diff --git a/rivetkit-typescript/packages/rivetkit/src/db/native-database.test.ts b/rivetkit-typescript/packages/rivetkit/src/db/native-database.test.ts
new file mode 100644
index 0000000000..1415a1535d
--- /dev/null
+++ b/rivetkit-typescript/packages/rivetkit/src/db/native-database.test.ts
@@ -0,0 +1,60 @@
+import { describe, expect, test } from "vitest";
+import { wrapJsNativeDatabase, type JsNativeDatabaseLike } from "./native-database";
+
+function createDatabase(
+	overrides: Partial<JsNativeDatabaseLike> = {},
+): JsNativeDatabaseLike {
+	return {
+		async exec() {
+			return { columns: [], rows: [] };
+		},
+		async query() {
+			return { columns: [], rows: [] };
+		},
+		async run() {
+			return { changes: 0 };
+		},
+		async close() {},
+		...overrides,
+	};
+}
+
+describe("wrapJsNativeDatabase", () => {
+	test("appends native sqlite kv errors to generic sqlite I/O failures", async () => {
+		const db = wrapJsNativeDatabase(
+			createDatabase({
+				async run() {
+					throw new Error(
+						"failed to execute sqlite statement: disk I/O error",
+					);
+				},
+				takeLastKvError() {
+					return "envoy channel closed while writing sqlite page";
+				},
+			}),
+		);
+
+		await expect(db.run("INSERT INTO foo VALUES (1)")).rejects.toThrow(
+			"failed to execute sqlite statement: disk I/O error (native sqlite kv error: envoy channel closed while writing sqlite page)",
+		);
+	});
+
+	test("does not attach native sqlite kv errors to unrelated sqlite failures", async () => {
+		const db = wrapJsNativeDatabase(
+			createDatabase({
+				async run() {
+					throw new Error(
+						"failed to execute sqlite statement: no such table: foo",
+					);
+				},
+				takeLastKvError() {
+					return "envoy channel closed while writing sqlite page";
+				},
+			}),
+		);
+
+		await expect(db.run("INSERT INTO foo VALUES (1)")).rejects.toThrow(
+			"failed to execute sqlite statement: no such table: foo",
+		);
+	});
+});
diff --git a/rivetkit-typescript/packages/rivetkit/src/db/native-database.ts b/rivetkit-typescript/packages/rivetkit/src/db/native-database.ts
index cfd69ad08d..04603de464 100644
--- a/rivetkit-typescript/packages/rivetkit/src/db/native-database.ts
+++ b/rivetkit-typescript/packages/rivetkit/src/db/native-database.ts
@@ -26,9 +26,30 @@ export interface JsNativeDatabaseLike {
 	exec(sql: string): Promise<NativeExecResult>;
 	query(sql: string, params?: NativeBindParam[] | null): Promise<NativeQueryResult>;
 	run(sql: string, params?: NativeBindParam[] | null): Promise<NativeRunResult>;
+	takeLastKvError?(): string | null;
 	close(): Promise<void>;
 }
 
+function shouldAttachNativeKvError(message: string): boolean {
+	return /i\/o error|unable to open database file/i.test(message);
+}
+
+function enrichNativeDatabaseError(
+	database: JsNativeDatabaseLike,
+	error: unknown,
+): never {
+	const kvError = database.takeLastKvError?.();
+	if (
+		error instanceof Error &&
+		kvError &&
+		shouldAttachNativeKvError(error.message) &&
+		!error.message.includes(kvError)
+	) {
+		error.message = `${error.message} (native sqlite kv error: ${kvError})`;
+	}
+	throw error;
+}
+
 function toNativeBinding(arg: unknown): NativeBindParam {
 	if (arg === null || arg === undefined) {
 		return { kind: "null" };
@@ -126,7 +147,12 @@ export function wrapJsNativeDatabase(
 			sql: string,
 			callback?: (row: unknown[], columns: string[]) => void,
 		): Promise<void> {
-			const result = await database.exec(sql);
+			let result: NativeExecResult;
+			try {
+				result = await database.exec(sql);
+			} catch (error) {
+				enrichNativeDatabaseError(database, error);
+			}
 			if (!callback) {
 				return;
 			}
@@ -135,10 +161,18 @@ export function wrapJsNativeDatabase(
 			}
 		},
 		async run(sql: string, params?: SqliteBindings): Promise<void> {
-			await database.run(sql, toNativeBindings(sql, params));
+			try {
+				await database.run(sql, toNativeBindings(sql, params));
+			} catch (error) {
+				enrichNativeDatabaseError(database, error);
+			}
 		},
 		async query(sql: string, params?: SqliteBindings) {
-			return await database.query(sql, toNativeBindings(sql, params));
+			try {
+				return await database.query(sql, toNativeBindings(sql, params));
+			} catch (error) {
+				enrichNativeDatabaseError(database, error);
+			}
 		},
 		async close(): Promise<void> {
 			await database.close();