I know this has been addressed many times and either the solutions don’t apply to me or I cant wrap my head around the solution. I get the error whenever I send my data to the client, It is partially time sensitive. Thanks for the help.

import tkinter as tk
import tkinter.filedialog
from tkinter import *
from tkinter import ttk
import os
import socket
import pickle


def main(TYPE, IP, PORT):
    clientsocket = socket.socket(socket.AF_INET, socket.SOCK_STREAM)

    try:
        clientsocket.connect((IP, PORT))
        print("Client Connected to:", IP + ":" + str(PORT))
    except socket.error as e:
        print(f"Connection error: {e}")
        return

    def send_data():
        files = tkinter.filedialog.askopenfiles(
            filetypes=[("Portable Network Graphics", "*.png"), ("JavaScript Object Notation", "*.json"),
                       ("Vorbis Compressed Audio File", "*.ogg")])
        files_data = []

        for file in files:
            file_path = file.name
            try:
                with open(file_path, "rb") as f:
                    file_data = f.read()
                    files_data.append((file_path, file_data))
            except IOError as e:
                print(f"Error reading file {file_path}: {e}")

        try:
            if clientsocket:
                clientsocket.send(pickle.dumps(files_data))
                print("Data sent successfully.")
            else:
                print("Socket is not connected.")
        except socket.error as e:
            print(f"Send error: {e}")

    def recv_data():
        try:
            data = clientsocket.recv(2048)
            if not data:
                print("No data received or socket might be closed.")
                return

            files = pickle.loads(data)
            for data_bundle in files:
                file_path = data_bundle[0]
                file_data = data_bundle[1]

                file_path_minus_name = os.path.dirname(file_path)

                try:
                    os.makedirs(file_path_minus_name, exist_ok=True)
                except OSError as e:
                    print(f"Error creating directory {file_path_minus_name}: {e}")

                try:
                    with open(file_path, "wb") as new_file:
                        new_file.write(file_data)
                        print(f"File received and written: {file_path}")
                except IOError as e:
                    print(f"Error writing file {file_path}: {e}")
        except socket.error as e:
            print(f"Receive error: {e}")
        except pickle.PickleError as e:
            print(f"Pickle error: {e}")

    def choose_resource_folder():
        global file_path
        file_path = tkinter.filedialog.askdirectory()
        print(f"Selected folder: {file_path}")
        folder_label = ttk.Label(main_frame, text=file_path).grid(column=0, row=1)

    main_window = Tk()
    main_window.resizable(0, 0)
    main_window.geometry("590x590")

    main_frame = ttk.Frame(main_window, padding=10)
    main_frame.grid()

    choose_folder = ttk.Button(main_frame, text="Choose Folder", command=choose_resource_folder).grid(column=0, row=0)
    send_button = ttk.Button(main_frame, text="Send Files", command=send_data).grid(column=1, row=0)
    recv_button = ttk.Button(main_frame, text="Recv Files", command=recv_data).grid(column=2, row=0)

    main_window.mainloop()


if __name__ == "__main__":
    main("server", "127.0.0.1", 8080)

Tried a million more tries and exceptions then i needed to. I don’t know why i thought it would help.