diff --git a/surfsense_web/tests/documents/file-upload/journey.spec.ts b/surfsense_web/tests/documents/file-upload/journey.spec.ts
new file mode 100644
index 000000000..9a7de04c5
--- /dev/null
+++ b/surfsense_web/tests/documents/file-upload/journey.spec.ts
@@ -0,0 +1,95 @@
+import path from "node:path";
+import type { APIRequestContext, Page } from "@playwright/test";
+import { expect, test } from "../../fixtures";
+import { getEditorContent, listDocuments } from "../../helpers/api/documents";
+import { CANARY_TOKENS } from "../../helpers/canary";
+import { waitForDocumentByTitle } from "../../helpers/waits/indexing";
+
+type UploadFixture = {
+	path: string;
+	name: string;
+	canary: string;
+};
+
+type SearchSpace = {
+	id: number;
+};
+
+const MD_FILE: UploadFixture = {
+	path: path.join(__dirname, "fixtures", "canary.md"),
+	name: "canary.md",
+	canary: CANARY_TOKENS.manualUploadMdCanary,
+};
+
+const PDF_FILE: UploadFixture = {
+	path: path.join(__dirname, "fixtures", "canary.pdf"),
+	name: "canary.pdf",
+	canary: CANARY_TOKENS.manualUploadPdfCanary,
+};
+
+async function uploadAndAssert({
+	page,
+	request,
+	apiToken,
+	searchSpace,
+	file,
+}: {
+	page: Page;
+	request: APIRequestContext;
+	apiToken: string;
+	searchSpace: SearchSpace;
+	file: UploadFixture;
+}) {
+	await page.goto(`/dashboard/${searchSpace.id}/new-chat`, {
+		waitUntil: "domcontentloaded",
+	});
+
+	await page.getByRole("button", { name: "Upload" }).click();
+	const dialog = page.getByRole("dialog", { name: "Upload Documents" });
+	await expect(dialog).toBeVisible();
+
+	await dialog.locator('input[type="file"]').first().setInputFiles(file.path);
+	await dialog.getByRole("button", { name: /Upload 1 file/i }).click();
+
+	await expect(page.getByText(/Upload Task Initiated/i)).toBeVisible({
+		timeout: 15_000,
+	});
+
+	await waitForDocumentByTitle(request, apiToken, searchSpace.id, file.name, {
+		timeoutMs: 200_000,
+	});
+
+	const docs = await listDocuments(request, apiToken, searchSpace.id);
+	const uploaded = docs.find((d) => d.title === file.name);
+	expect(uploaded, `${file.name} must exist after indexing`).toBeDefined();
+	if (!uploaded) throw new Error("unreachable: uploaded asserted defined above");
+	expect(uploaded.document_type).toBe("FILE");
+
+	const editor = await getEditorContent(request, apiToken, searchSpace.id, uploaded.id);
+	expect(editor.source_markdown).toContain(file.canary);
+	expect(editor.chunk_count).toBeGreaterThan(0);
+}
+
+test.describe("Manual file upload journey", () => {
+	test("user uploads a markdown file (PLAINTEXT branch)", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+	}) => {
+		test.setTimeout(180_000);
+
+		await uploadAndAssert({ page, request, apiToken, searchSpace, file: MD_FILE });
+	});
+
+	test("user uploads a PDF (DOCUMENT branch via real Docling)", async ({
+		page,
+		request,
+		apiToken,
+		searchSpace,
+	}) => {
+		test.setTimeout(240_000); // Docling cold-start can take 30-60s on first invocation.
+
+		await uploadAndAssert({ page, request, apiToken, searchSpace, file: PDF_FILE });
+	});
+});