diff --git a/easyinstall.sh b/easyinstall.sh
index 499476d0..37084a61 100755
--- a/easyinstall.sh
+++ b/easyinstall.sh
@@ -710,6 +710,29 @@ function setupWirelessNetworking() {
     sudo reboot
 }
 
+# Detects or creates the file sharing directory
+function createFileSharingDir() {
+    if [ ! -d "$FILE_SHARE_PATH" ] && [ -d "$HOME/afpshare" ]; then
+        echo
+        echo "File server dir $HOME/afpshare detected. This script will rename it to $FILE_SHARE_PATH."
+        echo
+        echo "Do you want to proceed with the installation? [y/N]"
+        read -r REPLY
+        if [ "$REPLY" == "y" ] || [ "$REPLY" == "Y" ]; then
+            sudo mv "$HOME/afpshare" "$FILE_SHARE_PATH" || exit 1
+        else
+            exit 0
+        fi
+    elif [ -d "$FILE_SHARE_PATH" ]; then
+        echo "Found a $FILE_SHARE_PATH directory; will use it for file sharing."
+    else
+        echo "Creating the $FILE_SHARE_PATH directory and granting read/write permissions to all users..."
+        sudo mkdir -p "$FILE_SHARE_PATH"
+        sudo chown -R "$USER:$USER" "$FILE_SHARE_PATH"
+        chmod -Rv 775 "$FILE_SHARE_PATH"
+    fi
+}
+
 # Downloads, compiles, and installs Netatalk (AppleShare server)
 function installNetatalk() {
     NETATALK_VERSION="230301"
@@ -729,19 +752,6 @@ function installNetatalk() {
         fi
     fi
 
-    if [ ! -d "$FILE_SHARE_PATH" ] && [ -d "$HOME/afpshare" ]; then
-        echo
-        echo "File server dir $HOME/afpshare detected. This script will rename it to $FILE_SHARE_PATH."
-        echo
-        echo "Do you want to proceed with the installation? [y/N]"
-        read -r REPLY
-        if [ "$REPLY" == "y" ] || [ "$REPLY" == "Y" ]; then
-            sudo mv "$HOME/afpshare" "$FILE_SHARE_PATH" || exit 1
-        else
-            exit 0
-        fi
-    fi
-
     echo
     echo "Downloading tarball to $HOME..."
     cd $HOME || exit 1
@@ -874,26 +884,6 @@ function installSamba() {
         fi
     fi
 
-    if [ ! -d "$FILE_SHARE_PATH" ] && [ -d "$HOME/afpshare" ]; then
-        echo
-        echo "File server dir $HOME/afpshare detected. This script will rename it to $FILE_SHARE_PATH."
-        echo
-        echo "Do you want to proceed with the installation? [y/N]"
-        read -r REPLY
-        if [ "$REPLY" == "y" ] || [ "$REPLY" == "Y" ]; then
-            sudo mv "$HOME/afpshare" "$FILE_SHARE_PATH" || exit 1
-        else
-            exit 0
-        fi
-    elif [ -d "$FILE_SHARE_PATH" ]; then
-        echo "Found a $FILE_SHARE_PATH directory; will use it for file sharing."
-    else
-        echo "Creating the $FILE_SHARE_PATH directory and granting read/write permissions to all users..."
-        sudo mkdir -p "$FILE_SHARE_PATH"
-        sudo chown -R "$USER:$USER" "$FILE_SHARE_PATH"
-        chmod -Rv 775 "$FILE_SHARE_PATH"
-    fi
-
     echo ""
     echo "Installing dependencies..."
     sudo apt-get update || true
@@ -1279,6 +1269,7 @@ function runChoice() {
           ;;
           7)
               echo "Installing AppleShare File Server"
+              createFileSharingDir
               installNetatalk
               echo "Installing AppleShare File Server - Complete!"
           ;;
@@ -1290,6 +1281,7 @@ function runChoice() {
               echo "WARNING: The FTP server may transfer unencrypted data over the network."
               echo "Proceed with this installation only if you are on a private, secure network."
               sudoCheck
+              createFileSharingDir
               installFtp
               echo "Installing FTP File Server - Complete!"
           ;;
@@ -1301,6 +1293,7 @@ function runChoice() {
               echo " - Create a directory in the current user's home directory where shared files will be stored"
               echo " - Create a Samba user for the current user"
               sudoCheck
+              createFileSharingDir
               installSamba
               echo "Installing SMB File Server - Complete!"
           ;;
diff --git a/python/web/src/templates/index.html b/python/web/src/templates/index.html
index b9d74cc4..f6364c92 100644
--- a/python/web/src/templates/index.html
+++ b/python/web/src/templates/index.html
@@ -383,8 +383,11 @@
     </summary>
     <ul>
         <li>{{ _("Disk Images") }} = {{ env["image_dir"] }}</li>
+	{% if file_server_dir_exists %}
         <li>{{ _("Shared Files") }} = {{ FILE_SERVER_DIR }}</li>
-        <li>{{ _("To access shared files remotely, you may have to install one of the file servers first.") }}</li>
+	{% else %}
+        <li>{{ _("Install a file server and create the shared files directory in order to share files between the Pi and your vintage computers.") }}</li>
+	{% endif %}
     </ul>
 </details>
 
@@ -399,6 +402,7 @@
     {% endfor %}
     <option value="/" selected>/</option>
     </select>
+    {% if file_server_dir_exists %}
     <input type="radio" name="destination" id="shared_files" value="shared_files">
     <label for="shared_files">{{ _("Shared Files") }}</label>
     <select name="shared_subdir" id="shared_subdir">
@@ -407,6 +411,7 @@
     {% endfor %}
     <option value="/" selected>/</option>
     </select>
+    {% endif %}
     <input type="submit" value="{{ _("Download") }}" onclick="processNotify('{{ _("Downloading File...") }}')">
 </form>
 </section>
diff --git a/python/web/src/templates/upload.html b/python/web/src/templates/upload.html
index 67d6b57f..c572469e 100644
--- a/python/web/src/templates/upload.html
+++ b/python/web/src/templates/upload.html
@@ -6,7 +6,9 @@
     <li>{{ _("The largest file size accepted in this form is %(max_file_size)s MiB. Use other file transfer means for larger files.", max_file_size=max_file_size) }}</li>
     <li>{{ _("You have to manually clean up partially uploaded files, as a result of cancelling the upload or closing this page.") }}</li>
     <li>{{ _("Disk Images") }} = {{ env["image_dir"] }}</li>
+    {% if file_server_dir_exists %}
     <li>{{ _("Shared Files") }} = {{ FILE_SERVER_DIR }}</li>
+    {% endif %}
     <li>{{ _("PiSCSI Config") }} = {{ CFG_DIR }}</li>
 </ul>
 
@@ -20,6 +22,7 @@
     {% endfor %}
     <option value="/" selected>/</option>
     </select>
+    {% if file_server_dir_exists %}
     <input type="radio" name="destination" id="shared_files" value="shared_files">
     <label for="shared_files">{{ _("Shared Files") }}</label>
     <select name="shared_subdir" id="shared_subdir">
@@ -28,6 +31,7 @@
     {% endfor %}
     <option value="/" selected>/</option>
     </select>
+    {% endif %}
     <input type="radio" name="destination" id="piscsi_config" value="piscsi_config">
     <label for="piscsi_config">{{ _("PiSCSI Config") }}</label>
 </form>
diff --git a/python/web/src/web.py b/python/web/src/web.py
index 40d9b032..5ac8ea22 100644
--- a/python/web/src/web.py
+++ b/python/web/src/web.py
@@ -24,7 +24,6 @@ from flask import (
     send_from_directory,
     make_response,
     session,
-    abort,
     jsonify,
 )
 
@@ -44,6 +43,7 @@ from return_code_mapper import ReturnCodeMapper
 from socket_cmds_flask import SocketCmdsFlask
 
 from web_utils import (
+    working_dirs_exist,
     sort_and_format_devices,
     get_valid_scsi_ids,
     map_device_types_and_names,
@@ -209,16 +209,9 @@ def index():
     """
     Sets up data structures for and renders the index page
     """
-    if not piscsi_cmd.is_token_auth()["status"] and not APP.config["PISCSI_TOKEN"]:
-        abort(
-            403,
-            _(
-                "PiSCSI is password protected. "
-                "Start the Web Interface with the --password parameter."
-            ),
-        )
-
     server_info = piscsi_cmd.get_server_info()
+    working_dirs_exist((server_info["image_dir"], CFG_DIR))
+
     devices = piscsi_cmd.list_devices()
     device_types = map_device_types_and_names(piscsi_cmd.get_device_types()["device_types"])
     image_files = file_cmd.list_images()
@@ -277,6 +270,7 @@ def index():
         drive_properties=format_drive_properties(APP.config["PISCSI_DRIVE_PROPERTIES"]),
         images_subdirs=file_cmd.list_subdirs(server_info["image_dir"]),
         shared_subdirs=file_cmd.list_subdirs(FILE_SERVER_DIR),
+        file_server_dir_exists=Path(FILE_SERVER_DIR).exists(),
         RESERVATIONS=RESERVATIONS,
         CFG_DIR=CFG_DIR,
         FILE_SERVER_DIR=FILE_SERVER_DIR,
@@ -302,6 +296,8 @@ def drive_list():
     """
     Sets up the data structures and kicks off the rendering of the drive list page
     """
+    server_info = piscsi_cmd.get_server_info()
+    working_dirs_exist((server_info["image_dir"], CFG_DIR))
 
     return response(
         template="drives.html",
@@ -317,12 +313,14 @@ def upload_page():
     Sets up the data structures and kicks off the rendering of the file uploading page
     """
     server_info = piscsi_cmd.get_server_info()
+    working_dirs_exist((server_info["image_dir"], CFG_DIR))
 
     return response(
         template="upload.html",
         page_title=_("PiSCSI File Upload"),
         images_subdirs=file_cmd.list_subdirs(server_info["image_dir"]),
         shared_subdirs=file_cmd.list_subdirs(FILE_SERVER_DIR),
+        file_server_dir_exists=Path(FILE_SERVER_DIR).exists(),
         max_file_size=int(int(MAX_FILE_SIZE) / 1024 / 1024),
         CFG_DIR=CFG_DIR,
         FILE_SERVER_DIR=FILE_SERVER_DIR,
@@ -516,6 +514,7 @@ def show_diskinfo():
     if not safe_path["status"]:
         return response(error=True, message=safe_path["msg"])
     server_info = piscsi_cmd.get_server_info()
+    working_dirs_exist((server_info["image_dir"], CFG_DIR))
     returncode, diskinfo = sys_cmd.get_diskinfo(Path(server_info["image_dir"]) / file_name)
     if returncode == 0:
         return response(
@@ -1474,6 +1473,12 @@ if __name__ == "__main__":
     file_cmd = FileCmds(sock_cmd=sock_cmd, piscsi=piscsi_cmd, token=APP.config["PISCSI_TOKEN"])
     sys_cmd = SysCmds()
 
+    if not piscsi_cmd.is_token_auth()["status"] and not APP.config["PISCSI_TOKEN"]:
+        raise Exception(
+            "PiSCSI is password protected. "
+            "Start the Web Interface with the --password parameter."
+        )
+
     if Path(f"{CFG_DIR}/{DEFAULT_CONFIG}").is_file():
         file_cmd.read_config(DEFAULT_CONFIG)
     if Path(f"{DRIVE_PROPERTIES_FILE}").is_file():
diff --git a/python/web/src/web_utils.py b/python/web/src/web_utils.py
index 3cf71b3e..d085510f 100644
--- a/python/web/src/web_utils.py
+++ b/python/web/src/web_utils.py
@@ -9,13 +9,26 @@ from pathlib import Path
 from ua_parser import user_agent_parser
 from re import findall
 
-from flask import request, make_response
+from flask import request, make_response, abort
 from flask_babel import _
 from werkzeug.utils import secure_filename
 
 from piscsi.sys_cmds import SysCmds
 
 
+def working_dirs_exist(working_dirs):
+    """
+    Method for validating that working dirs exist.
+    Takes (tuple) of (str) working_dirs with paths to required dirs.
+    """
+    for dir_path in working_dirs:
+        if not Path(dir_path).exists():
+            abort(
+                503,
+                _(f"Please create directory: {dir_path}"),
+            )
+
+
 def get_valid_scsi_ids(devices, reserved_ids):
     """
     Takes a list of (dict)s devices, and list of (int)s reserved_ids.