diff --git a/esphome/__main__.py b/esphome/__main__.py
index 0164e2eeb3..c9e4862e48 100644
--- a/esphome/__main__.py
+++ b/esphome/__main__.py
@@ -628,6 +628,50 @@ def _check_and_emit_build_info() -> None:
     )
 
 
+def _get_configured_xtal_freq() -> int | None:
+    """Read the configured crystal frequency from the sdkconfig file."""
+    sdkconfig_path = CORE.relative_build_path(f"sdkconfig.{CORE.name}")
+    if not sdkconfig_path.is_file():
+        return None
+    try:
+        content = sdkconfig_path.read_text()
+        for line in content.splitlines():
+            if line.startswith("CONFIG_XTAL_FREQ="):
+                return int(line.split("=", 1)[1])
+    except (OSError, ValueError):
+        pass
+    return None
+
+
+def _make_crystal_freq_callback(
+    configured_freq: int,
+) -> Callable[[str], str | None]:
+    """Create a callback that checks esptool crystal frequency output."""
+    crystal_re = re.compile(r"Crystal frequency:\s+(\d+(?:\.\d+)?)\s*MHz")
+
+    def check_crystal_line(line: str) -> str | None:
+        if match := crystal_re.search(line):
+            detected = int(float(match.group(1)))
+            if detected != configured_freq:
+                return (
+                    f"\n\033[33mWARNING: Crystal frequency mismatch! "
+                    f"Device reports {detected}MHz but firmware is configured "
+                    f"for {configured_freq}MHz.\n"
+                    f"UART logging and other clock-dependent features will not "
+                    f"work correctly.\n"
+                    f"Set the correct crystal frequency with sdkconfig_options:\n"
+                    f"  esp32:\n"
+                    f"    framework:\n"
+                    f"      sdkconfig_options:\n"
+                    f"        CONFIG_XTAL_FREQ_{detected}: 'y'\n"
+                    f"        CONFIG_XTAL_FREQ_{configured_freq}: 'n'\n"
+                    f'        CONFIG_XTAL_FREQ: "{detected}"\033[0m\n\n'
+                )
+        return None
+
+    return check_crystal_line
+
+
 def upload_using_esptool(
     config: ConfigType, port: str, file: str, speed: int
 ) -> str | int:
@@ -656,6 +700,12 @@ def upload_using_esptool(
 
         mcu = get_esp32_variant().lower()
 
+    line_callbacks = []
+    if CORE.is_esp32:
+        configured_freq = _get_configured_xtal_freq()
+        if configured_freq is not None:
+            line_callbacks.append(_make_crystal_freq_callback(configured_freq))
+
     def run_esptool(baud_rate):
         cmd = [
             "esptool",
@@ -680,7 +730,9 @@ def upload_using_esptool(
         if os.environ.get("ESPHOME_USE_SUBPROCESS") is None:
             import esptool
 
-            return run_external_command(esptool.main, *cmd)  # pylint: disable=no-member
+            return run_external_command(
+                esptool.main, *cmd, line_callbacks=line_callbacks
+            )  # pylint: disable=no-member
 
         return run_external_process(*cmd)
 
diff --git a/esphome/util.py b/esphome/util.py
index 686aa74306..f9ef9bbbc3 100644
--- a/esphome/util.py
+++ b/esphome/util.py
@@ -124,7 +124,12 @@ ANSI_ESCAPE = re.compile(r"\033[@-_][0-?]*[ -/]*[@-~]")
 
 
 class RedirectText:
-    def __init__(self, out, filter_lines=None):
+    def __init__(
+        self,
+        out,
+        filter_lines: str | None = None,
+        line_callbacks: list[Callable[[str], str | None]] | None = None,
+    ) -> None:
         self._out = out
         if filter_lines is None:
             self._filter_pattern = None
@@ -132,6 +137,7 @@ class RedirectText:
             pattern = r"|".join(r"(?:" + pattern + r")" for pattern in filter_lines)
             self._filter_pattern = re.compile(pattern)
         self._line_buffer = ""
+        self._line_callbacks = line_callbacks or []
 
     def __getattr__(self, item):
         return getattr(self._out, item)
@@ -180,6 +186,9 @@ class RedirectText:
                     and (help_msg := get_esp32_arduino_flash_error_help())
                 ):
                     self._write_color_replace(help_msg)
+                for callback in self._line_callbacks:
+                    if msg := callback(line_without_end):
+                        self._write_color_replace(msg)
         else:
             self._write_color_replace(s)
 
@@ -193,7 +202,11 @@ class RedirectText:
 
 
 def run_external_command(
-    func, *cmd, capture_stdout: bool = False, filter_lines: str = None
+    func,
+    *cmd,
+    capture_stdout: bool = False,
+    filter_lines: str = None,
+    line_callbacks: list | None = None,
 ) -> int | str:
     """
     Run a function from an external package that acts like a main method.
@@ -217,9 +230,13 @@ def run_external_command(
     _LOGGER.debug("Running:  %s", full_cmd)
 
     orig_stdout = sys.stdout
-    sys.stdout = RedirectText(sys.stdout, filter_lines=filter_lines)
+    sys.stdout = RedirectText(
+        sys.stdout, filter_lines=filter_lines, line_callbacks=line_callbacks
+    )
     orig_stderr = sys.stderr
-    sys.stderr = RedirectText(sys.stderr, filter_lines=filter_lines)
+    sys.stderr = RedirectText(
+        sys.stderr, filter_lines=filter_lines, line_callbacks=line_callbacks
+    )
 
     if capture_stdout:
         cap_stdout = sys.stdout = io.StringIO()