diff --git a/playground/server/main.py b/playground/server/main.py
index ec1301e47d..405fe6d503 100644
--- a/playground/server/main.py
+++ b/playground/server/main.py
@@ -436,6 +436,16 @@ async def _dispatch_query(self, system_name: str, sql: bytes
                 if attempt == 1:
                     self.sink.write_event(system=system_name, kind="ensure-failed",
                                           detail=f"attempt {attempt}: {e!r}")
+                    # Belt-and-suspenders: even though vm_manager's
+                    # _restore_snapshot + _boot except handlers reap
+                    # their own fc process on failure, corners we don't
+                    # yet cover (e.g. a network-level ServerDisconnect
+                    # while waiting for the guest agent) can still
+                    # leave an fc process alive holding fc-tap-<slot>.
+                    # Force a clean teardown before the second attempt
+                    # so ensure_tap can recreate the TAP.
+                    with contextlib.suppress(Exception):
+                        await self.vmm.kick(system_name, "ensure-failed-retry")
                     await asyncio.sleep(0.5)
                     continue
                 raise
diff --git a/playground/server/vm_manager.py b/playground/server/vm_manager.py
index 600731225e..40f39cb0e5 100644
--- a/playground/server/vm_manager.py
+++ b/playground/server/vm_manager.py
@@ -660,11 +660,26 @@ async def _restore_snapshot(self, vm: VM) -> None:
         if vm.system.name in DATALAKE_FILTERED:
             await net.enable_filtered_internet(vm.slot)
         await self._boot(vm, restore_snapshot=True)
-        await self._wait_for_agent(vm, timeout=60)
-        # Block here until the system's daemon reports ready, so the
-        # first user query doesn't time out mid-startup. Big upper bound
-        # for slow JVMs (Doris/Druid/Trino).
-        await self._wait_for_daemon_ready(vm, timeout=600)
+        try:
+            await self._wait_for_agent(vm, timeout=60)
+            # Block here until the system's daemon reports ready, so the
+            # first user query doesn't time out mid-startup. Big upper
+            # bound for slow JVMs (Doris/Druid/Trino).
+            await self._wait_for_daemon_ready(vm, timeout=600)
+        except Exception:
+            # _boot's own except handler covers _configure_boot failure,
+            # but if the guest agent never comes up or the daemon never
+            # reports ready, the fc process is left alive holding
+            # fc-tap-<slot>. The next /query then hits
+            #   Open tap device failed: … Resource busy (os error 16)
+            # even though vm.state was left at "snapshotted". Reap the
+            # process + delete the TAP so ensure_tap can recreate a
+            # fresh one on the next attempt.
+            with contextlib.suppress(Exception):
+                await self._shutdown(vm)
+            with contextlib.suppress(Exception):
+                await net.teardown_tap(vm.slot)
+            raise
         vm.state = "ready"
         vm.ready_since = time.time()
         # Baseline the firecracker's current jiffy counter so the