diff --git a/backend/tests/services/context/test_compression.py b/backend/tests/services/context/test_compression.py
index b2fde38..c37ca10 100644
--- a/backend/tests/services/context/test_compression.py
+++ b/backend/tests/services/context/test_compression.py
@@ -212,3 +212,80 @@ class TestContextCompressor:
         assert compressor._get_strategy_for_type(ContextType.KNOWLEDGE) == "sentence"
         assert compressor._get_strategy_for_type(ContextType.CONVERSATION) == "end"
         assert compressor._get_strategy_for_type(ContextType.TOOL) == "middle"
+
+
+class TestTruncationEdgeCases:
+    """Tests for edge cases in truncation to prevent regressions."""
+
+    @pytest.mark.asyncio
+    async def test_truncation_ratio_with_zero_original_tokens(self) -> None:
+        """Test that truncation ratio handles zero original tokens without division by zero."""
+        strategy = TruncationStrategy()
+
+        # Empty content should not raise ZeroDivisionError
+        result = await strategy.truncate_to_tokens("", max_tokens=100)
+
+        assert result.truncation_ratio == 0.0
+        assert result.original_tokens == 0
+
+    @pytest.mark.asyncio
+    async def test_truncate_end_with_zero_available_tokens(self) -> None:
+        """Test truncation when marker tokens exceed max_tokens."""
+        strategy = TruncationStrategy()
+        content = "Some content to truncate"
+
+        # max_tokens less than marker tokens should return just marker
+        result = await strategy.truncate_to_tokens(content, max_tokens=1, strategy="end")
+
+        # Should handle gracefully without crashing
+        assert strategy.TRUNCATION_MARKER in result.content or result.content == content
+
+    @pytest.mark.asyncio
+    async def test_truncate_with_content_that_has_zero_tokens(self) -> None:
+        """Test truncation when content estimates to zero tokens."""
+        strategy = TruncationStrategy()
+
+        # Very short content that might estimate to 0 tokens
+        result = await strategy.truncate_to_tokens("a", max_tokens=100)
+
+        # Should not raise ZeroDivisionError
+        assert result.content in ("a", "a" + strategy.TRUNCATION_MARKER)
+
+    @pytest.mark.asyncio
+    async def test_get_content_for_tokens_zero_target(self) -> None:
+        """Test _get_content_for_tokens with zero target tokens."""
+        strategy = TruncationStrategy()
+
+        result = await strategy._get_content_for_tokens(
+            content="Some content",
+            target_tokens=0,
+            from_start=True,
+        )
+
+        assert result == ""
+
+    @pytest.mark.asyncio
+    async def test_sentence_truncation_with_no_sentences(self) -> None:
+        """Test sentence truncation with content that has no sentence boundaries."""
+        strategy = TruncationStrategy()
+        content = "this is content without any sentence ending punctuation"
+
+        result = await strategy.truncate_to_tokens(
+            content, max_tokens=5, strategy="sentence"
+        )
+
+        # Should handle gracefully
+        assert result is not None
+
+    @pytest.mark.asyncio
+    async def test_middle_truncation_very_short_content(self) -> None:
+        """Test middle truncation with content shorter than preserved portions."""
+        strategy = TruncationStrategy(preserve_ratio_start=0.7)
+        content = "ab"  # Very short
+
+        result = await strategy.truncate_to_tokens(
+            content, max_tokens=1, strategy="middle"
+        )
+
+        # Should handle gracefully without negative indices
+        assert result is not None
diff --git a/backend/tests/services/context/test_scoring.py b/backend/tests/services/context/test_scoring.py
index 6fea92f..1feeea6 100644
--- a/backend/tests/services/context/test_scoring.py
+++ b/backend/tests/services/context/test_scoring.py
@@ -616,6 +616,66 @@ class TestCompositeScorer:
         scorer.set_mcp_manager(mock_mcp)
         assert scorer._relevance_scorer._mcp is mock_mcp
 
+    @pytest.mark.asyncio
+    async def test_concurrent_scoring_same_context_no_race(self) -> None:
+        """Test that concurrent scoring of the same context doesn't cause race conditions.
+
+        This verifies that the per-context locking mechanism prevents the same context
+        from being scored multiple times when scored concurrently.
+        """
+        import asyncio
+
+        scorer = CompositeScorer()
+
+        # Create a single context that will be scored multiple times concurrently
+        context = KnowledgeContext(
+            content="Test content for race condition test",
+            source="docs",
+            relevance_score=0.75,
+        )
+
+        # Score the same context many times in parallel
+        num_concurrent = 50
+        tasks = [scorer.score(context, "test query") for _ in range(num_concurrent)]
+        scores = await asyncio.gather(*tasks)
+
+        # All scores should be identical (the same context scored the same way)
+        assert all(s == scores[0] for s in scores)
+
+        # The context should have its _score cached
+        assert context._score is not None
+
+    @pytest.mark.asyncio
+    async def test_concurrent_scoring_different_contexts(self) -> None:
+        """Test that concurrent scoring of different contexts works correctly.
+
+        Different contexts should not interfere with each other during parallel scoring.
+        """
+        import asyncio
+
+        scorer = CompositeScorer()
+
+        # Create many different contexts
+        contexts = [
+            KnowledgeContext(
+                content=f"Test content {i}",
+                source="docs",
+                relevance_score=i / 10,
+            )
+            for i in range(10)
+        ]
+
+        # Score all contexts concurrently
+        tasks = [scorer.score(ctx, "test query") for ctx in contexts]
+        scores = await asyncio.gather(*tasks)
+
+        # Each context should have a different score based on its relevance
+        assert len(set(scores)) > 1  # Not all the same
+
+        # All contexts should have cached scores
+        for ctx in contexts:
+            assert ctx._score is not None
+
 
 class TestScoredContext:
     """Tests for ScoredContext dataclass."""