diff --git a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
index 9b285db81ec..7ff99d7d448 100644
--- a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
+++ b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
@@ -146,6 +146,11 @@ export function VercelOnboardingModal({
       }
       return "project-selection";
     }
+    // If onboarding was already completed but GitHub is not connected,
+    // go directly to the github-connection step (e.g., returning from GitHub App installation)
+    if (onboardingData?.isOnboardingComplete && !onboardingData?.isGitHubConnected) {
+      return "github-connection";
+    }
     // For marketplace origin, skip env-mapping step and go directly to env-var-sync
     if (!fromMarketplaceContext) {
       const customEnvs = (onboardingData?.customEnvironments?.length ?? 0) > 0 && hasStagingEnvironment;
@@ -1159,26 +1164,7 @@ export function VercelOnboardingModal({
                     >
                       Complete
                     </Button>
-                  ) : (
-                    <Button
-                      variant="tertiary/medium"
-                      onClick={() => {
-                        trackOnboarding("vercel onboarding github skipped");
-                        setState("completed");
-                        if (fromMarketplaceContext && nextUrl) {
-                          const validUrl = safeRedirectUrl(nextUrl);
-                          if (validUrl) {
-                            window.location.href = validUrl;
-                          }
-                        }
-                      }}
-                    >
-                      Skip for now
-                    </Button>
-                  )
-                }
-                cancelButton={
-                  isGitHubConnectedForOnboarding && fromMarketplaceContext && nextUrl ? (
+                  ) : !fromMarketplaceContext ? (
                     <Button
                       variant="tertiary/medium"
                       onClick={() => {
diff --git a/apps/webapp/app/routes/login._index/route.tsx b/apps/webapp/app/routes/login._index/route.tsx
index 592ecd3f7c0..72901fa5ddb 100644
--- a/apps/webapp/app/routes/login._index/route.tsx
+++ b/apps/webapp/app/routes/login._index/route.tsx
@@ -80,6 +80,7 @@ export async function loader({ request }: LoaderFunctionArgs) {
         showGoogleAuth: isGoogleAuthSupported,
         lastAuthMethod,
         authError: null,
+        isVercelMarketplace: redirectTo.startsWith("/vercel/callback"),
       },
       {
         headers: {
@@ -106,6 +107,7 @@ export async function loader({ request }: LoaderFunctionArgs) {
       showGoogleAuth: isGoogleAuthSupported,
       lastAuthMethod,
       authError,
+      isVercelMarketplace: false,
     });
   }
 }
@@ -164,19 +166,21 @@ export default function LoginPage() {
                 </Form>
               </div>
             )}
-            <div className="relative w-full">
-              {data.lastAuthMethod === "email" && <LastUsedBadge />}
-              <LinkButton
-                to={data.redirectTo ? `/login/magic?redirectTo=${encodeURIComponent(data.redirectTo)}` : "/login/magic"}
-                variant="secondary/extra-large"
-                fullWidth
-                data-action="continue with email"
-                className="text-text-bright"
-              >
-                <EnvelopeIcon className="mr-2 size-5 text-text-bright" />
-                Continue with Email
-              </LinkButton>
-            </div>
+            {!data.isVercelMarketplace && (
+              <div className="relative w-full">
+                {data.lastAuthMethod === "email" && <LastUsedBadge />}
+                <LinkButton
+                  to={data.redirectTo ? `/login/magic?redirectTo=${encodeURIComponent(data.redirectTo)}` : "/login/magic"}
+                  variant="secondary/extra-large"
+                  fullWidth
+                  data-action="continue with email"
+                  className="text-text-bright"
+                >
+                  <EnvelopeIcon className="mr-2 size-5 text-text-bright" />
+                  Continue with Email
+                </LinkButton>
+              </div>
+            )}
             {data.authError && <FormError>{data.authError}</FormError>}
           </div>
           <Paragraph variant="extra-small" className="mt-2 text-center">
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 c806381f1aa..15062a718bc 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
@@ -41,6 +41,7 @@ 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 { VercelIntegrationService } from "~/services/vercelIntegration.server";
 import { requireUserId } from "~/services/session.server";
 import {
   githubAppInstallPath,
@@ -210,16 +211,22 @@ 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
+      // Trigger initial deployment for marketplace flows now that GitHub is connected.
+      // We check the persisted onboardingOrigin on the Vercel integration rather than
+      // the redirectUrl, because the redirect URL loses the marketplace context when
+      // the user installs the GitHub App for the first time (full-page redirect cycle).
+      try {
+        const vercelService = new VercelIntegrationService();
+        const vercelIntegration = await vercelService.getVercelProjectIntegration(projectId);
+        if (
+          vercelIntegration?.parsedIntegrationData.onboardingCompleted &&
+          vercelIntegration.parsedIntegrationData.onboardingOrigin === "marketplace"
+        ) {
+          logger.info("Marketplace flow detected, triggering initial deployment", { projectId });
+          await triggerInitialDeployment(projectId, { environment: "prod" });
         }
+      } catch (error) {
+        logger.error("Failed to check Vercel integration or trigger initial deployment", { projectId, error });
       }
 
       return redirectWithMessage(
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 9f5be039e44..d1c4715a1c6 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
@@ -293,6 +293,7 @@ export async function action({ request, params }: ActionFunctionArgs) {
         syncEnvVarsMapping,
         next,
         skipRedirect,
+        origin,
       } = submission.value;
 
       const parsedStagingEnv = parseVercelStagingEnvironment(vercelStagingEnvironment);
@@ -306,6 +307,7 @@ export async function action({ request, params }: ActionFunctionArgs) {
         atomicBuilds,
         discoverEnvVars,
         syncEnvVarsMapping: parsedSyncEnvVarsMapping,
+        origin: origin === "marketplace" ? "marketplace" : "dashboard",
       });
 
       if (result) {
diff --git a/apps/webapp/app/services/vercelIntegration.server.ts b/apps/webapp/app/services/vercelIntegration.server.ts
index 5e9155a6b25..cf9e634afbb 100644
--- a/apps/webapp/app/services/vercelIntegration.server.ts
+++ b/apps/webapp/app/services/vercelIntegration.server.ts
@@ -526,6 +526,7 @@ export class VercelIntegrationService {
       atomicBuilds?: EnvSlug[] | null;
       discoverEnvVars?: EnvSlug[] | null;
       syncEnvVarsMapping?: SyncEnvVarsMapping;
+      origin?: "marketplace" | "dashboard";
     }
   ): Promise<VercelProjectIntegrationWithParsedData | null> {
     const existing = await this.getVercelProjectIntegration(projectId);
@@ -544,8 +545,9 @@ export class VercelIntegrationService {
         vercelStagingEnvironment: params.vercelStagingEnvironment ?? null,
       },
       //This is intentionally not updated here, in case of resetting the onboarding it should not override the existing mapping with an empty one
-      syncEnvVarsMapping: existing.parsedIntegrationData.syncEnvVarsMapping, 
+      syncEnvVarsMapping: existing.parsedIntegrationData.syncEnvVarsMapping,
       onboardingCompleted: true,
+      onboardingOrigin: params.origin ?? existing.parsedIntegrationData.onboardingOrigin,
     };
 
     const updated = await this.#prismaClient.organizationProjectIntegration.update({
diff --git a/apps/webapp/app/v3/vercel/vercelProjectIntegrationSchema.ts b/apps/webapp/app/v3/vercel/vercelProjectIntegrationSchema.ts
index fd23f10c995..9e39febe0ab 100644
--- a/apps/webapp/app/v3/vercel/vercelProjectIntegrationSchema.ts
+++ b/apps/webapp/app/v3/vercel/vercelProjectIntegrationSchema.ts
@@ -72,6 +72,7 @@ export const VercelProjectIntegrationDataSchema = z.object({
   vercelTeamSlug: z.string().optional(),
   vercelProjectId: z.string(),
   onboardingCompleted: z.boolean().optional(),
+  onboardingOrigin: z.enum(["marketplace", "dashboard"]).optional(),
 });
 
 export type VercelProjectIntegrationData = z.infer<typeof VercelProjectIntegrationDataSchema>;