diff --git a/apps/web/src/app/admin-console/organizations/guards/is-paid-org.guard.ts b/apps/web/src/app/admin-console/organizations/guards/is-paid-org.guard.ts
index f6968daca9..aaf24e4834 100644
--- a/apps/web/src/app/admin-console/organizations/guards/is-paid-org.guard.ts
+++ b/apps/web/src/app/admin-console/organizations/guards/is-paid-org.guard.ts
@@ -27,15 +27,26 @@ export class IsPaidOrgGuard implements CanActivate {
       // Users without billing permission can't access billing
       if (!org.canEditSubscription) {
         await this.dialogService.openSimpleDialog({
-          title: { key: "upgradeOrganization" },
-          content: { key: "notAvailableForFreeOrganization" },
+          title: { key: "upgradeOrganizationCloseSecurityGaps" },
+          content: { key: "upgradeOrganizationCloseSecurityGapsDesc" },
           acceptButtonText: { key: "ok" },
           cancelButtonText: null,
           type: "info",
         });
         return false;
       } else {
-        this.messagingService.send("upgradeOrganization", { organizationId: org.id });
+        const upgradeConfirmed = await this.dialogService.openSimpleDialog({
+          title: { key: "upgradeOrganizationCloseSecurityGaps" },
+          content: { key: "upgradeOrganizationCloseSecurityGapsDesc" },
+          acceptButtonText: { key: "upgradeOrganization" },
+          type: "info",
+          icon: "bwi-arrow-circle-up",
+        });
+        if (upgradeConfirmed) {
+          await this.router.navigate(["organizations", org.id, "billing", "subscription"], {
+            queryParams: { upgrade: true },
+          });
+        }
       }
     }
 
diff --git a/apps/web/src/locales/en/messages.json b/apps/web/src/locales/en/messages.json
index 3afd318266..fb1c30e546 100644
--- a/apps/web/src/locales/en/messages.json
+++ b/apps/web/src/locales/en/messages.json
@@ -8222,5 +8222,11 @@
   },
   "protectYourFamilyOrBusiness": {
     "message": "Protect your family or business"
+  },
+  "upgradeOrganizationCloseSecurityGaps": {
+    "message": "Close security gaps with monitoring reports"
+  },
+  "upgradeOrganizationCloseSecurityGapsDesc": {
+    "message": "Stay ahead of security vulnerabilities by upgrading to a paid plan for enhanced monitoring."
   }
 }