diff --git a/src/codegen/cli/auth/auth_session.py b/src/codegen/cli/auth/auth_session.py
deleted file mode 100644
index e2984f470..000000000
--- a/src/codegen/cli/auth/auth_session.py
+++ /dev/null
@@ -1,82 +0,0 @@
-from dataclasses import dataclass
-from pathlib import Path
-
-from codegen.cli.api.client import RestAPI
-from codegen.cli.auth.session import CodegenSession
-from codegen.cli.auth.token_manager import get_current_token
-from codegen.cli.errors import AuthError, NoTokenError
-
-
-@dataclass
-class User:
-    full_name: str
-    email: str
-    github_username: str
-
-
-@dataclass
-class Identity:
-    token: str
-    expires_at: str
-    status: str
-    user: "User"
-
-
-class CodegenAuthenticatedSession(CodegenSession):
-    """Represents an authenticated codegen session with user and repository context"""
-
-    # =====[ Instance attributes ]=====
-    _token: str | None = None
-
-    # =====[ Lazy instance attributes ]=====
-    _identity: Identity | None = None
-
-    def __init__(self, token: str | None = None, repo_path: Path | None = None):
-        # TODO: fix jank.
-        # super().__init__(repo_path)
-        self._token = token
-
-    @property
-    def token(self) -> str | None:
-        """Get the current authentication token"""
-        if self._token:
-            return self._token
-        return get_current_token()
-
-    @property
-    def identity(self) -> Identity | None:
-        """Get the identity of the user, if a token has been provided"""
-        if self._identity:
-            return self._identity
-        if not self.token:
-            msg = "No authentication token found"
-            raise NoTokenError(msg)
-
-        identity = RestAPI(self.token).identify()
-        if not identity:
-            return None
-
-        self._identity = Identity(
-            token=self.token,
-            expires_at=identity.auth_context.expires_at,
-            status=identity.auth_context.status,
-            user=User(
-                full_name=identity.user.full_name,
-                email=identity.user.email,
-                github_username=identity.user.github_username,
-            ),
-        )
-        return self._identity
-
-    def is_authenticated(self) -> bool:
-        """Check if the session is fully authenticated, including token expiration"""
-        return bool(self.identity and self.identity.status == "active")
-
-    def assert_authenticated(self) -> None:
-        """Raise an AuthError if the session is not fully authenticated"""
-        if not self.identity:
-            msg = "No identity found for session"
-            raise AuthError(msg)
-        if self.identity.status != "active":
-            msg = "Current session is not active. API Token may be invalid or may have expired."
-            raise AuthError(msg)
diff --git a/src/codegen/cli/auth/decorators.py b/src/codegen/cli/auth/decorators.py
index 640bb98c5..d91674121 100644
--- a/src/codegen/cli/auth/decorators.py
+++ b/src/codegen/cli/auth/decorators.py
@@ -4,9 +4,10 @@
 import click
 import rich
 
-from codegen.cli.auth.auth_session import CodegenAuthenticatedSession
 from codegen.cli.auth.login import login_routine
-from codegen.cli.errors import AuthError, InvalidTokenError, NoTokenError
+from codegen.cli.auth.session import CodegenSession
+from codegen.cli.auth.token_manager import TokenManager, get_current_token
+from codegen.cli.errors import AuthError
 from codegen.cli.rich.pretty_print import pretty_print_error
 
 
@@ -15,22 +16,23 @@ def requires_auth(f: Callable) -> Callable:
 
     @functools.wraps(f)
     def wrapper(*args, **kwargs):
-        session = CodegenAuthenticatedSession.from_active_session()
+        session = CodegenSession.from_active_session()
 
         # Check for valid session
-        if not session.is_valid():
-            pretty_print_error(f"The session at path {session.repo_path} is missing or corrupt.\nPlease run 'codegen init' to re-initialize the project.")
+        if session is None or not session.is_valid():
+            pretty_print_error("There is currently no active session.\nPlease run 'codegen init' to initialize the project.")
             raise click.Abort()
 
-        try:
-            if not session.is_authenticated():
-                rich.print("[yellow]Not authenticated. Let's get you logged in first![/yellow]\n")
-                session = login_routine()
-        except (InvalidTokenError, NoTokenError) as e:
-            rich.print("[yellow]Authentication token is invalid or expired. Let's get you logged in again![/yellow]\n")
-            session = login_routine()
-        except AuthError as e:
-            raise click.ClickException(str(e))
+        if (token := get_current_token()) is None:
+            rich.print("[yellow]Not authenticated. Let's get you logged in first![/yellow]\n")
+            login_routine()
+        else:
+            try:
+                token_manager = TokenManager()
+                token_manager.authenticate_token(token)
+            except AuthError:
+                rich.print("[yellow]Authentication token is invalid or expired. Let's get you logged in again![/yellow]\n")
+                login_routine()
 
         return f(*args, session=session, **kwargs)
 
diff --git a/src/codegen/cli/auth/login.py b/src/codegen/cli/auth/login.py
index 7e4b0e7ff..3843dbad3 100644
--- a/src/codegen/cli/auth/login.py
+++ b/src/codegen/cli/auth/login.py
@@ -4,48 +4,45 @@
 import rich_click as click
 
 from codegen.cli.api.webapp_routes import USER_SECRETS_ROUTE
-from codegen.cli.auth.auth_session import CodegenAuthenticatedSession
 from codegen.cli.auth.token_manager import TokenManager
 from codegen.cli.env.global_env import global_env
 from codegen.cli.errors import AuthError
 
 
-def login_routine(token: str | None = None) -> CodegenAuthenticatedSession:
+def login_routine(token: str | None = None) -> str:
     """Guide user through login flow and return authenticated session.
 
     Args:
-        console: Optional console for output. Creates new one if not provided.
+        token: Codegen user access token associated with github account
 
     Returns:
-        CodegenSession: Authenticated session
+        str: The authenticated token
 
     Raises:
         click.ClickException: If login fails
 
     """
     # Try environment variable first
-
-    _token = token or global_env.CODEGEN_USER_ACCESS_TOKEN
+    token = token or global_env.CODEGEN_USER_ACCESS_TOKEN
 
     # If no token provided, guide user through browser flow
-    if not _token:
+    if not token:
         rich.print(f"Opening {USER_SECRETS_ROUTE} to get your authentication token...")
         webbrowser.open_new(USER_SECRETS_ROUTE)
-        _token = click.prompt("Please enter your authentication token from the browser", hide_input=False)
+        token = click.prompt("Please enter your authentication token from the browser", hide_input=False)
 
-    if not _token:
+    if not token:
         msg = "Token must be provided via CODEGEN_USER_ACCESS_TOKEN environment variable or manual input"
         raise click.ClickException(msg)
 
     # Validate and store token
-    token_manager = TokenManager()
-    session = CodegenAuthenticatedSession(token=_token)
-
     try:
-        session.assert_authenticated()
-        token_manager.save_token(_token)
+        token_manager = TokenManager()
+        token_manager.authenticate_token(token)
         rich.print(f"[green]✓ Stored token to:[/green] {token_manager.token_file}")
-        return session
+        rich.print("[cyan]📊 Hey![/cyan] We collect anonymous usage data to improve your experience 🔒")
+        rich.print("To opt out, set [green]telemetry_enabled = false[/green] in [cyan]~/.config/codegen-sh/analytics.json[/cyan] ✨")
+        return token
     except AuthError as e:
         msg = f"Error: {e!s}"
         raise click.ClickException(msg)
diff --git a/src/codegen/cli/auth/token_manager.py b/src/codegen/cli/auth/token_manager.py
index 04d61c823..7e6b6470c 100644
--- a/src/codegen/cli/auth/token_manager.py
+++ b/src/codegen/cli/auth/token_manager.py
@@ -2,7 +2,9 @@
 import os
 from pathlib import Path
 
+from codegen.cli.api.client import RestAPI
 from codegen.cli.auth.constants import AUTH_FILE, CONFIG_DIR
+from codegen.cli.errors import AuthError
 
 
 class TokenManager:
@@ -19,6 +21,17 @@ def _ensure_config_dir(self):
         if not os.path.exists(self.config_dir):
             Path(self.config_dir).mkdir(parents=True, exist_ok=True)
 
+    def authenticate_token(self, token: str) -> None:
+        """Authenticate the token with the api."""
+        identity = RestAPI(token).identify()
+        if not identity:
+            msg = "No identity found for session"
+            raise AuthError(msg)
+        if identity.auth_context.status != "active":
+            msg = "Current session is not active. API Token may be invalid or may have expired."
+            raise AuthError(msg)
+        self.save_token(token)
+
     def save_token(self, token: str) -> None:
         """Save api token to disk."""
         try:
diff --git a/src/codegen/cli/commands/create/main.py b/src/codegen/cli/commands/create/main.py
index a7a6f0b13..551d85e85 100644
--- a/src/codegen/cli/commands/create/main.py
+++ b/src/codegen/cli/commands/create/main.py
@@ -5,14 +5,15 @@
 
 from codegen.cli.api.client import RestAPI
 from codegen.cli.auth.constants import PROMPTS_DIR
+from codegen.cli.auth.decorators import requires_auth
 from codegen.cli.auth.session import CodegenSession
+from codegen.cli.auth.token_manager import get_current_token
 from codegen.cli.codemod.convert import convert_to_cli
 from codegen.cli.errors import ServerError
 from codegen.cli.rich.codeblocks import format_command, format_path
 from codegen.cli.rich.pretty_print import pretty_print_error
 from codegen.cli.rich.spinners import create_spinner
 from codegen.cli.utils.default_code import DEFAULT_CODEMOD
-from codegen.cli.workspace.decorators import requires_init
 
 
 def get_prompts_dir() -> Path:
@@ -65,7 +66,7 @@ def make_relative(path: Path) -> str:
 
 
 @click.command(name="create")
-@requires_init
+@requires_auth
 @click.argument("name", type=str)
 @click.argument("path", type=click.Path(path_type=Path), default=Path.cwd())
 @click.option("--description", "-d", default=None, help="Description of what this codemod does.")
@@ -92,7 +93,7 @@ def create_command(session: CodegenSession, name: str, path: Path, description:
         if description:
             # Use API to generate implementation
             with create_spinner("Generating function (using LLM, this will take ~10s)") as status:
-                response = RestAPI(session.token).create(name=name, query=description)
+                response = RestAPI(get_current_token()).create(name=name, query=description)
                 code = convert_to_cli(response.code, session.config.repository.language, name)
                 prompt_path.parent.mkdir(parents=True, exist_ok=True)
                 prompt_path.write_text(response.context)
diff --git a/src/codegen/cli/commands/deploy/main.py b/src/codegen/cli/commands/deploy/main.py
index 8963a3385..9b0e3c873 100644
--- a/src/codegen/cli/commands/deploy/main.py
+++ b/src/codegen/cli/commands/deploy/main.py
@@ -6,21 +6,21 @@
 
 from codegen.cli.api.client import RestAPI
 from codegen.cli.auth.decorators import requires_auth
-from codegen.cli.auth.session import CodegenSession
+from codegen.cli.auth.token_manager import get_current_token
 from codegen.cli.rich.codeblocks import format_command
 from codegen.cli.rich.spinners import create_spinner
 from codegen.cli.utils.codemod_manager import CodemodManager
 from codegen.cli.utils.function_finder import DecoratedFunction
 
 
-def deploy_functions(session: CodegenSession, functions: list[DecoratedFunction], message: str | None = None) -> None:
+def deploy_functions(functions: list[DecoratedFunction], message: str | None = None) -> None:
     """Deploy a list of functions."""
     if not functions:
         rich.print("\n[yellow]No @codegen.function decorators found.[/yellow]\n")
         return
 
     # Deploy each function
-    api_client = RestAPI(session.token)
+    api_client = RestAPI(get_current_token())
     rich.print()  # Add a blank line before deployments
 
     for func in functions:
@@ -47,7 +47,7 @@ def deploy_functions(session: CodegenSession, functions: list[DecoratedFunction]
 @click.argument("name", required=False)
 @click.option("-d", "--directory", type=click.Path(exists=True, path_type=Path), help="Directory to search for functions")
 @click.option("-m", "--message", help="Optional message to include with the deploy")
-def deploy_command(session: CodegenSession, name: str | None = None, directory: Path | None = None, message: str | None = None):
+def deploy_command(name: str | None = None, directory: Path | None = None, message: str | None = None):
     """Deploy codegen functions.
 
     If NAME is provided, deploys a specific function by that name.
@@ -70,11 +70,11 @@ def deploy_command(session: CodegenSession, name: str | None = None, directory:
                     rich.print(f"  • {func.filepath}")
                 msg = "Please specify the exact directory with --directory"
                 raise click.ClickException(msg)
-            deploy_functions(session, matching, message=message)
+            deploy_functions(matching, message=message)
         else:
             # Deploy all functions in the directory
             functions = CodemodManager.get_decorated(search_path)
-            deploy_functions(session, functions)
+            deploy_functions(functions)
     except Exception as e:
         msg = f"Failed to deploy: {e!s}"
         raise click.ClickException(msg)
diff --git a/src/codegen/cli/commands/expert/main.py b/src/codegen/cli/commands/expert/main.py
index d8e55d9d2..bbbfdbd1f 100644
--- a/src/codegen/cli/commands/expert/main.py
+++ b/src/codegen/cli/commands/expert/main.py
@@ -4,7 +4,7 @@
 
 from codegen.cli.api.client import RestAPI
 from codegen.cli.auth.decorators import requires_auth
-from codegen.cli.auth.session import CodegenSession
+from codegen.cli.auth.token_manager import get_current_token
 from codegen.cli.errors import ServerError
 from codegen.cli.workspace.decorators import requires_init
 
@@ -13,13 +13,13 @@
 @click.option("--query", "-q", help="The question to ask the expert.")
 @requires_auth
 @requires_init
-def expert_command(session: CodegenSession, query: str):
+def expert_command(query: str):
     """Asks a codegen expert a question."""
     status = Status("Asking expert...", spinner="dots", spinner_style="purple")
     status.start()
 
     try:
-        response = RestAPI(session.token).ask_expert(query)
+        response = RestAPI(get_current_token()).ask_expert(query)
         status.stop()
         rich.print("[bold green]✓ Response received[/bold green]")
         rich.print(response.response)
diff --git a/src/codegen/cli/commands/init/main.py b/src/codegen/cli/commands/init/main.py
index e52f53a8b..d79cc6261 100644
--- a/src/codegen/cli/commands/init/main.py
+++ b/src/codegen/cli/commands/init/main.py
@@ -24,6 +24,7 @@ def init_command(path: str | None = None, token: str | None = None, language: st
     # Print a message if not in a git repo
     path = Path.cwd() if path is None else Path(path)
     repo_path = get_git_root_path(path)
+    rich.print(f"Found git repository at: {repo_path}")
     if repo_path is None:
         rich.print(f"\n[bold red]Error:[/bold red] Path={path} is not in a git repository")
         rich.print("[white]Please run this command from within a git repository.[/white]")
diff --git a/src/codegen/cli/commands/login/main.py b/src/codegen/cli/commands/login/main.py
index da096bfe3..27448df42 100644
--- a/src/codegen/cli/commands/login/main.py
+++ b/src/codegen/cli/commands/login/main.py
@@ -1,11 +1,7 @@
-import sys
-
-import rich
 import rich_click as click
 
-from codegen.cli.auth.auth_session import CodegenAuthenticatedSession
 from codegen.cli.auth.login import login_routine
-from codegen.cli.auth.token_manager import TokenManager, get_current_token
+from codegen.cli.auth.token_manager import get_current_token
 
 
 @click.command(name="login")
@@ -17,19 +13,4 @@ def login_command(token: str):
         msg = "Already authenticated. Use 'codegen logout' to clear the token."
         raise click.ClickException(msg)
 
-    if not token:
-        login_routine()
-        sys.exit(1)
-
-    # Use provided token or go through login flow
-    token_manager = TokenManager()
-    session = CodegenAuthenticatedSession(token=token)
-    try:
-        session.assert_authenticated()
-        token_manager.save_token(token)
-        rich.print(f"[green]✓ Stored token to:[/green] {token_manager.token_file}")
-        rich.print("[cyan]📊 Hey![/cyan] We collect anonymous usage data to improve your experience 🔒")
-        rich.print("To opt out, set [green]telemetry_enabled = false[/green] in [cyan]~/.config/codegen-sh/analytics.json[/cyan] ✨")
-    except ValueError as e:
-        msg = f"Error: {e!s}"
-        raise click.ClickException(msg)
+    login_routine(token)
diff --git a/src/codegen/cli/commands/notebook/main.py b/src/codegen/cli/commands/notebook/main.py
index d00447288..e37599205 100644
--- a/src/codegen/cli/commands/notebook/main.py
+++ b/src/codegen/cli/commands/notebook/main.py
@@ -4,7 +4,6 @@
 
 import rich_click as click
 
-from codegen.cli.auth.constants import CODEGEN_DIR
 from codegen.cli.auth.session import CodegenSession
 from codegen.cli.rich.spinners import create_spinner
 from codegen.cli.utils.notebooks import create_notebook
@@ -12,9 +11,9 @@
 from codegen.cli.workspace.venv_manager import VenvManager
 
 
-def create_jupyter_dir() -> Path:
+def create_jupyter_dir(codegen_dir: Path) -> Path:
     """Create and return the jupyter directory."""
-    jupyter_dir = Path.cwd() / CODEGEN_DIR / "jupyter"
+    jupyter_dir = codegen_dir / "jupyter"
     jupyter_dir.mkdir(parents=True, exist_ok=True)
     return jupyter_dir
 
@@ -26,12 +25,12 @@ def create_jupyter_dir() -> Path:
 def notebook_command(session: CodegenSession, background: bool, demo: bool):
     """Launch Jupyter Lab with a pre-configured notebook for exploring your codebase."""
     with create_spinner("Setting up Jupyter environment...") as status:
-        venv = VenvManager()
+        venv = VenvManager(codegen_dir=session.codegen_dir)
 
         status.update("Checking Jupyter installation...")
         venv.ensure_jupyter()
 
-        jupyter_dir = create_jupyter_dir()
+        jupyter_dir = create_jupyter_dir(session.codegen_dir)
         notebook_path = create_notebook(jupyter_dir, demo=demo)
 
         status.update("Running Jupyter Lab...")
diff --git a/src/codegen/cli/commands/run/main.py b/src/codegen/cli/commands/run/main.py
index 13e9cf843..d34d93784 100644
--- a/src/codegen/cli/commands/run/main.py
+++ b/src/codegen/cli/commands/run/main.py
@@ -25,7 +25,7 @@ def run_command(
 ):
     """Run a codegen function by its label."""
     # Ensure venv is initialized
-    venv = VenvManager()
+    venv = VenvManager(session.codegen_dir)
     if not venv.is_initialized():
         msg = "Virtual environment not found. Please run 'codegen init' first."
         raise click.ClickException(msg)
diff --git a/src/codegen/cli/commands/run/run_cloud.py b/src/codegen/cli/commands/run/run_cloud.py
index e066b3967..d9e4e3533 100644
--- a/src/codegen/cli/commands/run/run_cloud.py
+++ b/src/codegen/cli/commands/run/run_cloud.py
@@ -6,6 +6,7 @@
 
 from codegen.cli.api.client import RestAPI
 from codegen.cli.auth.session import CodegenSession
+from codegen.cli.auth.token_manager import get_current_token
 from codegen.cli.errors import ServerError
 from codegen.cli.git.patch import apply_patch
 from codegen.cli.rich.codeblocks import format_command
@@ -24,7 +25,7 @@ def run_cloud(session: CodegenSession, function, apply_local: bool = False, diff
     """
     with create_spinner(f"Running {function.name}...") as status:
         try:
-            run_output = RestAPI(session.token).run(
+            run_output = RestAPI(get_current_token()).run(
                 function=function,
             )
 
diff --git a/src/codegen/cli/commands/run_on_pr/main.py b/src/codegen/cli/commands/run_on_pr/main.py
index 97bd003e9..c3882466f 100644
--- a/src/codegen/cli/commands/run_on_pr/main.py
+++ b/src/codegen/cli/commands/run_on_pr/main.py
@@ -4,6 +4,7 @@
 from codegen.cli.api.client import RestAPI
 from codegen.cli.auth.decorators import requires_auth
 from codegen.cli.auth.session import CodegenSession
+from codegen.cli.auth.token_manager import get_current_token
 from codegen.cli.rich.spinners import create_spinner
 from codegen.cli.utils.codemod_manager import CodemodManager
 
@@ -18,7 +19,7 @@ def run_on_pr(session: CodegenSession, codemod_name: str, pr_number: int) -> Non
 
     with create_spinner(f"Testing webhook '{codemod_name}' on PR #{pr_number}...") as status:
         try:
-            response = RestAPI(session.token).run_on_pr(
+            response = RestAPI(get_current_token()).run_on_pr(
                 codemod_name=codemod_name,
                 repo_full_name=session.config.repository.full_name,
                 github_pr_number=pr_number,
diff --git a/src/codegen/cli/workspace/initialize_workspace.py b/src/codegen/cli/workspace/initialize_workspace.py
index 178150745..b29c2e423 100644
--- a/src/codegen/cli/workspace/initialize_workspace.py
+++ b/src/codegen/cli/workspace/initialize_workspace.py
@@ -55,7 +55,7 @@ def initialize_codegen(session: CodegenSession, status: Status | str = "Initiali
 
         # Initialize virtual environment
         status_obj.update(f"   {'Creating' if isinstance(status, str) else 'Checking'} virtual environment...")
-        venv = VenvManager()
+        venv = VenvManager(session.codegen_dir)
         if not venv.is_initialized():
             venv.create_venv()
             venv.install_packages("codegen")
diff --git a/src/codegen/cli/workspace/venv_manager.py b/src/codegen/cli/workspace/venv_manager.py
index 6dc1bd86e..22467dc1a 100644
--- a/src/codegen/cli/workspace/venv_manager.py
+++ b/src/codegen/cli/workspace/venv_manager.py
@@ -2,14 +2,12 @@
 import subprocess
 from pathlib import Path
 
-from codegen.cli.auth.constants import CODEGEN_DIR
-
 
 class VenvManager:
     """Manages the virtual environment for codegen."""
 
-    def __init__(self):
-        self.codegen_dir = Path.cwd() / CODEGEN_DIR
+    def __init__(self, codegen_dir: Path):
+        self.codegen_dir = codegen_dir
         self.venv_dir = self.codegen_dir / ".venv"
 
     def is_initialized(self) -> bool: