast.parse_to_ast(
-                file.source_code, module_path=str(path_vy), module_name=alias
-            )
+            module_ast = self.__class__._ast_from_file(file, alias)
+
             with override_global_namespace(Namespace()):
-                validate_semantics(module_ast, self.input_bundle)
+                with tag_exceptions(node):
+                    validate_semantics_r(
+                        module_ast, self.input_bundle, import_graph=self._import_graph
+                    )
                 module_t = module_ast._metadata["type"]
 
                 return ModuleInfo(module_t, decl_node=node)
@@ -376,6 +408,14 @@ def _load_import(self, node: vy_ast.VyperNode, level: int, module_str: str, alia
             raise ModuleNotFoundError(module_str)
 
 
+@contextlib.contextmanager
+def tag_exceptions(node: vy_ast.VyperNode) -> Any:
+    try:
+        yield
+    except VyperException as e:
+        raise e.with_annotation(node) from None
+
+
 # convert an import to a path (without suffix)
 def _import_to_path(level: int, module_str: str) -> PurePath:
     base_path = ""