diff --git a/apps/desktop/src/components/generate/DataGenerateDialog.vue b/apps/desktop/src/components/generate/DataGenerateDialog.vue
index 3979aa77b7..205eff296a 100644
--- a/apps/desktop/src/components/generate/DataGenerateDialog.vue
+++ b/apps/desktop/src/components/generate/DataGenerateDialog.vue
@@ -607,8 +607,11 @@ function sqlStatementsForTable(r: GeneratedTableResult): string[] {
     stmts.push(...r.statements);
   } else {
     const colList = r.columns.map((c) => quoteTableIdentifier(dbType.value, c)).join(", ");
+    // Match by column name: rows may carry a leading tbname (TDengine stable),
+    // so positional indexes into resolvedColumns would drift.
+    const dataTypeByName = new Map(r.resolvedColumns.map((c) => [c.columnName.toLowerCase(), c.dataType]));
     for (const row of r.rows) {
-      const vals = row.map((value) => formatGeneratedValue(value)).join(", ");
+      const vals = row.map((value, index) => formatGeneratedValue(value, dbType.value, dataTypeByName.get(r.columns[index]?.toLowerCase() ?? ""))).join(", ");
       stmts.push(`INSERT INTO ${targetTable} (${colList}) VALUES (${vals});`);
     }
   }
diff --git a/apps/desktop/src/lib/dataGrid/dataGenerate.ts b/apps/desktop/src/lib/dataGrid/dataGenerate.ts
index 8e8571d365..66777e3069 100644
--- a/apps/desktop/src/lib/dataGrid/dataGenerate.ts
+++ b/apps/desktop/src/lib/dataGrid/dataGenerate.ts
@@ -1758,9 +1758,37 @@ export function formatGeneratedValue(value: unknown, databaseType?: DatabaseType
     const temporalValue = formatOracleTemporalValue(stringValue, dataType);
     if (temporalValue) return temporalValue;
   }
+  if (isJsonType(dataType)) {
+    // MySQL (and MariaDB) reject any non-JSON text in a JSON column, so free
+    // text from a string generator must land as a JSON string scalar; values
+    // that are already valid JSON pass through untouched.
+    const jsonText = isWellFormedJson(stringValue) ? stringValue : JSON.stringify(stringValue);
+    // MySQL's lexer consumes backslash escapes inside '...' literals, so the
+    // JSON escape sequences must double their backslashes to survive the trip.
+    if (databaseType === "mysql") return quoteGeneratedString(jsonText.replace(/\\/g, "\\\\"));
+    return quoteGeneratedString(jsonText);
+  }
   return quoteGeneratedString(stringValue);
 }
 
+function isJsonType(dataType: string | undefined): boolean {
+  return !!dataType && dataType.toLowerCase().includes("json");
+}
+
+function isWellFormedJson(value: string): boolean {
+  // Cheap pre-filter: plain prose (the common case from string generators)
+  // can't be JSON, so skip the parse for it.
+  if (!/^".*"$/.test(value) && !/^\{.*\}$/.test(value) && !/^\[.*\]$/.test(value) && !/^(true|false|null|-?\d+(\.\d+)?([eE][+-]?\d+)?)$/.test(value)) {
+    return false;
+  }
+  try {
+    JSON.parse(value);
+    return true;
+  } catch {
+    return false;
+  }
+}
+
 export function displayGeneratedValue(value: unknown): string {
   if (isGeneratedSqlExpression(value)) return value.display;
   if (value === null || value === undefined) return "NULL";
diff --git a/packages/app-tests/dataGenerate.test.ts b/packages/app-tests/dataGenerate.test.ts
index 3438a4ff44..1f735aec5b 100644
--- a/packages/app-tests/dataGenerate.test.ts
+++ b/packages/app-tests/dataGenerate.test.ts
@@ -1,6 +1,6 @@
 import { strict as assert } from "node:assert";
 import { test, vi } from "vitest";
-import { defaultGeneratorParams, displayGeneratedValue, findGeneratorKey, generateTableData, generateValue, supportsGeneratedMultiRowValues } from "../../apps/desktop/src/lib/dataGrid/dataGenerate.ts";
+import { defaultGeneratorParams, displayGeneratedValue, findGeneratorKey, formatGeneratedValue, generateTableData, generateValue, supportsGeneratedMultiRowValues } from "../../apps/desktop/src/lib/dataGrid/dataGenerate.ts";
 
 test("recognizes Oracle-compatible NUMBER column types as numeric", () => {
   assert.equal(findGeneratorKey("value", "NUMBER"), "number");
@@ -423,3 +423,40 @@ test("keeps ordinary TDengine table generation unchanged", () => {
   assert.deepEqual(result.rows, [[1]]);
   assert.doesNotMatch(result.sql, /tbname/);
 });
+
+test("formats generated values for MySQL JSON columns as JSON literals", () => {
+  const result = generateTableData(
+    {
+      tableName: "events",
+      schema: "app",
+      database: "app",
+      rowCount: 1,
+      columns: [
+        {
+          columnName: "ext_json",
+          dataType: "json",
+          rowCount: 1,
+          generatorKey: "uuid",
+        },
+      ],
+    },
+    "mysql",
+  );
+
+  // The generated uuid must land as a JSON string scalar ("..."), not a bare
+  // SQL string — MySQL rejects the latter in a JSON column (#9011).
+  assert.match(result.sql, /VALUES\n\('"[0-9a-f-]{36}"'\);$/);
+});
+
+test("JSON-encodes generated strings for json columns but not for varchar", () => {
+  // Plain prose lands as a JSON string scalar (still a SQL string, so valid).
+  assert.equal(formatGeneratedValue("plain", "mysql", "json"), `'"plain"'`);
+  // Embedded double quotes are JSON-escaped; MySQL's lexer consumes '\' escapes
+  // inside '...' literals, so backslashes double to survive the roundtrip.
+  assert.equal(formatGeneratedValue('say "hi"', "mysql", "json"), `'"say \\\\"hi\\\\""'`);
+  // Already-valid JSON passes through with the same backslash doubling.
+  assert.equal(formatGeneratedValue('{"a":1}', "mysql", "json"), `'{"a":1}'`);
+  assert.equal(formatGeneratedValue('{"a":"b\\"c"}', "mysql", "json"), `'{"a":"b\\\\"c"}'`);
+  // Non-JSON columns keep plain string quoting.
+  assert.equal(formatGeneratedValue("plain", "mysql", "varchar(16)"), `'plain'`);
+});