diff --git a/cli/onionshare_cli/web/chat_mode.py b/cli/onionshare_cli/web/chat_mode.py
index 385972fe..91c41d2f 100644
--- a/cli/onionshare_cli/web/chat_mode.py
+++ b/cli/onionshare_cli/web/chat_mode.py
@@ -39,6 +39,12 @@ class ChatModeWeb:
         # This tracks the history id
         self.cur_history_id = 0
 
+        # Whether or not we can send REQUEST_INDIVIDUAL_FILE_STARTED
+        # and maybe other events when requests come in to this mode
+        # Chat mode has no concept of individual file requests that
+        # turn into history widgets in the GUI, so set it to False
+        self.supports_file_requests = False
+
         self.define_routes()
 
     def define_routes(self):
diff --git a/cli/onionshare_cli/web/receive_mode.py b/cli/onionshare_cli/web/receive_mode.py
index b3a146e3..76abb0a8 100644
--- a/cli/onionshare_cli/web/receive_mode.py
+++ b/cli/onionshare_cli/web/receive_mode.py
@@ -64,6 +64,10 @@ class ReceiveModeWeb:
         # This tracks the history id
         self.cur_history_id = 0
 
+        # Whether or not we can send REQUEST_INDIVIDUAL_FILE_STARTED
+        # and maybe other events when requests come in to this mode
+        self.supports_file_requests = True
+
         self.define_routes()
 
     def define_routes(self):
diff --git a/cli/onionshare_cli/web/send_base_mode.py b/cli/onionshare_cli/web/send_base_mode.py
index 2f3e0bbd..e448d2dd 100644
--- a/cli/onionshare_cli/web/send_base_mode.py
+++ b/cli/onionshare_cli/web/send_base_mode.py
@@ -52,6 +52,10 @@ class SendBaseModeWeb:
         # This tracks the history id
         self.cur_history_id = 0
 
+        # Whether or not we can send REQUEST_INDIVIDUAL_FILE_STARTED
+        # and maybe other events when requests come in to this mode
+        self.supports_file_requests = True
+
         self.define_routes()
         self.init()
 
diff --git a/cli/onionshare_cli/web/web.py b/cli/onionshare_cli/web/web.py
index b947b491..56e307b4 100644
--- a/cli/onionshare_cli/web/web.py
+++ b/cli/onionshare_cli/web/web.py
@@ -152,7 +152,6 @@ class Web:
         self.receive_mode = None
         self.website_mode = None
         self.chat_mode = None
-        self.mode_supports_file_requests = True
         if self.mode == "share":
             self.share_mode = ShareModeWeb(self.common, self)
         elif self.mode == "receive":
@@ -163,9 +162,6 @@ class Web:
             self.socketio = SocketIO()
             self.socketio.init_app(self.app)
             self.chat_mode = ChatModeWeb(self.common, self)
-            # Chat mode has no concept of individual file requests that
-            # turn into history widgets in the GUI
-            self.mode_supports_file_requests = False
 
         self.cleanup_filenames = []
 
@@ -298,7 +294,8 @@ class Web:
         return self.add_security_headers(r)
 
     def error404(self, history_id):
-        if self.mode_supports_file_requests:
+        mode = self.get_mode()
+        if mode.supports_file_requests:
             self.add_request(
                 self.REQUEST_INDIVIDUAL_FILE_STARTED,
                 request.path,
@@ -312,7 +309,8 @@ class Web:
         return self.add_security_headers(r)
 
     def error405(self, history_id):
-        if self.mode_supports_file_requests:
+        mode = self.get_mode()
+        if mode.supports_file_requests:
             self.add_request(
                 self.REQUEST_INDIVIDUAL_FILE_STARTED,
                 request.path,
@@ -326,7 +324,8 @@ class Web:
         return self.add_security_headers(r)
 
     def error500(self, history_id):
-        if self.mode_supports_file_requests:
+        mode = self.get_mode()
+        if mode.supports_file_requests:
             self.add_request(
                 self.REQUEST_INDIVIDUAL_FILE_STARTED,
                 request.path,