diff --git a/core/services/helpers/download_file.py b/core/services/helpers/download_file.py
index 8d62a9d..17dc07d 100644
--- a/core/services/helpers/download_file.py
+++ b/core/services/helpers/download_file.py
@@ -77,13 +77,19 @@ def download_file_and_verify(
 
 def _get_httpx_client(target_app_name: str, connection_observer: Optional[ConnectionObserver]) -> httpx.Client:
     connection_type = ConfigurationController.get_connection_enum()
-    did_it_work = connect.make_client(connection_type, connection_observer) # always gets boolean
+    made_client = connect.make_client(connection_type, connection_observer) # always gets boolean
 
-    if not did_it_work:
-        raise ConnectionError(f'Could not connect, to download {target_app_name}.')
-    else:
-        client = httpx_client.get_http_session()
-        logger.info(f"client type is {type(client)}")
+    if not made_client:
+        if connection_type == ConnectionChoice.SYSTEM:
+            raise ConnectionError(f'Could not connect, to download {target_app_name}.')
+        else: # Tor:
+            if connection_observer:
+                connection_observer.notify('message', "Tor Bootstrap..")
+            bootstrap_results = connect.coordinate_bootstrap(connection_observer)
+            if not bootstrap_results.valid:
+                raise ConnectionError(f'Could not connect, to download {target_app_name}.')
+
+    client = httpx_client.get_http_session()
     return client
 
 def __calculate_file_hash(file):
diff --git a/core/services/helpers/install_dependencies.py b/core/services/helpers/install_dependencies.py
index 989fe21..87928b4 100644
--- a/core/services/helpers/install_dependencies.py
+++ b/core/services/helpers/install_dependencies.py
@@ -11,6 +11,7 @@ from core.models.orm_models.Dependency import Dependency
 from core.models.orm_calls.dependency_calls import get_dependency_version
 from core.controllers.ConfigurationController import ConfigurationController
 from core.utils.basic_operations.compare_versions import version_update_required
+from core.observers.ConnectionObserver import ConnectionObserver
 
 import httpx
 from io import BytesIO
@@ -21,7 +22,10 @@ import os
 
 SUDO_SINGBOX_LOCATION = f"{Constants.SUDO_TARGET_FOLDER}/sing-box"
 
-def setup_singbox_binary(application_version_observer: Optional[ApplicationVersionObserver]) -> Result:
+def setup_singbox_binary(
+    application_version_observer: Optional[ApplicationVersionObserver],
+    connection_observer: Optional[ConnectionObserver]
+) -> Result:
     """
     Rank:
         Module's Main Orchestrator
diff --git a/core/services/networking/httpx/connect.py b/core/services/networking/httpx/connect.py
index 804f014..a78527b 100644
--- a/core/services/networking/httpx/connect.py
+++ b/core/services/networking/httpx/connect.py
@@ -5,6 +5,7 @@ from core.services.networking.tor_tools.tor_orchestrator import establish_tor_co
 from core.services.networking.tor_tools.tor_dns import setup_SINGLE_use_resolver
 
 from core.services.networking.api_requests.ApiResponseModel import ApiResponse, ErrorType
+from core.models.Result import Result, ResultError
 from core.services.networking.httpx.async_batch_requests import async_parallel
 from core.services.networking.tor_tools.pre_bootstrap import get_bootstrap_port
 from core.services.networking.api_requests.subtools.get_connection_type import get_connection_type
@@ -164,6 +165,24 @@ def bootstrap_and_try_again(method: str, url: str, observer: ConnectionObserver,
     Called by:
         single_endpoint
     """
+    bootstrap_results = coordinate_bootstrap(observer)
+    if not bootstrap_results.valid:
+        return bootstrap_results
+
+    observer.notify('message', "Tor Confirmed")
+
+    client = httpx_client.get_http_session()
+    observer.notify('message', "Making Request..")
+    return make_request(
+        method=method,
+        url=url,
+        client=client,
+        payload=payload,
+        billing_code=billing_code
+    )
+
+
+def coordinate_bootstrap(observer: ConnectionObserver) -> ApiResponse:
     global _port_used
     
     if _port_used is None:
@@ -178,22 +197,13 @@ def bootstrap_and_try_again(method: str, url: str, observer: ConnectionObserver,
     # BOOTSTRAP SUCCESS
     _port_used = bootstrap_results.port
 
-    observer.notify('message', "Testing Tor..")
+    if observer:
+        observer.notify('message', "Testing Tor..")
     made_client = httpx_client.init_tor_session(_port_used)
     if not made_client:
         return bootstrap_results
-    observer.notify('message', "Tor Confirmed")
-
-    client = httpx_client.get_http_session()
-    observer.notify('message', "Making Request..")
-    return make_request(
-        method=method,
-        url=url,
-        client=client,
-        payload=payload,
-        billing_code=billing_code
-    )
-
+    else:
+        return ApiResponse(valid=True)
 
 
 def bulk_async(wanted_list: list, observer: ConnectionObserver, client_observer: ClientObserver) -> ApiResponse: