diff --git a/homeassistant/components/cloud/__init__.py b/homeassistant/components/cloud/__init__.py
index 6a948c0ad15..0662487b765 100644
--- a/homeassistant/components/cloud/__init__.py
+++ b/homeassistant/components/cloud/__init__.py
@@ -3,6 +3,7 @@ from __future__ import annotations
 
 import asyncio
 from collections.abc import Awaitable, Callable
+from datetime import timedelta
 from enum import Enum
 
 from hass_nabucasa import Cloud
@@ -26,6 +27,7 @@ from homeassistant.helpers.dispatcher import (
     async_dispatcher_connect,
     async_dispatcher_send,
 )
+from homeassistant.helpers.event import async_call_later
 from homeassistant.helpers.service import async_register_admin_service
 from homeassistant.helpers.typing import ConfigType
 from homeassistant.loader import bind_hass
@@ -55,6 +57,8 @@ from .const import (
     MODE_PROD,
 )
 from .prefs import CloudPreferences
+from .repairs import async_manage_legacy_subscription_issue
+from .subscription import async_subscription_info
 
 DEFAULT_MODE = MODE_PROD
 
@@ -258,6 +262,14 @@ async def async_setup(hass: HomeAssistant, config: ConfigType) -> bool:
 
     loaded = False
 
+    async def async_startup_repairs(_=None) -> None:
+        """Create repair issues after startup."""
+        if not cloud.is_logged_in:
+            return
+
+        if subscription_info := await async_subscription_info(cloud):
+            async_manage_legacy_subscription_issue(hass, subscription_info)
+
     async def _on_connect():
         """Discover RemoteUI binary sensor."""
         nonlocal loaded
@@ -294,6 +306,12 @@ async def async_setup(hass: HomeAssistant, config: ConfigType) -> bool:
 
     account_link.async_setup(hass)
 
+    async_call_later(
+        hass=hass,
+        delay=timedelta(hours=1),
+        action=async_startup_repairs,
+    )
+
     return True
 
 
diff --git a/homeassistant/components/cloud/http_api.py b/homeassistant/components/cloud/http_api.py
index 01b6cd17508..76d8bea1664 100644
--- a/homeassistant/components/cloud/http_api.py
+++ b/homeassistant/components/cloud/http_api.py
@@ -9,7 +9,7 @@ from typing import Any
 import aiohttp
 import async_timeout
 import attr
-from hass_nabucasa import Cloud, auth, cloud_api, thingtalk
+from hass_nabucasa import Cloud, auth, thingtalk
 from hass_nabucasa.const import STATE_DISCONNECTED
 from hass_nabucasa.voice import MAP_VOICE
 import voluptuous as vol
@@ -38,6 +38,8 @@ from .const import (
     PREF_TTS_DEFAULT_VOICE,
     REQUEST_TIMEOUT,
 )
+from .repairs import async_manage_legacy_subscription_issue
+from .subscription import async_subscription_info
 
 _LOGGER = logging.getLogger(__name__)
 
@@ -328,15 +330,14 @@ async def websocket_subscription(
 ) -> None:
     """Handle request for account info."""
     cloud = hass.data[DOMAIN]
-    try:
-        async with async_timeout.timeout(REQUEST_TIMEOUT):
-            data = await cloud_api.async_subscription_info(cloud)
-    except aiohttp.ClientError:
+    if (data := await async_subscription_info(cloud)) is None:
         connection.send_error(
             msg["id"], "request_failed", "Failed to request subscription"
         )
-    else:
-        connection.send_result(msg["id"], data)
+        return
+
+    connection.send_result(msg["id"], data)
+    async_manage_legacy_subscription_issue(hass, data)
 
 
 @_require_cloud_login
diff --git a/homeassistant/components/cloud/repairs.py b/homeassistant/components/cloud/repairs.py
new file mode 100644
index 00000000000..779c0eb64b0
--- /dev/null
+++ b/homeassistant/components/cloud/repairs.py
@@ -0,0 +1,121 @@
+"""Repairs implementation for the cloud integration."""
+from __future__ import annotations
+
+import asyncio
+from typing import Any
+
+from hass_nabucasa import Cloud
+import voluptuous as vol
+
+from homeassistant.components.repairs import RepairsFlow, repairs_flow_manager
+from homeassistant.core import HomeAssistant, callback
+from homeassistant.data_entry_flow import FlowResult
+from homeassistant.helpers import issue_registry as ir
+
+from .const import DOMAIN
+from .subscription import async_subscription_info
+
+BACKOFF_TIME = 5
+MAX_RETRIES = 60  # This allows for 10 minutes of retries
+
+
+@callback
+def async_manage_legacy_subscription_issue(
+    hass: HomeAssistant,
+    subscription_info: dict[str, Any],
+) -> None:
+    """
+    Manage the legacy subscription issue.
+
+    If the provider is "legacy" create an issue,
+    in all other cases remove the issue.
+    """
+    if subscription_info["provider"] == "legacy":
+        ir.async_create_issue(
+            hass=hass,
+            domain=DOMAIN,
+            issue_id="legacy_subscription",
+            is_fixable=True,
+            severity=ir.IssueSeverity.WARNING,
+            translation_key="legacy_subscription",
+        )
+        return
+    ir.async_delete_issue(hass=hass, domain=DOMAIN, issue_id="legacy_subscription")
+
+
+class LegacySubscriptionRepairFlow(RepairsFlow):
+    """Handler for an issue fixing flow."""
+
+    wait_task: asyncio.Task | None = None
+    _data: dict[str, Any] | None = None
+
+    async def async_step_init(self, _: None = None) -> FlowResult:
+        """Handle the first step of a fix flow."""
+        return await self.async_step_confirm_change_plan()
+
+    async def async_step_confirm_change_plan(
+        self,
+        user_input: dict[str, str] | None = None,
+    ) -> FlowResult:
+        """Handle the confirm step of a fix flow."""
+        if user_input is not None:
+            return await self.async_step_change_plan()
+
+        return self.async_show_form(
+            step_id="confirm_change_plan", data_schema=vol.Schema({})
+        )
+
+    async def async_step_change_plan(self, _: None = None) -> FlowResult:
+        """Wait for the user to authorize the app installation."""
+
+        async def _async_wait_for_plan_change() -> None:
+            flow_manager = repairs_flow_manager(self.hass)
+            # We can not get here without a flow manager
+            assert flow_manager is not None
+
+            cloud: Cloud = self.hass.data[DOMAIN]
+
+            retries = 0
+            while retries < MAX_RETRIES:
+                self._data = await async_subscription_info(cloud)
+                if self._data is not None and self._data["provider"] != "legacy":
+                    break
+
+                retries += 1
+                await asyncio.sleep(BACKOFF_TIME)
+
+            self.hass.async_create_task(
+                flow_manager.async_configure(flow_id=self.flow_id)
+            )
+
+        if not self.wait_task:
+            self.wait_task = self.hass.async_create_task(_async_wait_for_plan_change())
+            return self.async_external_step(
+                step_id="change_plan",
+                url="https://account.nabucasa.com/",
+            )
+
+        await self.wait_task
+
+        if self._data is None or self._data["provider"] == "legacy":
+            # If we get here we waited too long.
+            return self.async_external_step_done(next_step_id="timeout")
+
+        return self.async_external_step_done(next_step_id="complete")
+
+    async def async_step_complete(self, _: None = None) -> FlowResult:
+        """Handle the final step of a fix flow."""
+        return self.async_create_entry(title="", data={})
+
+    async def async_step_timeout(self, _: None = None) -> FlowResult:
+        """Handle the final step of a fix flow."""
+        return self.async_abort(reason="operation_took_too_long")
+
+
+async def async_create_fix_flow(
+    hass: HomeAssistant,
+    issue_id: str,
+    data: dict[str, str | int | float | None] | None,
+) -> RepairsFlow:
+    """Create flow."""
+    return LegacySubscriptionRepairFlow()
diff --git a/homeassistant/components/cloud/strings.json b/homeassistant/components/cloud/strings.json
index a799a8cee59..e437fca9ed3 100644
--- a/homeassistant/components/cloud/strings.json
+++ b/homeassistant/components/cloud/strings.json
@@ -13,5 +13,20 @@
       "logged_in": "Logged In",
       "subscription_expiration": "Subscription Expiration"
     }
+  },
+  "issues": {
+    "legacy_subscription": {
+      "title": "Legacy subscription detected",
+      "fix_flow": {
+        "step": {
+          "confirm_change_plan": {
+            "description": "We've recently updated our subscription system. To continue using Home Assistant Cloud you need to one-time approve the change in PayPal.\n\nThis takes 1 minute and will not increase the price."
+          }
+        },
+        "abort": {
+          "operation_took_too_long": "The operation took too long. Please try again later."
+        }
+      }
+    }
   }
 }
diff --git a/homeassistant/components/cloud/subscription.py b/homeassistant/components/cloud/subscription.py
new file mode 100644
index 00000000000..9a2e5bd87cf
--- /dev/null
+++ b/homeassistant/components/cloud/subscription.py
@@ -0,0 +1,24 @@
+"""Subscription information."""
+from __future__ import annotations
+
+import logging
+from typing import Any
+
+from aiohttp.client_exceptions import ClientError
+import async_timeout
+from hass_nabucasa import Cloud, cloud_api
+
+from .const import REQUEST_TIMEOUT
+
+_LOGGER = logging.getLogger(__name__)
+
+
+async def async_subscription_info(cloud: Cloud) -> dict[str, Any] | None:
+    """Fetch the subscription info."""
+    try:
+        async with async_timeout.timeout(REQUEST_TIMEOUT):
+            return await cloud_api.async_subscription_info(cloud)
+    except ClientError:
+        _LOGGER.error("Failed to fetch subscription information")
+
+    return None
diff --git a/homeassistant/components/cloud/translations/en.json b/homeassistant/components/cloud/translations/en.json
index 7577a9a51e4..fa7376f80c8 100644
--- a/homeassistant/components/cloud/translations/en.json
+++ b/homeassistant/components/cloud/translations/en.json
@@ -1,4 +1,19 @@
 {
+    "issues": {
+        "legacy_subscription": {
+            "fix_flow": {
+                "abort": {
+                    "operation_took_too_long": "The operation took too long. Please try again later."
+                },
+                "step": {
+                    "confirm_change_plan": {
+                        "description": "We've recently updated our subscription system. To continue using Home Assistant Cloud you need to one-time approve the change in PayPal.\n\nThis takes 1 minute and will not increase the price."
+                    }
+                }
+            },
+            "title": "Legacy subscription detected"
+        }
+    },
     "system_health": {
         "info": {
             "alexa_enabled": "Alexa Enabled",
diff --git a/tests/components/cloud/conftest.py b/tests/components/cloud/conftest.py
index 4bd5868db5f..e16fb63b34a 100644
--- a/tests/components/cloud/conftest.py
+++ b/tests/components/cloud/conftest.py
@@ -52,6 +52,15 @@ def mock_cloud_login(hass, mock_cloud_setup):
         yield
 
 
+@pytest.fixture(name="mock_auth")
+def mock_auth_fixture():
+    """Mock check token."""
+    with patch("hass_nabucasa.auth.CognitoAuth.async_check_token"), patch(
+        "hass_nabucasa.auth.CognitoAuth.async_renew_access_token"
+    ):
+        yield
+
+
 @pytest.fixture
 def mock_expired_cloud_login(hass, mock_cloud_setup):
     """Mock cloud is logged in."""
diff --git a/tests/components/cloud/test_http_api.py b/tests/components/cloud/test_http_api.py
index 4d0729d72b2..1f9af960f08 100644
--- a/tests/components/cloud/test_http_api.py
+++ b/tests/components/cloud/test_http_api.py
@@ -24,13 +24,6 @@ from tests.components.google_assistant import MockConfig
 SUBSCRIPTION_INFO_URL = "https://api-test.hass.io/subscription_info"
 
 
-@pytest.fixture(name="mock_auth")
-def mock_auth_fixture():
-    """Mock check token."""
-    with patch("hass_nabucasa.auth.CognitoAuth.async_check_token"):
-        yield
-
-
 @pytest.fixture(name="mock_cloud_login")
 def mock_cloud_login_fixture(hass, setup_api):
     """Mock cloud is logged in."""
diff --git a/tests/components/cloud/test_repairs.py b/tests/components/cloud/test_repairs.py
new file mode 100644
index 00000000000..ef96efaa402
--- /dev/null
+++ b/tests/components/cloud/test_repairs.py
@@ -0,0 +1,232 @@
+"""Test cloud repairs."""
+from collections.abc import Awaitable, Callable, Generator
+from datetime import timedelta
+from http import HTTPStatus
+from unittest.mock import AsyncMock, patch
+
+from aiohttp import ClientSession
+
+from homeassistant.components.cloud import DOMAIN
+import homeassistant.components.cloud.repairs as cloud_repairs
+from homeassistant.components.repairs import DOMAIN as REPAIRS_DOMAIN
+from homeassistant.core import HomeAssistant
+import homeassistant.helpers.issue_registry as ir
+from homeassistant.setup import async_setup_component
+from homeassistant.util import dt
+
+from . import mock_cloud
+
+from tests.common import async_fire_time_changed
+from tests.test_util.aiohttp import AiohttpClientMocker
+
+
+async def test_do_not_create_repair_issues_at_startup_if_not_logged_in(
+    hass: HomeAssistant,
+):
+    """Test that we create repair issue at startup if we are logged in."""
+    issue_registry: ir.IssueRegistry = ir.async_get(hass)
+
+    with patch("homeassistant.components.cloud.Cloud.is_logged_in", False):
+        await mock_cloud(hass)
+
+        async_fire_time_changed(hass, dt.utcnow() + timedelta(hours=1))
+        await hass.async_block_till_done()
+
+    assert not issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+
+
+async def test_create_repair_issues_at_startup_if_logged_in(
+    hass: HomeAssistant,
+    aioclient_mock: AiohttpClientMocker,
+    mock_auth: Generator[None, AsyncMock, None],
+):
+    """Test that we create repair issue at startup if we are logged in."""
+    issue_registry: ir.IssueRegistry = ir.async_get(hass)
+    aioclient_mock.get(
+        "https://accounts.nabucasa.com/payments/subscription_info",
+        json={"provider": "legacy"},
+    )
+
+    with patch("homeassistant.components.cloud.Cloud.is_logged_in", True):
+        await mock_cloud(hass)
+
+        async_fire_time_changed(hass, dt.utcnow() + timedelta(hours=1))
+        await hass.async_block_till_done()
+
+    assert issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+
+
+async def test_legacy_subscription_delete_issue_if_no_longer_legacy(
+    hass: HomeAssistant,
+):
+    """Test that we delete the legacy subscription issue if no longer legacy."""
+    issue_registry: ir.IssueRegistry = ir.async_get(hass)
+    cloud_repairs.async_manage_legacy_subscription_issue(hass, {"provider": "legacy"})
+    assert issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+
+    cloud_repairs.async_manage_legacy_subscription_issue(hass, {"provider": None})
+    assert not issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+
+
+async def test_legacy_subscription_repair_flow(
+    hass: HomeAssistant,
+    aioclient_mock: AiohttpClientMocker,
+    mock_auth: Generator[None, AsyncMock, None],
+    hass_client: Callable[..., Awaitable[ClientSession]],
+):
+    """Test desired flow of the fix flow for legacy subscription."""
+    issue_registry: ir.IssueRegistry = ir.async_get(hass)
+    aioclient_mock.get(
+        "https://accounts.nabucasa.com/payments/subscription_info",
+        json={"provider": None},
+    )
+
+    cloud_repairs.async_manage_legacy_subscription_issue(hass, {"provider": "legacy"})
+    repair_issue = issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+    assert repair_issue
+
+    assert await async_setup_component(hass, REPAIRS_DOMAIN, {REPAIRS_DOMAIN: {}})
+    await mock_cloud(hass)
+    await hass.async_block_till_done()
+    await hass.async_start()
+
+    client = await hass_client()
+
+    resp = await client.post(
+        "/api/repairs/issues/fix",
+        json={"handler": DOMAIN, "issue_id": repair_issue.issue_id},
+    )
+
+    assert resp.status == HTTPStatus.OK
+    data = await resp.json()
+
+    flow_id = data["flow_id"]
+    assert data == {
+        "type": "form",
+        "flow_id": flow_id,
+        "handler": DOMAIN,
+        "step_id": "confirm_change_plan",
+        "data_schema": [],
+        "errors": None,
+        "description_placeholders": None,
+        "last_step": None,
+    }
+
+    resp = await client.post(f"/api/repairs/issues/fix/{flow_id}")
+
+    assert resp.status == HTTPStatus.OK
+    data = await resp.json()
+
+    flow_id = data["flow_id"]
+    assert data == {
+        "type": "external",
+        "flow_id": flow_id,
+        "handler": DOMAIN,
+        "step_id": "change_plan",
+        "url": "https://account.nabucasa.com/",
+        "description_placeholders": None,
+    }
+
+    resp = await client.post(f"/api/repairs/issues/fix/{flow_id}")
+
+    assert resp.status == HTTPStatus.OK
+    data = await resp.json()
+
+    flow_id = data["flow_id"]
+    assert data == {
+        "version": 1,
+        "type": "create_entry",
+        "flow_id": flow_id,
+        "handler": DOMAIN,
+        "title": "",
+        "description": None,
+        "description_placeholders": None,
+    }
+
+    assert not issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+
+
+async def test_legacy_subscription_repair_flow_timeout(
+    hass: HomeAssistant,
+    hass_client: Callable[..., Awaitable[ClientSession]],
+):
+    """Test timeout flow of the fix flow for legacy subscription."""
+    issue_registry: ir.IssueRegistry = ir.async_get(hass)
+
+    cloud_repairs.async_manage_legacy_subscription_issue(hass, {"provider": "legacy"})
+    repair_issue = issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )
+    assert repair_issue
+
+    assert await async_setup_component(hass, REPAIRS_DOMAIN, {REPAIRS_DOMAIN: {}})
+    await mock_cloud(hass)
+    await hass.async_block_till_done()
+    await hass.async_start()
+
+    client = await hass_client()
+
+    resp = await client.post(
+        "/api/repairs/issues/fix",
+        json={"handler": DOMAIN, "issue_id": repair_issue.issue_id},
+    )
+
+    assert resp.status == HTTPStatus.OK
+    data = await resp.json()
+
+    flow_id = data["flow_id"]
+    assert data == {
+        "type": "form",
+        "flow_id": flow_id,
+        "handler": DOMAIN,
+        "step_id": "confirm_change_plan",
+        "data_schema": [],
+        "errors": None,
+        "description_placeholders": None,
+        "last_step": None,
+    }
+
+    with patch("homeassistant.components.cloud.repairs.MAX_RETRIES", new=0):
+        resp = await client.post(f"/api/repairs/issues/fix/{flow_id}")
+        assert resp.status == HTTPStatus.OK
+        data = await resp.json()
+
+        flow_id = data["flow_id"]
+        assert data == {
+            "type": "external",
+            "flow_id": flow_id,
+            "handler": DOMAIN,
+            "step_id": "change_plan",
+            "url": "https://account.nabucasa.com/",
+            "description_placeholders": None,
+        }
+
+    resp = await client.post(f"/api/repairs/issues/fix/{flow_id}")
+    assert resp.status == HTTPStatus.OK
+    data = await resp.json()
+
+    flow_id = data["flow_id"]
+    assert data == {
+        "type": "abort",
+        "flow_id": flow_id,
+        "handler": "cloud",
+        "reason": "operation_took_too_long",
+        "description_placeholders": None,
+        "result": None,
+    }
+
+    assert issue_registry.async_get_issue(
+        domain="cloud", issue_id="legacy_subscription"
+    )