diff --git a/postgres/changelog.d/23645.added b/postgres/changelog.d/23645.added
new file mode 100644
index 0000000000000..949d76193e287
--- /dev/null
+++ b/postgres/changelog.d/23645.added
@@ -0,0 +1 @@
+Run `diagnose` when the main Postgres check fails then emit any warnings and failures as Agent Health events.
\ No newline at end of file
diff --git a/postgres/datadog_checks/postgres/diagnose.py b/postgres/datadog_checks/postgres/diagnose.py
index 9044799e911f7..eb6c5970fc059 100644
--- a/postgres/datadog_checks/postgres/diagnose.py
+++ b/postgres/datadog_checks/postgres/diagnose.py
@@ -16,8 +16,15 @@
       health event instead.
 """
 
+from __future__ import annotations
+
+from typing import TYPE_CHECKING
+
 import psycopg
 
+if TYPE_CHECKING:
+    from .postgres import PostgreSql
+
 from .util import (
     DIAGNOSTIC_METADATA,
     DatabaseConfigurationError,
@@ -35,7 +42,7 @@
 class PostgresDiagnose:
     """Explicit pre-flight diagnostics for `datadog-agent diagnose`."""
 
-    def __init__(self, check):
+    def __init__(self, check: PostgreSql):
         self._check = check
         # Codes that have FAIL'd in the current explicit run. Used for cascade skipping so we
         # don't emit downstream-effect FAILs with nonsensical remediations (e.g. "CREATE EXTENSION"
diff --git a/postgres/datadog_checks/postgres/health.py b/postgres/datadog_checks/postgres/health.py
index e900ad9d55032..4c7ef041748eb 100644
--- a/postgres/datadog_checks/postgres/health.py
+++ b/postgres/datadog_checks/postgres/health.py
@@ -5,6 +5,8 @@
 
 from typing import TYPE_CHECKING
 
+from datadog_checks.base.utils.diagnose import Diagnosis
+
 if TYPE_CHECKING:
     from datadog_checks.postgres import PostgreSql
 
@@ -62,3 +64,20 @@ def submit_health_event(
             },
             **kwargs,
         )
+
+    def diagnose(self):
+        """
+        Run the diagnostics for the Postgres check.
+        """
+        self.check.diagnose.run()
+        for diagnosis in self.check.diagnosis.diagnoses:
+            if diagnosis.result == Diagnosis.DIAGNOSIS_FAIL:
+                self.submit_health_event(
+                    name=diagnosis.name,
+                    status=HealthStatus.WARNING
+                    if diagnosis.result == Diagnosis.DIAGNOSIS_WARNING
+                    else HealthStatus.ERROR,
+                    data={
+                        "diagnosis": diagnosis,
+                    },
+                )
diff --git a/postgres/datadog_checks/postgres/postgres.py b/postgres/datadog_checks/postgres/postgres.py
index 113e4402af133..f269ca671a413 100644
--- a/postgres/datadog_checks/postgres/postgres.py
+++ b/postgres/datadog_checks/postgres/postgres.py
@@ -192,7 +192,8 @@ def __init__(self, name, init_config, instances):
         )  # type: TTLCache
 
         # Register explicit pre-flight diagnostics for `datadog-agent diagnose`.
-        PostgresDiagnose(self).register()
+        self.diagnose = PostgresDiagnose(self)
+        self.diagnose.register()
 
     def _submit_initialization_health_event(self):
         try:
@@ -492,6 +493,7 @@ def cancel(self):
             if self.data_observability._job_loop_future:
                 self.data_observability._job_loop_future.result()
         self._close_db_pool()
+        self.diagnose = None
 
     def _clean_state(self):
         self.log.debug("Cleaning state")
@@ -1206,6 +1208,9 @@ def check(self, _):
                 hostname=self.reported_hostname,
                 raw=True,
             )
+
+            self.health.diagnose()
+
             raise e
         else:
             self.service_check(