diff --git a/esphome/__main__.py b/esphome/__main__.py
index 70d5cacd72..e1f683397f 100644
--- a/esphome/__main__.py
+++ b/esphome/__main__.py
@@ -398,28 +398,27 @@ def check_permissions(port: str):
 
 def upload_program(
     config: ConfigType, args: ArgsProtocol, devices: list[str]
-) -> int | str:
+) -> tuple[int, str | None]:
     host = devices[0]
     try:
         module = importlib.import_module("esphome.components." + CORE.target_platform)
         if getattr(module, "upload_program")(config, args, host):
-            return 0
+            return 0, host
     except AttributeError:
         pass
 
     if get_port_type(host) == "SERIAL":
         check_permissions(host)
+
+        exit_code = 1
         if CORE.target_platform in (PLATFORM_ESP32, PLATFORM_ESP8266):
             file = getattr(args, "file", None)
-            return upload_using_esptool(config, host, file, args.upload_speed)
+            exit_code = upload_using_esptool(config, host, file, args.upload_speed)
+        elif CORE.target_platform == PLATFORM_RP2040 or CORE.is_libretiny:
+            exit_code = upload_using_platformio(config, host)
+        # else: Unknown target platform, exit_code remains 1
 
-        if CORE.target_platform in (PLATFORM_RP2040):
-            return upload_using_platformio(config, host)
-
-        if CORE.is_libretiny:
-            return upload_using_platformio(config, host)
-
-        return 1  # Unknown target platform
+        return exit_code, host if exit_code == 0 else None
 
     ota_conf = {}
     for ota_item in config.get(CONF_OTA, []):
@@ -553,7 +552,7 @@ def command_upload(args: ArgsProtocol, config: ConfigType) -> int | None:
         purpose="uploading",
     )
 
-    exit_code = upload_program(config, args, devices)
+    exit_code, _ = upload_program(config, args, devices)
     if exit_code == 0:
         _LOGGER.info("Successfully uploaded program.")
     else:
@@ -610,19 +609,11 @@ def command_run(args: ArgsProtocol, config: ConfigType) -> int | None:
         purpose="uploading",
     )
 
-    # Try each device for upload until one succeeds
-    successful_device: str | None = None
-    for device in devices:
-        _LOGGER.info("Uploading to %s", device)
-        exit_code = upload_program(config, args, device)
-        if exit_code == 0:
-            _LOGGER.info("Successfully uploaded program.")
-            successful_device = device
-            break
-        if len(devices) > 1:
-            _LOGGER.warning("Failed to upload to %s", device)
-
-    if successful_device is None:
+    exit_code, successful_device = upload_program(config, args, devices)
+    if exit_code == 0:
+        _LOGGER.info("Successfully uploaded program.")
+    else:
+        _LOGGER.warning("Failed to upload to %s", devices)
         return exit_code
 
     if args.no_logs:
diff --git a/esphome/espota2.py b/esphome/espota2.py
index d83f25a303..3d25af985b 100644
--- a/esphome/espota2.py
+++ b/esphome/espota2.py
@@ -310,7 +310,7 @@ def perform_ota(
 
 def run_ota_impl_(
     remote_host: str | list[str], remote_port: int, password: str, filename: str
-) -> int:
+) -> tuple[int, str | None]:
     # Handle both single host and list of hosts
     try:
         # Resolve all hosts at once for parallel DNS resolution
@@ -344,21 +344,22 @@ def run_ota_impl_(
                 perform_ota(sock, password, file_handle, filename)
             except OTAError as err:
                 _LOGGER.error(str(err))
-                return 1
+                return 1, None
             finally:
                 sock.close()
 
-        return 0
+        # Successfully uploaded to sa[0]
+        return 0, sa[0]
 
     _LOGGER.error("Connection failed.")
-    return 1
+    return 1, None
 
 
 def run_ota(
     remote_host: str | list[str], remote_port: int, password: str, filename: str
-) -> int:
+) -> tuple[int, str | None]:
     try:
         return run_ota_impl_(remote_host, remote_port, password, filename)
     except OTAError as err:
         _LOGGER.error(err)
-        return 1
+        return 1, None