diff --git a/enginetest/queries/json_scripts.go b/enginetest/queries/json_scripts.go
index cb981cd1c8..3c0b09744e 100644
--- a/enginetest/queries/json_scripts.go
+++ b/enginetest/queries/json_scripts.go
@@ -17,11 +17,35 @@ package queries
 import (
 	"github.com/dolthub/vitess/go/vt/sqlparser"
 
+	"github.com/dolthub/go-mysql-server/sql/plan"
+
 	"github.com/dolthub/go-mysql-server/sql"
 	"github.com/dolthub/go-mysql-server/sql/types"
 )
 
 var JsonScripts = []ScriptTest{
+	{
+		// https://github.com/dolthub/dolt/issues/10050
+		Name: "TextStorage converts to JSON when using dolt wrapper",
+		SetUpScript: []string{
+			"CREATE TABLE pages (id INT PRIMARY KEY, text_col TEXT, text_json JSON)",
+			"INSERT INTO pages VALUES (1, '{\"message\":\"hello\"}', NULL)",
+		},
+		Assertions: []ScriptTestAssertion{
+			{
+				Query: "UPDATE pages SET text_json = text_col",
+				Expected: []sql.Row{
+					{types.OkResult{RowsAffected: 1, Info: plan.UpdateInfo{Matched: 1, Updated: 1}}},
+				},
+			},
+			{
+				Query: "SELECT text_json FROM pages",
+				Expected: []sql.Row{
+					{types.MustJSON("{\"message\":\"hello\"}")},
+				},
+			},
+		},
+	},
 	{
 		Name: "json_type scripts",
 		Assertions: []ScriptTestAssertion{
diff --git a/sql/types/json.go b/sql/types/json.go
index 44cb3434f9..64ba15842c 100644
--- a/sql/types/json.go
+++ b/sql/types/json.go
@@ -45,29 +45,55 @@ func (t JsonType) Compare(ctx context.Context, a interface{}, b interface{}) (in
 	return CompareJSON(ctx, a, b)
 }
 
+// convertJSONValue parses JSON-encoded data if the input is a string or []byte, returning the resulting JSONDocument. For
+// other types, the value is returned if it can be marshalled.
+func convertJSONValue(v interface{}) (interface{}, sql.ConvertInRange, error) {
+	var data []byte
+	var charsetMaxLength int64 = 1
+	switch x := v.(type) {
+	case []byte:
+		data = x
+	case string:
+		data = []byte(x)
+		charsetMaxLength = sql.Collation_Default.CharacterSet().MaxLength()
+	default:
+		// if |v| can be marshalled, it contains
+		// a valid JSON document representation
+		if b, berr := json.Marshal(v); berr == nil {
+			data = b
+		} else {
+			return nil, sql.InRange, nil
+		}
+	}
+
+	if int64(len(data))*charsetMaxLength > MaxJsonFieldByteLength {
+		return nil, sql.InRange, ErrLengthTooLarge.New(len(data), MaxJsonFieldByteLength)
+	}
+
+	var val interface{}
+	if err := json.Unmarshal(data, &val); err != nil {
+		return nil, sql.OutOfRange, sql.ErrInvalidJson.New(err.Error())
+	}
+
+	return JSONDocument{Val: val}, sql.InRange, nil
+}
+
 // Convert implements Type interface.
-func (t JsonType) Convert(c context.Context, v interface{}) (doc interface{}, inRange sql.ConvertInRange, err error) {
+func (t JsonType) Convert(c context.Context, v interface{}) (interface{}, sql.ConvertInRange, error) {
 	switch v := v.(type) {
 	case sql.JSONWrapper:
 		return v, sql.InRange, nil
 	case []byte:
-		if int64(len(v)) > MaxJsonFieldByteLength {
-			return nil, sql.InRange, ErrLengthTooLarge.New(len(v), MaxJsonFieldByteLength)
-		}
-		err = json.Unmarshal(v, &doc)
-		if err != nil {
-			return nil, sql.OutOfRange, sql.ErrInvalidJson.New(err.Error())
-		}
+		return convertJSONValue(v)
 	case string:
-		charsetMaxLength := sql.Collation_Default.CharacterSet().MaxLength()
-		length := int64(len(v)) * charsetMaxLength
-		if length > MaxJsonFieldByteLength {
-			return nil, sql.InRange, ErrLengthTooLarge.New(length, MaxJsonFieldByteLength)
-		}
-		err = json.Unmarshal([]byte(v), &doc)
+		return convertJSONValue(v)
+	// Text values may be stored in wrappers (e.g. Dolt's TextStorage), so unwrap to the raw string before decoding.
+	case sql.StringWrapper:
+		str, err := v.Unwrap(c)
 		if err != nil {
-			return nil, sql.OutOfRange, sql.ErrInvalidJson.New(err.Error())
+			return nil, sql.OutOfRange, err
 		}
+		return convertJSONValue(str)
 	case int8:
 		return JSONDocument{Val: int64(v)}, sql.InRange, nil
 	case int16:
@@ -91,22 +117,8 @@ func (t JsonType) Convert(c context.Context, v interface{}) (doc interface{}, in
 	case decimal.Decimal:
 		return JSONDocument{Val: v}, sql.InRange, nil
 	default:
-		// if |v| can be marshalled, it contains
-		// a valid JSON document representation
-		if b, berr := json.Marshal(v); berr == nil {
-			if int64(len(b)) > MaxJsonFieldByteLength {
-				return nil, sql.InRange, ErrLengthTooLarge.New(len(b), MaxJsonFieldByteLength)
-			}
-			err = json.Unmarshal(b, &doc)
-			if err != nil {
-				return nil, sql.OutOfRange, sql.ErrInvalidJson.New(err.Error())
-			}
-		}
-	}
-	if err != nil {
-		return nil, sql.OutOfRange, err
+		return convertJSONValue(v)
 	}
-	return JSONDocument{Val: doc}, sql.InRange, nil
 }
 
 // Equals implements the Type interface.
diff --git a/sql/types/jsontests/json_test.go b/sql/types/jsontests/json_test.go
index e83aa4005d..1540106e0e 100644
--- a/sql/types/jsontests/json_test.go
+++ b/sql/types/jsontests/json_test.go
@@ -28,6 +28,34 @@ import (
 	"github.com/dolthub/go-mysql-server/sql/types"
 )
 
+type mockStringWrapper struct {
+	val string
+}
+
+func (m mockStringWrapper) Unwrap(ctx context.Context) (string, error) {
+	return m.val, nil
+}
+
+func (m mockStringWrapper) UnwrapAny(ctx context.Context) (interface{}, error) {
+	return m.val, nil
+}
+
+func (m mockStringWrapper) IsExactLength() bool {
+	return false
+}
+
+func (m mockStringWrapper) MaxByteLength() int64 {
+	return int64(len(m.val))
+}
+
+func (m mockStringWrapper) Compare(ctx context.Context, other interface{}) (int, bool, error) {
+	return 0, false, nil
+}
+
+func (m mockStringWrapper) Hash() interface{} {
+	return m.val
+}
+
 func TestJsonCompare(t *testing.T) {
 	RunJsonCompareTests(t, JsonCompareTests, func(t *testing.T, left, right interface{}) (interface{}, interface{}) {
 		return ConvertToJson(t, left), ConvertToJson(t, right)
@@ -58,6 +86,7 @@ func TestJsonConvert(t *testing.T) {
 		{types.MustJSON(`{"field":"test"}`), types.MustJSON(`{"field":"test"}`), false},
 		{[]string{}, types.MustJSON(`[]`), false},
 		{[]string{`555-555-5555`}, types.MustJSON(`["555-555-5555"]`), false},
+		{mockStringWrapper{val: `{"c": 1}`}, types.MustJSON(`{"c":1}`), false},
 	}
 
 	for _, test := range tests {