diff --git a/backend/src/agents/memory/prompt.py b/backend/src/agents/memory/prompt.py
index 3982a2e..dd27476 100644
--- a/backend/src/agents/memory/prompt.py
+++ b/backend/src/agents/memory/prompt.py
@@ -1,5 +1,6 @@
 """Prompt templates for memory update and injection."""
 
+import re
 from typing import Any
 
 try:
@@ -108,6 +109,9 @@ Important Rules:
 - For history sections, integrate new information chronologically into appropriate time period
 - Preserve technical accuracy - keep exact names of technologies, companies, projects
 - Focus on information useful for future interactions and personalization
+- IMPORTANT: Do NOT record file upload events in memory. Uploaded files are
+  session-specific and ephemeral — they will not be accessible in future sessions.
+  Recording upload events causes confusion in subsequent conversations.
 
 Return ONLY valid JSON, no explanation or markdown."""
 
@@ -249,6 +253,16 @@ def format_conversation_for_update(messages: list[Any]) -> str:
             text_parts = [p.get("text", "") for p in content if isinstance(p, dict) and "text" in p]
             content = " ".join(text_parts) if text_parts else str(content)
 
+        # Strip uploaded_files tags from human messages to avoid persisting
+        # ephemeral file path info into long-term memory.  Skip the turn entirely
+        # when nothing remains after stripping (upload-only message).
+        if role == "human":
+            content = re.sub(
+                r"<uploaded_files>[\s\S]*?</uploaded_files>\n*", "", str(content)
+            ).strip()
+            if not content:
+                continue
+
         # Truncate very long messages
         if len(str(content)) > 1000:
             content = str(content)[:1000] + "..."
diff --git a/backend/src/agents/memory/updater.py b/backend/src/agents/memory/updater.py
index a9ad72a..b82da30 100644
--- a/backend/src/agents/memory/updater.py
+++ b/backend/src/agents/memory/updater.py
@@ -1,6 +1,7 @@
 """Memory updater for reading, writing, and updating memory data."""
 
 import json
+import re
 import uuid
 from datetime import datetime
 from pathlib import Path
@@ -135,6 +136,47 @@ def _load_memory_from_file(agent_name: str | None = None) -> dict[str, Any]:
         return _create_empty_memory()
 
 
+# Matches sentences that describe a file-upload *event* rather than general
+# file-related work.  Deliberately narrow to avoid removing legitimate facts
+# such as "User works with CSV files" or "prefers PDF export".
+_UPLOAD_SENTENCE_RE = re.compile(
+    r"[^.!?]*\b(?:"
+    r"upload(?:ed|ing)?(?:\s+\w+){0,3}\s+(?:file|files?|document|documents?|attachment|attachments?)"
+    r"|file\s+upload"
+    r"|/mnt/user-data/uploads/"
+    r"|<uploaded_files>"
+    r")[^.!?]*[.!?]?\s*",
+    re.IGNORECASE,
+)
+
+
+def _strip_upload_mentions_from_memory(memory_data: dict[str, Any]) -> dict[str, Any]:
+    """Remove sentences about file uploads from all memory summaries and facts.
+
+    Uploaded files are session-scoped; persisting upload events in long-term
+    memory causes the agent to search for non-existent files in future sessions.
+    """
+    # Scrub summaries in user/history sections
+    for section in ("user", "history"):
+        section_data = memory_data.get(section, {})
+        for _key, val in section_data.items():
+            if isinstance(val, dict) and "summary" in val:
+                cleaned = _UPLOAD_SENTENCE_RE.sub("", val["summary"]).strip()
+                cleaned = re.sub(r"  +", " ", cleaned)
+                val["summary"] = cleaned
+
+    # Also remove any facts that describe upload events
+    facts = memory_data.get("facts", [])
+    if facts:
+        memory_data["facts"] = [
+            f
+            for f in facts
+            if not _UPLOAD_SENTENCE_RE.search(f.get("content", ""))
+        ]
+
+    return memory_data
+
+
 def _save_memory_to_file(memory_data: dict[str, Any], agent_name: str | None = None) -> bool:
     """Save memory data to file and update cache.
 
@@ -244,6 +286,12 @@ class MemoryUpdater:
             # Apply updates
             updated_memory = self._apply_updates(current_memory, update_data, thread_id)
 
+            # Strip file-upload mentions from all summaries before saving.
+            # Uploaded files are session-scoped and won't exist in future sessions,
+            # so recording upload events in long-term memory causes the agent to
+            # try (and fail) to locate those files in subsequent conversations.
+            updated_memory = _strip_upload_mentions_from_memory(updated_memory)
+
             # Save
             return _save_memory_to_file(updated_memory, agent_name)
 
diff --git a/backend/src/agents/middlewares/memory_middleware.py b/backend/src/agents/middlewares/memory_middleware.py
index c7c74ea..8c88650 100644
--- a/backend/src/agents/middlewares/memory_middleware.py
+++ b/backend/src/agents/middlewares/memory_middleware.py
@@ -1,5 +1,6 @@
 """Middleware for memory mechanism."""
 
+import re
 from typing import Any, override
 
 from langchain.agents import AgentState
@@ -22,10 +23,16 @@ def _filter_messages_for_memory(messages: list[Any]) -> list[Any]:
     This filters out:
     - Tool messages (intermediate tool call results)
     - AI messages with tool_calls (intermediate steps, not final responses)
+    - The <uploaded_files> block injected by UploadsMiddleware into human messages
+      (file paths are session-scoped and must not persist in long-term memory).
+      The user's actual question is preserved; only turns whose content is entirely
+      the upload block (nothing remains after stripping) are dropped along with
+      their paired assistant response.
 
     Only keeps:
-    - Human messages (user input)
-    - AI messages without tool_calls (final assistant responses)
+    - Human messages (with the ephemeral upload block removed)
+    - AI messages without tool_calls (final assistant responses), unless the
+      paired human turn was upload-only and had no real user text.
 
     Args:
         messages: List of all conversation messages.
@@ -33,17 +40,47 @@ def _filter_messages_for_memory(messages: list[Any]) -> list[Any]:
     Returns:
         Filtered list containing only user inputs and final assistant responses.
     """
+    _UPLOAD_BLOCK_RE = re.compile(
+        r"<uploaded_files>[\s\S]*?</uploaded_files>\n*", re.IGNORECASE
+    )
+
     filtered = []
+    skip_next_ai = False
     for msg in messages:
         msg_type = getattr(msg, "type", None)
 
         if msg_type == "human":
-            # Always keep user messages
-            filtered.append(msg)
+            content = getattr(msg, "content", "")
+            if isinstance(content, list):
+                content = " ".join(
+                    p.get("text", "") for p in content if isinstance(p, dict)
+                )
+            content_str = str(content)
+            if "<uploaded_files>" in content_str:
+                # Strip the ephemeral upload block; keep the user's real question.
+                stripped = _UPLOAD_BLOCK_RE.sub("", content_str).strip()
+                if not stripped:
+                    # Nothing left — the entire turn was upload bookkeeping;
+                    # skip it and the paired assistant response.
+                    skip_next_ai = True
+                    continue
+                # Rebuild the message with cleaned content so the user's question
+                # is still available for memory summarisation.
+                from copy import copy
+
+                clean_msg = copy(msg)
+                clean_msg.content = stripped
+                filtered.append(clean_msg)
+                skip_next_ai = False
+            else:
+                filtered.append(msg)
+                skip_next_ai = False
         elif msg_type == "ai":
-            # Only keep AI messages that are final responses (no tool_calls)
             tool_calls = getattr(msg, "tool_calls", None)
             if not tool_calls:
+                if skip_next_ai:
+                    skip_next_ai = False
+                    continue
                 filtered.append(msg)
         # Skip tool messages and AI messages with tool_calls
 
diff --git a/backend/tests/test_memory_upload_filtering.py b/backend/tests/test_memory_upload_filtering.py
new file mode 100644
index 0000000..e100842
--- /dev/null
+++ b/backend/tests/test_memory_upload_filtering.py
@@ -0,0 +1,232 @@
+"""Tests for upload-event filtering in the memory pipeline.
+
+Covers two functions introduced to prevent ephemeral file-upload context from
+persisting in long-term memory:
+
+  - _filter_messages_for_memory  (memory_middleware)
+  - _strip_upload_mentions_from_memory  (updater)
+"""
+
+from langchain_core.messages import AIMessage, HumanMessage, ToolMessage
+
+from src.agents.memory.updater import _strip_upload_mentions_from_memory
+from src.agents.middlewares.memory_middleware import _filter_messages_for_memory
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+_UPLOAD_BLOCK = (
+    "<uploaded_files>\n"
+    "The following files have been uploaded and are available for use:\n\n"
+    "- filename: secret.txt\n"
+    "  path: /mnt/user-data/uploads/abc123/secret.txt\n"
+    "  size: 42 bytes\n"
+    "</uploaded_files>"
+)
+
+
+def _human(text: str) -> HumanMessage:
+    return HumanMessage(content=text)
+
+
+def _ai(text: str, tool_calls=None) -> AIMessage:
+    msg = AIMessage(content=text)
+    if tool_calls:
+        msg.tool_calls = tool_calls
+    return msg
+
+
+# ===========================================================================
+# _filter_messages_for_memory
+# ===========================================================================
+
+
+class TestFilterMessagesForMemory:
+    # --- upload-only turns are excluded ---
+
+    def test_upload_only_turn_is_excluded(self):
+        """A human turn containing only <uploaded_files> (no real question)
+        and its paired AI response must both be dropped."""
+        msgs = [
+            _human(_UPLOAD_BLOCK),
+            _ai("I have read the file. It says: Hello."),
+        ]
+        result = _filter_messages_for_memory(msgs)
+        assert result == []
+
+    def test_upload_with_real_question_preserves_question(self):
+        """When the user asks a question alongside an upload, the question text
+        must reach the memory queue (upload block stripped, AI response kept)."""
+        combined = _UPLOAD_BLOCK + "\n\nWhat does this file contain?"
+        msgs = [
+            _human(combined),
+            _ai("The file contains: Hello DeerFlow."),
+        ]
+        result = _filter_messages_for_memory(msgs)
+
+        assert len(result) == 2
+        human_result = result[0]
+        assert "<uploaded_files>" not in human_result.content
+        assert "What does this file contain?" in human_result.content
+        assert result[1].content == "The file contains: Hello DeerFlow."
+
+    # --- non-upload turns pass through unchanged ---
+
+    def test_plain_conversation_passes_through(self):
+        msgs = [
+            _human("What is the capital of France?"),
+            _ai("The capital of France is Paris."),
+        ]
+        result = _filter_messages_for_memory(msgs)
+        assert len(result) == 2
+        assert result[0].content == "What is the capital of France?"
+        assert result[1].content == "The capital of France is Paris."
+
+    def test_tool_messages_are_excluded(self):
+        """Intermediate tool messages must never reach memory."""
+        msgs = [
+            _human("Search for something"),
+            _ai("Calling search tool", tool_calls=[{"name": "search", "id": "1", "args": {}}]),
+            ToolMessage(content="Search results", tool_call_id="1"),
+            _ai("Here are the results."),
+        ]
+        result = _filter_messages_for_memory(msgs)
+        human_msgs = [m for m in result if m.type == "human"]
+        ai_msgs = [m for m in result if m.type == "ai"]
+        assert len(human_msgs) == 1
+        assert len(ai_msgs) == 1
+        assert ai_msgs[0].content == "Here are the results."
+
+    def test_multi_turn_with_upload_in_middle(self):
+        """Only the upload turn is dropped; surrounding non-upload turns survive."""
+        msgs = [
+            _human("Hello, how are you?"),
+            _ai("I'm doing well, thank you!"),
+            _human(_UPLOAD_BLOCK),           # upload-only → dropped
+            _ai("I read the uploaded file."),  # paired AI → dropped
+            _human("What is 2 + 2?"),
+            _ai("4"),
+        ]
+        result = _filter_messages_for_memory(msgs)
+        human_contents = [m.content for m in result if m.type == "human"]
+        ai_contents = [m.content for m in result if m.type == "ai"]
+
+        assert "Hello, how are you?" in human_contents
+        assert "What is 2 + 2?" in human_contents
+        assert _UPLOAD_BLOCK not in human_contents
+        assert "I'm doing well, thank you!" in ai_contents
+        assert "4" in ai_contents
+        # The upload-paired AI response must NOT appear
+        assert "I read the uploaded file." not in ai_contents
+
+    def test_multimodal_content_list_handled(self):
+        """Human messages with list-style content (multimodal) are handled."""
+        msg = HumanMessage(content=[
+            {"type": "text", "text": _UPLOAD_BLOCK},
+        ])
+        msgs = [msg, _ai("Done.")]
+        result = _filter_messages_for_memory(msgs)
+        assert result == []
+
+    def test_file_path_not_in_filtered_content(self):
+        """After filtering, no upload file path should appear in any message."""
+        combined = _UPLOAD_BLOCK + "\n\nSummarise the file please."
+        msgs = [_human(combined), _ai("It says hello.")]
+        result = _filter_messages_for_memory(msgs)
+        all_content = " ".join(
+            m.content for m in result if isinstance(m.content, str)
+        )
+        assert "/mnt/user-data/uploads/" not in all_content
+        assert "<uploaded_files>" not in all_content
+
+
+# ===========================================================================
+# _strip_upload_mentions_from_memory
+# ===========================================================================
+
+
+class TestStripUploadMentionsFromMemory:
+    def _make_memory(self, summary: str, facts: list[dict] | None = None) -> dict:
+        return {
+            "user": {"topOfMind": {"summary": summary}},
+            "history": {"recentMonths": {"summary": ""}},
+            "facts": facts or [],
+        }
+
+    # --- summaries ---
+
+    def test_upload_event_sentence_removed_from_summary(self):
+        mem = self._make_memory(
+            "User is interested in AI. "
+            "User uploaded a test file for verification purposes. "
+            "User prefers concise answers."
+        )
+        result = _strip_upload_mentions_from_memory(mem)
+        summary = result["user"]["topOfMind"]["summary"]
+        assert "uploaded a test file" not in summary
+        assert "User is interested in AI" in summary
+        assert "User prefers concise answers" in summary
+
+    def test_upload_path_sentence_removed_from_summary(self):
+        mem = self._make_memory(
+            "User uses Python. "
+            "User uploaded file to /mnt/user-data/uploads/tid/data.csv. "
+            "User likes clean code."
+        )
+        result = _strip_upload_mentions_from_memory(mem)
+        summary = result["user"]["topOfMind"]["summary"]
+        assert "/mnt/user-data/uploads/" not in summary
+        assert "User uses Python" in summary
+
+    def test_legitimate_csv_mention_is_preserved(self):
+        """'User works with CSV files' must NOT be deleted — it's not an upload event."""
+        mem = self._make_memory("User regularly works with CSV files for data analysis.")
+        result = _strip_upload_mentions_from_memory(mem)
+        assert "CSV files" in result["user"]["topOfMind"]["summary"]
+
+    def test_pdf_export_preference_preserved(self):
+        """'Prefers PDF export' is a legitimate preference, not an upload event."""
+        mem = self._make_memory("User prefers PDF export for reports.")
+        result = _strip_upload_mentions_from_memory(mem)
+        assert "PDF export" in result["user"]["topOfMind"]["summary"]
+
+    def test_uploading_a_test_file_removed(self):
+        """'uploading a test file' (with intervening words) must be caught."""
+        mem = self._make_memory(
+            "User conducted a hands-on test by uploading a test file titled "
+            "'test_deerflow_memory_bug.txt'. User is also learning Python."
+        )
+        result = _strip_upload_mentions_from_memory(mem)
+        summary = result["user"]["topOfMind"]["summary"]
+        assert "test_deerflow_memory_bug.txt" not in summary
+        assert "uploading a test file" not in summary
+
+    # --- facts ---
+
+    def test_upload_fact_removed_from_facts(self):
+        facts = [
+            {"content": "User uploaded a file titled secret.txt", "category": "behavior"},
+            {"content": "User prefers dark mode", "category": "preference"},
+            {"content": "User is uploading document attachments regularly", "category": "behavior"},
+        ]
+        mem = self._make_memory("summary", facts=facts)
+        result = _strip_upload_mentions_from_memory(mem)
+        remaining = [f["content"] for f in result["facts"]]
+        assert "User prefers dark mode" in remaining
+        assert not any("uploaded a file" in c for c in remaining)
+        assert not any("uploading document" in c for c in remaining)
+
+    def test_non_upload_facts_preserved(self):
+        facts = [
+            {"content": "User graduated from Peking University", "category": "context"},
+            {"content": "User prefers Python over JavaScript", "category": "preference"},
+        ]
+        mem = self._make_memory("", facts=facts)
+        result = _strip_upload_mentions_from_memory(mem)
+        assert len(result["facts"]) == 2
+
+    def test_empty_memory_handled_gracefully(self):
+        mem = {"user": {}, "history": {}, "facts": []}
+        result = _strip_upload_mentions_from_memory(mem)
+        assert result == {"user": {}, "history": {}, "facts": []}