diff --git a/esptool/cmds.py b/esptool/cmds.py
index 5fd652cc6..8809974be 100644
--- a/esptool/cmds.py
+++ b/esptool/cmds.py
@@ -13,6 +13,7 @@
 import itertools
 
 from esptool.intelhex import IntelHex
+from serial import SerialException
 
 from .bin_image import ELFFile, ImageSegment, LoadFirmwareImage
 from .bin_image import (
@@ -579,56 +580,89 @@ def write_flash(esp, args):
         if compress:
             uncimage = image
             image = zlib.compress(uncimage, 9)
-            # Decompress the compressed binary a block at a time,
-            # to dynamically calculate the timeout based on the real write size
-            decompress = zlib.decompressobj()
-            blocks = esp.flash_defl_begin(uncsize, len(image), address)
-        else:
-            blocks = esp.flash_begin(uncsize, address, begin_rom_encrypted=encrypted)
-        argfile.seek(0)  # in case we need it again
-        seq = 0
-        bytes_sent = 0  # bytes sent on wire
-        bytes_written = 0  # bytes written to flash
-        t = time.time()
-
-        timeout = DEFAULT_TIMEOUT
-
-        while len(image) > 0:
-            print_overwrite(
-                "Writing at 0x%08x... (%d %%)"
-                % (address + bytes_written, 100 * (seq + 1) // blocks)
-            )
-            sys.stdout.flush()
-            block = image[0 : esp.FLASH_WRITE_SIZE]
-            if compress:
-                # feeding each compressed block into the decompressor lets us
-                # see block-by-block how much will be written
-                block_uncompressed = len(decompress.decompress(block))
-                bytes_written += block_uncompressed
-                block_timeout = max(
-                    DEFAULT_TIMEOUT,
-                    timeout_per_mb(ERASE_WRITE_TIMEOUT_PER_MB, block_uncompressed),
-                )
-                if not esp.IS_STUB:
-                    timeout = (
-                        block_timeout  # ROM code writes block to flash before ACKing
+        original_image = image  # Save the whole image in case retry is needed
+        # Try again if reconnect was successful
+        for attempt in range(1, esp.WRITE_FLASH_ATTEMPTS + 1):
+            try:
+                if compress:
+                    # Decompress the compressed binary a block at a time,
+                    # to dynamically calculate the timeout based on the real write size
+                    decompress = zlib.decompressobj()
+                    blocks = esp.flash_defl_begin(uncsize, len(image), address)
+                else:
+                    blocks = esp.flash_begin(
+                        uncsize, address, begin_rom_encrypted=encrypted
                     )
-                esp.flash_defl_block(block, seq, timeout=timeout)
-                if esp.IS_STUB:
-                    # Stub ACKs when block is received,
-                    # then writes to flash while receiving the block after it
-                    timeout = block_timeout
-            else:
-                # Pad the last block
-                block = block + b"\xff" * (esp.FLASH_WRITE_SIZE - len(block))
-                if encrypted:
-                    esp.flash_encrypt_block(block, seq)
+                argfile.seek(0)  # in case we need it again
+                seq = 0
+                bytes_sent = 0  # bytes sent on wire
+                bytes_written = 0  # bytes written to flash
+                t = time.time()
+
+                timeout = DEFAULT_TIMEOUT
+
+                while len(image) > 0:
+                    print_overwrite(
+                        "Writing at 0x%08x... (%d %%)"
+                        % (address + bytes_written, 100 * (seq + 1) // blocks)
+                    )
+                    sys.stdout.flush()
+                    block = image[0 : esp.FLASH_WRITE_SIZE]
+                    if compress:
+                        # feeding each compressed block into the decompressor lets us
+                        # see block-by-block how much will be written
+                        block_uncompressed = len(decompress.decompress(block))
+                        bytes_written += block_uncompressed
+                        block_timeout = max(
+                            DEFAULT_TIMEOUT,
+                            timeout_per_mb(
+                                ERASE_WRITE_TIMEOUT_PER_MB, block_uncompressed
+                            ),
+                        )
+                        if not esp.IS_STUB:
+                            timeout = block_timeout  # ROM code writes block to flash before ACKing
+                        esp.flash_defl_block(block, seq, timeout=timeout)
+                        if esp.IS_STUB:
+                            # Stub ACKs when block is received,
+                            # then writes to flash while receiving the block after it
+                            timeout = block_timeout
+                    else:
+                        # Pad the last block
+                        block = block + b"\xff" * (esp.FLASH_WRITE_SIZE - len(block))
+                        if encrypted:
+                            esp.flash_encrypt_block(block, seq)
+                        else:
+                            esp.flash_block(block, seq)
+                        bytes_written += len(block)
+                    bytes_sent += len(block)
+                    image = image[esp.FLASH_WRITE_SIZE :]
+                    seq += 1
+                break
+            except SerialException:
+                if attempt == esp.WRITE_FLASH_ATTEMPTS or encrypted:
+                    # Already retried once or encrypted mode is disabled because of security reasons
+                    raise
+                print("\nLost connection, retrying...")
+                esp._port.close()
+                print("Waiting for the chip to reconnect", end="")
+                for _ in range(DEFAULT_CONNECT_ATTEMPTS):
+                    try:
+                        time.sleep(1)
+                        esp._port.open()
+                        print()  # Print new line which was suppressed by print(".")
+                        esp.connect()
+                        if esp.IS_STUB:
+                            # Hack to bypass the stub overwrite check
+                            esp.IS_STUB = False
+                            # Reflash stub because chip was reset
+                            esp = esp.run_stub()
+                        image = original_image
+                        break
+                    except SerialException:
+                        print(".", end="")
+                        sys.stdout.flush()
                 else:
-                    esp.flash_block(block, seq)
-                bytes_written += len(block)
-            bytes_sent += len(block)
-            image = image[esp.FLASH_WRITE_SIZE :]
-            seq += 1
+                    raise  # Reconnect limit reached
 
         if esp.IS_STUB:
             # Stub only writes each block to flash after 'ack'ing the receive,
diff --git a/esptool/loader.py b/esptool/loader.py
index 2b2785db4..8cfc3a43e 100644
--- a/esptool/loader.py
+++ b/esptool/loader.py
@@ -278,6 +278,9 @@ class ESPLoader(object):
     # Chip IDs that are no longer supported by esptool
     UNSUPPORTED_CHIPS = {6: "ESP32-S3(beta 3)"}
 
+    # Number of attempts to write flash data
+    WRITE_FLASH_ATTEMPTS = 2
+
     def __init__(self, port=DEFAULT_PORT, baud=ESP_ROM_BAUD, trace_enabled=False):
         """Base constructor for ESPLoader bootloader interaction