diff --git a/surfsense_web/tests/connectors/onedrive/journey.spec.ts b/surfsense_web/tests/connectors/onedrive/journey.spec.ts
new file mode 100644
index 000000000..81a9a52ff
--- /dev/null
+++ b/surfsense_web/tests/connectors/onedrive/journey.spec.ts
@@ -0,0 +1,129 @@
+import { expect, nativeOneDriveWithChatTest as test } from "../../fixtures";
+import { streamChatToCompletion } from "../../helpers/api/chat";
+import {
+	listConnectors,
+	triggerIndex,
+	updateConnectorConfig,
+} from "../../helpers/api/connectors";
+import { getEditorContent, listDocuments } from "../../helpers/api/documents";
+import { CANARY_TOKENS, FAKE_ONEDRIVE_FILES } from "../../helpers/canary";
+import { openConnectorPopup } from "../../helpers/ui/connector-popup";
+import {
+	waitForDocumentByTitle,
+	waitForIndexingComplete,
+} from "../../helpers/waits/indexing";
+
+/**
+ * Proves the native OneDrive wiring from Microsoft OAuth fixture -> selection
+ * persistence -> OneDrive Graph API indexing -> stored source_markdown -> chat.
+ *
+ * The folder picker is intentionally bypassed; this journey exercises the
+ * persisted config and indexing contract the picker ultimately feeds.
+ */
+test.describe("Native OneDrive journey", () => {
+	test(
+		"user connects OneDrive, selects a file, indexes it, and chats with the canary token",
+		async ({
+			page,
+			request,
+			apiToken,
+			searchSpace,
+			nativeOneDriveConnector,
+			chatThread,
+		}) => {
+			test.setTimeout(180_000); // worker cold-start + summarize + embed + chunk
+
+			expect(nativeOneDriveConnector.connector_type).toBe("ONEDRIVE_CONNECTOR");
+			expect(nativeOneDriveConnector.is_indexable).toBe(true);
+			expect(nativeOneDriveConnector.config._token_encrypted).toBe(true);
+			expect(nativeOneDriveConnector.config.composio_connected_account_id).toBeUndefined();
+
+			await page.goto(`/dashboard/${searchSpace.id}/new-chat`, {
+				waitUntil: "domcontentloaded",
+			});
+			await openConnectorPopup(page);
+			const connectorDialog = page.getByRole("dialog", { name: "Manage Connectors" });
+			await expect(connectorDialog).toBeVisible();
+
+			const selectedFiles = [
+				{
+					id: FAKE_ONEDRIVE_FILES.canary.id,
+					name: FAKE_ONEDRIVE_FILES.canary.name,
+					mimeType: FAKE_ONEDRIVE_FILES.canary.mimeType,
+				},
+			];
+			// Keep the shared Drive-style body shape. OneDrive currently defaults
+			// these internally because the indexer expects max_files/use_delta_sync.
+			const indexingOptions = {
+				max_files_per_folder: 10,
+				incremental_sync: false,
+				include_subfolders: false,
+			};
+
+			await updateConnectorConfig(request, apiToken, nativeOneDriveConnector.id, {
+				...nativeOneDriveConnector.config,
+				selected_folders: [],
+				selected_files: selectedFiles,
+				indexing_options: indexingOptions,
+			});
+
+			await triggerIndex(request, apiToken, nativeOneDriveConnector.id, searchSpace.id, {
+				files: selectedFiles,
+				indexing_options: indexingOptions,
+			});
+
+			await waitForIndexingComplete(
+				request,
+				apiToken,
+				nativeOneDriveConnector.id,
+				searchSpace.id,
+				{
+					timeoutMs: 150_000,
+					intervalMs: 1_500,
+					minDocuments: 1,
+				}
+			);
+
+			await waitForDocumentByTitle(
+				request,
+				apiToken,
+				searchSpace.id,
+				FAKE_ONEDRIVE_FILES.canary.name,
+				{ timeoutMs: 30_000 }
+			);
+
+			const docs = await listDocuments(request, apiToken, searchSpace.id);
+			const canaryDoc = docs.find((d) => d.title === FAKE_ONEDRIVE_FILES.canary.name);
+
+			expect(canaryDoc, "OneDrive canary document must exist after indexing").toBeDefined();
+			if (!canaryDoc) throw new Error("unreachable: canaryDoc asserted defined above");
+			expect(canaryDoc.document_type).toBe("ONEDRIVE_FILE");
+
+			const editor = await getEditorContent(request, apiToken, searchSpace.id, canaryDoc.id);
+			expect(
+				editor.source_markdown,
+				`canary token ${CANARY_TOKENS.onedriveCanary} should appear in editor source_markdown; ` +
+					`got first 200 chars: ${editor.source_markdown.slice(0, 200)}`
+			).toContain(CANARY_TOKENS.onedriveCanary);
+			expect(editor.document_type).toBe("ONEDRIVE_FILE");
+			expect(editor.chunk_count).toBeGreaterThan(0);
+
+			const refreshedConnectors = await listConnectors(request, apiToken, searchSpace.id);
+			const refreshed = refreshedConnectors.find((c) => c.id === nativeOneDriveConnector.id);
+			expect(refreshed?.connector_type).toBe("ONEDRIVE_CONNECTOR");
+			expect(refreshed?.is_indexable).toBe(true);
+			expect(refreshed?.last_indexed_at).not.toBeNull();
+
+			const chat = await streamChatToCompletion(request, apiToken, {
+				searchSpaceId: searchSpace.id,
+				threadId: chatThread.id,
+				query: "What is in my e2e-onedrive-canary.txt OneDrive file?",
+			});
+			expect(
+				chat.assistantText,
+				"chat agent should surface OneDrive canary token after indexing; " +
+					`got: ${chat.assistantText.slice(0, 200)}`
+			).toContain(CANARY_TOKENS.onedriveCanary);
+		}
+	);
+});
diff --git a/surfsense_web/tests/fixtures/connectors/native-onedrive.fixture.ts b/surfsense_web/tests/fixtures/connectors/native-onedrive.fixture.ts
new file mode 100644
index 000000000..bdcd9ec86
--- /dev/null
+++ b/surfsense_web/tests/fixtures/connectors/native-onedrive.fixture.ts
@@ -0,0 +1,32 @@
+import {
+	type ConnectorRow,
+	deleteConnector,
+	runNativeOneDriveOAuth,
+} from "../../helpers/api/connectors";
+import { searchSpaceFixtures } from "../search-space.fixture";
+
+export type NativeOneDriveFixtures = {
+	/**
+	 * A pre-connected native Microsoft OneDrive connector inside the
+	 * fixture's `searchSpace`. OAuth uses E2E Microsoft Graph fakes and is
+	 * cleaned up automatically after the test.
+	 */
+	nativeOneDriveConnector: ConnectorRow;
+};
+
+export const nativeOneDriveFixtures = searchSpaceFixtures.extend<NativeOneDriveFixtures>({
+	nativeOneDriveConnector: async ({ request, apiToken, searchSpace }, use) => {
+		const { connector } = await runNativeOneDriveOAuth(request, apiToken, searchSpace.id);
+		if (!connector) {
+			throw new Error(
+				"nativeOneDriveConnector fixture: OAuth completed but no ONEDRIVE_CONNECTOR was created. " +
+					"Check the backend log — the OneDrive fake likely rejected an unmodelled call."
+			);
+		}
+		try {
+			await use(connector);
+		} finally {
+			await deleteConnector(request, apiToken, connector.id);
+		}
+	},
+});
diff --git a/surfsense_web/tests/fixtures/index.ts b/surfsense_web/tests/fixtures/index.ts
index 4020bdd12..e1099762c 100644
--- a/surfsense_web/tests/fixtures/index.ts
+++ b/surfsense_web/tests/fixtures/index.ts
@@ -20,6 +20,8 @@
  *             └─ nativeGmailWithChatTest — chatThread
  *         └─ nativeCalendarFixtures — nativeCalendarConnector
  *             └─ nativeCalendarWithChatTest — chatThread
+ *         └─ nativeOneDriveFixtures — nativeOneDriveConnector
+ *             └─ nativeOneDriveWithChatTest — chatThread
  *         └─ notionFixtures — notionConnector
  *             └─ notionWithChatTest — chatThread
  *         └─ confluenceFixtures — confluenceConnector
@@ -47,6 +49,7 @@ export { linearFixtures } from "./connectors/linear.fixture";
 export { nativeCalendarFixtures } from "./connectors/native-calendar.fixture";
 export { nativeDriveFixtures } from "./connectors/native-drive.fixture";
 export { nativeGmailFixtures } from "./connectors/native-gmail.fixture";
+export { nativeOneDriveFixtures } from "./connectors/native-onedrive.fixture";
 export { notionFixtures } from "./connectors/notion.fixture";
 export { searchSpaceFixtures } from "./search-space.fixture";
 export { slackFixtures } from "./connectors/slack.fixture";
@@ -61,6 +64,7 @@ import { linearFixtures } from "./connectors/linear.fixture";
 import { nativeCalendarFixtures } from "./connectors/native-calendar.fixture";
 import { nativeDriveFixtures } from "./connectors/native-drive.fixture";
 import { nativeGmailFixtures } from "./connectors/native-gmail.fixture";
+import { nativeOneDriveFixtures } from "./connectors/native-onedrive.fixture";
 import { notionFixtures } from "./connectors/notion.fixture";
 import { searchSpaceFixtures } from "./search-space.fixture";
 import { slackFixtures } from "./connectors/slack.fixture";
@@ -97,6 +101,11 @@ export const nativeCalendarTest = nativeCalendarFixtures;
 /** `test` for native Calendar specs that also need a chat thread. */
 export const nativeCalendarWithChatTest =
 	nativeCalendarFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);
+/** `test` for specs that also need a pre-connected native OneDrive connector. */
+export const nativeOneDriveTest = nativeOneDriveFixtures;
+/** `test` for native OneDrive specs that also need a chat thread. */
+export const nativeOneDriveWithChatTest =
+	nativeOneDriveFixtures.extend<ChatThreadFixtures>(chatThreadFixtures);
 /** `test` for specs that also need a pre-connected Notion connector. */
 export const notionTest = notionFixtures;
 /** `test` for Notion specs that also need a chat thread. */
diff --git a/surfsense_web/tests/helpers/api/connectors.ts b/surfsense_web/tests/helpers/api/connectors.ts
index ec3f6ac45..a638d18b6 100644
--- a/surfsense_web/tests/helpers/api/connectors.ts
+++ b/surfsense_web/tests/helpers/api/connectors.ts
@@ -256,6 +256,62 @@ export async function runNativeGoogleDriveOAuth(
 	return { authUrl: auth_url, finalUrl: location, connector };
 }
 
+/**
+ * Drives the native Microsoft OneDrive OAuth flow programmatically.
+ *
+ * The OneDrive authorization URL is off-origin, so the helper extracts the
+ * signed state and calls the backend callback directly. The E2E backend fakes
+ * Microsoft's token and profile HTTP responses inside that callback.
+ */
+export async function runNativeOneDriveOAuth(
+	request: APIRequestContext,
+	token: string,
+	searchSpaceId: number
+): Promise<{
+	authUrl: string;
+	finalUrl: string;
+	connector: ConnectorRow | null;
+}> {
+	const initiateResp = await request.get(
+		`${BACKEND_URL}/api/v1/auth/onedrive/connector/add?space_id=${searchSpaceId}`,
+		{ headers: authHeaders(token) }
+	);
+	if (!initiateResp.ok()) {
+		throw new Error(
+			`native OneDrive initiate failed (${initiateResp.status()}): ${await initiateResp.text()}`
+		);
+	}
+	const { auth_url } = (await initiateResp.json()) as { auth_url: string };
+	if (!auth_url) {
+		throw new Error("native OneDrive initiate response missing auth_url");
+	}
+
+	const state = new URL(auth_url).searchParams.get("state");
+	if (!state) {
+		throw new Error(`native OneDrive auth_url missing state: ${auth_url}`);
+	}
+
+	const callbackResp = await request.get(
+		`${BACKEND_URL}/api/v1/auth/onedrive/connector/callback?code=fake-onedrive-oauth-code&state=${encodeURIComponent(state)}`,
+		{
+			headers: authHeaders(token),
+			maxRedirects: 0,
+			failOnStatusCode: false,
+		}
+	);
+	if (callbackResp.status() >= 400) {
+		throw new Error(
+			`native OneDrive callback failed (${callbackResp.status()}): ${await callbackResp.text()}`
+		);
+	}
+	const location = callbackResp.headers().location ?? auth_url;
+
+	const connectors = await listConnectors(request, token, searchSpaceId);
+	const connector = connectors.find((c) => c.connector_type === "ONEDRIVE_CONNECTOR") ?? null;
+
+	return { authUrl: auth_url, finalUrl: location, connector };
+}
+
 /**
  * Drives the native Google Gmail OAuth flow programmatically.
  *
diff --git a/surfsense_web/tests/helpers/canary.ts b/surfsense_web/tests/helpers/canary.ts
index 480842c10..82c41f339 100644
--- a/surfsense_web/tests/helpers/canary.ts
+++ b/surfsense_web/tests/helpers/canary.ts
@@ -20,6 +20,7 @@ export const CANARY_TOKENS = {
 	driveArchive: "SURFSENSE_E2E_ARCHIVE_MARKER",
 	gmailCanary: "SURFSENSE_E2E_CANARY_TOKEN_GMAIL_001",
 	calendarCanary: "SURFSENSE_E2E_CANARY_TOKEN_CALENDAR_001",
+	onedriveCanary: "SURFSENSE_E2E_CANARY_TOKEN_ONEDRIVE_001",
 	notionCanary: "SURFSENSE_E2E_CANARY_TOKEN_NOTION_001",
 	confluenceCanary: "SURFSENSE_E2E_CANARY_TOKEN_CONFLUENCE_001",
 	linearCanary: "SURFSENSE_E2E_CANARY_TOKEN_LINEAR_001",
@@ -50,6 +51,18 @@ export const FAKE_DRIVE_FOLDERS = {
 	},
 } as const;
 
+/**
+ * Fake OneDrive file IDs that match the Microsoft Graph-shaped backend
+ * fake in onedrive_files.json.
+ */
+export const FAKE_ONEDRIVE_FILES = {
+	canary: {
+		id: "fake-onedrive-canary",
+		name: "e2e-onedrive-canary.txt",
+		mimeType: "text/plain",
+	},
+} as const;
+
 /**
  * Fake Gmail message IDs that match what the backend fake returns from
  * GMAIL_FETCH_EMAILS / GMAIL_FETCH_MESSAGE_BY_MESSAGE_ID.