diff --git a/apps/cli/src/commands/server.ts b/apps/cli/src/commands/server.ts
index 3384d7092..17e6301f1 100644
--- a/apps/cli/src/commands/server.ts
+++ b/apps/cli/src/commands/server.ts
@@ -348,6 +348,14 @@ export const start = Command.make("start", {
 			)
 			const pidPath = pidFilePath(dataDir)
 
+			// First run: `~/.maple` does not exist yet, and everything startup touches
+			// before the data dir itself — the PID file, the `--background` log, the
+			// restore/reset transactions, the migration journal, the maintenance lock —
+			// is a *sibling* of the data dir, i.e. lives in that missing parent. Create
+			// it up front so first-run ordering is a stated precondition rather than a
+			// side effect of whichever helper happens to run first.
+			yield* fs.makeDirectory(dirname(dataDir), { recursive: true })
+
 			// Already-running guard.
 			const existingPid = yield* readPid(fs, pidPath)
 			if (Option.isSome(existingPid) && isProcessAlive(existingPid.value)) {
diff --git a/apps/cli/test/archive-pins.test.ts b/apps/cli/test/archive-pins.test.ts
index 639ae9eb8..b0e4c742b 100644
--- a/apps/cli/test/archive-pins.test.ts
+++ b/apps/cli/test/archive-pins.test.ts
@@ -241,6 +241,23 @@ describe("maintenance lock", () => {
 		})
 	})
 
+	// First run on a clean machine: `~/.maple` does not exist, so the lock — a
+	// *sibling* of `~/.maple/data` — has no parent to be created in. `maple start`
+	// reconciles checkpoint recovery under this lock before it creates any
+	// directory, so an ENOENT here is a hard startup failure, not a warning.
+	it("acquires the lock when the data dir's parent does not exist yet", async () => {
+		const root = mkdtempSync(join(tmpdir(), "maple-first-run-lock-test-"))
+		const dataDir = join(root, ".maple", "data")
+		try {
+			ok(!existsSync(dirname(dataDir)), "precondition: the maple home is absent")
+			const result = await withMaintenanceLock(dataDir, newCheckpointId(), async () => "done")
+			strictEqual(result, "done")
+			ok(!existsSync(`${dataDir}.maple-maintenance-lock`), "maintenance lock released")
+		} finally {
+			rmSync(root, { recursive: true, force: true })
+		}
+	})
+
 	it("releases the lock even when the task throws", async () => {
 		await withDataDir(async (dataDir) => {
 			await rejects(
diff --git a/apps/cli/test/checkpoints.test.ts b/apps/cli/test/checkpoints.test.ts
index 720403aa1..d09b6385f 100644
--- a/apps/cli/test/checkpoints.test.ts
+++ b/apps/cli/test/checkpoints.test.ts
@@ -805,6 +805,21 @@ describe("live restore transaction reconciliation", () => {
 		})
 	})
 
+	// `maple start` reconciles recovery before it creates any directory, so on a
+	// clean machine this runs with `~/.maple` itself absent — and every path it
+	// touches (transaction journal, quarantine, maintenance lock) is a sibling of
+	// the data dir, living in that missing parent.
+	it("is a no-op on first run, when the data dir's parent does not exist yet", async () => {
+		const root = mkdtempSync(join(tmpdir(), "maple-first-run-recovery-test-"))
+		const dataDir = join(root, ".maple", "data")
+		try {
+			ok(!existsSync(dirname(dataDir)), "precondition: the maple home is absent")
+			await Effect.runPromise(reconcileCheckpointRecovery(dataDir))
+		} finally {
+			rmSync(root, { recursive: true, force: true })
+		}
+	})
+
 	it("preserves an interrupted pre-ready restore and leaves the old live store selected", async () => {
 		await withDataDir(async (dataDir) => {
 			const operationId = newCheckpointOperationId()