diff --git a/airbyte/http_caching/proxy.py b/airbyte/http_caching/proxy.py
index a2e9f1f6..fd457a22 100644
--- a/airbyte/http_caching/proxy.py
+++ b/airbyte/http_caching/proxy.py
@@ -107,7 +107,9 @@ def _get_cache_path(self, key: str, *, is_read: bool = False) -> Path:
             The path to the cache file.
         """
         base_dir = self.read_dir if is_read else self.cache_dir
+
         extension = ".json" if self.serialization_format == SerializationFormat.JSON else ".mitm"
+
         return base_dir / f"{key}{extension}"
 
     def request(self, flow: HTTPFlow) -> None:
@@ -127,14 +129,15 @@ def request(self, flow: HTTPFlow) -> None:
             if cache_path.exists():
                 try:
                     cached_data: dict[str, Any] = self.serializer.deserialize(cache_path)
+
                     cached_flow = HTTPFlow.from_state(cached_data)
+
                     if hasattr(cached_flow, "response") and cached_flow.response:
                         flow.response = cached_flow.response
-                    logger.info(f"Serving {flow.request.url} from cache")
+                        logger.info(f"Serving {flow.request.url} from cache")
+                        return
                 except Exception as e:
-                    logger.warning(f"Failed to load cached response: {e}")
-                else:
-                    return
+                    logger.warning(f"Failed to load cached response: {e}", exc_info=True)
 
             if self.mode == HttpCacheMode.READ_ONLY_FAIL_ON_MISS:
                 flow.response = Response.make(
@@ -154,7 +157,9 @@ def response(self, flow: HTTPFlow) -> None:
             cache_path = self._get_cache_path(key, is_read=False)
 
             try:
+                cache_path.parent.mkdir(parents=True, exist_ok=True)
+
                 self.serializer.serialize(flow.get_state(), cache_path)
                 logger.info(f"Cached response for {flow.request.url}")
             except Exception as e:
-                logger.warning(f"Failed to cache response: {e}")
+                logger.warning(f"Failed to cache response: {e}", exc_info=True)
diff --git a/airbyte/http_caching/serialization.py b/airbyte/http_caching/serialization.py
index b3257d8e..d37df456 100644
--- a/airbyte/http_caching/serialization.py
+++ b/airbyte/http_caching/serialization.py
@@ -4,12 +4,16 @@
 from __future__ import annotations
 
 import json
+import logging
 from enum import Enum
 from typing import TYPE_CHECKING, Any, Protocol
 
 from mitmproxy.io import io
 
 
+logger = logging.getLogger(__name__)
+
+
 if TYPE_CHECKING:
     from pathlib import Path
 
@@ -88,12 +92,14 @@ def serialize(self, data: T_SerializedData, path: Path) -> None:
         """
         path.parent.mkdir(parents=True, exist_ok=True)
 
-        if not str(path).endswith(".mitm"):
+        if path.suffix != ".mitm":
             path = path.with_suffix(".mitm")
 
+        flows = data.get("flows", [])
+
         with path.open("wb") as f:
             fw = io.FlowWriter(f)
-            for flow in data.get("flows", []):
+            for flow in flows:
                 fw.add(flow)
 
     def deserialize(self, path: Path) -> T_SerializedData:
@@ -105,14 +111,18 @@ def deserialize(self, path: Path) -> T_SerializedData:
         Returns:
             The deserialized data.
         """
-        if not str(path).endswith(".mitm"):
+        if path.suffix != ".mitm":
             path = path.with_suffix(".mitm")
 
         if not path.exists():
             return {"flows": []}
 
-        with path.open("rb") as f:
-            fr = io.FlowReader(f)
-            flows = list(fr.stream())
-
-        return {"flows": flows}
+        try:
+            with path.open("rb") as f:
+                fr = io.FlowReader(f)
+                flows = list(fr.stream())
+        except Exception as e:
+            logger.warning(f"Error reading flow file {path}: {e}")
+            return {"flows": []}
+        else:
+            return {"flows": flows}