diff --git a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
index 28bfe5672c..9b285db81e 100644
--- a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
+++ b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
@@ -541,6 +541,9 @@ export function VercelOnboardingModal({
     formData.append("atomicBuilds", JSON.stringify(atomicBuilds));
     formData.append("discoverEnvVars", JSON.stringify(discoverEnvVars));
     formData.append("syncEnvVarsMapping", JSON.stringify(syncEnvVarsMapping));
+    if (fromMarketplaceContext) {
+      formData.append("origin", "marketplace");
+    }
     if (nextUrl && fromMarketplaceContext && isGitHubConnectedForOnboarding) {
       formData.append("next", nextUrl);
     }
diff --git a/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.github.tsx b/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.github.tsx
index 38ef50126c..c806381f1a 100644
--- a/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.github.tsx
+++ b/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.github.tsx
@@ -3,7 +3,8 @@ import { parse } from "@conform-to/zod";
 import { CheckCircleIcon, LockClosedIcon, PlusIcon } from "@heroicons/react/20/solid";
 import { Form, useActionData, useNavigation, useNavigate, useSearchParams, useLocation } from "@remix-run/react";
 import { type ActionFunctionArgs, type LoaderFunctionArgs, json } from "@remix-run/server-runtime";
-import { typedjson, useTypedFetcher } from "remix-typedjson";
+import { redirect,
+typedjson, useTypedFetcher } from "remix-typedjson";
 import { z } from "zod";
 import { OctoKitty } from "~/components/GitHubLoginButton";
 import { Dialog, DialogContent, DialogHeader, DialogTrigger } from "~/components/primitives/Dialog";
@@ -39,6 +40,7 @@ import { findProjectBySlug } from "~/models/project.server";
 import { findEnvironmentBySlug } from "~/models/runtimeEnvironment.server";
 import { ProjectSettingsService } from "~/services/projectSettings.server";
 import { logger } from "~/services/logger.server";
+import { triggerInitialDeployment } from "~/services/platform.v3.server";
 import { requireUserId } from "~/services/session.server";
 import {
   githubAppInstallPath,
@@ -208,6 +210,18 @@ export async function action({ request, params }: ActionFunctionArgs) {
     );
 
     if (resultOrFail.isOk()) {
+      // Trigger initial deployment for marketplace flows now that GitHub is connected
+      if (redirectUrl) {
+        try {
+          if (redirectUrl.includes("origin=marketplace")) {
+            await triggerInitialDeployment(projectId, { environment: "prod" });
+          }
+        } catch (error) {
+          logger.error("Invalid redirect URL, skipping initial deployment trigger", { redirectUrl, error });
+          // Invalid redirectUrl, skip initial deployment check
+        }
+      }
+
       return redirectWithMessage(
         request,
         redirectUrl,
diff --git a/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.vercel.tsx b/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.vercel.tsx
index 1857a4abdf..9f5be039e4 100644
--- a/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.vercel.tsx
+++ b/apps/webapp/app/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.vercel.tsx
@@ -113,6 +113,7 @@ const CompleteOnboardingFormSchema = z.object({
   syncEnvVarsMapping: z.string().optional(),
   next: z.string().optional(),
   skipRedirect: z.string().optional().transform((val) => val === "true"),
+  origin: z.string().optional(),
 });
 
 const SkipOnboardingFormSchema = z.object({
diff --git a/apps/webapp/app/services/vercelIntegration.server.ts b/apps/webapp/app/services/vercelIntegration.server.ts
index e2c118ffd3..5e9155a6b2 100644
--- a/apps/webapp/app/services/vercelIntegration.server.ts
+++ b/apps/webapp/app/services/vercelIntegration.server.ts
@@ -413,7 +413,7 @@ export class VercelIntegrationService {
       });
 
       if (upsertResult.isErr()) {
-        logger.error("Failed to sync staging TRIGGER_SECRET_KEY to custom environment", {
+        logger.warn("Failed to sync staging TRIGGER_SECRET_KEY to custom environment", {
           projectId,
           newCustomEnvironmentId,
           error: upsertResult.error.message,