diff --git a/ingestion/internal/frontmatter/frontmatter.go b/ingestion/internal/frontmatter/frontmatter.go
index 0b6f959..e18079a 100644
--- a/ingestion/internal/frontmatter/frontmatter.go
+++ b/ingestion/internal/frontmatter/frontmatter.go
@@ -101,21 +101,23 @@ func quoteScalars(block []byte) []byte {
 	return []byte(strings.Join(lines, "\n"))
 }
 
-// needsQuoting reports whether a scalar value must be quoted to parse as the
-// string it plainly is. Only the colon case is handled: it is the one this
-// package exists for, and every other special case risks rewriting a value
-// that was deliberately structured (a nested mapping, an anchor, a number).
+// needsQuoting reports whether a scalar value has to be quoted to load as the
+// string it plainly is.
+//
+// The test is YAML's own parser rather than a pattern: ask whether the value
+// stands alone as the right-hand side of a mapping. Heuristics get this wrong
+// in both directions — `title: "Foo" — bar` opens with a quote but is not
+// quoted, and a value may contain a colon inside quotes and be perfectly fine.
+//
+// Anything that already parses is left alone, whatever it parses into — a flow
+// collection, a number, a bool. It is not broken, and quoting would change its
+// type.
 func needsQuoting(value string) bool {
-	if strings.HasPrefix(value, "'") || strings.HasPrefix(value, `"`) {
-		return false
-	}
 	if strings.HasPrefix(value, "|") || strings.HasPrefix(value, ">") {
 		return false // block scalar; its content is not parsed as YAML
 	}
-	if strings.HasPrefix(value, "{") || strings.HasPrefix(value, "[") {
-		return false // flow collection; quoting would silently make it a string
-	}
-	return strings.Contains(value, ": ") || strings.HasSuffix(value, ":")
+	var probe map[string]any
+	return yaml.Unmarshal([]byte("v: "+value+"\n"), &probe) != nil
 }
 
 // block returns the raw YAML between the opening and closing fences.
diff --git a/ingestion/internal/frontmatter/frontmatter_test.go b/ingestion/internal/frontmatter/frontmatter_test.go
index 7edebbf..8f0c8a4 100644
--- a/ingestion/internal/frontmatter/frontmatter_test.go
+++ b/ingestion/internal/frontmatter/frontmatter_test.go
@@ -90,6 +90,17 @@ func TestFix(t *testing.T) {
 			wantKey:     "title",
 			wantValue:   "Don't do this: it breaks",
 		},
+		{
+			// The value opens with a double quote and then keeps going after
+			// the closing one, so YAML reads it as a quoted scalar followed by
+			// junk. Treating "starts with a quote" as "already quoted" leaves
+			// this broken forever.
+			name:        "quotes a value that only looks quoted",
+			doc:         "---\ntitle: \"Evaluation Driven Generation\" — a TDD-style scaffold\ntags: [a, b]\n---\n\nbody\n",
+			wantChanged: true,
+			wantKey:     "title",
+			wantValue:   "\"Evaluation Driven Generation\" — a TDD-style scaffold",
+		},
 		{
 			name:        "leaves an already-valid document untouched",
 			doc:         "---\ntitle: 'Already quoted: fine'\nwing: homelab\n---\n\nbody\n",
@@ -129,6 +140,25 @@ func TestFix(t *testing.T) {
 	}
 }
 
+func TestFix_LeavesStructuredValuesStructured(t *testing.T) {
+	// Only the broken scalar may be touched. A flow sequence on a neighbouring
+	// line still has to load as a sequence afterwards, not as a string.
+	doc := "---\ntitle: Broken: here\ntags: [prompting, llm]\ncount: 3\n---\n\nbody\n"
+
+	got, changed, err := Fix([]byte(doc))
+	require.NoError(t, err)
+	require.True(t, changed)
+
+	b, ok := block(got)
+	require.True(t, ok)
+	var m map[string]any
+	require.NoError(t, yaml.Unmarshal(b, &m))
+
+	assert.Equal(t, "Broken: here", m["title"])
+	assert.Equal(t, []any{"prompting", "llm"}, m["tags"])
+	assert.Equal(t, 3, m["count"])
+}
+
 func TestFix_PreservesBodyExactly(t *testing.T) {
 	body := "\nThe body has: colons, 'quotes', and\n---\na horizontal rule.\n"
 	doc := "---\ntitle: Broken: title\n---" + body