diff --git a/esphome/build_gen/arduino8266.py b/esphome/build_gen/arduino8266.py
index fd198b2e0c..5b14af5a1d 100644
--- a/esphome/build_gen/arduino8266.py
+++ b/esphome/build_gen/arduino8266.py
@@ -1065,10 +1065,10 @@ def write_project(paths: InstalledPaths, ccache: str | None) -> bool:
         "  rspfile_content = $in_newline",
         "  description = LINK $out",
         "rule elf2bin",
-        # --flash_size deliberately stays board-derived, as under
-        # PlatformIO (which reads upload.maximum_size, not the ldscript).
+        # --flash_size follows PlatformIO: ldscript filename first, then
+        # upload.maximum_size, so the header always matches the layout.
         # -W: the framework's own elf2bin.py trips SyntaxWarning on 3.12+.
-        f"  command = $python -W ignore::SyntaxWarning {_q(framework / 'tools' / 'elf2bin.py')} --eboot {_q(framework / 'bootloaders' / 'eboot' / 'eboot.elf')} --app $in --flash_mode {flash_mode} --flash_freq {_FLASH_FREQ_MHZ} --flash_size {_flash_size_str(BOARDS[board][KEY_FLASH_SIZE])} --path {_q(toolchain_bin)} --out $out",
+        f"  command = $python -W ignore::SyntaxWarning {_q(framework / 'tools' / 'elf2bin.py')} --eboot {_q(framework / 'bootloaders' / 'eboot' / 'eboot.elf')} --app $in --flash_mode {flash_mode} --flash_freq {_FLASH_FREQ_MHZ} --flash_size {_elf2bin_flash_size(board, flash_ld_name)} --path {_q(toolchain_bin)} --out $out",
         "  description = BIN $out",
         "rule copy",
         "  command = $python $buildtool copy $in $out",
@@ -1189,3 +1189,28 @@ def _flash_size_str(flash_size: int) -> str:
     """Flash size argument for elf2bin (e.g. ``4M``, ``512K``)."""
     mb = 1024 * 1024
     return f"{flash_size // mb}M" if flash_size >= mb else f"{flash_size // 1024}K"
+
+
+# Same pattern PlatformIO's _get_flash_size applies to the ldscript path
+_LD_FLASH_SIZE_RE = re.compile(r"\.flash\.(\d+[mk]).*\.ld")
+# The framework elf2bin.py's --flash_size choices
+_ELF2BIN_FLASH_SIZES = frozenset({"256K", "512K", "1M", "2M", "4M", "8M", "16M"})
+
+
+def _elf2bin_flash_size(board: str, flash_ld_name: str) -> str:
+    """Image-header flash size as PlatformIO derives it: ldscript filename,
+    else board_upload.maximum_size, else the board table. The SDK clamps the
+    chip to the header size at boot, so a header smaller than the linked
+    layout breaks OTA writes on the running device."""
+    if match := _LD_FLASH_SIZE_RE.search(flash_ld_name):
+        token = match.group(1)
+        base = 1024 if token[-1] == "k" else 1024 * 1024
+        return _flash_size_str(int(token[:-1]) * base)
+    if max_size := _pio_option("board_upload.maximum_size", ""):
+        if (
+            not max_size.isdigit()
+            or (size := _flash_size_str(int(max_size))) not in _ELF2BIN_FLASH_SIZES
+        ):
+            raise EsphomeError(f"Invalid board_upload.maximum_size value {max_size!r}")
+        return size
+    return _flash_size_str(BOARDS[board][KEY_FLASH_SIZE])
diff --git a/esphome/core/config.py b/esphome/core/config.py
index bb3f03d366..281d430410 100644
--- a/esphome/core/config.py
+++ b/esphome/core/config.py
@@ -549,7 +549,9 @@ def _add_library_str(lib: str) -> None:
 # platformio_options keys the native ESP8266 Arduino generator (a later PR
 # in this chain) will honor; its ignored-option warning will consume the same
 # list so the two cannot drift
-NATIVE_ARDUINO_PIO_OPTIONS = frozenset({"board_build.f_cpu", "board_build.ldscript"})
+NATIVE_ARDUINO_PIO_OPTIONS = frozenset(
+    {"board_build.f_cpu", "board_build.ldscript", "board_upload.maximum_size"}
+)
 # The full set that survives into CORE.platformio_options under the native
 # arduino toolchain: lib_ignore is the only specially-translated key below
 # that is stored rather than translated away. Consumed by the esp8266 native
@@ -609,9 +611,13 @@ async def _add_platformio_options(pio_options: dict[str, str | list[str]]) -> No
                 # through to the ignored-option warning). Other native
                 # toolchains have no equivalent and fall through too.
                 cg.add_platformio_option(key, vals[-1])
-            elif key != "upload_speed":
-                # upload_speed needs no handling: it is read from the raw
-                # config at upload time (upload_using_esptool)
+            elif key != "upload_speed" and not (
+                key == "board_upload.flash_size" and CORE.using_toolchain_arduino
+            ):
+                # upload_speed is read from the raw config at upload time.
+                # board_upload.flash_size is dropped silently on arduino:
+                # PlatformIO's esp8266 builder never reads it either, and
+                # published configs (Athom) commonly set it.
                 _LOGGER.warning(
                     "esphome->platformio_options->%s is ignored when building with "
                     "the native '%s' toolchain",
diff --git a/tests/unit_tests/build_gen/test_arduino8266.py b/tests/unit_tests/build_gen/test_arduino8266.py
index 4a0355fd01..066746d36d 100644
--- a/tests/unit_tests/build_gen/test_arduino8266.py
+++ b/tests/unit_tests/build_gen/test_arduino8266.py
@@ -21,12 +21,18 @@ from esphome.arduino8266.framework import InstalledPaths, toolchain_tool
 from esphome.build_gen import arduino8266
 from esphome.build_gen.arduino8266 import (
     _defines_flags,
+    _elf2bin_flash_size,
     _flag_defines,
     _flash_size_str,
     _resolve_build_config,
     get_flash_ld_path,
 )
-from esphome.components.esp8266.boards import BOARDS, ESP8266_BOARD_BUILD
+from esphome.components.esp8266.boards import (
+    BOARDS,
+    ESP8266_BOARD_BUILD,
+    KEY_FLASH_SIZE,
+    board_ld_script,
+)
 from esphome.components.esp8266.build_surgery import RATETABLE_RULE
 from esphome.components.esp8266.const import KEY_BOARD, KEY_ESP8266, KEY_SCANF_FLOAT
 import esphome.config_validation as cv
@@ -747,6 +753,54 @@ def test_flash_size_str() -> None:
     assert _flash_size_str(512 * 1024) == "512K"
 
 
+def test_elf2bin_flash_size() -> None:
+    """The image-header size follows the ldscript filename like PlatformIO,
+    falling back to board_upload.maximum_size and then the board table."""
+    assert _elf2bin_flash_size("esp8285", "eagle.flash.2m.ld") == "2M"
+    assert _elf2bin_flash_size("esp01", "eagle.flash.512k.ld") == "512K"
+    assert _elf2bin_flash_size("nodemcuv2", "eagle.flash.4m1m.ld") == "4M"
+    # The testing-mode prefix still matches (search, not match)
+    assert _elf2bin_flash_size("esp8285", "testing_eagle.flash.2m.ld") == "2M"
+    # Custom ldscript name: board_upload.maximum_size wins over the board
+    CORE.platformio_options["board_upload.maximum_size"] = "2097152"
+    assert _elf2bin_flash_size("esp8285", "custom.ld") == "2M"
+    del CORE.platformio_options["board_upload.maximum_size"]
+    assert _elf2bin_flash_size("esp8285", "custom.ld") == "1M"
+
+
+@pytest.mark.parametrize("bad", ["2MB", "3145728", "-1"])
+def test_elf2bin_flash_size_rejects_bad_maximum_size(bad: str) -> None:
+    """A non-numeric or unsupported board_upload.maximum_size fails by name
+    instead of a ValueError or a late elf2bin choices error."""
+    CORE.platformio_options["board_upload.maximum_size"] = bad
+    with pytest.raises(EsphomeError, match="board_upload.maximum_size"):
+        _elf2bin_flash_size("esp8285", "custom.ld")
+
+
+def test_elf2bin_flash_size_default_matches_board_table() -> None:
+    """Without an ldscript override, every board's own ldscript parses to
+    the board-table size, so the emitted --flash_size is unchanged."""
+    for board, entry in BOARDS.items():
+        assert _elf2bin_flash_size(board, board_ld_script(entry)) == _flash_size_str(
+            entry[KEY_FLASH_SIZE]
+        ), board
+
+
+def test_write_project_flash_size_follows_ldscript_override(
+    tmp_path: Path,
+) -> None:
+    """An ldscript overriding the board's flash size drives the image header
+    too (the Athom shape: esp8285 with eagle.flash.2m.ld). A 1M header over
+    a 2M layout clamps the chip below the OTA scratch area and bricks OTA."""
+    paths = _make_framework(tmp_path)
+    (paths.framework / "variants" / "esp8285").mkdir()
+    CORE.data[KEY_ESP8266][KEY_BOARD] = "esp8285"
+    CORE.platformio_options["board_build.ldscript"] = "eagle.flash.2m.ld"
+    content = _write_ninja(paths)
+    assert "--flash_size 2M" in content
+    assert "eagle.flash.2m.ld" in content
+
+
 def test_write_project_testing_mode(tmp_path: Path) -> None:
     paths = _make_framework(tmp_path)
     CORE.testing_mode = True
diff --git a/tests/unit_tests/core/test_config.py b/tests/unit_tests/core/test_config.py
index 189c024b3a..cfb9651e6b 100644
--- a/tests/unit_tests/core/test_config.py
+++ b/tests/unit_tests/core/test_config.py
@@ -1341,6 +1341,8 @@ async def test_add_platformio_options_native_idf(
             "lib_ignore": "libsodium",
             "upload_speed": "115200",
             "board_build.f_flash": "80000000L",
+            # Silently dropped on arduino only; warns here
+            "board_upload.flash_size": "2MB",
         }
     )
 
@@ -1351,6 +1353,9 @@ async def test_add_platformio_options_native_idf(
     # nothing else lands in platformio_options on the native toolchain.
     assert CORE.platformio_options == {"lib_ignore": ["libsodium"]}
     assert "esphome->platformio_options->board_build.f_flash is ignored" in caplog.text
+    assert (
+        "esphome->platformio_options->board_upload.flash_size is ignored" in caplog.text
+    )
     assert "upload_speed" not in caplog.text
     # build_flags has a first-class esphome equivalent, so it is deprecated.
     # lib_deps/lib_ignore are kept as valid platformio_options (no warning).
@@ -1464,13 +1469,21 @@ async def test_add_platformio_options_native_arduino(
             "board_build.ldscript": ["eagle.flash.2m.ld", "eagle.flash.4m2m.ld"],
             "board_build.filesystem": "littlefs",
             "upload_speed": "115200",
+            # The Athom shape: maximum_size is the elf2bin fallback,
+            # flash_size is dropped silently (PlatformIO never reads it)
+            "board_upload.maximum_size": "2097152",
+            "board_upload.flash_size": "2MB",
         }
     )
 
     assert CORE.platformio_options["board_build.f_cpu"] == "160000000L"
     assert CORE.platformio_options["board_build.ldscript"] == "eagle.flash.4m2m.ld"
+    assert CORE.platformio_options["board_upload.maximum_size"] == "2097152"
+    assert "board_upload.flash_size" not in CORE.platformio_options
     assert "board_build.f_cpu is ignored" not in caplog.text
     assert "board_build.ldscript is ignored" not in caplog.text
+    assert "board_upload.maximum_size is ignored" not in caplog.text
+    assert "board_upload.flash_size is ignored" not in caplog.text
     assert (
         "esphome->platformio_options->board_build.filesystem is ignored" in caplog.text
     )