diff --git a/backend/app/dependencies.py b/backend/app/dependencies.py
index 845d602..e43790c 100644
--- a/backend/app/dependencies.py
+++ b/backend/app/dependencies.py
@@ -47,6 +47,22 @@ from .schemas import (
 )
 
 
+def _normalize_pypi_package_name(name: str) -> str:
+    """
+    Normalize a PyPI package name for comparison.
+
+    - Strips extras brackets (e.g., "package[extra]" -> "package")
+    - Replaces sequences of hyphens, underscores, and dots with a single hyphen
+    - Lowercases the result
+
+    This follows PEP 503 normalization rules.
+    """
+    # Strip extras brackets like [test], [dev], etc.
+    base_name = re.sub(r'\[.*\]', '', name)
+    # Normalize separators and lowercase
+    return re.sub(r'[-_.]+', '-', base_name).lower()
+
+
 class DependencyError(Exception):
     """Base exception for dependency errors."""
     pass
@@ -514,10 +530,16 @@ def _detect_package_cycle(
     Returns:
         Cycle path if detected, None otherwise
     """
-    pkg_key = f"{project_name}/{package_name}"
+    # Normalize names for comparison (handles extras like [test] and separators)
+    pkg_normalized = _normalize_pypi_package_name(package_name)
+    target_pkg_normalized = _normalize_pypi_package_name(target_package)
+
+    # Use normalized key for tracking
+    pkg_key = f"{project_name.lower()}/{pkg_normalized}"
 
     # Check if we've reached the target package (cycle detected)
-    if project_name == target_project and package_name == target_package:
+    # Use normalized comparison to handle extras and naming variations
+    if project_name.lower() == target_project.lower() and pkg_normalized == target_pkg_normalized:
         return path + [pkg_key]
 
     if pkg_key in visiting:
@@ -619,12 +641,15 @@ def check_circular_dependencies(
     else:
         return None
 
+    # Normalize the initial path for consistency with _detect_package_cycle
+    normalized_path = f"{target_project.lower()}/{_normalize_pypi_package_name(target_package)}"
+
     # For each new dependency, check if it would create a cycle back to our package
     for dep in new_dependencies:
         # Check if this dependency (transitively) depends on us at the package level
         visiting: Set[str] = set()
         visited: Set[str] = set()
-        path: List[str] = [current_path]
+        path: List[str] = [normalized_path]
 
         # Check from the dependency's package
         cycle = _detect_package_cycle(
@@ -782,11 +807,11 @@ def resolve_dependencies(
         # Resolve each dependency first (depth-first)
         for dep in deps:
             # Skip self-dependencies (can happen with PyPI extras like pytest[testing])
-            # Use case-insensitive comparison and normalize for PyPI naming conventions
+            # Use normalized comparison for PyPI naming conventions (handles extras, separators)
             dep_proj_normalized = dep.dependency_project.lower()
-            dep_pkg_normalized = re.sub(r'[-_.]+', '-', dep.dependency_package).lower()
+            dep_pkg_normalized = _normalize_pypi_package_name(dep.dependency_package)
             curr_proj_normalized = proj_name.lower()
-            curr_pkg_normalized = re.sub(r'[-_.]+', '-', pkg_name).lower()
+            curr_pkg_normalized = _normalize_pypi_package_name(pkg_name)
             if dep_proj_normalized == curr_proj_normalized and dep_pkg_normalized == curr_pkg_normalized:
                 continue