diff --git a/homeassistant/components/recorder/migration.py b/homeassistant/components/recorder/migration.py
index 927097b18fd..931422b64f4 100644
--- a/homeassistant/components/recorder/migration.py
+++ b/homeassistant/components/recorder/migration.py
@@ -297,6 +297,19 @@ def _create_index(
     _LOGGER.debug("Finished creating %s", index_name)
 
 
+def _execute_or_collect_error(
+    session_maker: Callable[[], Session], query: str, errors: list[str]
+) -> bool:
+    """Execute a query or collect an error."""
+    with session_scope(session=session_maker()) as session:
+        try:
+            session.connection().execute(text(query))
+            return True
+        except SQLAlchemyError as err:
+            errors.append(str(err))
+    return False
+
+
 def _drop_index(
     session_maker: Callable[[], Session],
     table_name: str,
@@ -322,74 +335,45 @@ def _drop_index(
         index_name,
         table_name,
     )
-    success = False
+    index_to_drop: str | None = None
+    with session_scope(session=session_maker()) as session:
+        index_to_drop = get_index_by_name(session, table_name, index_name)
 
-    # Engines like DB2/Oracle
-    with session_scope(session=session_maker()) as session, contextlib.suppress(
-        SQLAlchemyError
-    ):
-        connection = session.connection()
-        connection.execute(text(f"DROP INDEX {index_name}"))
-        success = True
-
-    # Engines like SQLite, SQL Server
-    if not success:
-        with session_scope(session=session_maker()) as session, contextlib.suppress(
-            SQLAlchemyError
-        ):
-            connection = session.connection()
-            connection.execute(
-                text(
-                    "DROP INDEX {table}.{index}".format(
-                        index=index_name, table=table_name
-                    )
-                )
-            )
-            success = True
-
-    if not success:
-        # Engines like MySQL, MS Access
-        with session_scope(session=session_maker()) as session, contextlib.suppress(
-            SQLAlchemyError
-        ):
-            connection = session.connection()
-            connection.execute(
-                text(
-                    "DROP INDEX {index} ON {table}".format(
-                        index=index_name, table=table_name
-                    )
-                )
-            )
-            success = True
-
-    if not success:
-        # Engines like postgresql may have a prefix
-        # ex idx_16532_ix_events_event_type_time_fired
-        with session_scope(session=session_maker()) as session, contextlib.suppress(
-            SQLAlchemyError
-        ):
-            if index_to_drop := get_index_by_name(session, table_name, index_name):
-                connection.execute(text(f"DROP INDEX {index_to_drop}"))
-                success = True
-
-    if success:
+    if index_to_drop is None:
         _LOGGER.debug(
-            "Finished dropping index %s from table %s", index_name, table_name
+            "The index %s on table %s no longer exists", index_name, table_name
         )
         return
 
-    if quiet:
-        return
+    errors: list[str] = []
+    for query in (
+        # Engines like DB2/Oracle
+        f"DROP INDEX {index_name}",
+        # Engines like SQLite, SQL Server
+        f"DROP INDEX {table_name}.{index_name}",
+        # Engines like MySQL, MS Access
+        f"DROP INDEX {index_name} ON {table_name}",
+        # Engines like postgresql may have a prefix
+        # ex idx_16532_ix_events_event_type_time_fired
+        f"DROP INDEX {index_to_drop}",
+    ):
+        if _execute_or_collect_error(session_maker, query, errors):
+            _LOGGER.debug(
+                "Finished dropping index %s from table %s", index_name, table_name
+            )
+            return
 
-    _LOGGER.warning(
-        (
-            "Failed to drop index `%s` from table `%s`. Schema "
-            "Migration will continue; this is not a "
-            "critical operation"
-        ),
-        index_name,
-        table_name,
-    )
+    if not quiet:
+        _LOGGER.warning(
+            (
+                "Failed to drop index `%s` from table `%s`. Schema "
+                "Migration will continue; this is not a "
+                "critical operation: %s"
+            ),
+            index_name,
+            table_name,
+            errors,
+        )
 
 
 def _add_columns(
diff --git a/tests/components/recorder/test_migrate.py b/tests/components/recorder/test_migrate.py
index b23b7a2dfc9..fe4f1e016f5 100644
--- a/tests/components/recorder/test_migrate.py
+++ b/tests/components/recorder/test_migrate.py
@@ -15,6 +15,7 @@ from sqlalchemy.exc import (
     InternalError,
     OperationalError,
     ProgrammingError,
+    SQLAlchemyError,
 )
 from sqlalchemy.orm import Session
 from sqlalchemy.pool import StaticPool
@@ -492,7 +493,51 @@ def test_forgiving_add_index(recorder_db_url: str) -> None:
     with Session(engine) as session:
         instance = Mock()
         instance.get_session = Mock(return_value=session)
-        migration._create_index(instance.get_session, "states", "ix_states_context_id")
+        migration._create_index(
+            instance.get_session, "states", "ix_states_context_id_bin"
+        )
+    engine.dispose()
+
+
+def test_forgiving_drop_index(
+    recorder_db_url: str, caplog: pytest.LogCaptureFixture
+) -> None:
+    """Test that drop index will continue if index drop fails."""
+    engine = create_engine(recorder_db_url, poolclass=StaticPool)
+    db_schema.Base.metadata.create_all(engine)
+    with Session(engine) as session:
+        instance = Mock()
+        instance.get_session = Mock(return_value=session)
+        migration._drop_index(
+            instance.get_session, "states", "ix_states_context_id_bin"
+        )
+        migration._drop_index(
+            instance.get_session, "states", "ix_states_context_id_bin"
+        )
+
+        with patch(
+            "homeassistant.components.recorder.migration.get_index_by_name",
+            return_value="ix_states_context_id_bin",
+        ), patch.object(
+            session, "connection", side_effect=SQLAlchemyError("connection failure")
+        ):
+            migration._drop_index(
+                instance.get_session, "states", "ix_states_context_id_bin"
+            )
+        assert "Failed to drop index" in caplog.text
+        assert "connection failure" in caplog.text
+        caplog.clear()
+        with patch(
+            "homeassistant.components.recorder.migration.get_index_by_name",
+            return_value="ix_states_context_id_bin",
+        ), patch.object(
+            session, "connection", side_effect=SQLAlchemyError("connection failure")
+        ):
+            migration._drop_index(
+                instance.get_session, "states", "ix_states_context_id_bin", quiet=True
+            )
+        assert "Failed to drop index" not in caplog.text
+        assert "connection failure" not in caplog.text
     engine.dispose()