diff --git a/packages/db/migrations/mysql/0044_add_assistant.sql b/packages/db/migrations/mysql/0044_add_assistant.sql
index 511ab6a81..46315c4aa 100644
--- a/packages/db/migrations/mysql/0044_add_assistant.sql
+++ b/packages/db/migrations/mysql/0044_add_assistant.sql
@@ -26,7 +26,7 @@ CREATE TABLE `assistant_message` (
 	`thread_id` varchar(64) NOT NULL,
 	`parent_id` varchar(128),
 	`format` varchar(64) DEFAULT 'ai-sdk/v6' NOT NULL,
-	`content` text DEFAULT ('{"json": {}}') NOT NULL,
+	`content` mediumtext DEFAULT ('{"json": {}}') NOT NULL,
 	`created_at` timestamp DEFAULT (now()) NOT NULL,
 	CONSTRAINT `assistant_message_id` PRIMARY KEY(`id`)
 );
diff --git a/packages/db/schema/mysql.ts b/packages/db/schema/mysql.ts
index cfe52485a..9f2fc8701 100644
--- a/packages/db/schema/mysql.ts
+++ b/packages/db/schema/mysql.ts
@@ -8,6 +8,7 @@ import {
   customType,
   index,
   int,
+  mediumtext,
   mysqlTable,
   primaryKey,
   smallint,
@@ -536,7 +537,9 @@ export const assistantMessages = mysqlTable(
       .references(() => assistantThreads.id, { onDelete: "cascade" }),
     parentId: varchar({ length: 128 }),
     format: varchar({ length: 64 }).notNull().default("ai-sdk/v6"),
-    content: text().default(emptySuperJSON).notNull(),
+    // `text` only holds 64KB on MySQL, which a single base64 image attachment already exceeds.
+    // `mediumtext` holds 16MB, comfortably above the 2MB request cap enforced by the chat route.
+    content: mediumtext().default(emptySuperJSON).notNull(),
     createdAt: timestamp().notNull().defaultNow(),
   },
   (message) => ({
diff --git a/packages/db/test/mysql-migration.spec.ts b/packages/db/test/mysql-migration.spec.ts
index b781a9531..9e86e2003 100644
--- a/packages/db/test/mysql-migration.spec.ts
+++ b/packages/db/test/mysql-migration.spec.ts
@@ -1,9 +1,10 @@
 import path from "path";
 import { MySqlContainer } from "@testcontainers/mysql";
+import { eq } from "drizzle-orm";
 import { drizzle } from "drizzle-orm/mysql2";
 import { migrate } from "drizzle-orm/mysql2/migrator";
 import mysql from "mysql2";
-import { describe, test } from "vitest";
+import { describe, expect, test } from "vitest";
 
 import { DB_CASING } from "@homarr/core/infrastructure/db/constants";
 
@@ -35,6 +36,22 @@ describe("Mysql Migration", () => {
     // Check if users table exists
     await database.query.users.findMany();
 
+    // A single base64 image attachment already exceeds the 64KB that `text` holds on MySQL, so
+    // `assistant_message.content` has to be `mediumtext`. Everything below 64KB passes either way.
+    const largeContent = "x".repeat(200_000);
+    await database.insert(mysqlSchema.users).values({ id: "size-check-user", name: "size-check" });
+    await database.insert(mysqlSchema.assistantThreads).values({ id: "size-check-thread", userId: "size-check-user" });
+    await database.insert(mysqlSchema.assistantMessages).values({
+      id: "size-check-message",
+      threadId: "size-check-thread",
+      parentId: null,
+      content: largeContent,
+    });
+    const [storedMessage] = await database.query.assistantMessages.findMany({
+      where: eq(mysqlSchema.assistantMessages.id, "size-check-message"),
+    });
+    expect(storedMessage?.content).toHaveLength(largeContent.length);
+
     connection.end();
     await mysqlContainer.stop();
   }, 120_000);