diff --git a/sqlserver/assets/configuration/spec.yaml b/sqlserver/assets/configuration/spec.yaml
index 11088e12ddc40..18f5bd6bc3724 100644
--- a/sqlserver/assets/configuration/spec.yaml
+++ b/sqlserver/assets/configuration/spec.yaml
@@ -686,7 +686,9 @@ files:
         type: string
         example: master
     - name: ignore_missing_database
-      description: If the DB specified doesn't exist on the server then don't do the check
+      description: |
+        DEPRECATED - use `database_autodiscovery` instead, when database name is uncertain.
+        If the DB specified doesn't exist on the server then don't do the check
       value:
         type: boolean
         example: false
diff --git a/sqlserver/changelog.d/17300.fixed b/sqlserver/changelog.d/17300.fixed
new file mode 100644
index 0000000000000..63e4d0a501aba
--- /dev/null
+++ b/sqlserver/changelog.d/17300.fixed
@@ -0,0 +1 @@
+Remove db exist check if ignore_missing_database is set to false. In this case throw SQLConnectionError instead of ConfigurationError when database does not exist. 
diff --git a/sqlserver/datadog_checks/sqlserver/config.py b/sqlserver/datadog_checks/sqlserver/config.py
index fa8a20b86893b..d37297c36f59d 100644
--- a/sqlserver/datadog_checks/sqlserver/config.py
+++ b/sqlserver/datadog_checks/sqlserver/config.py
@@ -29,6 +29,12 @@ def __init__(self, init_config, instance, log):
         self.include_index_usage_metrics_tempdb: bool = is_affirmative(
             instance.get('include_index_usage_metrics_tempdb', False)
         )
+        self.ignore_missing_database = is_affirmative(instance.get("ignore_missing_database", False))
+        if self.ignore_missing_database:
+            self.log.warning(
+                "The parameter 'ignore_missing_database' is deprecated"
+                "if you are unsure about the database name please use 'database_autodiscovery'"
+            )
 
         # DBM
         self.dbm_enabled: bool = is_affirmative(instance.get('dbm', False))
diff --git a/sqlserver/datadog_checks/sqlserver/data/conf.yaml.example b/sqlserver/datadog_checks/sqlserver/data/conf.yaml.example
index f28d03cb33c28..303df58f2e522 100644
--- a/sqlserver/datadog_checks/sqlserver/data/conf.yaml.example
+++ b/sqlserver/datadog_checks/sqlserver/data/conf.yaml.example
@@ -644,6 +644,7 @@ instances:
     # proc_only_if_database: master
 
     ## @param ignore_missing_database - boolean - optional - default: false
+    ## DEPRECATED - use `database_autodiscovery` instead, when database name is uncertain.
     ## If the DB specified doesn't exist on the server then don't do the check
     #
     # ignore_missing_database: false
diff --git a/sqlserver/datadog_checks/sqlserver/sqlserver.py b/sqlserver/datadog_checks/sqlserver/sqlserver.py
index 56c6f0b44f189..b55882a1fdd3f 100644
--- a/sqlserver/datadog_checks/sqlserver/sqlserver.py
+++ b/sqlserver/datadog_checks/sqlserver/sqlserver.py
@@ -11,7 +11,7 @@
 import six
 from cachetools import TTLCache
 
-from datadog_checks.base import AgentCheck, ConfigurationError
+from datadog_checks.base import AgentCheck
 from datadog_checks.base.config import is_affirmative
 from datadog_checks.base.utils.db import QueryExecutor, QueryManager
 from datadog_checks.base.utils.db.utils import default_json_event_encoding, resolve_db_host, tracked_query
@@ -332,31 +332,27 @@ def initialize_connection(self):
     def make_metric_list_to_collect(self):
         # Pre-process the list of metrics to collect
         try:
-            # check to see if the database exists before we try any connections to it
-            db_exists, context = self.connection.check_database()
-            if db_exists:
-                if self.instance.get('stored_procedure') is None:
-                    with self.connection.open_managed_default_connection():
-                        with self.connection.get_managed_cursor() as cursor:
-                            self.autodiscover_databases(cursor)
-                        self._make_metric_list_to_collect(self._config.custom_metrics)
-            else:
-                # How much do we care that the DB doesn't exist?
-                ignore = is_affirmative(self.instance.get("ignore_missing_database", False))
-                if ignore is not None and ignore:
-                    # not much : we expect it. leave checks disabled
-                    self.do_check = False
-                    self.log.warning("Database %s does not exist. Disabling checks for this instance.", context)
-                else:
-                    # yes we do. Keep trying
-                    msg = "Database {} does not exist. Please resolve invalid database and restart agent".format(
-                        context
-                    )
-                    raise ConfigurationError(msg)
-
-        except SQLConnectionError as e:
-            self.log.exception("Error connecting to database: %s", e)
-        except ConfigurationError:
+            if self._config.ignore_missing_database:
+                # self.connection.check_database() will try to connect to 'master'.
+                # If this is an Azure SQL Database this function will throw.
+                # For this reason we avoid calling self.connection.check_database()
+                # for this config as it will be a false negative.
+                engine_edition = self.static_info_cache.get(STATIC_INFO_ENGINE_EDITION)
+                if not is_azure_sql_database(engine_edition):
+                    # Do the database exist check that will allow to disable _check as a whole
+                    # as otherwise the first call to open_managed_default_connection will throw the
+                    # SQLConnectionError.
+                    db_exists, context = self.connection.check_database()
+                    if not db_exists:
+                        self.do_check = False
+                        self.log.warning("Database %s does not exist. Disabling checks for this instance.", context)
+                        return
+            if self.instance.get('stored_procedure') is None:
+                with self.connection.open_managed_default_connection():
+                    with self.connection.get_managed_cursor() as cursor:
+                        self.autodiscover_databases(cursor)
+                    self._make_metric_list_to_collect(self._config.custom_metrics)
+        except SQLConnectionError:
             raise
         except Exception as e:
             self.log.exception("Initialization exception %s", e)
diff --git a/sqlserver/tests/test_metrics.py b/sqlserver/tests/test_metrics.py
index b9118eb03cc75..d02d8bb29f4f0 100644
--- a/sqlserver/tests/test_metrics.py
+++ b/sqlserver/tests/test_metrics.py
@@ -203,6 +203,7 @@ def test_check_index_usage_metrics(
 ):
     instance_docker_metrics['database'] = 'datadog_test'
     instance_docker_metrics['include_index_usage_metrics'] = True
+    instance_docker_metrics['ignore_missing_database'] = True
 
     # Cause an index seek
     bob_conn.execute_with_retries(
@@ -379,6 +380,7 @@ def test_check_incr_fraction_metrics(
     bob_conn_raw,
 ):
     instance_docker_metrics['database'] = 'datadog_test'
+    instance_docker_metrics['ignore_missing_database'] = True
     sqlserver_check = SQLServer(CHECK_NAME, init_config, [instance_docker_metrics])
 
     sqlserver_check.run()
diff --git a/sqlserver/tests/test_unit.py b/sqlserver/tests/test_unit.py
index dd0af7b9c4bf4..0f65e631a01cc 100644
--- a/sqlserver/tests/test_unit.py
+++ b/sqlserver/tests/test_unit.py
@@ -9,7 +9,6 @@
 import mock
 import pytest
 
-from datadog_checks.base.errors import ConfigurationError
 from datadog_checks.dev import EnvVars
 from datadog_checks.sqlserver import SQLServer
 from datadog_checks.sqlserver.connection import split_sqlserver_host_port
@@ -43,8 +42,12 @@ def test_get_cursor(instance_docker):
 def test_missing_db(instance_docker, dd_run_check):
     instance = copy.copy(instance_docker)
     instance['ignore_missing_database'] = False
-    with mock.patch('datadog_checks.sqlserver.connection.Connection.check_database', return_value=(False, 'db')):
-        with pytest.raises(ConfigurationError):
+
+    with mock.patch(
+        'datadog_checks.sqlserver.connection.Connection.open_managed_default_connection',
+        side_effect=SQLConnectionError(Exception("couldnt connect")),
+    ):
+        with pytest.raises(SQLConnectionError):
             check = SQLServer(CHECK_NAME, {}, [instance])
             check.initialize_connection()
             check.make_metric_list_to_collect()
@@ -79,13 +82,13 @@ def test_db_exists(get_cursor, mock_connect, instance_docker_defaults, dd_run_ch
     instance = copy.copy(instance_docker_defaults)
     # make sure check doesn't try to add metrics
     instance['stored_procedure'] = 'fake_proc'
+    instance['ignore_missing_database'] = True
 
     # check base case of lowercase for lowercase and case-insensitive db
     check = SQLServer(CHECK_NAME, {}, [instance])
     check.initialize_connection()
     check.make_metric_list_to_collect()
     assert check.do_check is True
-
     # check all caps for case insensitive db
     instance['database'] = 'MASTER'
     check = SQLServer(CHECK_NAME, {}, [instance])
@@ -110,9 +113,9 @@ def test_db_exists(get_cursor, mock_connect, instance_docker_defaults, dd_run_ch
     # check case sensitive but mismatched db
     instance['database'] = 'cASEsENSITIVE2018'
     check = SQLServer(CHECK_NAME, {}, [instance])
-    with pytest.raises(ConfigurationError):
-        check.initialize_connection()
-        check.make_metric_list_to_collect()
+    check.initialize_connection()
+    check.make_metric_list_to_collect()
+    assert check.do_check is False
 
     # check offline but exists db
     instance['database'] = 'Offlinedb'