diff --git a/.vscode/launch.json b/.vscode/launch.json
index d135aa70a2..71a76904a2 100644
--- a/.vscode/launch.json
+++ b/.vscode/launch.json
@@ -31,6 +31,15 @@
       "cwd": "${workspaceFolder}/apps/webapp",
       "sourceMaps": true
     },
+    {
+      "type": "node-terminal",
+      "request": "launch",
+      "name": "Debug opened test file",
+      "command": "pnpm run test -- ./${relativeFile}",
+      "envFile": "${workspaceFolder}/.env",
+      "cwd": "${workspaceFolder}",
+      "sourceMaps": true
+    },
     {
       "type": "chrome",
       "request": "launch",
diff --git a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
index c2a5bfec43..dc6996dab1 100644
--- a/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
+++ b/apps/webapp/app/components/integrations/VercelOnboardingModal.tsx
@@ -47,6 +47,7 @@ import { type VercelOnboardingData } from "~/presenters/v3/VercelSettingsPresent
 import { vercelAppInstallPath, v3ProjectSettingsPath, githubAppInstallPath, vercelResourcePath } from "~/utils/pathBuilder";
 import type { loader } from "~/routes/resources.orgs.$organizationSlug.projects.$projectParam.env.$envParam.vercel";
 import { useEffect, useState, useCallback, useRef } from "react";
+import { usePostHogTracking } from "~/hooks/usePostHog";
 
 function safeRedirectUrl(url: string): string | null {
   try {
@@ -114,6 +115,7 @@ export function VercelOnboardingModal({
   nextUrl?: string;
   onDataReload?: (vercelStagingEnvironment?: string) => void;
 }) {
+  const { capture, startSessionRecording } = usePostHogTracking();
   const navigation = useNavigation();
   const fetcher = useTypedFetcher<typeof loader>();
   const envMappingFetcher = useFetcher();
@@ -172,6 +174,33 @@ export function VercelOnboardingModal({
     prevIsOpenRef.current = isOpen;
   }, [isOpen, state, computeInitialState]);
 
+  const trackOnboarding = useCallback(
+    (eventName: string, extraProperties?: Record<string, unknown>) => {
+      capture(eventName, {
+        origin: fromMarketplaceContext ? "marketplace" : "dashboard",
+        step: state,
+        organization_slug: organizationSlug,
+        project_slug: projectSlug,
+        ...extraProperties,
+      });
+    },
+    [capture, fromMarketplaceContext, state, organizationSlug, projectSlug]
+  );
+
+  const hasTrackedStartRef = useRef(false);
+  const hasTrackedCompletionRef = useRef(false);
+  useEffect(() => {
+    if (isOpen && state === "project-selection" && !hasTrackedStartRef.current) {
+      hasTrackedStartRef.current = true;
+      startSessionRecording();
+      trackOnboarding("vercel onboarding started");
+    }
+    if (!isOpen) {
+      hasTrackedStartRef.current = false;
+      hasTrackedCompletionRef.current = false;
+    }
+  }, [isOpen, state, trackOnboarding, startSessionRecording]);
+
   const [selectedVercelProject, setSelectedVercelProject] = useState<{
     id: string;
     name: string;
@@ -337,6 +366,9 @@ export function VercelOnboardingModal({
 
   useEffect(() => {
     if (state === "project-selection" && fetcher.data && "success" in fetcher.data && fetcher.data.success && fetcher.state === "idle") {
+      trackOnboarding("vercel onboarding project selected", {
+        vercel_project_name: selectedVercelProject?.name,
+      });
       setState("loading-env-mapping");
       if (onDataReload) {
         onDataReload();
@@ -344,7 +376,7 @@ export function VercelOnboardingModal({
     } else if (fetcher.data && "error" in fetcher.data && typeof fetcher.data.error === "string") {
       setProjectSelectionError(fetcher.data.error);
     }
-  }, [state, fetcher.data, fetcher.state, onDataReload]);
+  }, [state, fetcher.data, fetcher.state, onDataReload, trackOnboarding, selectedVercelProject?.name]);
 
   // For marketplace origin, skip env-mapping step
   useEffect(() => {
@@ -449,14 +481,23 @@ export function VercelOnboardingModal({
       method: "post",
       action: actionUrl,
     });
-  }, [actionUrl, fetcher, onClose, nextUrl, fromMarketplaceContext]);
+  }, [actionUrl, fetcher, onClose, fromMarketplaceContext]);
 
   const handleSkipEnvMapping = useCallback(() => {
+    trackOnboarding("vercel onboarding env mapping completed", {
+      skipped: true,
+      staging_environment: null,
+    });
     setVercelStagingEnvironment(null);
     setState("loading-env-vars");
-  }, []);
+  }, [trackOnboarding]);
 
   const handleUpdateEnvMapping = useCallback(() => {
+    trackOnboarding("vercel onboarding env mapping completed", {
+      skipped: false,
+      staging_environment: vercelStagingEnvironment?.displayName ?? null,
+    });
+
     if (!vercelStagingEnvironment) {
       setState("loading-env-vars");
       return;
@@ -471,9 +512,11 @@ export function VercelOnboardingModal({
       action: actionUrl,
     });
 
-  }, [vercelStagingEnvironment, envMappingFetcher, actionUrl]);
+  }, [vercelStagingEnvironment, envMappingFetcher, actionUrl, trackOnboarding]);
 
   const handleBuildSettingsNext = useCallback(() => {
+    trackOnboarding("vercel onboarding build settings completed");
+
     if (nextUrl && fromMarketplaceContext && isGitHubConnectedForOnboarding) {
       setIsRedirecting(true);
     }
@@ -501,7 +544,7 @@ export function VercelOnboardingModal({
     if (!isGitHubConnectedForOnboarding) {
       setState("github-connection");
     }
-  }, [vercelStagingEnvironment, pullEnvVarsBeforeBuild, atomicBuilds, discoverEnvVars, syncEnvVarsMapping, nextUrl, fromMarketplaceContext, isGitHubConnectedForOnboarding, completeOnboardingFetcher, actionUrl]);
+  }, [vercelStagingEnvironment, pullEnvVarsBeforeBuild, atomicBuilds, discoverEnvVars, syncEnvVarsMapping, nextUrl, fromMarketplaceContext, isGitHubConnectedForOnboarding, completeOnboardingFetcher, actionUrl, trackOnboarding]);
 
   const handleFinishOnboarding = useCallback((e: React.FormEvent<HTMLFormElement>) => {
     e.preventDefault();
@@ -530,10 +573,14 @@ export function VercelOnboardingModal({
   }, [completeOnboardingFetcher.data, completeOnboardingFetcher.state, state]);
 
   useEffect(() => {
-    if (state === "completed") {
+    if (state === "completed" && !hasTrackedCompletionRef.current) {
+      hasTrackedCompletionRef.current = true;
+      trackOnboarding("vercel onboarding completed", {
+        github_connected: isGitHubConnectedForOnboarding,
+      });
       onClose();
     }
-  }, [state, onClose]);
+  }, [state, onClose, trackOnboarding, isGitHubConnectedForOnboarding]);
 
   useEffect(() => {
     if (state === "installing") {
@@ -565,6 +612,12 @@ export function VercelOnboardingModal({
     }
   }, [state, customEnvironments, vercelStagingEnvironment]);
 
+  useEffect(() => {
+    if (state === "project-selection" && availableProjects.length > 0 && !selectedVercelProject) {
+      setSelectedVercelProject(availableProjects[0]);
+    }
+  }, [state, availableProjects, selectedVercelProject]);
+
   if (!isOpen || onboardingData?.authInvalid) {
     return null;
   }
@@ -578,7 +631,14 @@ export function VercelOnboardingModal({
 
   if (isLoadingState) {
     return (
-      <Dialog open={isOpen} onOpenChange={(open) => !open && !fromMarketplaceContext && onClose()}>
+      <Dialog open={isOpen} onOpenChange={(open) => {
+        if (!open && !fromMarketplaceContext) {
+          if (state as string !== "completed") {
+            trackOnboarding("vercel onboarding abandoned");
+          }
+          onClose();
+        }
+      }}>
         <DialogContent className="max-w-lg">
           <DialogHeader>
             <div className="flex items-center gap-2">
@@ -601,7 +661,14 @@ export function VercelOnboardingModal({
   const showGitHubConnection = state === "github-connection";
 
   return (
-    <Dialog open={isOpen} onOpenChange={(open) => !open && !fromMarketplaceContext && onClose()}>
+    <Dialog open={isOpen} onOpenChange={(open) => {
+      if (!open && !fromMarketplaceContext) {
+        if (state !== "completed") {
+          trackOnboarding("vercel onboarding abandoned");
+        }
+        onClose();
+      }
+    }}>
       <DialogContent className="max-w-lg">
         <DialogHeader>
           <div className="flex items-center gap-2">
@@ -625,6 +692,7 @@ export function VercelOnboardingModal({
                 </Callout>
               ) : (
                 <Select
+                  disabled={availableProjects.length === 1}
                   value={selectedVercelProject?.id || ""}
                   setValue={(value) => {
                     if (!Array.isArray(value)) {
@@ -634,6 +702,7 @@ export function VercelOnboardingModal({
                     }
                   }}
                   items={availableProjects}
+                  filter={availableProjects.length > 5 ? { keys: ["name"] } : undefined}
                   variant="tertiary/medium"
                   placeholder="Select a Vercel project"
                   dropdownIcon
@@ -894,6 +963,10 @@ export function VercelOnboardingModal({
                   <Button
                     variant="primary/medium"
                     onClick={() => {
+                      trackOnboarding("vercel onboarding env vars configured", {
+                        env_vars_enabled: enabledEnvVars.length,
+                        env_vars_total: syncableEnvVars.length,
+                      });
                       if (fromMarketplaceContext) {
                         handleBuildSettingsNext();
                       } else {
diff --git a/apps/webapp/app/hooks/usePostHog.ts b/apps/webapp/app/hooks/usePostHog.ts
index 99e2597dfe..f52663ec01 100644
--- a/apps/webapp/app/hooks/usePostHog.ts
+++ b/apps/webapp/app/hooks/usePostHog.ts
@@ -1,6 +1,6 @@
 import { useLocation } from "@remix-run/react";
 import posthog from "posthog-js";
-import { useEffect, useRef } from "react";
+import { useCallback, useEffect, useRef } from "react";
 import { useOrganizationChanged } from "./useOrganizations";
 import { useOptionalUser, useUserChanged } from "./useUser";
 import { useProjectChanged } from "./useProject";
@@ -68,3 +68,18 @@ export const usePostHog = (apiKey?: string, logging = false, debug = false): voi
     posthog.capture("$pageview");
   }, [location, logging]);
 };
+
+export function usePostHogTracking() {
+  const capture = useCallback(
+    (eventName: string, properties?: Record<string, unknown>) => {
+      posthog.capture(eventName, properties);
+    },
+    []
+  );
+
+  const startSessionRecording = useCallback(() => {
+    posthog.startSessionRecording();
+  }, []);
+
+  return { capture, startSessionRecording };
+}
diff --git a/apps/webapp/app/routes/api.v1.deployments.$deploymentId.progress.ts b/apps/webapp/app/routes/api.v1.deployments.$deploymentId.progress.ts
index 64f20f4f64..2c78c59f55 100644
--- a/apps/webapp/app/routes/api.v1.deployments.$deploymentId.progress.ts
+++ b/apps/webapp/app/routes/api.v1.deployments.$deploymentId.progress.ts
@@ -48,6 +48,7 @@ export async function action({ request, params }: ActionFunctionArgs) {
       contentHash: body.data.contentHash,
       git: body.data.gitMeta,
       runtime: body.data.runtime,
+      buildServerMetadata: body.data.buildServerMetadata,
     })
     .match(
       () => {
diff --git a/apps/webapp/app/v3/services/deployment.server.ts b/apps/webapp/app/v3/services/deployment.server.ts
index 848c06c453..56888284ba 100644
--- a/apps/webapp/app/v3/services/deployment.server.ts
+++ b/apps/webapp/app/v3/services/deployment.server.ts
@@ -2,7 +2,12 @@ import { type AuthenticatedEnvironment } from "~/services/apiAuth.server";
 import { BaseService } from "./baseService.server";
 import { errAsync, fromPromise, okAsync, type ResultAsync } from "neverthrow";
 import { type WorkerDeployment, type Project } from "@trigger.dev/database";
-import { BuildServerMetadata, logger, type GitMeta, type DeploymentEvent } from "@trigger.dev/core/v3";
+import {
+  BuildServerMetadata,
+  logger,
+  type GitMeta,
+  type DeploymentEvent,
+} from "@trigger.dev/core/v3";
 import { TimeoutDeploymentService } from "./timeoutDeployment.server";
 import { env } from "~/env.server";
 import { createRemoteImageBuild } from "../remoteImageBuilder.server";
@@ -38,9 +43,20 @@ export class DeploymentService extends BaseService {
   public progressDeployment(
     authenticatedEnv: AuthenticatedEnvironment,
     friendlyId: string,
-    updates: Partial<Pick<WorkerDeployment, "contentHash" | "runtime"> & { git: GitMeta }>
+    updates: Partial<
+      Pick<WorkerDeployment, "contentHash" | "runtime"> & {
+        git: GitMeta;
+        buildServerMetadata: BuildServerMetadata;
+      }
+    >
   ) {
-    const validateDeployment = (deployment: Pick<WorkerDeployment, "id" | "status"> & { buildServerMetadata?: BuildServerMetadata }) => {
+    const { buildServerMetadata: newBuildServerMetadata, ...restUpdates } = updates;
+
+    const validateDeployment = (
+      deployment: Pick<WorkerDeployment, "id" | "status"> & {
+        buildServerMetadata?: BuildServerMetadata;
+      }
+    ) => {
       if (deployment.status !== "PENDING" && deployment.status !== "INSTALLING") {
         logger.warn(
           "Attempted progressing deployment that is not in PENDING or INSTALLING status",
@@ -54,12 +70,24 @@ export class DeploymentService extends BaseService {
       return okAsync(deployment);
     };
 
-    const progressToInstalling = (deployment: Pick<WorkerDeployment, "id">) =>
-      fromPromise(
+    const progressToInstalling = (
+      deployment: Pick<WorkerDeployment, "id"> & { buildServerMetadata?: BuildServerMetadata }
+    ) => {
+      const existingBuildServerMetadata = deployment.buildServerMetadata;
+
+      return fromPromise(
         this._prisma.workerDeployment.updateMany({
           where: { id: deployment.id, status: "PENDING" }, // status could've changed in the meantime, we're not locking the row
           data: {
-            ...updates,
+            ...restUpdates,
+            ...(newBuildServerMetadata
+              ? {
+                  buildServerMetadata: {
+                    ...(existingBuildServerMetadata ?? {}),
+                    ...newBuildServerMetadata,
+                  },
+                }
+              : {}),
             status: "INSTALLING",
             startedAt: new Date(),
           },
@@ -74,6 +102,7 @@ export class DeploymentService extends BaseService {
         }
         return okAsync({ id: deployment.id, status: "INSTALLING" as const });
       });
+    };
 
     const progressToBuilding = (
       deployment: Pick<WorkerDeployment, "id"> & { buildServerMetadata?: BuildServerMetadata }
@@ -85,13 +114,26 @@ export class DeploymentService extends BaseService {
           cause: error,
         }));
 
+      const existingBuildServerMetadata = deployment.buildServerMetadata as
+        | BuildServerMetadata
+        | null
+        | undefined;
+
       return createRemoteBuildIfNeeded
         .andThen((externalBuildData) =>
           fromPromise(
             this._prisma.workerDeployment.updateMany({
               where: { id: deployment.id, status: "INSTALLING" }, // status could've changed in the meantime, we're not locking the row
               data: {
-                ...updates,
+                ...restUpdates,
+                ...(newBuildServerMetadata
+                  ? {
+                      buildServerMetadata: {
+                        ...(existingBuildServerMetadata ?? {}),
+                        ...newBuildServerMetadata,
+                      },
+                    }
+                  : {}),
                 externalBuildData,
                 status: "BUILDING",
                 installedAt: new Date(),
diff --git a/apps/webapp/app/v3/services/initializeDeployment.server.ts b/apps/webapp/app/v3/services/initializeDeployment.server.ts
index 96439d94d6..939cfd7e6f 100644
--- a/apps/webapp/app/v3/services/initializeDeployment.server.ts
+++ b/apps/webapp/app/v3/services/initializeDeployment.server.ts
@@ -200,6 +200,7 @@ export class InitializeDeploymentService extends BaseService {
                     artifactKey: payload.artifactKey,
                     skipPromotion: payload.skipPromotion,
                     configFilePath: payload.configFilePath,
+                    skipEnqueue: payload.skipEnqueue,
                   }
                 : {}),
             }
@@ -238,7 +239,8 @@ export class InitializeDeploymentService extends BaseService {
         new Date(Date.now() + timeoutMs)
       );
 
-      if (payload.isNativeBuild) {
+      // For github integration there is no artifactKey, hence we skip it here
+      if (payload.isNativeBuild && payload.artifactKey && !payload.skipEnqueue) {
         const result = await deploymentService
           .enqueueBuild(environment, deployment, payload.artifactKey, {
             skipPromotion: payload.skipPromotion,
diff --git a/packages/core/src/v3/schemas/api-type.test.ts b/packages/core/src/v3/schemas/api-type.test.ts
new file mode 100644
index 0000000000..c936b3c769
--- /dev/null
+++ b/packages/core/src/v3/schemas/api-type.test.ts
@@ -0,0 +1,141 @@
+import { describe, it, expect } from "vitest";
+import { InitializeDeploymentRequestBody } from "./api.js";
+import type { InitializeDeploymentRequestBody as InitializeDeploymentRequestBodyType } from "./api.js";
+
+describe("InitializeDeploymentRequestBody", () => {
+  const base = { contentHash: "abc123" };
+
+  describe("non-native build variant (isNativeBuild omitted or false)", () => {
+    it("parses with only required fields", () => {
+      const result = InitializeDeploymentRequestBody.safeParse(base);
+      expect(result.success).toBe(true);
+      if (result.success) {
+        expect(result.data.isNativeBuild).toBe(false);
+      }
+    });
+
+    it("parses with isNativeBuild explicitly false", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({ ...base, isNativeBuild: false });
+      expect(result.success).toBe(true);
+    });
+
+    it("parses with optional base fields", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        userId: "user_1",
+        type: "MANAGED",
+        runtime: "node",
+        initialStatus: "PENDING",
+      });
+      expect(result.success).toBe(true);
+    });
+
+    it("strips native-only fields when isNativeBuild is false", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        isNativeBuild: false,
+        skipPromotion: true,
+      });
+      // Zod discriminatedUnion matches the non-native branch and strips unknown keys
+      expect(result.success).toBe(true);
+      if (result.success) {
+        expect("skipPromotion" in result.data).toBe(false);
+      }
+    });
+  });
+
+  describe("native build variant (isNativeBuild: true)", () => {
+    it("parses with isNativeBuild true", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        isNativeBuild: true,
+      });
+      expect(result.success).toBe(true);
+      if (result.success) {
+        expect(result.data.isNativeBuild).toBe(true);
+      }
+    });
+
+    it("parses with native-specific optional fields", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        isNativeBuild: true,
+        skipPromotion: true,
+        artifactKey: "artifact_abc",
+        configFilePath: "trigger.config.ts",
+        skipEnqueue: true,
+      });
+      expect(result.success).toBe(true);
+      if (result.success) {
+        expect(result.data.skipPromotion).toBe(true);
+        expect(result.data.artifactKey).toBe("artifact_abc");
+        expect(result.data.configFilePath).toBe("trigger.config.ts");
+        expect(result.data.skipEnqueue).toBe(true);
+      }
+    });
+
+    it("skipEnqueue defaults to false when omitted", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        isNativeBuild: true,
+      });
+      expect(result.success).toBe(true);
+      if (result.success) {
+        expect(result.data.skipEnqueue).toBe(false);
+      }
+    });
+  });
+
+  describe("rejects invalid inputs", () => {
+    it("rejects missing contentHash", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({});
+      expect(result.success).toBe(false);
+    });
+
+    it("rejects invalid type enum value", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        type: "INVALID",
+      });
+      expect(result.success).toBe(false);
+    });
+
+    it("rejects invalid initialStatus enum value", () => {
+      const result = InitializeDeploymentRequestBody.safeParse({
+        ...base,
+        initialStatus: "RUNNING",
+      });
+      expect(result.success).toBe(false);
+    });
+  });
+
+  describe("type-level checks", () => {
+    it("native variant exposes native-specific fields", () => {
+      const result = InitializeDeploymentRequestBody.parse({
+        ...base,
+        isNativeBuild: true,
+        skipPromotion: true,
+      });
+
+      if (result.isNativeBuild === true) {
+        const _skipPromotion: boolean | undefined = result.skipPromotion;
+        const _artifactKey: string | undefined = result.artifactKey;
+        const _configFilePath: string | undefined = result.configFilePath;
+        expect(_skipPromotion).toBe(true);
+        expect(_artifactKey).toBeUndefined();
+        expect(_configFilePath).toBeUndefined();
+      }
+    });
+
+    it("non-native variant narrows correctly", () => {
+      const result: InitializeDeploymentRequestBodyType =
+        InitializeDeploymentRequestBody.parse(base);
+
+      if (!result.isNativeBuild) {
+        // Should only have base fields — native-specific fields should not exist
+        const narrowed: { isNativeBuild?: false; contentHash: string } = result;
+        expect(narrowed.contentHash).toBe("abc123");
+      }
+    });
+  });
+});
diff --git a/packages/core/src/v3/schemas/api.ts b/packages/core/src/v3/schemas/api.ts
index 4cb5c96503..76f93af3ff 100644
--- a/packages/core/src/v3/schemas/api.ts
+++ b/packages/core/src/v3/schemas/api.ts
@@ -485,10 +485,22 @@ export const FinalizeDeploymentRequestBody = z.object({
 
 export type FinalizeDeploymentRequestBody = z.infer<typeof FinalizeDeploymentRequestBody>;
 
+export const BuildServerMetadata = z.object({
+  buildId: z.string().optional(),
+  isNativeBuild: z.boolean().optional(),
+  artifactKey: z.string().optional(),
+  skipPromotion: z.boolean().optional(),
+  configFilePath: z.string().optional(),
+  skipEnqueue: z.boolean().optional(),
+});
+
+export type BuildServerMetadata = z.infer<typeof BuildServerMetadata>;
+
 export const ProgressDeploymentRequestBody = z.object({
   contentHash: z.string().optional(),
   gitMeta: GitMeta.optional(),
   runtime: z.string().optional(),
+  buildServerMetadata: BuildServerMetadata.optional(),
 });
 
 export type ProgressDeploymentRequestBody = z.infer<typeof ProgressDeploymentRequestBody>;
@@ -528,16 +540,6 @@ export const DeploymentTriggeredVia = z
 
 export type DeploymentTriggeredVia = z.infer<typeof DeploymentTriggeredVia>;
 
-export const BuildServerMetadata = z.object({
-  buildId: z.string().optional(),
-  isNativeBuild: z.boolean().optional(),
-  artifactKey: z.string().optional(),
-  skipPromotion: z.boolean().optional(),
-  configFilePath: z.string().optional(),
-});
-
-export type BuildServerMetadata = z.infer<typeof BuildServerMetadata>;
-
 export const UpsertBranchRequestBody = z.object({
   git: GitMeta.optional(),
   env: z.enum(["preview"]),
@@ -590,41 +592,53 @@ export const InitializeDeploymentResponseBody = z.object({
 
 export type InitializeDeploymentResponseBody = z.infer<typeof InitializeDeploymentResponseBody>;
 
-export const InitializeDeploymentRequestBody = z
-  .object({
-    contentHash: z.string(),
-    userId: z.string().optional(),
-    /** @deprecated This is now determined by the webapp. This is only used to warn users with old CLI versions. */
-    selfHosted: z.boolean().optional(),
-    gitMeta: GitMeta.optional(),
-    type: z.enum(["MANAGED", "UNMANAGED", "V1"]).optional(),
-    runtime: z.string().optional(),
-    initialStatus: z.enum(["PENDING", "BUILDING"]).optional(),
-    triggeredVia: DeploymentTriggeredVia.optional(),
-    buildId: z.string().optional(),
-  })
-  .and(
-    z.preprocess(
-      (val) => {
-        const obj = val as any;
-        if (!obj || !obj.isNativeBuild) {
-          return { ...obj, isNativeBuild: false };
-        }
-        return obj;
-      },
-      z.discriminatedUnion("isNativeBuild", [
-        z.object({
-          isNativeBuild: z.literal(true),
-          skipPromotion: z.boolean(),
-          artifactKey: z.string(),
-          configFilePath: z.string().optional(),
-        }),
-        z.object({
-          isNativeBuild: z.literal(false),
-        }),
-      ])
-    )
-  );
+const InitializeDeploymentRequestBodyBase = z.object({
+  contentHash: z.string(),
+  userId: z.string().optional(),
+  /** @deprecated This is now determined by the webapp. This is only used to warn users with old CLI versions. */
+  selfHosted: z.boolean().optional(),
+  gitMeta: GitMeta.optional(),
+  type: z.enum(["MANAGED", "UNMANAGED", "V1"]).optional(),
+  runtime: z.string().optional(),
+  initialStatus: z.enum(["PENDING", "BUILDING"]).optional(),
+  triggeredVia: DeploymentTriggeredVia.optional(),
+  buildId: z.string().optional()
+});
+type BaseOutput = z.output<typeof InitializeDeploymentRequestBodyBase>;
+
+type NativeBuildOutput = BaseOutput & {
+  isNativeBuild: true;
+  skipPromotion?: boolean;
+  artifactKey?: string;
+  configFilePath?: string;
+  skipEnqueue?: boolean;
+};
+
+type NonNativeBuildOutput = BaseOutput & {
+  isNativeBuild: false;
+  skipPromotion?: never;
+  artifactKey?: never;
+  configFilePath?: never;
+  skipEnqueue?: never;
+};
+
+const InitializeDeploymentRequestBodyFull = InitializeDeploymentRequestBodyBase.extend({
+  isNativeBuild: z.boolean().default(false),
+  skipPromotion: z.boolean().optional(),
+  artifactKey: z.string().optional(),
+  configFilePath: z.string().optional(),
+  skipEnqueue: z.boolean().optional().default(false),
+});
+
+export const InitializeDeploymentRequestBody = InitializeDeploymentRequestBodyFull.transform(
+  (data): NativeBuildOutput | NonNativeBuildOutput => {
+    if (data.isNativeBuild) {
+      return { ...data, isNativeBuild: true as const };
+    }
+    const { skipPromotion, artifactKey, configFilePath, skipEnqueue, ...rest } = data;
+    return { ...rest, isNativeBuild: false as const };
+  }
+);
 
 export type InitializeDeploymentRequestBody = z.infer<typeof InitializeDeploymentRequestBody>;