diff --git a/esphome/espidf/bootloader.py b/esphome/espidf/bootloader.py
index 65237a371ac..b0d58d1a981 100644
--- a/esphome/espidf/bootloader.py
+++ b/esphome/espidf/bootloader.py
@@ -75,9 +75,13 @@ def _compute_enabled() -> bool:
             _LOGGER.info("IDF changed its bootloader macro; building in-tree")
             return False
         return True
-    except (OSError, KeyError, ValueError, EsphomeError) as err:
+    except (OSError, EsphomeError) as err:
         _LOGGER.info("Bootloader cache disabled: %s", err)
         return False
+    except (KeyError, ValueError) as err:
+        # More likely a regression than the environment; still fail safe.
+        _LOGGER.warning("Bootloader cache disabled: %s", err)
+        return False
 
 
 def _snapshot_blocks_cache(sdkconfig_path: Path) -> bool:
diff --git a/tests/unit_tests/test_espidf_bootloader.py b/tests/unit_tests/test_espidf_bootloader.py
index 2a86e76b21c..c570b4325f6 100644
--- a/tests/unit_tests/test_espidf_bootloader.py
+++ b/tests/unit_tests/test_espidf_bootloader.py
@@ -118,14 +118,25 @@ def test_enabled_readonly_tools_prefix_disables(tmp_path: Path) -> None:
         assert bootloader._compute_enabled() is False
 
 
-def test_enabled_swallows_errors_as_disabled(tmp_path: Path) -> None:
-    """Any failure while deciding must read as disabled, never raise."""
+@pytest.mark.parametrize(
+    ("err", "level"),
+    [(OSError("boom"), "INFO"), (ValueError("bad"), "WARNING")],
+    ids=["environment", "regression"],
+)
+def test_enabled_swallows_errors_as_disabled(
+    tmp_path: Path, caplog: pytest.LogCaptureFixture, err: Exception, level: str
+) -> None:
+    """Any failure while deciding must read as disabled, never raise;
+    likely regressions log louder than environmental errors."""
     _write_snapshot("CONFIG_APP_REPRODUCIBLE_BUILD=y\n")
     with (
         _tools_prefix(tmp_path),
-        patch.object(toolchain, "_get_idf_path", side_effect=OSError("boom")),
+        patch.object(toolchain, "_get_idf_path", side_effect=err),
+        caplog.at_level("INFO"),
     ):
         assert bootloader._compute_enabled() is False
+    record = next(r for r in caplog.records if "cache disabled" in r.message)
+    assert record.levelname == level
 
 
 def test_bootloader_cache_enabled_is_cached_per_run() -> None: