diff --git a/docs/en/esptool/configuration-file.rst b/docs/en/esptool/configuration-file.rst
index c538c608a..d93037495 100644
--- a/docs/en/esptool/configuration-file.rst
+++ b/docs/en/esptool/configuration-file.rst
@@ -109,6 +109,8 @@ Complete list configurable options:
 +------------------------------+-----------------------------------------------------------+----------+
 | custom_reset_sequence        | Custom reset sequence for resetting into the bootloader   |          |
 +------------------------------+-----------------------------------------------------------+----------+
+| retry_open_serial            | Retry opening the serial port indefinitely                | False    |
++------------------------------+-----------------------------------------------------------+----------+
 
 Custom Reset Sequence
 ---------------------
diff --git a/esptool/__init__.py b/esptool/__init__.py
index 46dad3582..146e9eec9 100644
--- a/esptool/__init__.py
+++ b/esptool/__init__.py
@@ -35,6 +35,7 @@
 import os
 import shlex
 import sys
+import termios
 import time
 import traceback
 
@@ -66,7 +67,13 @@
     write_mem,
 )
 from esptool.config import load_config_file
-from esptool.loader import DEFAULT_CONNECT_ATTEMPTS, StubFlasher, ESPLoader, list_ports
+from esptool.loader import (
+    DEFAULT_CONNECT_ATTEMPTS,
+    StubFlasher,
+    ESPLoader,
+    list_ports,
+    cfg,
+)
 from esptool.targets import CHIP_DEFS, CHIP_LIST, ESP32ROM
 from esptool.util import (
     FatalError,
@@ -77,6 +84,9 @@
 
 import serial
 
+# Retry opening the serial port indefinitely
+DEFAULT_RETRY_OPEN_SERIAL = cfg.getboolean("retry_open_serial", False)
+
 
 def main(argv=None, esp=None):
     """
@@ -768,6 +778,9 @@ def add_spi_flash_subparsers(
             port=args.port,
             connect_attempts=args.connect_attempts,
             initial_baud=initial_baud,
+            retry_open_serial=os.environ.get(
+                "ESPTOOL_RETRY_OPEN_SERIAL", DEFAULT_RETRY_OPEN_SERIAL
+            ),
             chip=args.chip,
             trace=args.trace,
             before=args.before,
@@ -1092,11 +1105,49 @@ def expand_file_arguments(argv):
     return argv
 
 
+def get_default_specific_connected_device(
+    chip, each_port, initial_baud, trace, before, connect_attempts, retry_open_serial
+):
+    retry_attempts = 0
+    _esp = None
+    while True:
+        try:
+            chip_class = CHIP_DEFS[chip]
+            _esp = chip_class(each_port, initial_baud, trace)
+            _esp.connect(before, connect_attempts)
+            if retry_attempts > 0:
+                # break the retrying line
+                print("")
+            return _esp
+        except (
+            FatalError,
+            serial.serialutil.SerialException,
+            IOError,
+            OSError,
+            termios.error,
+        ) as e:
+            if not retry_open_serial:
+                raise
+            if _esp and _esp._port:
+                _esp._port.close()
+            _esp = None
+            if retry_attempts == 0:
+                print(e)
+                print("Retrying failed connection ", end="", flush=True)
+            else:
+                if retry_attempts % 9 == 0:
+                    # print a dot every second
+                    print(".", end="", flush=True)
+            time.sleep(0.1)
+            retry_attempts += 1
+
+
 def get_default_connected_device(
     serial_list,
     port,
     connect_attempts,
     initial_baud,
+    retry_open_serial=False,
     chip="auto",
     trace=False,
     before="default_reset",
@@ -1110,9 +1161,15 @@ def get_default_connected_device(
                     each_port, initial_baud, before, trace, connect_attempts
                 )
             else:
-                chip_class = CHIP_DEFS[chip]
-                _esp = chip_class(each_port, initial_baud, trace)
-                _esp.connect(before, connect_attempts)
+                _esp = get_default_specific_connected_device(
+                    chip,
+                    each_port,
+                    initial_baud,
+                    trace,
+                    before,
+                    connect_attempts,
+                    retry_open_serial and port is not None,
+                )
             break
         except (FatalError, OSError) as err:
             if port is not None:
@@ -1229,6 +1286,7 @@ def _main():
     try:
         main()
     except FatalError as e:
+        print(traceback.format_exc())
         print(f"\nA fatal error occurred: {e}")
         sys.exit(2)
     except serial.serialutil.SerialException as e:
diff --git a/esptool/config.py b/esptool/config.py
index 5566becca..56f27d5e3 100644
--- a/esptool/config.py
+++ b/esptool/config.py
@@ -20,6 +20,7 @@
     "write_block_attempts",
     "reset_delay",
     "custom_reset_sequence",
+    "retry_open_serial",
 ]