From e1b01abf9b3b7a90864d7d6417b7dc197a322b7c Mon Sep 17 00:00:00 2001
From: Mondo Diaz <armando.m.diaz@boeing.com>
Date: Fri, 30 Jan 2026 15:34:19 -0600
Subject: [PATCH] Add PEP 440 version constraint matching for dependency
 resolution

- Parse version constraints like >=1.9, <2.0 using packaging library
- Find the latest version that satisfies the constraint
- Support wildcard (*) to get latest version
- Fall back to exact version and tag matching
---
 backend/app/dependencies.py | 124 ++++++++++++++++++++++++++++++++----
 1 file changed, 113 insertions(+), 11 deletions(-)

diff --git a/backend/app/dependencies.py b/backend/app/dependencies.py
index 196a927..24569fe 100644
--- a/backend/app/dependencies.py
+++ b/backend/app/dependencies.py
@@ -10,11 +10,20 @@ Handles:
 - Conflict detection
 """
 
+import re
 import yaml
 from typing import List, Dict, Any, Optional, Set, Tuple
 from sqlalchemy.orm import Session
 from sqlalchemy import and_
 
+# Import packaging for PEP 440 version matching
+try:
+    from packaging.specifiers import SpecifierSet, InvalidSpecifier
+    from packaging.version import Version, InvalidVersion
+    HAS_PACKAGING = True
+except ImportError:
+    HAS_PACKAGING = False
+
 from .models import (
     Project,
     Package,
@@ -304,6 +313,87 @@ def get_reverse_dependencies(
     )
 
 
+def _is_version_constraint(version_str: str) -> bool:
+    """Check if a version string contains constraint operators."""
+    if not version_str:
+        return False
+    # Check for common constraint operators
+    return any(op in version_str for op in ['>=', '<=', '!=', '~=', '>', '<', '==', '*'])
+
+
+def _resolve_version_constraint(
+    db: Session,
+    package: Package,
+    constraint: str,
+) -> Optional[Tuple[str, str, int]]:
+    """
+    Resolve a version constraint (e.g., '>=1.9') to a specific version.
+
+    Uses PEP 440 version matching to find the best matching version.
+
+    Args:
+        db: Database session
+        package: Package to search versions in
+        constraint: Version constraint string (e.g., '>=1.9', '<2.0,>=1.5')
+
+    Returns:
+        Tuple of (artifact_id, resolved_version, size) or None if not found
+    """
+    if not HAS_PACKAGING:
+        # Fallback: if packaging not available, can't do constraint matching
+        return None
+
+    # Handle wildcard - return latest version
+    if constraint == '*':
+        # Get the latest version by created_at
+        latest = db.query(PackageVersion).filter(
+            PackageVersion.package_id == package.id,
+        ).order_by(PackageVersion.created_at.desc()).first()
+        if latest:
+            artifact = db.query(Artifact).filter(Artifact.id == latest.artifact_id).first()
+            if artifact:
+                return (artifact.id, latest.version, artifact.size)
+        return None
+
+    try:
+        specifier = SpecifierSet(constraint)
+    except InvalidSpecifier:
+        # Invalid constraint, try as exact version
+        return None
+
+    # Get all versions for this package
+    all_versions = db.query(PackageVersion).filter(
+        PackageVersion.package_id == package.id,
+    ).all()
+
+    if not all_versions:
+        return None
+
+    # Find matching versions
+    matching = []
+    for pv in all_versions:
+        try:
+            v = Version(pv.version)
+            if v in specifier:
+                matching.append((pv, v))
+        except InvalidVersion:
+            # Skip invalid versions
+            continue
+
+    if not matching:
+        return None
+
+    # Sort by version (descending) and return the latest matching
+    matching.sort(key=lambda x: x[1], reverse=True)
+    best_match = matching[0][0]
+
+    artifact = db.query(Artifact).filter(Artifact.id == best_match.artifact_id).first()
+    if artifact:
+        return (artifact.id, best_match.version, artifact.size)
+
+    return None
+
+
 def _resolve_dependency_to_artifact(
     db: Session,
     project_name: str,
@@ -314,11 +404,17 @@ def _resolve_dependency_to_artifact(
     """
     Resolve a dependency constraint to an artifact ID.
 
+    Supports:
+    - Exact version matching (e.g., '1.2.3')
+    - Version constraints (e.g., '>=1.9', '<2.0,>=1.5')
+    - Tag matching
+    - Wildcard ('*' for any version)
+
     Args:
         db: Database session
         project_name: Project name
         package_name: Package name
-        version: Version constraint (exact)
+        version: Version or version constraint
         tag: Tag constraint
 
     Returns:
@@ -337,17 +433,23 @@ def _resolve_dependency_to_artifact(
         return None
 
     if version:
-        # Look up by version
-        pkg_version = db.query(PackageVersion).filter(
-            PackageVersion.package_id == package.id,
-            PackageVersion.version == version,
-        ).first()
-        if pkg_version:
-            artifact = db.query(Artifact).filter(
-                Artifact.id == pkg_version.artifact_id
+        # Check if this is a version constraint (>=, <, etc.) or exact version
+        if _is_version_constraint(version):
+            result = _resolve_version_constraint(db, package, version)
+            if result:
+                return result
+        else:
+            # Look up by exact version
+            pkg_version = db.query(PackageVersion).filter(
+                PackageVersion.package_id == package.id,
+                PackageVersion.version == version,
             ).first()
-            if artifact:
-                return (artifact.id, version, artifact.size)
+            if pkg_version:
+                artifact = db.query(Artifact).filter(
+                    Artifact.id == pkg_version.artifact_id
+                ).first()
+                if artifact:
+                    return (artifact.id, version, artifact.size)
 
         # Also check if there's a tag with this exact name
         tag_record = db.query(Tag).filter(