From 48d3b7ababe8f245d74f59d3696fbe80a68bb860 Mon Sep 17 00:00:00 2001
From: Afonso Coutinho <116525378+afonsopc@users.noreply.github.com>
Date: Tue, 2 Jun 2026 03:42:04 +0100
Subject: [PATCH] fix: topic analysis false-matches keywords as substrings
 (e.g. 'ai' in 'email') (#687)

* fix: match topic keywords on word boundaries, not substrings

* fix: apply word-boundary matching to topic example snippets too

* test: topic keywords match whole words, not substrings
---
 src/topic_analyzer.py        |  4 ++--
 tests/test_topic_analyzer.py | 30 ++++++++++++++++++++++++++++++
 2 files changed, 32 insertions(+), 2 deletions(-)
 create mode 100644 tests/test_topic_analyzer.py

diff --git a/src/topic_analyzer.py b/src/topic_analyzer.py
index 73666ae..e8563df 100644
--- a/src/topic_analyzer.py
+++ b/src/topic_analyzer.py
@@ -60,11 +60,11 @@ def analyze_topics(session_manager, owner: str = None) -> Dict[str, Any]:
 
             for topic, keywords in TOPIC_KEYWORDS.items():
                 for kw in keywords:
-                    if kw in content:
+                    if re.search(rf"\b{re.escape(kw)}\b", content):
                         topic_counts[topic] += 1
                         sentences = re.split(r'[.!?]', str(content_raw))
                         for sentence in sentences:
-                            if kw in sentence.lower():
+                            if re.search(rf"\b{re.escape(kw)}\b", sentence.lower()):
                                 topic_matches[topic].append({
                                     "session_id": session_id,
                                     "session_name": session_name,
diff --git a/tests/test_topic_analyzer.py b/tests/test_topic_analyzer.py
new file mode 100644
index 0000000..ba55db0
--- /dev/null
+++ b/tests/test_topic_analyzer.py
@@ -0,0 +1,30 @@
+"""Tests for topic keyword matching (src/topic_analyzer.py)."""
+from types import SimpleNamespace
+
+from src.topic_analyzer import analyze_topics
+
+
+def _sm(*messages):
+    history = [{"role": "user", "content": c} for c in messages]
+    return SimpleNamespace(sessions={"s1": {"owner": None, "name": "S", "history": history}})
+
+
+def _freq(result):
+    return {t["topic"]: t["frequency"] for t in result["topics"]}
+
+
+def test_substring_does_not_false_match_technology():
+    # Regression: "ai" matched inside "email"/"again"/"rain"/"wait", flagging
+    # Technology for messages with no technical content at all.
+    result = analyze_topics(_sm("Can you send me an email again about the rain? I will wait."))
+    assert "Technology" not in _freq(result)
+
+
+def test_real_keywords_still_match():
+    result = analyze_topics(_sm("I wrote some Python code to test the algorithm."))
+    assert _freq(result).get("Technology", 0) >= 1
+
+
+def test_multiword_keyword_matches():
+    result = analyze_topics(_sm("Can you explain how to set this up?"))
+    assert "Learning" in _freq(result)