diff --git a/flomo/cli.py b/flomo/cli.py
index a7b5bb6..abdbada 100644
--- a/flomo/cli.py
+++ b/flomo/cli.py
@@ -1,9 +1,10 @@
 import datetime
-import sqlite3
 
 import click
 import click_aliases
 
+import flomo.config as config
+import flomo.errors as errors
 import flomo.tracker as tracker
 import flomo.ui as ui
 
@@ -16,6 +17,19 @@ def flomo():
     pass
 
 
+@flomo.command(aliases=["i"])
+def init():
+    """
+    Initialize the required files for Flomo.
+    """
+    db = tracker.Tracker(initializing=True)
+    db.create_table()
+    db.conn.close()
+
+    conf = config.Config(initializing=True)
+    conf.create_config()
+
+
 @flomo.command(aliases=["s"])
 @click.option("-t", "--tag", default="Default", help="Session tag name.")
 @click.option("-n", "--name", default="Work", help="Session Name")
@@ -23,11 +37,14 @@ def start(tag: str, name: str):
     """
     Start a Flowmodoro session.
     """
-    db = tracker.Tracker()
-    db.create_table()
-    session_id = db.create_session(tag, name, datetime.datetime.now())
-    db.conn.close()
-    ui.main(tag.lower(), name, session_id)
+    try:
+        db = tracker.Tracker()
+        db.create_table()
+        session_id = db.create_session(tag, name, datetime.datetime.now())
+        db.conn.close()
+        ui.main(tag.lower(), name, session_id)
+    except (errors.DBFileNotFoundError, errors.NoConfigError) as e:
+        print(e)
 
 
 @flomo.command(aliases=["t"])
@@ -37,8 +54,29 @@ def tracking():
     """
     try:
         tracker.show_sessions()
-    except sqlite3.OperationalError:
-        print("No sessions were found.")
+    except (
+        errors.DBFileNotFoundError,
+        errors.NoSessionsError,
+        errors.NoSessionError,
+    ) as e:
+        print(e)
+
+
+@flomo.command(aliases=["d"])
+@click.argument("session_id")
+def delete(session_id: str):
+    """
+    Delete a session.
+    """
+    try:
+        db = tracker.Tracker()
+        db.delete_session(int(session_id))
+        db.conn.close()
+    except (
+        errors.DBFileNotFoundError,
+        errors.NoSessionError,
+    ) as e:
+        print(e)
 
 
 if __name__ == "__main__":
diff --git a/flomo/config.py b/flomo/config.py
new file mode 100644
index 0000000..ed7c7ab
--- /dev/null
+++ b/flomo/config.py
@@ -0,0 +1,18 @@
+import os
+
+import flomo.errors as errors
+import flomo.helpers as helpers
+
+
+class Config:
+    def __init__(self, initializing: bool = False):
+        self.path = helpers.get_path("config.json", in_data=True)
+
+        if not initializing and not self._config_file_exists():
+            raise errors.NoConfigError()
+
+    def _config_file_exists(self):
+        return os.path.exists(self.path)  # TODO: Check if file contents are proper.
+
+    def create_config(self):
+        pass
diff --git a/flomo/errors.py b/flomo/errors.py
new file mode 100644
index 0000000..d2b4097
--- /dev/null
+++ b/flomo/errors.py
@@ -0,0 +1,18 @@
+class DBFileNotFoundError(Exception):
+    def __init__(self):
+        super().__init__("Database file does not exist. Please run `flomo init`.")
+
+
+class NoConfigError(Exception):
+    def __init__(self):
+        super().__init__("No config file found. Please run `flomo init`.")
+
+
+class NoSessionsError(Exception):
+    def __init__(self):
+        super().__init__("No sessions were found.")
+
+
+class NoSessionError(Exception):
+    def __init__(self, session_id):
+        super().__init__(f"No session with ID {session_id} was found.")
diff --git a/flomo/helpers.py b/flomo/helpers.py
index 355704a..e1ae9f9 100644
--- a/flomo/helpers.py
+++ b/flomo/helpers.py
@@ -4,8 +4,6 @@
 
 from playsound import playsound
 
-import flomo.tracker as tracker
-
 
 def get_path(file_name: str, in_data: bool = False):
     dir_path = os.path.dirname(os.path.realpath(__file__))
@@ -33,7 +31,7 @@ def play_sound():
 
 
 def message_log(message: str):
-    path = get_path("message.log", True)
+    path = get_path("message.log", in_data=True)
 
     with open(path, "a") as f:
         f.write(message + "\n")
@@ -44,9 +42,3 @@ def format_time(seconds: int) -> str:
     mins, secs = divmod(remainder, 60)
 
     return f"{hours:02}:{mins:02}:{secs:02}"
-
-
-def update_session(session_id: float):
-    db = tracker.Tracker()
-    db.update_session(session_id, datetime.datetime.now())
-    db.conn.close()
diff --git a/flomo/tracker.py b/flomo/tracker.py
index 43a7633..743614c 100644
--- a/flomo/tracker.py
+++ b/flomo/tracker.py
@@ -4,26 +4,32 @@
 import pandas
 import tabulate
 
+import flomo.errors as errors
 import flomo.helpers as helpers
 
 
 class Tracker:
-    def __init__(self):
-        path = helpers.get_path("sessions.db", True)
+    def __init__(self, initializing: bool = False):
+        path = helpers.get_path("sessions.db", in_data=True)
 
         self.conn = sqlite3.connect(path)
         self.cursor = self.conn.cursor()
 
+        if not initializing and not self._db_file_exists():
+            raise errors.DBFileNotFoundError()
+
+    def _db_file_exists(self):
+        self.cursor.execute("SELECT name FROM sqlite_master WHERE type='table';")
+        return bool(self.cursor.fetchall())
+
     def create_table(self):
         self.cursor.execute(
             "CREATE TABLE IF NOT EXISTS sessions (id FLOAT PRIMARY KEY, date_time TEXT, tag TEXT, name TEXT, total_time TEXT)"
         )
         self.conn.commit()
 
-    def create_session(
-        self, tag: str, name: str, start_time: datetime.datetime
-    ) -> float:
-        session_id = start_time.timestamp() % 1000000
+    def create_session(self, tag: str, name: str, start_time: datetime.datetime) -> int:
+        session_id = int(start_time.timestamp() % 1000000)
         self.cursor.execute(
             "INSERT INTO sessions (id, date_time, tag, name) VALUES (?, ?, ?, ?)",
             (session_id, start_time.strftime("%Y-%m-%d %H:%M:%S"), tag, name),
@@ -31,7 +37,7 @@ def create_session(
         self.conn.commit()
         return session_id
 
-    def update_session(self, session_id: float, end_time: datetime.datetime):
+    def update_session(self, session_id: int, end_time: datetime.datetime):
         date_time = self.get_session(session_id)[1]
         total_time = end_time - datetime.datetime.strptime(
             date_time, "%Y-%m-%d %H:%M:%S"
@@ -49,10 +55,22 @@ def get_sessions(self):
         self.cursor.execute("SELECT * FROM sessions")
         return self.cursor.fetchall()
 
-    def get_session(self, session_id: float):
+    def get_session(self, session_id: int):
         self.cursor.execute("SELECT * FROM sessions WHERE id = ?", (session_id,))
         return self.cursor.fetchone()
 
+    def delete_session(self, session_id: int):
+        if not self.get_session(session_id):
+            raise errors.NoSessionError(session_id)
+        self.cursor.execute("DELETE FROM sessions WHERE id = ?", (session_id,))
+        self.conn.commit()
+
+
+def update_session(session_id: int):
+    db = Tracker()
+    db.update_session(session_id, datetime.datetime.now())
+    db.conn.close()
+
 
 def show_sessions():
     db = Tracker()
diff --git a/flomo/ui.py b/flomo/ui.py
index 5aa320b..f274809 100644
--- a/flomo/ui.py
+++ b/flomo/ui.py
@@ -10,6 +10,7 @@
 from rich.text import Text
 
 import flomo.helpers as helpers
+import flomo.tracker as tracker
 
 
 class UI:
@@ -63,7 +64,7 @@ def get_input(self):
             return self.terminal.inkey().lower()
 
 
-def main(tag: str, name: str, session_id: float):
+def main(tag: str, name: str, session_id: int):
     # TODO: Do something with the Terminal close issue
     try:
         while True:
@@ -123,5 +124,5 @@ def main(tag: str, name: str, session_id: float):
         if isinstance(e, Exception):
             helpers.message_log(f"{datetime.datetime.now()} - Error: {e}")
     finally:
-        helpers.update_session(session_id)
+        tracker.update_session(session_id)
         sys.exit()