diff --git a/esphome/cli/rotate_key.py b/esphome/cli/rotate_key.py
index f0d407e335..34d1ae1497 100644
--- a/esphome/cli/rotate_key.py
+++ b/esphome/cli/rotate_key.py
@@ -15,6 +15,7 @@ from esphome.components.noise import (
 from esphome.config_validation import Invalid
 from esphome.const import CONF_API, CONF_PASSWORD, CONF_PORT
 from esphome.core import CORE, EsphomeError
+from esphome.espota2 import ProbeResult
 from esphome.log import AnsiFore, color
 from esphome.ota_key_edit import locate_key_edits, old_key_edit, with_sharers
 from esphome.types import ConfigType
@@ -29,6 +30,24 @@ from esphome.util import (
 from esphome.yaml_edit import RestoreError, Snapshot, apply_line_edits, restore_files
 
 PRECHECK_TIMEOUT = 15.0
+# What to do when the device does not accept the key in the yaml before anything is written
+PRECHECK_ADVICE = {
+    ProbeResult.UNREACHABLE: (
+        "The device could not be reached; check that it is online, then try again."
+    ),
+    ProbeResult.REJECTED: (
+        "The device runs a different key than the yaml. Install the current "
+        "configuration first, presenting its key with --prompt-ota-key, then rotate."
+    ),
+    ProbeResult.NOT_OFFERED: (
+        "The device does not offer encryption: it runs a firmware older than "
+        "ESPHome 2026.9.0 or without a key. Install the current configuration "
+        "first, then rotate."
+    ),
+    ProbeResult.DEVICE_ERROR: (
+        "The device answered with an error (see the warning above); fix that first."
+    ),
+}
 
 
 def command_rotate_key(args: argparse.Namespace, config: ConfigType) -> int | None:
@@ -129,19 +148,15 @@ def command_rotate_key(args: argparse.Namespace, config: ConfigType) -> int | No
                 return 1
 
     safe_print("Checking that the device accepts the current key...")
-    if not espota2.probe_ota_key(
+    found = espota2.probe_ota_key(
         network_devices,
         remote_port,
         old_key,
         timeout=PRECHECK_TIMEOUT,
         retry_rejected=False,
-    ):
-        return fail(
-            "The device did not complete an encrypted handshake with the current "
-            "key (see the warning above for the reason). If it is reachable, it "
-            "has to run the key in the yaml on ESPHome 2026.9.0 or newer; install "
-            "the current configuration first, then rotate."
-        )
+    )
+    if found is not ProbeResult.ACCEPTED:
+        return fail(PRECHECK_ADVICE[found])
 
     # Both keys are shown only when a file could not be put back
     keys = f"Previous key: {old_key}\nNew key: {new_key}"
@@ -198,11 +213,16 @@ def command_rotate_key(args: argparse.Namespace, config: ConfigType) -> int | No
                 else "The upload did not reach the device."
             )
         safe_print("Waiting for the device to come back with the new key...")
-        if not espota2.probe_ota_key(network_devices, remote_port, new_key):
+        found = espota2.probe_ota_key(network_devices, remote_port, new_key)
+        if found is not ProbeResult.ACCEPTED:
             return fail(
-                "The device did not answer with the new key. The configuration "
-                "keeps it, with the previous key as old_key, so the next install "
-                "reaches the device either way."
+                (
+                    "The device still answers with the previous key."
+                    if found is ProbeResult.REJECTED
+                    else "The device did not come back to confirm the new key."
+                )
+                + " The configuration keeps the new key, with the previous one as "
+                "old_key, so the next install reaches the device either way."
             )
     except KeyboardInterrupt:
         return fail(
diff --git a/tests/unit_tests/cli/test_rotate_key.py b/tests/unit_tests/cli/test_rotate_key.py
index a2e4a1e8ab..4007065302 100644
--- a/tests/unit_tests/cli/test_rotate_key.py
+++ b/tests/unit_tests/cli/test_rotate_key.py
@@ -11,7 +11,7 @@ from unittest.mock import ANY, Mock, patch
 import pytest
 
 from esphome import yaml_util
-from esphome.cli.rotate_key import command_rotate_key
+from esphome.cli.rotate_key import PRECHECK_ADVICE, command_rotate_key
 from esphome.const import (
     CONF_API,
     CONF_ENCRYPTION,
@@ -26,6 +26,7 @@ from esphome.const import (
     PLATFORM_ESP32,
 )
 from esphome.core import CORE, EsphomeError, Toolchain
+from esphome.espota2 import ProbeResult
 from esphome.ota_key_edit import KeyEdit
 from esphome.upload_targets import PortType
 from esphome.util import ESPHOME_COMMAND
@@ -100,7 +101,9 @@ def env(tmp_path: Path) -> Generator[dict[str, Mock]]:
         patch("esphome.__main__.choose_upload_log_host", return_value=["dev.local"]),
         patch("esphome.__main__._resolve_network_devices", return_value=["dev.local"]),
         patch("esphome.cli.rotate_key.get_port_type", return_value=PortType.NETWORK),
-        patch("esphome.espota2.probe_ota_key", return_value=True) as probe,
+        patch(
+            "esphome.espota2.probe_ota_key", return_value=ProbeResult.ACCEPTED
+        ) as probe,
         patch(
             "esphome.cli.rotate_key.run_external_process", return_value=0
         ) as compile_,
@@ -233,11 +236,19 @@ def test_rejects_bad_new_key(env: dict[str, Mock], key: str) -> None:
 def test_precheck_fails_writes_nothing(
     env: dict[str, Mock], capfd: pytest.CaptureFixture[str]
 ) -> None:
-    env["probe"].return_value = False
+    env["probe"].return_value = ProbeResult.REJECTED
     assert command_rotate_key(MockArgs(), CORE.config) == 1
     assert CORE.config_path.read_text() == API_YAML
     env["compile"].assert_not_called()
-    assert "did not complete an encrypted handshake" in capfd.readouterr().out
+    assert "runs a different key than the yaml" in capfd.readouterr().out
+    for found in (
+        ProbeResult.UNREACHABLE,
+        ProbeResult.NOT_OFFERED,
+        ProbeResult.DEVICE_ERROR,
+    ):
+        env["probe"].return_value = found
+        assert command_rotate_key(MockArgs(), CORE.config) == 1
+        assert PRECHECK_ADVICE[found] in capfd.readouterr().out
 
 
 @pytest.mark.parametrize("step", ["compile", "interrupt"])
@@ -298,7 +309,7 @@ def test_an_interrupt_during_the_image_cleanup_shows_the_keys(
 def test_a_build_from_before_the_rotation_is_kept(
     env: dict[str, Mock], capfd: pytest.CaptureFixture[str]
 ) -> None:
-    env["probe"].return_value = False
+    env["probe"].return_value = ProbeResult.UNREACHABLE
     image = CORE.firmware_bin
     image.parent.mkdir(parents=True)
     image.write_bytes(b"built with the current key")
@@ -387,7 +398,7 @@ def test_reports_a_failed_restore(
     assert OLD_KEY in out and NEW_KEY in out
 
 
-@pytest.mark.parametrize("outcome", ["unconfirmed", "interrupted"])
+@pytest.mark.parametrize("outcome", ["unreachable", "rejected", "interrupted"])
 def test_keeps_the_new_key_after_the_upload(
     env: dict[str, Mock], capfd: pytest.CaptureFixture[str], outcome: str
 ) -> None:
@@ -395,8 +406,12 @@ def test_keeps_the_new_key_after_the_upload(
     and old_key covers the other case, so the files stay and the key is
     printed."""
     env["probe"].side_effect = [
-        True,
-        KeyboardInterrupt if outcome == "interrupted" else False,
+        ProbeResult.ACCEPTED,
+        {
+            "interrupted": KeyboardInterrupt,
+            "unreachable": ProbeResult.UNREACHABLE,
+            "rejected": ProbeResult.REJECTED,
+        }[outcome],
     ]
     assert command_rotate_key(MockArgs(), CORE.config) == 1
     assert NEW_KEY in CORE.config_path.read_text()
@@ -404,6 +419,8 @@ def test_keeps_the_new_key_after_the_upload(
     out = capfd.readouterr().out
     assert NEW_KEY in out
     assert ("Interrupted" in out) is (outcome == "interrupted")
+    assert ("still answers with the previous key" in out) is (outcome == "rejected")
+    assert ("did not come back" in out) is (outcome == "unreachable")
 
 
 def test_child_compile_gets_global_options_first(