diff --git a/src/meshapi/tests/test_install_create_signals.py b/src/meshapi/tests/test_install_create_signals.py
index 59b77f0d..1e9df8e6 100644
--- a/src/meshapi/tests/test_install_create_signals.py
+++ b/src/meshapi/tests/test_install_create_signals.py
@@ -159,3 +159,47 @@ def test_no_events_for_install_edit(self, request_mocker):
         install.save()
 
         self.assertEqual(len(request_mocker.request_history), 0)
+
+    @patch(
+        "meshapi.util.events.join_requests_slack_channel.SLACK_JOIN_REQUESTS_CHANNEL_WEBHOOK_URL",
+        "http://example.com/test-url-slack",
+    )
+    @patch(
+        "meshapi.util.events.osticket_creation.OSTICKET_NEW_TICKET_ENDPOINT",
+        "http://example.com/test-url-os-ticket",
+    )
+    @patch(
+        "meshapi.util.events.osticket_creation.OSTICKET_API_TOKEN",
+        "mock-token",
+    )
+    @requests_mock.Mocker()
+    def test_many_retry_no_crash_on_integration_404(self, request_mocker):
+        request_mocker.post("http://example.com/test-url-slack", text="Not found", status_code=404)
+        request_mocker.post("http://example.com/test-url-os-ticket", text="Not found", status_code=404)
+
+        enable_flag("INTEGRATION_ENABLED_SEND_JOIN_REQUEST_SLACK_MESSAGES")
+        enable_flag("INTEGRATION_ENABLED_CREATE_OSTICKET_TICKETS")
+
+        install = Install(**self.sample_install_copy)
+        install.save()
+
+        self.assertEqual(
+            len(
+                [
+                    request
+                    for request in request_mocker.request_history
+                    if request.url == "http://example.com/test-url-os-ticket"
+                ]
+            ),
+            4,
+        )
+        self.assertEqual(
+            len(
+                [
+                    request
+                    for request in request_mocker.request_history
+                    if request.url == "http://example.com/test-url-slack"
+                ]
+            ),
+            4,
+        )
diff --git a/src/meshapi/util/events/join_requests_slack_channel.py b/src/meshapi/util/events/join_requests_slack_channel.py
index 8c09acef..d2886308 100644
--- a/src/meshapi/util/events/join_requests_slack_channel.py
+++ b/src/meshapi/util/events/join_requests_slack_channel.py
@@ -1,5 +1,6 @@
 import logging
 import os
+import time
 
 import requests
 from django.db.models.base import ModelBase
@@ -29,14 +30,22 @@ def send_join_request_slack_message(sender: ModelBase, instance: Install, create
     building_height = str(int(install.building.altitude)) + "m" if install.building.altitude else "Altitude not found"
     roof_access = "Roof access" if install.roof_access else "No roof access"
 
-    response = requests.post(
-        SLACK_JOIN_REQUESTS_CHANNEL_WEBHOOK_URL,
-        json={
-            "text": f"*<https://www.nycmesh.net/map/nodes/{install.install_number}"
-            f"|{install.building.one_line_complete_address}>*\n"
-            f"{building_height} · {roof_access} · No LoS Data Available"
-        },
-    )
+    attempts = 0
+    while attempts < 4:
+        attempts += 1
+        response = requests.post(
+            SLACK_JOIN_REQUESTS_CHANNEL_WEBHOOK_URL,
+            json={
+                "text": f"*<https://www.nycmesh.net/map/nodes/{install.install_number}"
+                f"|{install.building.one_line_complete_address}>*\n"
+                f"{building_height} · {roof_access} · No LoS Data Available"
+            },
+        )
+
+        if response.status_code == 200:
+            break
+
+        time.sleep(1)
 
     if response.status_code != 200:
         logging.error(