diff --git a/model/criteria/json.go b/model/criteria/json.go
index ca47ceb95..beded9d1f 100644
--- a/model/criteria/json.go
+++ b/model/criteria/json.go
@@ -96,20 +96,32 @@ func normalizeBoolFields(m map[string]any) {
 	}
 }
 
-func normalizeBoolValue(v any) any {
+// ToBool coerces a criteria value to a bool, accepting the forms criteria values take: a real bool,
+// a strconv.ParseBool-parseable string, or a JSON number that is exactly 0 or 1. Any other value
+// (other numbers, slices, nil, unparseable strings) returns ok=false so callers can handle it.
+func ToBool(v any) (bool, bool) {
 	switch val := v.(type) {
+	case bool:
+		return val, true
 	case string:
-		if b, err := strconv.ParseBool(val); err == nil {
-			return b
-		}
+		b, err := strconv.ParseBool(val)
+		return b, err == nil
 	case float64:
-		if val == 1 {
-			return true
-		}
-		if val == 0 {
-			return false
+		switch val {
+		case 1:
+			return true, true
+		case 0:
+			return false, true
 		}
 	}
+	return false, false
+}
+
+// normalizeBoolValue leaves non-boolean values unchanged so they flow through to their own validation.
+func normalizeBoolValue(v any) any {
+	if b, ok := ToBool(v); ok {
+		return b
+	}
 	return v
 }
 
diff --git a/model/criteria/operators_test.go b/model/criteria/operators_test.go
index 17c4272ba..e5c8e1763 100644
--- a/model/criteria/operators_test.go
+++ b/model/criteria/operators_test.go
@@ -126,4 +126,25 @@ var _ = Describe("Operators", func() {
 			gomega.Expect(obj[0]).To(gomega.Equal(IsPresent{"genre": true}))
 		})
 	})
+
+	DescribeTable("ToBool",
+		func(in any, wantVal, wantOk bool) {
+			got, ok := ToBool(in)
+			gomega.Expect(ok).To(gomega.Equal(wantOk))
+			gomega.Expect(got).To(gomega.Equal(wantVal))
+		},
+		Entry("real bool true", true, true, true),
+		Entry("real bool false", false, false, true),
+		Entry("string true", "true", true, true),
+		Entry("string false", "false", false, true),
+		Entry("string 1", "1", true, true),
+		Entry("string t", "t", true, true),
+		Entry("string 0", "0", false, true),
+		Entry("string unparseable", "yes", false, false),
+		Entry("float64 1", float64(1), true, true),
+		Entry("float64 0", float64(0), false, true),
+		Entry("float64 other", float64(2), false, false),
+		Entry("slice", []any{true}, false, false),
+		Entry("nil", nil, false, false),
+	)
 })
diff --git a/persistence/criteria_sql.go b/persistence/criteria_sql.go
index b74f498d0..43cab4fdd 100644
--- a/persistence/criteria_sql.go
+++ b/persistence/criteria_sql.go
@@ -28,10 +28,11 @@ func (j smartPlaylistJoinType) has(other smartPlaylistJoinType) bool {
 }
 
 type smartPlaylistField struct {
-	expr        string
-	order       string
-	joinType    smartPlaylistJoinType
-	emptyValues []string // additional values that encode "missing" for string columns (e.g. '[]' for lyrics)
+	expr            string
+	order           string
+	joinType        smartPlaylistJoinType
+	emptyValues     []string // additional values that encode "missing" for string columns (e.g. '[]' for lyrics)
+	coalesceDefault any      // missing-row default for a nullable annotation column; nil = none. See annotationCond.
 }
 
 type smartPlaylistCriteria struct {
@@ -89,22 +90,22 @@ var smartPlaylistFields = map[string]smartPlaylistField{
 	"samplerate":           {expr: "media_file.sample_rate"},
 	"bpm":                  {expr: "media_file.bpm"},
 	"channels":             {expr: "media_file.channels"},
-	"loved":                {expr: "COALESCE(annotation.starred, false)"},
+	"loved":                {expr: "annotation.starred", coalesceDefault: false},
 	"dateloved":            {expr: "annotation.starred_at"},
 	"lastplayed":           {expr: "annotation.play_date"},
 	"daterated":            {expr: "annotation.rated_at"},
-	"playcount":            {expr: "COALESCE(annotation.play_count, 0)"},
-	"rating":               {expr: "COALESCE(annotation.rating, 0)"},
+	"playcount":            {expr: "annotation.play_count", coalesceDefault: 0},
+	"rating":               {expr: "annotation.rating", coalesceDefault: 0},
 	"averagerating":        {expr: "media_file.average_rating"},
-	"albumrating":          {expr: "COALESCE(album_annotation.rating, 0)", joinType: smartPlaylistJoinAlbumAnnotation},
-	"albumloved":           {expr: "COALESCE(album_annotation.starred, false)", joinType: smartPlaylistJoinAlbumAnnotation},
-	"albumplaycount":       {expr: "COALESCE(album_annotation.play_count, 0)", joinType: smartPlaylistJoinAlbumAnnotation},
+	"albumrating":          {expr: "album_annotation.rating", coalesceDefault: 0, joinType: smartPlaylistJoinAlbumAnnotation},
+	"albumloved":           {expr: "album_annotation.starred", coalesceDefault: false, joinType: smartPlaylistJoinAlbumAnnotation},
+	"albumplaycount":       {expr: "album_annotation.play_count", coalesceDefault: 0, joinType: smartPlaylistJoinAlbumAnnotation},
 	"albumlastplayed":      {expr: "album_annotation.play_date", joinType: smartPlaylistJoinAlbumAnnotation},
 	"albumdateloved":       {expr: "album_annotation.starred_at", joinType: smartPlaylistJoinAlbumAnnotation},
 	"albumdaterated":       {expr: "album_annotation.rated_at", joinType: smartPlaylistJoinAlbumAnnotation},
-	"artistrating":         {expr: "COALESCE(artist_annotation.rating, 0)", joinType: smartPlaylistJoinArtistAnnotation},
-	"artistloved":          {expr: "COALESCE(artist_annotation.starred, false)", joinType: smartPlaylistJoinArtistAnnotation},
-	"artistplaycount":      {expr: "COALESCE(artist_annotation.play_count, 0)", joinType: smartPlaylistJoinArtistAnnotation},
+	"artistrating":         {expr: "artist_annotation.rating", coalesceDefault: 0, joinType: smartPlaylistJoinArtistAnnotation},
+	"artistloved":          {expr: "artist_annotation.starred", coalesceDefault: false, joinType: smartPlaylistJoinArtistAnnotation},
+	"artistplaycount":      {expr: "artist_annotation.play_count", coalesceDefault: 0, joinType: smartPlaylistJoinArtistAnnotation},
 	"artistlastplayed":     {expr: "artist_annotation.play_date", joinType: smartPlaylistJoinArtistAnnotation},
 	"artistdateloved":      {expr: "artist_annotation.starred_at", joinType: smartPlaylistJoinArtistAnnotation},
 	"artistdaterated":      {expr: "artist_annotation.rated_at", joinType: smartPlaylistJoinArtistAnnotation},
@@ -152,27 +153,17 @@ func (c smartPlaylistCriteria) exprSQL(expr criteria.Expression) (squirrel.Sqliz
 		}
 		return mergeJsonConds(or), nil
 	case criteria.Is:
-		return mapExpr(e, func(fields map[string]any) squirrel.Sqlizer {
-			return squirrel.Eq(fields)
-		}, false)
+		return comparisonExpr(e, cmpEq)
 	case criteria.IsNot:
 		return isNotExpr(e)
 	case criteria.Gt:
-		return mapExpr(e, func(fields map[string]any) squirrel.Sqlizer {
-			return squirrel.Gt(fields)
-		}, false)
+		return comparisonExpr(e, cmpGt)
 	case criteria.Lt:
-		return mapExpr(e, func(fields map[string]any) squirrel.Sqlizer {
-			return squirrel.Lt(fields)
-		}, false)
+		return comparisonExpr(e, cmpLt)
 	case criteria.Before:
-		return mapExpr(e, func(fields map[string]any) squirrel.Sqlizer {
-			return squirrel.Lt(fields)
-		}, false)
+		return comparisonExpr(e, cmpLt)
 	case criteria.After:
-		return mapExpr(e, func(fields map[string]any) squirrel.Sqlizer {
-			return squirrel.Gt(fields)
-		}, false)
+		return comparisonExpr(e, cmpGt)
 	case criteria.Contains:
 		return likeExpr(e, "%%%v%%", false)
 	case criteria.NotContains:
@@ -204,11 +195,7 @@ func isNotExpr(values map[string]any) (squirrel.Sqlizer, error) {
 	if _, value, info, ok := singleField(values); ok && (info.IsTag || info.IsRole) {
 		return jsonExpr(info, squirrel.Eq{"value": value}, true), nil
 	}
-	fields, err := sqlFields(values)
-	if err != nil {
-		return nil, err
-	}
-	return squirrel.NotEq(fields), nil
+	return comparisonExpr(values, cmpNe)
 }
 
 func missingExpr(values map[string]any, checkAbsence bool) (squirrel.Sqlizer, error) {
@@ -259,20 +246,17 @@ func missingExpr(values map[string]any, checkAbsence bool) (squirrel.Sqlizer, er
 	}
 }
 
-func mapExpr(values map[string]any, makeCond func(map[string]any) squirrel.Sqlizer, negateJSON bool) (squirrel.Sqlizer, error) {
-	if _, value, info, ok := singleField(values); ok && (info.IsTag || info.IsRole) {
-		return jsonExpr(info, makeCond(map[string]any{"value": value}), negateJSON), nil
-	}
-	fields, err := sqlFields(values)
-	if err != nil {
-		return nil, err
-	}
-	return makeCond(fields), nil
-}
-
 func likeExpr(values map[string]any, pattern string, negate bool) (squirrel.Sqlizer, error) {
-	if _, value, info, ok := singleField(values); ok && (info.IsTag || info.IsRole) {
-		return jsonExpr(info, squirrel.Like{"value": fmt.Sprintf(pattern, value)}, negate), nil
+	if _, value, info, ok := singleField(values); ok {
+		if info.IsTag || info.IsRole {
+			return jsonExpr(info, squirrel.Like{"value": fmt.Sprintf(pattern, value)}, negate), nil
+		}
+		// LIKE can't use the column index, so annotation fields keep the COALESCE form: a NULL
+		// column never matches LIKE, which would silently drop missing-annotation rows the original
+		// COALESCE form included.
+		if f, isAnnotation := annotationField(info); isAnnotation {
+			return likeCond(f.coalesced(), fmt.Sprintf(pattern, value), negate), nil
+		}
 	}
 	fields, err := sqlFields(values)
 	if err != nil {
@@ -292,23 +276,36 @@ func likeExpr(values map[string]any, pattern string, negate bool) (squirrel.Sqli
 	return lk, nil
 }
 
+func likeCond(col, pattern string, negate bool) squirrel.Sqlizer {
+	if negate {
+		return squirrel.NotLike{col: pattern}
+	}
+	return squirrel.Like{col: pattern}
+}
+
 func rangeExpr(values map[string]any) (squirrel.Sqlizer, error) {
-	fields, err := sqlFields(values)
+	field, value, info, ok := singleField(values)
+	if !ok {
+		return nil, fmt.Errorf("invalid field in criteria: %s", field)
+	}
+	if info.IsTag || info.IsRole {
+		// Tags/roles are multi-valued JSON, so splitting a range into two independent EXISTS
+		// subqueries would let different values satisfy each bound. Ranges are unsupported there.
+		return nil, fmt.Errorf("range operator not supported for tag/role field: %s", field)
+	}
+	s := reflect.ValueOf(value)
+	if s.Kind() != reflect.Slice || s.Len() != 2 {
+		return nil, fmt.Errorf("range criteria for %q must be a [min, max] pair, got: %v", field, value)
+	}
+	low, err := comparisonExpr(map[string]any{field: s.Index(0).Interface()}, cmpGe)
 	if err != nil {
 		return nil, err
 	}
-	and := squirrel.And{}
-	for field, value := range fields {
-		s := reflect.ValueOf(value)
-		if s.Kind() != reflect.Slice || s.Len() != 2 {
-			return nil, fmt.Errorf("invalid range for 'in' operator: %s", value)
-		}
-		and = append(and,
-			squirrel.GtOrEq{field: s.Index(0).Interface()},
-			squirrel.LtOrEq{field: s.Index(1).Interface()},
-		)
+	high, err := comparisonExpr(map[string]any{field: s.Index(1).Interface()}, cmpLe)
+	if err != nil {
+		return nil, err
 	}
-	return and, nil
+	return squirrel.And{low, high}, nil
 }
 
 func periodExpr(values map[string]any, negate bool) (squirrel.Sqlizer, error) {
@@ -638,6 +635,139 @@ func fieldExpr(name string) (string, bool) {
 	return field.expr, ok
 }
 
+// comparator is a scalar SQL comparison operator used by smart playlist criteria.
+type comparator struct {
+	build   func(map[string]any) squirrel.Sqlizer
+	satisfy func(a, b float64) bool // the operator as a predicate, to reason about a column's COALESCE default
+	// ordering is false only for = and <>, the only operators with a clean bare form over bool columns.
+	ordering bool
+}
+
+var (
+	cmpEq = comparator{build: func(f map[string]any) squirrel.Sqlizer { return squirrel.Eq(f) }, satisfy: func(a, b float64) bool { return a == b }}
+	cmpNe = comparator{build: func(f map[string]any) squirrel.Sqlizer { return squirrel.NotEq(f) }, satisfy: func(a, b float64) bool { return a != b }}
+	cmpGt = comparator{build: func(f map[string]any) squirrel.Sqlizer { return squirrel.Gt(f) }, satisfy: func(a, b float64) bool { return a > b }, ordering: true}
+	cmpGe = comparator{build: func(f map[string]any) squirrel.Sqlizer { return squirrel.GtOrEq(f) }, satisfy: func(a, b float64) bool { return a >= b }, ordering: true}
+	cmpLt = comparator{build: func(f map[string]any) squirrel.Sqlizer { return squirrel.Lt(f) }, satisfy: func(a, b float64) bool { return a < b }, ordering: true}
+	cmpLe = comparator{build: func(f map[string]any) squirrel.Sqlizer { return squirrel.LtOrEq(f) }, satisfy: func(a, b float64) bool { return a <= b }, ordering: true}
+)
+
+// annotationField returns the field definition only for nullable annotation columns that have a
+// COALESCE default (playcount, rating, loved). Date annotation columns (lastplayed, dateloved, ...)
+// have no default and return ok=false.
+func annotationField(info criteria.FieldInfo) (smartPlaylistField, bool) {
+	f, ok := smartPlaylistFields[info.Name()]
+	if !ok || f.coalesceDefault == nil {
+		return smartPlaylistField{}, false
+	}
+	return f, true
+}
+
+// coalesced wraps the field in COALESCE(col, default) (bare expression if it has no default). Used
+// where index-friendliness does not apply (ORDER BY, list comparisons) and the missing-row-as-default
+// semantics must be kept.
+func (f smartPlaylistField) coalesced() string {
+	if f.coalesceDefault == nil {
+		return f.expr
+	}
+	return fmt.Sprintf("COALESCE(%s, %s)", f.expr, sqlLiteral(f.coalesceDefault))
+}
+
+func comparisonExpr(values map[string]any, cmp comparator) (squirrel.Sqlizer, error) {
+	if _, value, info, ok := singleField(values); ok {
+		if info.IsTag || info.IsRole {
+			return jsonExpr(info, cmp.build(map[string]any{"value": value}), false), nil
+		}
+		if f, isAnnotation := annotationField(info); isAnnotation {
+			return annotationCond(f, cmp, value), nil
+		}
+	}
+	fields, err := sqlFields(values)
+	if err != nil {
+		return nil, err
+	}
+	return cmp.build(fields), nil
+}
+
+// annotationCond builds a comparison against a nullable annotation column (see smartPlaylistField
+// for why). When bareNullInclusion can reason about the comparison exactly it emits the
+// index-friendly bare `col <cmp> ?`, adding `OR col IS NULL` only when the default would match;
+// otherwise it falls back to the COALESCE form, which can't use the index but is always equivalent.
+func annotationCond(f smartPlaylistField, cmp comparator, value any) squirrel.Sqlizer {
+	wrapNull, ok := bareNullInclusion(f.coalesceDefault, cmp, value)
+	if !ok {
+		return cmp.build(map[string]any{f.coalesced(): value})
+	}
+	base := cmp.build(map[string]any{f.expr: value})
+	if !wrapNull {
+		return base
+	}
+	// The default satisfies the predicate, so missing rows (NULL) must be included. All comparators
+	// (including <>) evaluate to false against NULL, so an explicit IS NULL restores them.
+	return squirrel.Or{base, squirrel.Eq{f.expr: nil}}
+}
+
+// bareNullInclusion decides whether the index-friendly bare form is safe for this comparison and,
+// if so, whether missing (NULL) rows must be re-included via `OR col IS NULL`. It returns ok=false
+// when the bare form can't be proven equivalent to COALESCE(col, default) <cmp> ? — i.e. the value
+// isn't a scalar the comparator can order exactly (lists, bool ordering, unparseable values) — in
+// which case the caller keeps the COALESCE form. When ok=true, wrapNull is true iff the default
+// value itself satisfies the predicate (so missing rows would match and must be preserved).
+func bareNullInclusion(defaultVal any, cmp comparator, value any) (wrapNull, ok bool) {
+	if b, isBool := defaultVal.(bool); isBool {
+		// Bool columns have an exact bare form only for equality; ordering operators fall back to
+		// COALESCE. Mapping both bools to 0/1 lets cmp.satisfy reuse the numeric eq/ne predicate.
+		if cmp.ordering {
+			return false, false
+		}
+		v, okV := criteria.ToBool(value)
+		if !okV {
+			return false, false
+		}
+		return cmp.satisfy(boolToFloat(b), boolToFloat(v)), true
+	}
+	d, okD := toFloat(defaultVal)
+	v, okV := toFloat(value)
+	if !okD || !okV {
+		// Non-scalar or unparseable value: no exact bare form, keep COALESCE.
+		return false, false
+	}
+	return cmp.satisfy(d, v), true
+}
+
+func boolToFloat(b bool) float64 {
+	if b {
+		return 1
+	}
+	return 0
+}
+
+// toFloat coerces a scalar criteria value to float64. Criteria values come from JSON (float64,
+// string) or are built in Go (int, float64), so only those types are handled; anything else —
+// including a slice or an unparseable string — reports ok=false so the caller keeps the COALESCE
+// form instead of an index-friendly bare comparison.
+func toFloat(v any) (float64, bool) {
+	switch n := v.(type) {
+	case float64:
+		return n, true
+	case int:
+		return float64(n), true
+	case int64:
+		return float64(n), true
+	case string:
+		f, err := strconv.ParseFloat(n, 64)
+		return f, err == nil
+	default:
+		return 0, false
+	}
+}
+
+// sqlLiteral renders an annotation field's COALESCE default (0 or false) as a SQL literal for ORDER
+// BY. %v renders both bool and numeric defaults correctly (false/true, 0).
+func sqlLiteral(v any) string {
+	return fmt.Sprintf("%v", v)
+}
+
 func fieldJoinType(name string) smartPlaylistJoinType {
 	info, ok := criteria.LookupField(name)
 	if !ok {
@@ -705,7 +835,9 @@ func sortExpr(sortField string) (string, bool) {
 		if !ok || field.expr == "" {
 			return "", false
 		}
-		mapped = field.expr
+		// Sorting keeps the COALESCE default so missing-annotation rows sort as that default
+		// (filtering drops COALESCE for index use, but ORDER BY has no index to preserve here).
+		mapped = field.coalesced()
 	}
 	if info.Numeric {
 		mapped = fmt.Sprintf("CAST(%s AS REAL)", mapped)
diff --git a/persistence/criteria_sql_test.go b/persistence/criteria_sql_test.go
index 9ff7f1f07..59bdc4452 100644
--- a/persistence/criteria_sql_test.go
+++ b/persistence/criteria_sql_test.go
@@ -30,16 +30,16 @@ var _ = Describe("Smart playlist criteria SQL", func() {
 		},
 		Entry("all group",
 			criteria.All{criteria.Contains{"title": "love"}, criteria.Gt{"rating": 3}},
-			"(media_file.title LIKE ? AND COALESCE(annotation.rating, 0) > ?)", "%love%", 3),
+			"(media_file.title LIKE ? AND annotation.rating > ?)", "%love%", 3),
 		Entry("any group",
 			criteria.Any{criteria.Is{"title": "Low Rider"}, criteria.Is{"album": "Best Of"}},
 			"(media_file.title = ? OR media_file.album = ?)", "Low Rider", "Best Of"),
 		Entry("is string", criteria.Is{"title": "Low Rider"}, "media_file.title = ?", "Low Rider"),
-		Entry("is bool", criteria.Is{"loved": true}, "COALESCE(annotation.starred, false) = ?", true),
+		Entry("is bool", criteria.Is{"loved": true}, "annotation.starred = ?", true),
 		Entry("is numeric list", criteria.Is{"library_id": []int{1, 2}}, "media_file.library_id IN (?,?)", 1, 2),
 		Entry("is not", criteria.IsNot{"title": "Low Rider"}, "media_file.title <> ?", "Low Rider"),
-		Entry("gt", criteria.Gt{"playCount": 10}, "COALESCE(annotation.play_count, 0) > ?", 10),
-		Entry("lt", criteria.Lt{"playCount": 10}, "COALESCE(annotation.play_count, 0) < ?", 10),
+		Entry("gt", criteria.Gt{"playCount": 10}, "annotation.play_count > ?", 10),
+		Entry("lt", criteria.Lt{"playCount": 10}, "(annotation.play_count < ? OR annotation.play_count IS NULL)", 10),
 		Entry("contains", criteria.Contains{"title": "Low Rider"}, "media_file.title LIKE ?", "%Low Rider%"),
 		Entry("not contains", criteria.NotContains{"title": "Low Rider"}, "media_file.title NOT LIKE ?", "%Low Rider%"),
 		Entry("starts with", criteria.StartsWith{"title": "Low Rider"}, "media_file.title LIKE ?", "Low Rider%"),
@@ -49,8 +49,51 @@ var _ = Describe("Smart playlist criteria SQL", func() {
 		Entry("after", criteria.After{"lastPlayed": time.Date(2021, 10, 1, 0, 0, 0, 0, time.Local)}, "annotation.play_date > ?", time.Date(2021, 10, 1, 0, 0, 0, 0, time.Local)),
 		Entry("in playlist", criteria.InPlaylist{"id": "deadbeef-dead-beef"}, "media_file.id IN (SELECT media_file_id FROM playlist_tracks pl LEFT JOIN playlist on pl.playlist_id = playlist.id WHERE (pl.playlist_id = ? AND playlist.public = ?))", "deadbeef-dead-beef", 1),
 		Entry("not in playlist", criteria.NotInPlaylist{"id": "deadbeef-dead-beef"}, "media_file.id NOT IN (SELECT media_file_id FROM playlist_tracks pl LEFT JOIN playlist on pl.playlist_id = playlist.id WHERE (pl.playlist_id = ? AND playlist.public = ?))", "deadbeef-dead-beef", 1),
-		Entry("album annotation", criteria.Gt{"albumRating": 3}, "COALESCE(album_annotation.rating, 0) > ?", 3),
-		Entry("artist annotation", criteria.Is{"artistLoved": true}, "COALESCE(artist_annotation.starred, false) = ?", true),
+		Entry("album annotation", criteria.Gt{"albumRating": 3}, "album_annotation.rating > ?", 3),
+		Entry("artist annotation", criteria.Is{"artistLoved": true}, "artist_annotation.starred = ?", true),
+		// Annotation fields use a COALESCE default (0 for numeric, false for bool) so that tracks
+		// with no annotation row behave as that default. To keep the annotation index usable, the
+		// COALESCE is dropped when the compared value cannot match the default (the missing-row
+		// case is then naturally excluded); otherwise an explicit `OR col IS NULL` preserves it.
+		Entry("is safe (value != default)", criteria.Is{"playCount": 3}, "annotation.play_count = ?", 3),
+		Entry("is unsafe (value == default)", criteria.Is{"playCount": 0},
+			"(annotation.play_count = ? OR annotation.play_count IS NULL)", 0),
+		Entry("is bool false (value == default)", criteria.Is{"loved": false},
+			"(annotation.starred = ? OR annotation.starred IS NULL)", false),
+		Entry("gt safe (value >= default)", criteria.Gt{"playCount": 0}, "annotation.play_count > ?", 0),
+		Entry("gt unsafe (value < default)", criteria.Gt{"playCount": -1},
+			"(annotation.play_count > ? OR annotation.play_count IS NULL)", -1),
+		Entry("lt safe (value <= default)", criteria.Lt{"playCount": 0}, "annotation.play_count < ?", 0),
+		Entry("lt unsafe (value > default)", criteria.Lt{"playCount": 5},
+			"(annotation.play_count < ? OR annotation.play_count IS NULL)", 5),
+		Entry("isNot annotation keeps null match", criteria.IsNot{"playCount": 3},
+			"(annotation.play_count <> ? OR annotation.play_count IS NULL)", 3),
+		Entry("isNot annotation value == default", criteria.IsNot{"playCount": 0},
+			"annotation.play_count <> ?", 0),
+		Entry("in range spanning default", criteria.InTheRange{"playCount": []int{-1, 5}},
+			"((annotation.play_count >= ? OR annotation.play_count IS NULL) AND (annotation.play_count <= ? OR annotation.play_count IS NULL))", -1, 5),
+		Entry("in range above default", criteria.InTheRange{"playCount": []int{1, 5}},
+			"(annotation.play_count >= ? AND (annotation.play_count <= ? OR annotation.play_count IS NULL))", 1, 5),
+		// A list value can't drive the index and a default-inclusive list has per-element NULL
+		// semantics, so the COALESCE form is kept to stay equivalent to the original.
+		Entry("is list keeps coalesce", criteria.Is{"playCount": []int{0, 3}},
+			"COALESCE(annotation.play_count, 0) IN (?,?)", 0, 3),
+		// LIKE operators can't use the column index, so annotation fields keep the COALESCE form to
+		// match missing-annotation rows exactly as before (a NULL column never matches LIKE).
+		Entry("contains annotation keeps coalesce", criteria.Contains{"playCount": 0},
+			"COALESCE(annotation.play_count, 0) LIKE ?", "%0%"),
+		Entry("starts with annotation keeps coalesce", criteria.StartsWith{"rating": 5},
+			"COALESCE(annotation.rating, 0) LIKE ?", "5%"),
+		Entry("not contains annotation keeps coalesce", criteria.NotContains{"playCount": 0},
+			"COALESCE(annotation.play_count, 0) NOT LIKE ?", "%0%"),
+		// Bool annotation fields only have a clean index-friendly form for equality; ordering
+		// comparators keep the COALESCE form so the missing-row default is honored exactly.
+		Entry("gt bool keeps coalesce", criteria.Gt{"loved": false},
+			"COALESCE(annotation.starred, false) > ?", false),
+		// A list value on a bool field is non-scalar, so it keeps the COALESCE form too (same as the
+		// numeric list case) — otherwise a NULL column would diverge from the original.
+		Entry("is bool list keeps coalesce", criteria.Is{"loved": []any{true}},
+			"COALESCE(annotation.starred, false) IN (?)", true),
 		Entry("tag is", criteria.Is{"genre": "Rock"}, "exists (select 1 from json_tree(media_file.tags, '$.genre') where key='value' and value = ?)", "Rock"),
 		Entry("tag is not", criteria.IsNot{"genre": "Rock"}, "not exists (select 1 from json_tree(media_file.tags, '$.genre') where key='value' and value = ?)", "Rock"),
 		Entry("tag contains", criteria.Contains{"genre": "Rock"}, "exists (select 1 from json_tree(media_file.tags, '$.genre') where key='value' and value LIKE ?)", "%Rock%"),
@@ -220,6 +263,16 @@ var _ = Describe("Smart playlist criteria SQL", func() {
 		Expect(err).To(MatchError(ContainSubstring("invalid boolean value for 'missing' expression")))
 	})
 
+	It("returns an error for a range over a tag/role field", func() {
+		_, err := newSmartPlaylistCriteria(criteria.Criteria{Expression: criteria.InTheRange{"rate": []int{1, 5}}}).Where()
+		Expect(err).To(MatchError(ContainSubstring("range operator not supported for tag/role field")))
+	})
+
+	It("returns a clear error for a malformed range value", func() {
+		_, err := newSmartPlaylistCriteria(criteria.Criteria{Expression: criteria.InTheRange{"playCount": []int{1, 2, 3}}}).Where()
+		Expect(err).To(MatchError(ContainSubstring("must be a [min, max] pair")))
+	})
+
 	Describe("sort", func() {
 		It("sorts by regular fields", func() {
 			Expect(newSmartPlaylistCriteria(criteria.Criteria{Sort: "title"}).OrderBy()).To(Equal("media_file.title asc"))