diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2dab338..8fd6d03 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,12 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## [1.4.5] - 2026-01-01
+
+### Fixed
+
+- Separate httpx and SQLAlchemy async contexts in bulk sync (fixes greenlet error)
+
 ## [1.4.4] - 2026-01-01
 
 ### Fixed
diff --git a/pyproject.toml b/pyproject.toml
index c603e46..d16023d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "core-api"
-version = "1.4.4"
+version = "1.4.5"
 description = "Core Code API - Infrastructure management and tools API"
 readme = "README.md"
 requires-python = ">=3.12"
diff --git a/src/auth/service.py b/src/auth/service.py
index 63ab50a..0117944 100644
--- a/src/auth/service.py
+++ b/src/auth/service.py
@@ -369,6 +369,8 @@ class AuthService:
         errors = []
         total_in_authentik = 0
 
+        # Step 1: Fetch all user data from Authentik API
+        authentik_users = []
         try:
             async with httpx.AsyncClient(timeout=30.0, follow_redirects=True) as client:
                 # Authenticate with Authentik to get session cookie
@@ -393,72 +395,73 @@ class AuthService:
                 authentik_users = data.get("results", [])
                 total_in_authentik = data.get("pagination", {}).get("count", len(authentik_users))
 
-                for auth_user in authentik_users:
-                    try:
-                        # Skip service accounts and inactive users
-                        if auth_user.get("type") in ("service_account", "internal_service_account"):
-                            continue
-                        if not auth_user.get("is_active", True):
-                            continue
-
-                        # Extract user data from Authentik
-                        authentik_id = uuid.UUID(auth_user["uuid"])
-                        email = auth_user.get("email") or f"{auth_user['username']}@local"
-                        name = auth_user.get("name") or auth_user.get("username", "Unknown")
-                        avatar_url = auth_user.get("avatar")
-
-                        # Get user's groups for role mapping
-                        groups = []
-                        groups_summary = auth_user.get("groups_obj", [])
-                        for group in groups_summary:
-                            groups.append(group.get("name", ""))
-
-                        # Check if user exists
-                        stmt = select(User).where(User.authentik_id == authentik_id)
-                        result = await self.session.execute(stmt)
-                        user = result.scalar_one_or_none()
-
-                        if user is None:
-                            # Create new user
-                            user = User(
-                                authentik_id=authentik_id,
-                                email=email,
-                                name=name,
-                                avatar_url=avatar_url,
-                            )
-                            self.session.add(user)
-                            await self.session.flush()
-
-                            # Create default preferences
-                            preferences = UserPreferences(user_id=user.id)
-                            self.session.add(preferences)
-                            created += 1
-                            logger.info(f"Created user from Authentik: {email}")
-                        else:
-                            # Update existing user
-                            user.email = email
-                            user.name = name
-                            user.avatar_url = avatar_url
-                            updated += 1
-                            logger.info(f"Updated user from Authentik: {email}")
-
-                        # Sync roles from groups
-                        await self.sync_roles(user, groups)
-
-                    except Exception as e:
-                        failed += 1
-                        error_msg = f"Failed to sync user {auth_user.get('username', 'unknown')}: {str(e)}"
-                        errors.append(error_msg)
-                        logger.warning(error_msg)
-
-                # Commit all changes
-                await self.session.commit()
-
         except httpx.HTTPStatusError as e:
             raise ValueError(f"Authentik API error: {e.response.status_code}")
         except httpx.RequestError as e:
             raise ValueError(f"Failed to connect to Authentik: {str(e)}")
 
+        # Step 2: Sync users to database (outside of httpx context to avoid greenlet issues)
+        for auth_user in authentik_users:
+            try:
+                # Skip service accounts and inactive users
+                if auth_user.get("type") in ("service_account", "internal_service_account"):
+                    continue
+                if not auth_user.get("is_active", True):
+                    continue
+
+                # Extract user data from Authentik
+                authentik_id = uuid.UUID(auth_user["uuid"])
+                email = auth_user.get("email") or f"{auth_user['username']}@local"
+                name = auth_user.get("name") or auth_user.get("username", "Unknown")
+                avatar_url = auth_user.get("avatar")
+
+                # Get user's groups for role mapping
+                groups = []
+                groups_summary = auth_user.get("groups_obj", [])
+                for group in groups_summary:
+                    groups.append(group.get("name", ""))
+
+                # Check if user exists
+                stmt = select(User).where(User.authentik_id == authentik_id)
+                result = await self.session.execute(stmt)
+                user = result.scalar_one_or_none()
+
+                if user is None:
+                    # Create new user
+                    user = User(
+                        authentik_id=authentik_id,
+                        email=email,
+                        name=name,
+                        avatar_url=avatar_url,
+                    )
+                    self.session.add(user)
+                    await self.session.flush()
+
+                    # Create default preferences
+                    preferences = UserPreferences(user_id=user.id)
+                    self.session.add(preferences)
+                    created += 1
+                    logger.info(f"Created user from Authentik: {email}")
+                else:
+                    # Update existing user
+                    user.email = email
+                    user.name = name
+                    user.avatar_url = avatar_url
+                    updated += 1
+                    logger.info(f"Updated user from Authentik: {email}")
+
+                # Sync roles from groups
+                await self.sync_roles(user, groups)
+
+            except Exception as e:
+                failed += 1
+                error_msg = f"Failed to sync user {auth_user.get('username', 'unknown')}: {str(e)}"
+                errors.append(error_msg)
+                logger.warning(error_msg)
+
+        # Commit all changes
+        await self.session.commit()
+
         return BulkSyncResultSchema(
             created=created,
             updated=updated,