diff --git a/.changeset/media-signed-upload-pending-rows.md b/.changeset/media-signed-upload-pending-rows.md
new file mode 100644
index 0000000000..d2f6526614
--- /dev/null
+++ b/.changeset/media-signed-upload-pending-rows.md
@@ -0,0 +1,5 @@
+---
+"emdash": patch
+---
+
+Fixes the media table filling up with hidden, unusable `pending` records — one per upload attempt — when storage cannot create signed upload URLs, which is always the case for local storage and for R2 accessed through a Worker binding.
diff --git a/packages/core/src/astro/routes/api/media/upload-url.ts b/packages/core/src/astro/routes/api/media/upload-url.ts
index edfa95ff2e..6d07ea2a8c 100644
--- a/packages/core/src/astro/routes/api/media/upload-url.ts
+++ b/packages/core/src/astro/routes/api/media/upload-url.ts
@@ -103,6 +103,15 @@ export const POST: APIRoute = async ({ request, locals }) => {
 		const ext = path.extname(body.filename) || "";
 		const storageKey = `${id}${ext}`;
 
+		// Get the signed upload URL before creating the pending row, so adapters
+		// that cannot pre-sign don't leave an orphaned `pending` record.
+		const signedUrl = await emdash.storage.getSignedUploadUrl({
+			key: storageKey,
+			contentType: body.contentType,
+			size: body.size,
+			expiresIn: 3600, // 1 hour
+		});
+
 		// Create pending media record with content hash
 		const mediaItem = await repo.createPending({
 			filename: body.filename,
@@ -113,14 +122,6 @@ export const POST: APIRoute = async ({ request, locals }) => {
 			authorId: user?.id,
 		});
 
-		// Get signed upload URL from storage
-		const signedUrl = await emdash.storage.getSignedUploadUrl({
-			key: storageKey,
-			contentType: body.contentType,
-			size: body.size,
-			expiresIn: 3600, // 1 hour
-		});
-
 		const response: UploadUrlResponse = {
 			uploadUrl: signedUrl.url,
 			method: signedUrl.method,
diff --git a/packages/core/tests/integration/api/media-upload-url-pending.test.ts b/packages/core/tests/integration/api/media-upload-url-pending.test.ts
new file mode 100644
index 0000000000..8f78595ecc
--- /dev/null
+++ b/packages/core/tests/integration/api/media-upload-url-pending.test.ts
@@ -0,0 +1,83 @@
+/** The signed-upload endpoint must not leave a pending media row behind when storage cannot pre-sign. */
+import { Role } from "@emdash-cms/auth";
+import type { APIContext } from "astro";
+import type { Kysely } from "kysely";
+import { afterEach, beforeEach, describe, expect, it } from "vitest";
+
+import { POST as requestUploadUrl } from "../../../src/astro/routes/api/media/upload-url.js";
+import type { DatabaseSchema } from "../../../src/database/types.js";
+import { EmDashStorageError } from "../../../src/storage/types.js";
+import type { Storage } from "../../../src/storage/types.js";
+import { setupTestDatabase, teardownTestDatabase } from "../../utils/test-db.js";
+
+/** Storage that behaves like local storage / an R2 binding: it cannot pre-sign. */
+function storageThatCannotPresign(): Storage {
+	return {
+		getSignedUploadUrl() {
+			throw new EmDashStorageError(
+				"Local storage does not support signed upload URLs. Upload files directly through the API.",
+				"NOT_SUPPORTED",
+			);
+		},
+	} as unknown as Storage;
+}
+
+function callRoute(db: Kysely<DatabaseSchema>, storage: Storage) {
+	const request = new Request("http://localhost:4321/_emdash/api/media/upload-url", {
+		method: "POST",
+		headers: { "Content-Type": "application/json" },
+		body: JSON.stringify({ filename: "photo.png", contentType: "image/png", size: 1024 }),
+	});
+
+	return requestUploadUrl({
+		request,
+		url: new URL(request.url),
+		params: {},
+		locals: {
+			emdash: { db, storage, config: {} },
+			user: { id: "admin-1", role: Role.ADMIN },
+		},
+		// eslint-disable-next-line typescript/no-unsafe-type-assertion -- minimal stub for tests
+	} as unknown as APIContext);
+}
+
+async function countMedia(db: Kysely<DatabaseSchema>, status: string): Promise<number> {
+	const rows = await db.selectFrom("media").select("id").where("status", "=", status).execute();
+	return rows.length;
+}
+
+describe("POST /_emdash/api/media/upload-url with storage that cannot pre-sign", () => {
+	let db: Kysely<DatabaseSchema>;
+
+	beforeEach(async () => {
+		db = await setupTestDatabase();
+	});
+
+	afterEach(async () => {
+		await teardownTestDatabase(db);
+	});
+
+	it("answers 501 NOT_SUPPORTED so the client falls back to direct upload", async () => {
+		const response = await callRoute(db, storageThatCannotPresign());
+
+		expect(response.status).toBe(501);
+		const body = (await response.json()) as { error: { code: string } };
+		expect(body.error.code).toBe("NOT_SUPPORTED");
+	});
+
+	it("does not create a pending media row", async () => {
+		await callRoute(db, storageThatCannotPresign());
+
+		expect(await countMedia(db, "pending")).toBe(0);
+	});
+
+	it("does not accumulate rows across repeated attempts", async () => {
+		for (let i = 0; i < 5; i++) {
+			// oxlint-disable-next-line no-await-in-loop -- sequential on purpose: the point is that repeats don't accumulate
+			await callRoute(db, storageThatCannotPresign());
+		}
+
+		const all = await db.selectFrom("media").select("id").execute();
+		expect(all).toHaveLength(0);
+	});
+});