diff --git a/server/routers/gerbil/updateHolePunch.ts b/server/routers/gerbil/updateHolePunch.ts
index 031cd23e..e0564fd6 100644
--- a/server/routers/gerbil/updateHolePunch.ts
+++ b/server/routers/gerbil/updateHolePunch.ts
@@ -150,7 +150,7 @@ export async function updateAndGenerateEndpointDestinations(
             throw new Error("Olm not found");
         }
 
-        const [client] = await db
+        const [updatedClient] = await db
             .update(clients)
             .set({
                 lastHolePunch: timestamp
@@ -158,10 +158,16 @@ export async function updateAndGenerateEndpointDestinations(
             .where(eq(clients.clientId, olm.clientId))
             .returning();
 
-        if (await checkExitNodeOrg(exitNode.exitNodeId, client.orgId) && checkOrg) {
+        if (
+            (await checkExitNodeOrg(
+                exitNode.exitNodeId,
+                updatedClient.orgId
+            )) &&
+            checkOrg
+        ) {
             // not allowed
             logger.warn(
-                `Exit node ${exitNode.exitNodeId} is not allowed for org ${client.orgId}`
+                `Exit node ${exitNode.exitNodeId} is not allowed for org ${updatedClient.orgId}`
             );
             throw new Error("Exit node not allowed");
         }
@@ -171,10 +177,14 @@ export async function updateAndGenerateEndpointDestinations(
             .select({
                 siteId: sites.siteId,
                 subnet: sites.subnet,
-                listenPort: sites.listenPort
+                listenPort: sites.listenPort,
+                endpoint: clientSitesAssociationsCache.endpoint
             })
             .from(sites)
-            .innerJoin(clientSitesAssociationsCache, eq(sites.siteId, clientSitesAssociationsCache.siteId))
+            .innerJoin(
+                clientSitesAssociationsCache,
+                eq(sites.siteId, clientSitesAssociationsCache.siteId)
+            )
             .where(
                 and(
                     eq(sites.exitNodeId, exitNode.exitNodeId),
@@ -188,7 +198,7 @@ export async function updateAndGenerateEndpointDestinations(
                 `Updating site ${site.siteId} on exit node ${exitNode.exitNodeId}`
             );
 
-            await db
+            const [updatedClientSitesAssociationsCache] = await db
                 .update(clientSitesAssociationsCache)
                 .set({
                     endpoint: `${ip}:${port}`
@@ -198,13 +208,27 @@ export async function updateAndGenerateEndpointDestinations(
                         eq(clientSitesAssociationsCache.clientId, olm.clientId),
                         eq(clientSitesAssociationsCache.siteId, site.siteId)
                     )
+                )
+                .returning();
+
+            if (
+                updatedClientSitesAssociationsCache.endpoint !== site.endpoint // this is the endpoint from the join table not the site
+            ) {
+                logger.info(
+                    `ClientSitesAssociationsCache for client ${olm.clientId} and site ${site.siteId} endpoint changed from ${site.endpoint} to ${updatedClientSitesAssociationsCache.endpoint}`
                 );
+                // Handle any additional logic for endpoint change
+                handleClientEndpointChange(
+                    olm.clientId,
+                    updatedClientSitesAssociationsCache.endpoint!
+                );
+            }
         }
 
         logger.debug(
             `Updated ${sitesOnExitNode.length} sites on exit node ${exitNode.exitNodeId}`
         );
-        if (!client) {
+        if (!updatedClient) {
             logger.warn(`Client not found for olm: ${olmId}`);
             throw new Error("Client not found");
         }
@@ -253,7 +277,10 @@ export async function updateAndGenerateEndpointDestinations(
             .where(eq(sites.siteId, newt.siteId))
             .limit(1);
 
-        if (await checkExitNodeOrg(exitNode.exitNodeId, site.orgId) && checkOrg) {
+        if (
+            (await checkExitNodeOrg(exitNode.exitNodeId, site.orgId)) &&
+            checkOrg
+        ) {
             // not allowed
             logger.warn(
                 `Exit node ${exitNode.exitNodeId} is not allowed for org ${site.orgId}`
@@ -273,6 +300,14 @@ export async function updateAndGenerateEndpointDestinations(
             .where(eq(sites.siteId, newt.siteId))
             .returning();
 
+        if (updatedSite.endpoint != site.endpoint) {
+            logger.info(
+                `Site ${newt.siteId} endpoint changed from ${site.endpoint} to ${updatedSite.endpoint}`
+            );
+            // Handle any additional logic for endpoint change
+            handleSiteEndpointChange(newt.siteId, updatedSite.endpoint!);
+        }
+
         if (!updatedSite || !updatedSite.subnet) {
             logger.warn(`Site not found: ${newt.siteId}`);
             throw new Error("Site not found");
@@ -326,3 +361,12 @@ export async function updateAndGenerateEndpointDestinations(
     }
     return destinations;
 }
+
+function handleSiteEndpointChange(siteId: number, newEndpoint: string) {
+    // just alert all of the clients connected to this site that the endpoint has changed but only if they are NOT relayed
+}
+
+function handleClientEndpointChange(clientId: number, newEndpoint: string) {
+    // just alert all of the sites connected to this client that the endpoint has changed but only if they are NOT relayed
+
+}