diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9e96101..ccba4e6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,9 @@ 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/)
 
 ## [0.6.0]
+### Changed
+- Updated CLI chat command to `vs chat`
+- Refactored CLI into separate modules
 
 ## [0.5.1]
 ### Fixed
diff --git a/README.md b/README.md
index 1f44779..88a53ee 100644
--- a/README.md
+++ b/README.md
@@ -70,7 +70,7 @@ Duration: 8.93 seconds
 
  Sync from a Zotero collection. Interactive selections are remembered for future sessions.
 ```bash
-vs sync -s zotero
+vs sync -source zotero
 
 Enter the path to your Zotero directory (Default: /Users/jbencina/Zotero): 
 
@@ -96,11 +96,11 @@ vs settings clear
 ```
 
 #### Chat Interactions
-Use `vs assistant chat` to chat with uploaded documents via the command line. The responding assistant is automatically linked to your
-vector store. Alternatively, you can use `vs assistant ui` to spawn a local Gradio instance.
+Use `vs chat` to chat with uploaded documents via the command line. The responding assistant is automatically linked to your
+vector store. Alternatively, you can use `vs chat -u` to spawn a local Gradio instance.
 
 ```bash
-vs assistant chat
+vs chat
 ✅ Assistant found: asst_123456789
 Type "exit" to quit at any time.
 
@@ -112,7 +112,7 @@ The contents of the vector store collection primarily focus on machine learning
 
 Conversations are remembered across sessions.
 ```bash
-vs assistant chat   
+vs chat   
 ✅ Assistant found: asst_123456789
 ✅ Thread found: thread_123456789
 Type "exit" to quit at any time.
@@ -123,7 +123,7 @@ Your last question to me was asking for a one sentence summary of the contents o
 
 Threads can be cleared using the `-n` flag.
 ```bash
-vs assistant chat -n
+vs chat -n
 ✅ Assistant found: asst_123456789
 Type "exit" to quit at any time.
 
diff --git a/pyproject.toml b/pyproject.toml
index 33c3638..1ed717d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -58,7 +58,7 @@ dependencies = [
 ]
 
 [project.scripts]
-vs = "vecsync.cli:cli"
+vs = "vecsync.cli.entry:cli"
 
 [project.urls]
 Homepage = "https://vecsync.io"
diff --git a/src/vecsync/cli/__init__.py b/src/vecsync/cli/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/src/vecsync/cli/chat.py b/src/vecsync/cli/chat.py
new file mode 100644
index 0000000..bf9bd05
--- /dev/null
+++ b/src/vecsync/cli/chat.py
@@ -0,0 +1,46 @@
+import click
+
+from vecsync.chat.clients.openai import OpenAIClient
+from vecsync.chat.interface import ConsoleInterface, GradioInterface
+from vecsync.constants import DEFAULT_STORE_NAME
+
+
+def start_console_chat(store_name: str, new_conversation: bool):
+    client = OpenAIClient(store_name=store_name, new_conversation=new_conversation)
+    ui = ConsoleInterface(client)
+    print('Type "exit" to quit at any time.')
+
+    while True:
+        print()
+        prompt = input("> ")
+        if prompt.lower() == "exit":
+            break
+        ui.prompt(prompt)
+
+
+def start_ui_chat(store_name: str, new_conversation: bool):
+    client = OpenAIClient(store_name=store_name, new_conversation=new_conversation)
+    ui = GradioInterface(client)
+    ui.chat_interface()
+
+
+@click.command("chat")
+@click.option(
+    "--new-conversation",
+    "-n",
+    is_flag=True,
+    help="Force the assistant to create a new thread.",
+)
+@click.option(
+    "--use-ui",
+    "-u",
+    is_flag=True,
+    help="Spawn an interactive UI instead of a console interface.",
+)
+def chat(new_conversation: bool, use_ui: bool):
+    """Chat with the assistant."""
+
+    if use_ui:
+        start_ui_chat(DEFAULT_STORE_NAME, new_conversation)
+    else:
+        start_console_chat(DEFAULT_STORE_NAME, new_conversation)
diff --git a/src/vecsync/cli/entry.py b/src/vecsync/cli/entry.py
new file mode 100644
index 0000000..8d7a84f
--- /dev/null
+++ b/src/vecsync/cli/entry.py
@@ -0,0 +1,19 @@
+import click
+
+from vecsync.cli.chat import chat
+from vecsync.cli.settings import group as settings_group
+from vecsync.cli.store import group as store_group
+from vecsync.cli.sync import sync
+
+
+@click.group()
+def cli():
+    """vecsync CLI tool"""
+    pass
+
+
+for group in [store_group, settings_group]:
+    cli.add_command(group)
+
+cli.add_command(sync)
+cli.add_command(chat)
diff --git a/src/vecsync/cli/settings.py b/src/vecsync/cli/settings.py
new file mode 100644
index 0000000..a0885f2
--- /dev/null
+++ b/src/vecsync/cli/settings.py
@@ -0,0 +1,30 @@
+import click
+from termcolor import colored
+
+from vecsync.settings import Settings
+
+
+@click.command()
+def clear():
+    """Clear the settings file."""
+    settings = Settings()
+    settings.delete()
+
+
+@click.command()
+def info():
+    """Get the location and data of the settings file."""
+    settings = Settings()
+    data = settings.info()
+    click.echo(f"Settings file location: {colored(data.location, 'yellow')}")
+    click.echo(f"Settings file data:\n{colored(data.data, 'yellow')}")
+
+
+@click.group(name="settings")
+def group():
+    """Commands to manage application settings"""
+    pass
+
+
+group.add_command(clear)
+group.add_command(info)
diff --git a/src/vecsync/cli/store.py b/src/vecsync/cli/store.py
new file mode 100644
index 0000000..76c7001
--- /dev/null
+++ b/src/vecsync/cli/store.py
@@ -0,0 +1,35 @@
+import click
+from termcolor import cprint
+
+from vecsync.constants import DEFAULT_STORE_NAME
+from vecsync.store.openai import OpenAiVectorStore
+
+
+@click.command()
+def list():
+    """List files in the remote vector store."""
+    store = OpenAiVectorStore(DEFAULT_STORE_NAME)
+    files = store.get_files()
+
+    num_total = len(files)
+
+    cprint(f"{num_total} Files in store '{store.name}':", "green")
+    for file in files:
+        cprint(f"\t✅{file.name}", "yellow")
+
+
+@click.command()
+def delete():
+    """Delete all files in the remote vector store."""
+    vstore = OpenAiVectorStore(DEFAULT_STORE_NAME)
+    vstore.delete()
+
+
+@click.group(name="store")
+def group():
+    """Commands to manage the vector store."""
+    pass
+
+
+group.add_command(list)
+group.add_command(delete)
diff --git a/src/vecsync/cli/sync.py b/src/vecsync/cli/sync.py
new file mode 100644
index 0000000..8dfb7a2
--- /dev/null
+++ b/src/vecsync/cli/sync.py
@@ -0,0 +1,44 @@
+import click
+from termcolor import cprint
+
+from vecsync.constants import DEFAULT_STORE_NAME
+from vecsync.store.file import FileStore
+from vecsync.store.openai import OpenAiVectorStore
+from vecsync.store.zotero import ZoteroStore
+
+
+@click.command()
+@click.option(
+    "--source",
+    type=str,
+    default="file",
+    help="Choose the source (file or zotero).",
+)
+def sync(source: str):
+    """Sync files from local to remote vector store."""
+    if source == "file":
+        store = FileStore()
+    elif source == "zotero":
+        try:
+            store = ZoteroStore.client()
+        except FileNotFoundError as e:
+            cprint(f'Zotero not found at "{str(e)}". Aborting.', "red")
+            return
+    else:
+        raise ValueError("Invalid source. Use 'file' or 'zotero'.")
+
+    vstore = OpenAiVectorStore(DEFAULT_STORE_NAME)
+    vstore.get_or_create()
+
+    files = store.get_files()
+
+    cprint(f"Syncing {len(files)} files from local to OpenAI", "green")
+
+    result = vstore.sync(files)
+    cprint("🏁 Sync results:", "green")
+    cprint(
+        f"Saved: {result.files_saved} | Deleted: {result.files_deleted} | Skipped: {result.files_skipped} ",
+        "yellow",
+    )
+    cprint(f"Remote count: {result.updated_count}", "yellow")
+    cprint(f"Duration: {result.duration:.2f} seconds", "yellow")
diff --git a/src/vecsync/constants.py b/src/vecsync/constants.py
new file mode 100644
index 0000000..371e39b
--- /dev/null
+++ b/src/vecsync/constants.py
@@ -0,0 +1 @@
+DEFAULT_STORE_NAME = "test"
diff --git a/src/vecsync/settings.py b/src/vecsync/settings.py
index 10830a2..d499d0f 100644
--- a/src/vecsync/settings.py
+++ b/src/vecsync/settings.py
@@ -15,6 +15,11 @@ class SettingMissing(BaseModel):
     key: str
 
 
+class SettingData(BaseModel):
+    location: str
+    data: str
+
+
 class Settings:
     def __init__(self, path: str | None = None):
         self.file = path or Path(user_config_dir("vecsync")) / "settings.json"
@@ -31,6 +36,10 @@ def delete(self):
         if self.file.exists():
             self.file.unlink()
 
+    def info(self) -> SettingData:
+        """Get the location and data of the settings file."""
+        return SettingData(location=str(self.file), data=self.file.read_text())
+
     def __getitem__(self, key: str) -> SettingExists | SettingMissing:
         with open(self.file) as f:
             data = json.load(f)
diff --git a/src/vecsync/store/base.py b/src/vecsync/store/base.py
index 2468086..88584e3 100644
--- a/src/vecsync/store/base.py
+++ b/src/vecsync/store/base.py
@@ -1,8 +1,16 @@
 # pragma: exclude file
 
+from enum import Enum
+
 from pydantic import BaseModel
 
 
+class FileStatus(str, Enum):
+    ATTACHED = "attached"
+    DETACHED = "detached"
+
+
 class StoredFile(BaseModel):
     id: str
     name: str
+    status: FileStatus
diff --git a/src/vecsync/store/openai.py b/src/vecsync/store/openai.py
index 4ec3b7a..551d414 100644
--- a/src/vecsync/store/openai.py
+++ b/src/vecsync/store/openai.py
@@ -6,7 +6,7 @@
 from termcolor import cprint
 from tqdm import tqdm
 
-from vecsync.store.base import StoredFile
+from vecsync.store.base import FileStatus, StoredFile
 
 
 class SyncOperationResult(BaseModel):
@@ -38,8 +38,24 @@ def get(self):
         raise ValueError(f"Vector store with name {self.name} not found.")
 
     def get_files(self) -> list[StoredFile]:
-        files = self.client.files.list()
-        return [StoredFile(id=file.id, name=file.filename) for file in files]
+        if not self.store:
+            self.get()
+
+        uploaded_files = self.client.files.list()
+        vector_store_files = set([f.id for f in self.client.vector_stores.files.list(vector_store_id=self.store.id)])
+
+        files = []
+
+        for file in uploaded_files:
+            files.append(
+                StoredFile(
+                    id=file.id,
+                    name=file.filename,
+                    status=FileStatus.ATTACHED if file.id in vector_store_files else FileStatus.DETACHED,
+                )
+            )
+
+        return files
 
     def get_or_create(self):
         try:
diff --git a/uv.lock b/uv.lock
index 34133e5..422d9cc 100644
--- a/uv.lock
+++ b/uv.lock
@@ -1,6 +1,12 @@
 version = 1
 revision = 2
-requires-python = ">=3.13"
+requires-python = ">=3.10"
+resolution-markers = [
+    "python_full_version >= '3.13'",
+    "python_full_version == '3.12.*'",
+    "python_full_version == '3.11.*'",
+    "python_full_version < '3.11'",
+]
 
 [[package]]
 name = "aiofiles"
@@ -25,8 +31,10 @@ name = "anyio"
 version = "4.9.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
+    { name = "exceptiongroup", marker = "python_full_version < '3.11'" },
     { name = "idna" },
     { name = "sniffio" },
+    { name = "typing-extensions", marker = "python_full_version < '3.13'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/95/7d/4c1bd541d4dffa1b52bd83fb8527089e097a106fc90b467a7313b105f840/anyio-4.9.0.tar.gz", hash = "sha256:673c0c244e15788651a4ff38710fea9675823028a6f08a5eda409e0c9840a028", size = 190949, upload_time = "2025-03-17T00:02:54.77Z" }
 wheels = [
@@ -106,6 +114,45 @@ version = "3.4.1"
 source = { registry = "https://pypi.org/simple" }
 sdist = { url = "https://files.pythonhosted.org/packages/16/b0/572805e227f01586461c80e0fd25d65a2115599cc9dad142fee4b747c357/charset_normalizer-3.4.1.tar.gz", hash = "sha256:44251f18cd68a75b56585dd00dae26183e102cd5e0f9f1466e6df5da2ed64ea3", size = 123188, upload_time = "2024-12-24T18:12:35.43Z" }
 wheels = [
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     { name = "anyio" },
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