diff --git a/CHANGELOG.md b/CHANGELOG.md
index 33c3cab..15ff6ad 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,10 @@ and this project adheres to [Semantic Versioning](https://semver.org/).
 ## [Unreleased]
 
 ### Fixed
+- `Diff` now sorts matches by `Similarity` descending before selecting the overall
+  suggestion. Previously, `KeywordSearch` ordered candidates by token overlap score,
+  so a high-keyword-score candidate classified as ADD could mask a lower-keyword-score
+  candidate with higher Jaccard similarity that should have been UPDATE or DUPLICATE.
 - Deduplication false positives on scientific and domain-specific text:
   - Removed bare `"not"` from negation words — it appears in virtually all
     scientific prose and caused unrelated records to be classified as CONFLICT.
diff --git a/internal/search/diff.go b/internal/search/diff.go
index 9d33c4a..c74473c 100644
--- a/internal/search/diff.go
+++ b/internal/search/diff.go
@@ -159,6 +159,14 @@ func Diff(insights []*model.Insight, newContent string, opts DiffOptions) DiffRe
 		}
 	}
 
+	// Sort by similarity descending so matches[0] is always the strongest candidate.
+	// KeywordSearch orders by token overlap score, which can differ from the final
+	// Jaccard-based Similarity — a high-keyword-score ADD would otherwise mask a
+	// lower-keyword-score UPDATE or DUPLICATE from a more similar candidate.
+	sort.Slice(matches, func(i, j int) bool {
+		return matches[i].Similarity > matches[j].Similarity
+	})
+
 	// Overall suggestion: take the strongest match
 	overall := DiffAdd
 	if len(matches) > 0 {
diff --git a/internal/search/diff_test.go b/internal/search/diff_test.go
index b63dd72..d10ba34 100644
--- a/internal/search/diff_test.go
+++ b/internal/search/diff_test.go
@@ -162,3 +162,29 @@ func TestDiff_LimitDefault(t *testing.T) {
 		t.Errorf("default limit 5: got %d matches", len(result.Matches))
 	}
 }
+
+func TestDiff_LowerKeywordScoreUpdateNotMasked(t *testing.T) {
+	// insightA: all of new's tokens are present (keyword score = 5/5 = 1.0),
+	// but Jaccard = 5/14 ≈ 0.36 → ADD. KeywordSearch puts this first.
+	insightA := &model.Insight{
+		ID:      "a",
+		Content: "project uses redis for caching database monitoring alerting logging tracing scaling replication failover clustering sharding",
+	}
+	// insightB: keyword score = 4/5 = 0.8 (ranks second), Jaccard = 4/6 ≈ 0.67 → UPDATE.
+	// Without sorting by Similarity, insightA's ADD masks this UPDATE.
+	insightB := &model.Insight{
+		ID:      "b",
+		Content: "project uses redis postgresql caching",
+	}
+
+	result := Diff(
+		[]*model.Insight{insightA, insightB},
+		"project uses redis for caching database",
+		DiffOptions{},
+	)
+
+	if result.Suggestion != DiffUpdate {
+		t.Errorf("want UPDATE (insightB is more similar by Jaccard), got %s — "+
+			"high-keyword-score ADD from insightA masked the UPDATE", result.Suggestion)
+	}
+}