diff --git a/enginetest/queries/script_queries.go b/enginetest/queries/script_queries.go
index 3e2fcc1631..2567274cf5 100644
--- a/enginetest/queries/script_queries.go
+++ b/enginetest/queries/script_queries.go
@@ -9355,7 +9355,7 @@ where
 		},
 	},
 	{
-		Name:    "enum conversion to strings",
+		Name:    "enum conversions",
 		Dialect: "mysql",
 		SetUpScript: []string{
 			"create table t (e enum('abc', 'defg', 'hijkl'));",
@@ -9491,6 +9491,38 @@ where
 					{"abc"},
 				},
 			},
+			{
+				Query: "select e, cast(e as unsigned) from t order by e;",
+				Expected: []sql.Row{
+					{"abc", uint64(1)},
+					{"defg", uint64(2)},
+					{"hijkl", uint64(3)},
+				},
+			},
+			{
+				Query: "select e, cast(e as decimal) from t order by e;",
+				Expected: []sql.Row{
+					{"abc", "1"},
+					{"defg", "2"},
+					{"hijkl", "3"},
+				},
+			},
+			{
+				Query: "select e, cast(e as float) from t order by e;",
+				Expected: []sql.Row{
+					{"abc", float32(1)},
+					{"defg", float32(2)},
+					{"hijkl", float32(3)},
+				},
+			},
+			{
+				Query: "select e, cast(e as double) from t order by e;",
+				Expected: []sql.Row{
+					{"abc", float64(1)},
+					{"defg", float64(2)},
+					{"hijkl", float64(3)},
+				},
+			},
 		},
 	},
 	{
@@ -9953,7 +9985,7 @@ where
 		},
 	},
 	{
-		Name:    "set conversion to strings",
+		Name:    "set conversions",
 		Dialect: "mysql",
 		SetUpScript: []string{
 			"create table t (s set('abc', 'defg', 'hijkl'));",
@@ -10077,25 +10109,59 @@ where
 				},
 			},
 			{
-				// https://github.com/dolthub/dolt/issues/9511
-				Skip:  true,
 				Query: "select s, cast(s as char) from t order by s;",
 				Expected: []sql.Row{
 					{"abc", "abc"},
+					{"defg", "defg"},
 					{"abc,defg", "abc,defg"},
 					{"abc,defg,hijkl", "abc,defg,hijkl"},
 				},
 			},
 			{
-				// https://github.com/dolthub/dolt/issues/9511
-				Skip:  true,
 				Query: "select s, cast(s as binary) from t order by s;",
 				Expected: []sql.Row{
 					{"abc", []uint8("abc")},
+					{"defg", []uint8("defg")},
 					{"abc,defg", []uint8("abc,defg")},
 					{"abc,defg,hijkl", []uint8("abc,defg,hijkl")},
 				},
 			},
+			{
+				Query: "select s, cast(s as unsigned) from t order by s;",
+				Expected: []sql.Row{
+					{"abc", uint64(1)},
+					{"defg", uint64(2)},
+					{"abc,defg", uint64(3)},
+					{"abc,defg,hijkl", uint64(7)},
+				},
+			},
+			{
+				Query: "select s, cast(s as decimal) from t order by s;",
+				Expected: []sql.Row{
+					{"abc", "1"},
+					{"defg", "2"},
+					{"abc,defg", "3"},
+					{"abc,defg,hijkl", "7"},
+				},
+			},
+			{
+				Query: "select s, cast(s as float) from t order by s;",
+				Expected: []sql.Row{
+					{"abc", float32(1)},
+					{"defg", float32(2)},
+					{"abc,defg", float32(3)},
+					{"abc,defg,hijkl", float32(7)},
+				},
+			},
+			{
+				Query: "select s, cast(s as double) from t order by s;",
+				Expected: []sql.Row{
+					{"abc", float64(1)},
+					{"defg", float64(2)},
+					{"abc,defg", float64(3)},
+					{"abc,defg,hijkl", float64(7)},
+				},
+			},
 		},
 	},
 	{
diff --git a/sql/expression/convert.go b/sql/expression/convert.go
index d115de49ca..d60df93c1e 100644
--- a/sql/expression/convert.go
+++ b/sql/expression/convert.go
@@ -278,17 +278,22 @@ func (c *Convert) Eval(ctx *sql.Context, row sql.Row) (interface{}, error) {
 	return casted, nil
 }
 
-// convertValue only returns an error if converting to JSON, Date, and Datetime;
-// the zero value is returned for float types. Nil is returned in all other cases.
+// convertValue converts a value from its current type to the specified target type for CAST/CONVERT operations.
+// It handles type-specific conversion logic and applies length/scale constraints where applicable.
 // If |typeLength| and |typeScale| are 0, they are ignored, otherwise they are used as constraints on the
 // converted type where applicable (e.g. Char conversion supports only |typeLength|, Decimal conversion supports
 // |typeLength| and |typeScale|).
+// Only returns an error if converting to JSON, Date, and Datetime; the zero value is returned for float types.
+// Nil is returned in all other cases.
 func convertValue(ctx *sql.Context, val interface{}, castTo string, originType sql.Type, typeLength, typeScale int) (interface{}, error) {
 	if val == nil {
 		return nil, nil
 	}
 	switch strings.ToLower(castTo) {
 	case ConvertToBinary:
+		if types.IsSet(originType) || types.IsEnum(originType) {
+			val, _ = types.TypeAwareConversion(ctx, val, originType, types.LongText)
+		}
 		b, _, err := types.LongBlob.Convert(ctx, val)
 		if err != nil {
 			return nil, nil
@@ -307,6 +312,7 @@ func convertValue(ctx *sql.Context, val interface{}, castTo string, originType s
 		}
 		return truncateConvertedValue(b, typeLength)
 	case ConvertToChar, ConvertToNChar:
+		val, _ = types.TypeAwareConversion(ctx, val, originType, types.LongText)
 		s, _, err := types.LongText.Convert(ctx, val)
 		if err != nil {
 			return nil, nil