diff --git a/esphome/compiled_config.py b/esphome/compiled_config.py
index be03eea965..066209b184 100644
--- a/esphome/compiled_config.py
+++ b/esphome/compiled_config.py
@@ -100,6 +100,22 @@ def _refresh_sidecar() -> bool:
             )
             return False
         if old is not None and old.can_apply_to_core():
+            if (
+                old.toolchain is not None
+                and CORE.toolchain is not None
+                and old.toolchain != CORE.toolchain.value
+            ):
+                # The config was validated under a different toolchain than
+                # the compile's, and platforms normalize toolchain-sensitive
+                # keys (e.g. the esp32 board name) differently; caching it
+                # would disagree with the sidecar until the next compile
+                _LOGGER.debug(
+                    "Not caching: config validated with toolchain %r but the "
+                    "last compile used %r",
+                    CORE.toolchain.value,
+                    old.toolchain,
+                )
+                return False
             # Compile-written; nothing to refresh.
             return True
         if CORE.build_path is not None and CORE.build_path.exists():
diff --git a/tests/unit_tests/test_compiled_config.py b/tests/unit_tests/test_compiled_config.py
index 77690a6897..62d043f480 100644
--- a/tests/unit_tests/test_compiled_config.py
+++ b/tests/unit_tests/test_compiled_config.py
@@ -68,6 +68,7 @@ def _write_storage(
     esp_platform: str | None = "ESP32",
     core_platform: str | None = "esp32",
     build_path: str | None = "/build/lite_test",
+    toolchain: str | None = None,
 ) -> None:
     """Write a vanilla StorageJSON sidecar for the cache tests."""
     storage_path.parent.mkdir(parents=True, exist_ok=True)
@@ -88,6 +89,7 @@ def _write_storage(
         "no_mdns": False,
         "framework": "arduino",
         "core_platform": core_platform,
+        "toolchain": toolchain,
     }
     storage_path.write_text(json.dumps(data), encoding="utf-8")
 
@@ -629,6 +631,36 @@ def test_save_compiled_config_and_sidecar_builds_real_sidecar(tmp_path: Path) ->
     assert load_compiled_config(yaml_path) is not None
 
 
+@pytest.mark.parametrize(
+    ("sidecar_toolchain", "saved"),
+    [
+        ("esp-idf", False),
+        ("platformio", True),
+        (None, True),  # legacy sidecar without the field: guard is inert
+    ],
+)
+def test_save_compiled_config_and_sidecar_toolchain_mismatch(
+    tmp_path: Path, sidecar_toolchain: str | None, saved: bool
+) -> None:
+    """A config validated under a different toolchain than the compile's
+    must not overwrite the cache: platforms normalize toolchain-sensitive
+    keys differently and the sidecar keeps the compile's toolchain."""
+    yaml_path = _bare_yaml(tmp_path)
+    _prime_core(tmp_path)
+    CORE.config = {CONF_ESPHOME: {CONF_NAME: "lite_test"}}
+    CORE.toolchain = Toolchain.PLATFORMIO
+    _write_storage(
+        tmp_path / ".esphome" / "storage" / "lite_test.yaml.json",
+        toolchain=sidecar_toolchain,
+    )
+
+    save_compiled_config_and_sidecar(CORE.config)
+
+    cache = tmp_path / ".esphome" / "storage" / "lite_test.yaml.validated.json"
+    assert cache.exists() is saved
+    assert (load_compiled_config(yaml_path) is not None) is saved
+
+
 @pytest.mark.parametrize("command", ["upload", "logs"])
 def test_run_esphome_upload_and_logs_refresh_cache_on_fallback(
     tmp_path: Path, command: str