diff --git a/aider/io.py b/aider/io.py
index f0000e965..ed6f22d51 100644
--- a/aider/io.py
+++ b/aider/io.py
@@ -308,6 +308,12 @@ class InputOutput:
         self.yes = yes
 
         self.input_history_file = input_history_file
+        if self.input_history_file:
+            try:
+                Path(self.input_history_file).parent.mkdir(parents=True, exist_ok=True)
+            except (PermissionError, OSError) as e:
+                self.tool_warning(f"Could not create directory for input history: {e}")
+                self.input_history_file = None
         self.llm_history_file = llm_history_file
         if chat_history_file is not None:
             self.chat_history_file = Path(chat_history_file)
@@ -731,7 +737,6 @@ class InputOutput:
         if not self.input_history_file:
             return
         try:
-            Path(self.input_history_file).parent.mkdir(parents=True, exist_ok=True)
             FileHistory(self.input_history_file).append_string(inp)
             # Also add to the in-memory history if it exists
             if self.prompt_session and self.prompt_session.history:
@@ -750,9 +755,14 @@ class InputOutput:
         if not self.llm_history_file:
             return
         timestamp = datetime.now().isoformat(timespec="seconds")
-        with open(self.llm_history_file, "a", encoding="utf-8") as log_file:
-            log_file.write(f"{role.upper()} {timestamp}\n")
-            log_file.write(content + "\n")
+        try:
+            Path(self.llm_history_file).parent.mkdir(parents=True, exist_ok=True)
+            with open(self.llm_history_file, "a", encoding="utf-8") as log_file:
+                log_file.write(f"{role.upper()} {timestamp}\n")
+                log_file.write(content + "\n")
+        except (PermissionError, OSError) as err:
+            self.tool_warning(f"Unable to write to llm history file {self.llm_history_file}: {err}")
+            self.llm_history_file = None
 
     def display_user_input(self, inp):
         if self.pretty and self.user_input_color: