diff --git a/.plans/files-gateway-asset-index.md b/.plans/files-gateway-asset-index.md
deleted file mode 100644
index 8cd0a3f6..00000000
--- a/.plans/files-gateway-asset-index.md
+++ /dev/null
@@ -1,450 +0,0 @@
-# Authenticated Files gateway and asset index
-
-## Status
-
-Implemented; awaiting review.
-
-## Objective
-
-Exercise one complete authenticated file lifecycle through the API application:
-
-1. an authenticated user uploads a file through Files SDK;
-2. the object is written to the configured S3-compatible bucket;
-3. a Files SDK `onAction` hook records the object's ownership and metadata in the
-   `storage.assets` table;
-4. another user cannot access the object; and
-5. deleting the object removes the asset record.
-
-Keep the Files SDK gateway at the versionless `/files` transport seam. Reserve
-`/v1/assets` for a future application-owned HTTP interface over asset IDs, ownership,
-organizations, metadata, and references.
-
-## Acceptance criteria
-
-- The Files SDK gateway is mounted at `/files`, not `/v1/files`.
-- `apps/api/src/routes/files.ts` owns the Files SDK router and authorization policy.
-- The existing Files SDK singleton in `apps/api/src/shared/files.ts` owns the inline
-  asset-index hook.
-- The `/v1` router contains only application-owned HTTP routes.
-- Hono's existing `contextStorage()` and `requireSession` middleware provide the
-  authenticated session, database, and logger to Files SDK callbacks.
-- Shared `context()` and `AuthenticatedAppContext` definitions provide typed access to
-  that request state outside ordinary Hono handlers.
-- The route does not perform a second Better Auth session lookup inside `authorize`.
-- Successful upload completion creates or updates one `storage.assets` row owned by
-  the authenticated user.
-- Successful deletion removes the matching asset row owned by the authenticated user.
-- `onAction` dispatches successful events to local `handleUpload` and `handleDelete`
-  functions in the singleton module; there is no persistence service or custom Files
-  SDK plugin.
-- Repeated upload-completion events are idempotent through the unique index on `key`.
-- Database failures from the fire-and-forget hook are caught and logged without
-  producing unhandled promise rejections.
-- The template contains exactly one baseline database migration generated from the
-  current schema.
-- Formatting, static checks, dependency analysis, and relevant build verification
-  pass.
-
-## Decisions
-
-### Treat `/files` as transport infrastructure
-
-The Files SDK gateway's wire format is controlled by Files SDK. It is transport and
-protocol plumbing, like Better Auth, tRPC, and Inngest, rather than an
-application-owned REST resource.
-
-Use this route split:
-
-| Route        | Ownership                                  |
-| ------------ | ------------------------------------------ |
-| `/files`     | Files SDK transport gateway                |
-| `/auth`      | Better Auth transport gateway              |
-| `/trpc`      | tRPC transport gateway                     |
-| `/workflows` | Inngest transport gateway                  |
-| `/v1/assets` | Future application-owned asset interface   |
-| `/v1/me`     | Application-owned authenticated HTTP route |
-
-Do not add `/v1/assets` as part of this slice. Its route is reserved for later domain
-behavior and should not proxy Files SDK operations.
-
-### Use the database as an eventually consistent asset index
-
-Object storage remains the source of truth for whether bytes exist. The assets table
-tracks which authenticated user owns each stored object and provides a stable asset ID
-for future references from other tables.
-
-Files SDK's `onAction` hook is observational and fire-and-forget: Files SDK does not
-await a promise returned by the hook, and a hook failure cannot fail the storage
-operation. Therefore:
-
-- the upload response does not guarantee that the asset row is already visible;
-- every hook-owned promise must have an explicit rejection handler;
-- stronger delivery guarantees or reconciliation are follow-up work, not hidden inside
-  this first slice.
-
-### Dispatch `onAction` events to local handlers
-
-Keep the persistence behavior local to the Files singleton. Do not introduce an
-`assetPersistence` plugin, repository wrapper, or callback adapter.
-
-Use a switch to keep the hook concise. Single upload and head events call
-`handleUpload`; delete events normalize their single or bulk keys and call
-`handleDelete`. These handlers remain private functions in `shared/files.ts` and
-execute the Drizzle operations directly.
-
-### Use a Files-SDK-shaped asset record
-
-The `storage.assets` table stores the stable asset ID, Files SDK metadata, and two
-distinct user roles:
-
-- `key`, `name`, `size`, `type`, `etag`, `lastModified`, and `metadata` mirror the
-  stored file returned by Files SDK;
-- `ownerId` records the user to whom the asset belongs; and
-- `uploaderId` records the user who placed the asset in managed storage.
-
-The current upload flow assigns the authenticated user to both roles. Keeping them
-separate preserves creation provenance if ownership changes later. The configured
-Files singleton owns one bucket, so the storage key is the unique object identity and
-bucket/provider columns are unnecessary.
-
-### Observe upload and head completion
-
-Handle successful `upload` events and successful `head` events. Direct/proxied uploads
-can produce an upload result, while completion of a direct or presigned upload can be
-confirmed through a follow-up `head`. The unique `key` conflict target makes both paths
-idempotent.
-
-Do not support copy or move until their destination-ownership behavior is explicitly
-defined. Do not build the index from list results.
-
-## Implementation plan
-
-### 1. Move the Files SDK gateway out of `/v1`
-
-Move:
-
-```text
-apps/api/src/routes/v1/files.ts
-```
-
-to:
-
-```text
-apps/api/src/routes/files.ts
-```
-
-Add the route to `apps/api/src/routes/index.ts`:
-
-```diff
-+import filesRoutes from "#routes/files.ts"
- import healthRoutes from "#routes/health.ts"
- import trpcRoutes from "#routes/trpc.ts"
- import v1Routes from "#routes/v1/index.ts"
- import workflowRoutes from "#routes/workflows.ts"
-
- export const router = app
-   // Keep the existing root and OpenAPI handlers.
-   .route("/health", healthRoutes)
-+  .route("/files", filesRoutes)
-   .route("/workflows", workflowRoutes)
-   .route("/trpc", trpcRoutes)
-   .route("/v1", v1Routes)
-```
-
-Remove the transport route from `apps/api/src/routes/v1/index.ts`:
-
-```diff
--import filesRoutes from "#routes/v1/files.ts"
- import { m } from "#shared/internationalization/messages.js"
-
- export default factory
-   .createApp()
--  .route("/files", filesRoutes)
-   .get(
-     "/hello",
-     // Keep the existing handler unchanged.
-   )
-   .get("/me", requireSession, (c) => c.json(c.var.session.user))
-```
-
-### 2. Add shared typed context access
-
-Add the authenticated refinement to `apps/api/src/shared/types.ts`:
-
-```ts
-export type AuthenticatedAppContext = DeepMerge<AppContext, { Variables: { session: Session } }>
-```
-
-Restore the context-storage helper in `apps/api/src/shared/utils.ts`, allowing callers
-to select a refined context while defaulting to `AppContext`:
-
-```ts
-export function context<T extends AppContext = AppContext>() {
-  return getContext<T>()
-}
-```
-
-Make `requireSession` consume the shared authenticated type instead of declaring the
-same merge inline:
-
-```ts
-export const requireSession = createMiddleware<AuthenticatedAppContext>(async (c, next) => {
-  // Keep the existing middleware implementation.
-})
-```
-
-### 3. Add `onAction` directly to the Files singleton
-
-Replace `apps/api/src/shared/files.ts` with this proposed implementation:
-
-```ts
-import { assets, type UserId } from "@init/db/schema"
-import * as z from "@init/utils/schema"
-import { helpers } from "@init/db/helpers"
-import type { DeleteManyResult, StoredFile, UploadResult } from "files-sdk"
-import { createFiles } from "files-sdk"
-import { bunS3 } from "files-sdk/bun-s3"
-import { contentType } from "files-sdk/content-type"
-import { signedUrlPolicy } from "files-sdk/signed-url-policy"
-import { validation } from "files-sdk/validation"
-import env from "#shared/env.ts"
-import type { AuthenticatedAppContext } from "#shared/types.ts"
-import { context } from "#shared/utils.ts"
-
-export const FILES_MAX_UPLOAD_SIZE = 10 * 1024 * 1024
-export const FILES_MAX_URL_AGE = 15 * 60
-
-export const files = createFiles({
-  adapter: bunS3({
-    accessKeyId: env.S3_ACCESS_KEY_ID,
-    bucket: env.S3_BUCKET,
-    endpoint: env.S3_ENDPOINT,
-    region: env.S3_REGION,
-    secretAccessKey: env.S3_SECRET_ACCESS_KEY,
-    virtualHostedStyle: !env.S3_ENDPOINT,
-  }),
-  hooks: {
-    onAction(event) {
-      if (event.status !== "success") return
-
-      switch (event.type) {
-        case "upload":
-          if (event.key) handleUpload(event.key, event.result as UploadResult)
-          break
-        case "head":
-          if (event.key) handleUpload(event.key, event.result as StoredFile)
-          break
-        case "delete": {
-          const keys = event.key ? [event.key] : (event.result as DeleteManyResult).deleted
-
-          handleDelete(keys)
-          break
-        }
-        default:
-          break
-      }
-    },
-  },
-  plugins: [
-    signedUrlPolicy({
-      maxExpiresIn: FILES_MAX_URL_AGE,
-      maxUploadSize: FILES_MAX_UPLOAD_SIZE,
-    }),
-    validation({
-      allowedTypes: ["image/*", "application/pdf"],
-      key: (key) =>
-        z
-          .string()
-          .regex(/^[\w.-]+(?:\/[\w.-]+)*$/u)
-          .refine((value) =>
-            value.split("/").every((segment) => segment !== "." && segment !== "..")
-          )
-          .safeParse(key).success,
-      maxSize: FILES_MAX_UPLOAD_SIZE,
-      minSize: 1,
-    }),
-    contentType({ onMismatch: "reject" }),
-  ],
-})
-
-function handleUpload(key: string, file: UploadResult | StoredFile) {
-  const ctx = context<AuthenticatedAppContext>()
-  const mimeType = "contentType" in file ? file.contentType : file.type
-  const name = "name" in file ? file.name : (key.split("/").at(-1) ?? key)
-
-  void ctx.var.db
-    .insert(assets)
-    .values({
-      etag: file.etag,
-      key,
-      lastModified: file.lastModified,
-      metadata: "metadata" in file ? file.metadata : undefined,
-      name,
-      ownerId: ctx.var.session.user.id as UserId,
-      size: file.size,
-      type: mimeType,
-      uploaderId: ctx.var.session.user.id as UserId,
-    })
-    .onConflictDoUpdate({
-      set: {
-        etag: file.etag,
-        lastModified: file.lastModified,
-        metadata: "metadata" in file ? file.metadata : undefined,
-        name,
-        size: file.size,
-        type: mimeType,
-        updatedAt: new Date(),
-      },
-      target: assets.key,
-    })
-    .catch((error: unknown) => {
-      ctx.var.logger.error(`Failed to record asset: ${String(error)}`)
-    })
-}
-
-function handleDelete(keys: string[]) {
-  if (keys.length === 0) return
-
-  const ctx = context<AuthenticatedAppContext>()
-
-  void ctx.var.db
-    .delete(assets)
-    .where(
-      helpers.and(
-        helpers.inArray(assets.key, keys),
-        helpers.eq(assets.ownerId, ctx.var.session.user.id as UserId)
-      )
-    )
-    .catch((error: unknown) => {
-      ctx.var.logger.error(`Failed to delete asset records: ${String(error)}`)
-    })
-}
-```
-
-The singleton is still constructed once at module initialization. Only the `onAction`
-callback reads Hono context, and it does so when Files SDK invokes the singleton during
-an authenticated request.
-
-This intentionally makes action-producing use of this singleton request-bound: a
-future caller that invokes it outside Hono context would not have a session to assign
-as `ownerId` and `uploaderId` and must use a separately configured Files instance or
-establish an equivalent ownership context.
-
-### 4. Implement the complete versionless gateway route
-
-Use this proposed implementation for `apps/api/src/routes/files.ts`:
-
-```ts
-import { createFilesRouter } from "files-sdk/api"
-import { createRouteHandler } from "files-sdk/hono"
-import env from "#shared/env.ts"
-import { files, FILES_MAX_UPLOAD_SIZE, FILES_MAX_URL_AGE } from "#shared/files.ts"
-import { requireSession } from "#shared/middleware.ts"
-import type { AuthenticatedAppContext } from "#shared/types.ts"
-import { context, factory } from "#shared/utils.ts"
-
-const router = createFilesRouter({
-  allowedOrigins: env.ALLOWED_API_ORIGINS,
-  authorize: () => {
-    const ctx = context<AuthenticatedAppContext>()
-
-    return {
-      disposition: "attachment",
-      keyPrefix: `users/${ctx.var.session.user.id}/`,
-      maxExpiresIn: FILES_MAX_URL_AGE,
-      maxResults: 100,
-    }
-  },
-  files,
-  maxListLimit: 100,
-  maxSearchResults: 100,
-  maxUploadSize: FILES_MAX_UPLOAD_SIZE,
-  operations: [
-    "capabilities",
-    "delete",
-    "download",
-    "exists",
-    "head",
-    "list",
-    "search",
-    "signedUploadUrl",
-    "upload",
-    "url",
-  ],
-  secret: env.FILES_API_SECRET,
-})
-
-export default factory.createApp().all("/", requireSession, createRouteHandler(router))
-```
-
-The installed Files SDK router applies `keyPrefix` before invoking `files.upload`,
-`files.head`, and `files.delete`. The hook therefore observes storage keys such as
-`users/<user-id>/avatar.png`, while gateway responses remove the prefix for clients.
-
-The singleton's `event.key` guards intentionally ignore bulk head events because reads
-are not the asset-creation seam. Bulk deletion uses `DeleteManyResult.deleted`, so only
-keys that were successfully removed change status.
-
-`requireSession` runs before `createRouteHandler`, allowing both `authorize` and
-`onAction` to read the session from Hono context storage. Remove the old direct `auth`
-import, `auth.api.getSession()` call, and `FilesError` authorization branch.
-
-### 5. Expose Drizzle through the database package
-
-Keep Drizzle's package identity behind `@init/db` and expose its helpers as a namespace
-from `packages/db/src/helpers.ts`:
-
-```ts
-export * as helpers from "drizzle-orm"
-```
-
-The API imports `helpers` from `@init/db/helpers`; it does not declare a separate direct
-Drizzle dependency.
-
-### 6. Limit the initial operation surface
-
-The concrete `operations` list above permits upload, direct/presigned upload, metadata,
-listing, download, URL, and deletion. It excludes `copy` and `move` because the hook
-does not update destination ownership, and excludes versioning and trash operations
-because the configured Files instance does not install those plugins.
-
-### 7. Regenerate the baseline migration
-
-Delete the existing migration SQL and metadata, then run `bun run generate` from
-`packages/db`. The template deliberately keeps one starting migration and does not
-preserve migration history for databases created from earlier template revisions.
-
-### 8. Verify the change
-
-Run the repository-managed static checks:
-
-```sh
-bun run format
-bun run check
-bun run analyze
-bun run check:monorepo
-```
-
-The API workspace currently has no build task, so do not add or invoke one as part of
-this change.
-
-## Explicitly out of scope
-
-- Implementing `/v1/assets`.
-- Making the asset table the source of truth for object existence.
-- Transactional guarantees between object storage and Postgres.
-- A reconciliation worker for missing or stale asset rows.
-- Copy and move ownership semantics.
-- Organization-owned asset authorization.
-- Asset labels, references, transformations, or processing pipelines.
-
-## Follow-up work
-
-- Design the application-owned `/v1/assets` interface around asset IDs rather than raw
-  storage keys.
-- Decide whether ownership should expand from a User owner to a polymorphic owner or
-  separate user/organization ownership records.
-- Add reconciliation if production requirements demand repair of missed hook writes.
-- Define database behavior for copy, move, bulk operations, and failed uploads.
-- Add domain references from future records to `assets.id` instead of duplicating
-  bucket keys.
diff --git a/apps/api/.env.template b/apps/api/.env.template
index 6413c99c..cc8888ea 100644
--- a/apps/api/.env.template
+++ b/apps/api/.env.template
@@ -1,8 +1,8 @@
 # ===========PROJECT===========
 # Add specific project environment variables here
 
-BASE_URL="http://localhost:3000"
-ALLOWED_API_ORIGINS="http://localhost:3001"
+BASE_URL="https://api.init.localhost"
+ALLOWED_API_ORIGINS="https://init.localhost"
 PORT="3000"
 
 # --- Files SDK / S3 ---
@@ -18,7 +18,7 @@ S3_SECRET_ACCESS_KEY="minioadmin"
 
 # --- Auth (@init/env/auth) ---
 AUTH_SECRET="dev-secret"
-AUTH_TRUSTED_ORIGINS="http://localhost:3001,http://localhost:3000"
+AUTH_TRUSTED_ORIGINS="https://init.localhost,https://api.init.localhost"
 
 # --- Auth Providers (@init/env/auth/providers) ---
 # GitHub OAuth
diff --git a/apps/api/package.json b/apps/api/package.json
index 531389f2..a9563c99 100644
--- a/apps/api/package.json
+++ b/apps/api/package.json
@@ -13,7 +13,8 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
     "codegen": "paraglide-js compile --project ../../tooling/internationalization/project.inlang --outdir ./src/shared/internationalization",
-    "dev": "bun --hot src/index.ts",
+    "dev": "portless",
+    "dev:app": "bun --hot src/index.ts",
     "start": "bun --bun src/index.ts"
   },
   "dependencies": {
@@ -43,5 +44,9 @@
     "@tooling/tsconfig": "workspace:*",
     "@types/bun": "1.3.14",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "api.init",
+    "script": "dev:app"
   }
 }
diff --git a/apps/api/src/routes/files.ts b/apps/api/src/routes/files.ts
index 364b6a41..58c5b3f2 100644
--- a/apps/api/src/routes/files.ts
+++ b/apps/api/src/routes/files.ts
@@ -4,10 +4,10 @@ import type { AuthenticatedAppContext } from "#shared/types.ts"
 import env from "#shared/env.ts"
 import { files, FILES_MAX_UPLOAD_SIZE, FILES_MAX_URL_AGE } from "#shared/files.ts"
 import { requireSession } from "#shared/middleware.ts"
-import { context, factory } from "#shared/utils.ts"
+import { allowedOrigins, context, factory } from "#shared/utils.ts"
 
 const router = createFilesRouter({
-  allowedOrigins: env.ALLOWED_API_ORIGINS,
+  allowedOrigins,
   authorize: () => {
     const ctx = context<AuthenticatedAppContext>()
 
diff --git a/apps/api/src/routes/index.ts b/apps/api/src/routes/index.ts
index 91d4b6e3..18ff83e7 100644
--- a/apps/api/src/routes/index.ts
+++ b/apps/api/src/routes/index.ts
@@ -14,11 +14,10 @@ import trpcRoutes from "#routes/trpc.ts"
 import v1Routes from "#routes/v1/index.ts"
 import workflowRoutes from "#routes/workflows.ts"
 import { auth } from "#shared/auth.ts"
-import env from "#shared/env.ts"
 import { files } from "#shared/files.ts"
 import { LoggerCategory, logger } from "#shared/logger.ts"
 import { withLanguageDetection } from "#shared/middleware.ts"
-import { factory } from "#shared/utils.ts"
+import { allowedOrigins, factory } from "#shared/utils.ts"
 
 const app = factory.createApp()
 
@@ -37,7 +36,7 @@ app.use(
     credentials: true,
     exposeHeaders: ["Content-Length"],
     maxAge: 600,
-    origin: env.ALLOWED_API_ORIGINS,
+    origin: allowedOrigins,
   })
 )
 
diff --git a/apps/api/src/shared/auth.ts b/apps/api/src/shared/auth.ts
index 7f69f99b..6e1ea7b0 100644
--- a/apps/api/src/shared/auth.ts
+++ b/apps/api/src/shared/auth.ts
@@ -10,12 +10,13 @@ import { database } from "@init/db/client"
 import { sendEmail } from "@init/email/client"
 import PasswordReset from "@init/email/templates/password-reset"
 import env from "#shared/env.ts"
+import { allowedOrigins, baseUrl } from "#shared/utils.ts"
 
 export const auth = createAuth({
   advanced: AUTH_ADVANCED_OPTIONS,
   appName: AUTH_APP_NAME,
   basePath: "/auth",
-  baseURL: env.BASE_URL,
+  baseURL: baseUrl,
   database: databaseAdapter(database()),
   emailAndPassword: {
     ...AUTH_EMAIL_AND_PASSWORD_OPTIONS,
@@ -41,7 +42,7 @@ export const auth = createAuth({
       enabled: true,
     },
   },
-  trustedOrigins: env.ALLOWED_API_ORIGINS,
+  trustedOrigins: allowedOrigins,
 })
 
 export type Auth = typeof auth
diff --git a/apps/api/src/shared/env.ts b/apps/api/src/shared/env.ts
index bce5d53d..fc1f617d 100644
--- a/apps/api/src/shared/env.ts
+++ b/apps/api/src/shared/env.ts
@@ -1,5 +1,5 @@
 import { createEnv } from "@init/env"
-import { auth, db, inngest, kv, resend, s3, sentry } from "@init/env/presets"
+import { auth, db, inngest, kv, portless, resend, s3, sentry } from "@init/env/presets"
 import * as z from "@init/utils/schema"
 import { isCI } from "std-env"
 
@@ -11,6 +11,7 @@ export default createEnv({
     auth.providers.google(),
     db(),
     kv(),
+    portless(),
     inngest(),
     resend(),
     s3(),
diff --git a/apps/api/src/shared/utils.ts b/apps/api/src/shared/utils.ts
index 728c22d0..65b4e7b5 100644
--- a/apps/api/src/shared/utils.ts
+++ b/apps/api/src/shared/utils.ts
@@ -1,6 +1,19 @@
 import { getContext } from "hono/context-storage"
 import { createFactory } from "hono/factory"
 import type { AppContext } from "#shared/types.ts"
+import env from "#shared/env.ts"
+
+export const baseUrl = env.PORTLESS_URL ?? env.BASE_URL
+
+export const allowedOrigins = env.PORTLESS_URL
+  ? env.ALLOWED_API_ORIGINS.map(
+      (origin) =>
+        new URL(
+          env.PORTLESS_URL?.replace(new URL(env.BASE_URL).hostname, new URL(origin).hostname) ??
+            origin
+        ).origin
+    )
+  : env.ALLOWED_API_ORIGINS
 
 /**
  * A utility function to create Hono apps and middlewares with the correct context type.
diff --git a/apps/app/.env.template b/apps/app/.env.template
index 70aa393b..12839f92 100644
--- a/apps/app/.env.template
+++ b/apps/app/.env.template
@@ -2,11 +2,11 @@
 # Add specific project environment variables here
 
 # Client-side variables (PUBLIC_ prefix for Vite)
-PUBLIC_BASE_URL="http://localhost:3001"
+PUBLIC_BASE_URL="https://init.localhost"
 
 # --- Auth (@init/env/auth) ---
 AUTH_SECRET="dev-secret"
-AUTH_TRUSTED_ORIGINS="http://localhost:3001"
+AUTH_TRUSTED_ORIGINS="https://init.localhost"
 
 # --- Auth Providers (@init/env/auth/providers) ---
 GITHUB_CLIENT_ID="dev-github-client-id"
diff --git a/apps/app/package.json b/apps/app/package.json
index 09be99d1..b2505761 100644
--- a/apps/app/package.json
+++ b/apps/app/package.json
@@ -11,7 +11,8 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
     "codegen": "paraglide-js compile --project ../../tooling/internationalization/project.inlang --outdir ./src/shared/internationalization",
-    "dev": "bun --bun vite dev",
+    "dev": "portless",
+    "dev:app": "bun --bun vite dev",
     "preview": "bun --bun vite preview",
     "start": "node .output/server/index.mjs"
   },
@@ -56,5 +57,9 @@
     "tailwindcss": "4.3.3",
     "typescript": "7.0.2",
     "vite": "8.1.5"
+  },
+  "portless": {
+    "name": "init",
+    "script": "dev:app"
   }
 }
diff --git a/apps/app/src/features/auth/server/index.ts b/apps/app/src/features/auth/server/index.ts
index aa252f5a..8d22223f 100644
--- a/apps/app/src/features/auth/server/index.ts
+++ b/apps/app/src/features/auth/server/index.ts
@@ -12,11 +12,15 @@ import { sendEmail } from "@init/email/client"
 import PasswordReset from "@init/email/templates/password-reset"
 import env from "#shared/env.ts"
 
+const trustedOrigins = env.PORTLESS_URL
+  ? [...new Set([...env.AUTH_TRUSTED_ORIGINS, env.PORTLESS_URL])]
+  : env.AUTH_TRUSTED_ORIGINS
+
 export const auth = createAuth({
   advanced: AUTH_ADVANCED_OPTIONS,
   appName: AUTH_APP_NAME,
   basePath: "/api/auth",
-  baseURL: env.PUBLIC_BASE_URL,
+  baseURL: env.PORTLESS_URL ?? env.PUBLIC_BASE_URL,
   database: databaseAdapter(database()),
   emailAndPassword: {
     ...AUTH_EMAIL_AND_PASSWORD_OPTIONS,
@@ -42,5 +46,5 @@ export const auth = createAuth({
       enabled: true,
     },
   },
-  trustedOrigins: env.AUTH_TRUSTED_ORIGINS,
+  trustedOrigins,
 })
diff --git a/apps/app/src/shared/env.ts b/apps/app/src/shared/env.ts
index 8d2f0471..f63b797a 100644
--- a/apps/app/src/shared/env.ts
+++ b/apps/app/src/shared/env.ts
@@ -1,5 +1,5 @@
 import { createEnv, REACT_PUBLIC_ENV_PREFIX } from "@init/env"
-import { auth, db, resend, sentry } from "@init/env/presets"
+import { auth, db, portless, resend, sentry } from "@init/env/presets"
 import * as z from "@init/utils/schema"
 import { env, isCI } from "std-env"
 
@@ -14,6 +14,7 @@ export default createEnv({
     auth.providers.github(),
     auth.providers.google(),
     db(),
+    portless(),
     resend(),
     sentry.client(),
   ],
diff --git a/apps/app/src/shared/utils.ts b/apps/app/src/shared/utils.ts
index b5205f99..ddcbe475 100644
--- a/apps/app/src/shared/utils.ts
+++ b/apps/app/src/shared/utils.ts
@@ -1,10 +1,14 @@
 import { createUrlBuilder } from "@init/utils/url"
+import { hasWindow } from "std-env"
 import env from "#shared/env.ts"
 
-const isProduction = import.meta.env.PROD
+const baseUrl = hasWindow ? globalThis.location.origin : (env.PORTLESS_URL ?? env.PUBLIC_BASE_URL)
 
-export const buildUrl = createUrlBuilder(env.PUBLIC_BASE_URL, isProduction ? "https" : "http")
-export const buildApiUrl = createUrlBuilder(
-  env.PUBLIC_API_URL ?? `${env.PUBLIC_BASE_URL}/api`,
-  isProduction ? "https" : "http"
-)
+export const buildUrl = createUrlBuilder(baseUrl, getProtocol(baseUrl))
+
+const apiUrl = env.PUBLIC_API_URL ?? `${baseUrl}/api`
+export const buildApiUrl = createUrlBuilder(apiUrl, getProtocol(apiUrl))
+
+function getProtocol(url: string) {
+  return new URL(url).protocol === "http:" ? "http" : "https"
+}
diff --git a/apps/app/vite.config.ts b/apps/app/vite.config.ts
index a5d45555..7d840b42 100644
--- a/apps/app/vite.config.ts
+++ b/apps/app/vite.config.ts
@@ -31,7 +31,7 @@ export default defineConfig(async ({ mode }) => {
       }),
     ],
     server: {
-      port: 3001,
+      port: Number(process.env.PORT ?? 3001),
     },
   }
 })
diff --git a/apps/desktop/package.json b/apps/desktop/package.json
index b354ac85..3da83653 100644
--- a/apps/desktop/package.json
+++ b/apps/desktop/package.json
@@ -11,7 +11,8 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
     "codegen": "paraglide-js compile --project ../../tooling/internationalization/project.inlang --outdir ./src/shared/internationalization",
-    "dev": "tauri dev"
+    "dev": "portless",
+    "dev:app": "tauri dev"
   },
   "dependencies": {
     "@init/env": "workspace:*",
@@ -46,5 +47,9 @@
     "babel-plugin-react-compiler": "1.0.0",
     "typescript": "7.0.2",
     "vite": "8.1.5"
+  },
+  "portless": {
+    "name": "desktop.init",
+    "script": "dev:app"
   }
 }
diff --git a/apps/desktop/src-tauri/tauri.conf.json b/apps/desktop/src-tauri/tauri.conf.json
index 0ee0d9d9..f303e1d8 100644
--- a/apps/desktop/src-tauri/tauri.conf.json
+++ b/apps/desktop/src-tauri/tauri.conf.json
@@ -6,7 +6,7 @@
   "build": {
     "beforeBuildCommand": "bun vite build",
     "beforeDevCommand": "bun vite dev",
-    "devUrl": "http://localhost:3003",
+    "devUrl": "https://desktop.init.localhost",
     "frontendDist": "../dist"
   },
   "app": {
diff --git a/apps/desktop/vite.config.ts b/apps/desktop/vite.config.ts
index 4a065a65..e6613150 100644
--- a/apps/desktop/vite.config.ts
+++ b/apps/desktop/vite.config.ts
@@ -38,12 +38,11 @@ export default defineConfig(async ({ mode }) => {
       hmr: host
         ? {
             host,
-            port: 4003,
             protocol: "ws",
           }
         : undefined,
       host: host ?? false,
-      port: 3003,
+      port: Number(process.env.PORT ?? 3003),
       strictPort: true,
       watch: {
         ignored: ["**/src-tauri/**"],
diff --git a/apps/docs/astro.config.ts b/apps/docs/astro.config.ts
index 5ce9adfe..46133387 100644
--- a/apps/docs/astro.config.ts
+++ b/apps/docs/astro.config.ts
@@ -46,7 +46,7 @@ export default defineConfig({
     }),
   ],
   server: {
-    port: 3004,
+    port: Number(process.env.PORT ?? 3004),
   },
   vite: {
     plugins: [
diff --git a/apps/docs/package.json b/apps/docs/package.json
index 98edf482..78612904 100644
--- a/apps/docs/package.json
+++ b/apps/docs/package.json
@@ -12,7 +12,8 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
     "codegen": "paraglide-js compile --project ../../tooling/internationalization/project.inlang --outdir ./src/shared/internationalization",
-    "dev": "astro dev",
+    "dev": "portless",
+    "dev:app": "astro dev",
     "preview": "astro preview",
     "typegen": "astro sync"
   },
@@ -29,5 +30,9 @@
     "@tooling/tsconfig": "workspace:*",
     "tailwindcss": "4.3.3",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "docs.init",
+    "script": "dev:app"
   }
 }
diff --git a/apps/extension/package.json b/apps/extension/package.json
index 23d3bc1c..ffcf344a 100644
--- a/apps/extension/package.json
+++ b/apps/extension/package.json
@@ -12,7 +12,8 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
     "codegen": "paraglide-js compile --project ../../tooling/internationalization/project.inlang --outdir ./src/shared/internationalization",
-    "dev": "wxt",
+    "dev": "portless",
+    "dev:app": "wxt",
     "dev:firefox": "wxt -b firefox",
     "postinstall": "wxt prepare",
     "typegen": "wxt prepare",
@@ -43,5 +44,9 @@
     "vite": "8.1.5",
     "web-ext": "10.5.0",
     "wxt": "0.21.1"
+  },
+  "portless": {
+    "name": "extension.init",
+    "script": "dev:app"
   }
 }
diff --git a/apps/extension/wxt.config.ts b/apps/extension/wxt.config.ts
index 4b313c05..3f1d505b 100644
--- a/apps/extension/wxt.config.ts
+++ b/apps/extension/wxt.config.ts
@@ -9,7 +9,7 @@ export default defineConfig({
     baseIconPath: "shared/assets/icon.svg",
   },
   dev: {
-    server: { port: 3005 },
+    server: { port: Number(process.env.PORT ?? 3005) },
   },
   imports: false,
   modules: ["@wxt-dev/module-react", "@wxt-dev/auto-icons"],
diff --git a/apps/mobile/package.json b/apps/mobile/package.json
index 8a0c1b6b..52419880 100644
--- a/apps/mobile/package.json
+++ b/apps/mobile/package.json
@@ -11,8 +11,9 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo .expo dist node_modules",
     "codegen": "bun run scripts/codegen.ts",
-    "dev": "expo start --port 3002",
+    "dev": "portless",
     "dev:android": "expo start --android",
+    "dev:app": "expo start --port ${PORT:-3002}",
     "dev:ios": "expo start --ios",
     "doctor": "expo-doctor",
     "install:check": "expo install --check",
@@ -71,5 +72,9 @@
     "babel-preset-expo": "~54.0.0",
     "expo-doctor": "1.17.14",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "mobile.init",
+    "script": "dev:app"
   }
 }
diff --git a/apps/web/.env.template b/apps/web/.env.template
index e0d74ee2..289cf6f0 100644
--- a/apps/web/.env.template
+++ b/apps/web/.env.template
@@ -2,7 +2,7 @@
 # Add specific project environment variables here
 
 # Client-side variables (PUBLIC_ prefix for Astro)
-PUBLIC_SITE_URL="http://localhost:3006"
+PUBLIC_SITE_URL="https://web.init.localhost"
 
 # ===========OPTIONAL===========
 # Optional packages that may be used in the future
diff --git a/apps/web/astro.config.ts b/apps/web/astro.config.ts
index c7ac7b22..53709834 100644
--- a/apps/web/astro.config.ts
+++ b/apps/web/astro.config.ts
@@ -12,7 +12,7 @@ const { default: env } = await import("./src/shared/env.ts")
 export default defineConfig({
   output: "static",
   server: {
-    port: 3006,
+    port: Number(process.env.PORT ?? 3006),
   },
   site: env.PUBLIC_SITE_URL ?? "https://init.now",
 
diff --git a/apps/web/package.json b/apps/web/package.json
index 50014c0f..cc1f4fcb 100644
--- a/apps/web/package.json
+++ b/apps/web/package.json
@@ -12,7 +12,8 @@
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
     "codegen": "paraglide-js compile --project ../../tooling/internationalization/project.inlang --outdir ./src/shared/internationalization",
-    "dev": "astro dev",
+    "dev": "portless",
+    "dev:app": "astro dev",
     "preview": "astro preview",
     "typegen": "astro sync"
   },
@@ -40,5 +41,9 @@
     "@types/react-dom": "19.1.9",
     "tailwindcss": "4.3.3",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "web.init",
+    "script": "dev:app"
   }
 }
diff --git a/bun.lock b/bun.lock
index 949414a1..41e6b3f4 100644
--- a/bun.lock
+++ b/bun.lock
@@ -15,6 +15,7 @@
         "oxfmt": "0.60.0",
         "oxlint": "1.75.0",
         "oxlint-tsgolint": "7.0.2001",
+        "portless": "0.15.5",
         "sherif": "1.13.0",
         "turbo": "2.10.7",
         "typescript": "7.0.2",
@@ -518,6 +519,7 @@
       },
       "devDependencies": {
         "@tooling/tsconfig": "workspace:*",
+        "inngest-cli": "1.40.0",
         "typescript": "7.0.2",
       },
     },
@@ -546,10 +548,11 @@
     },
   },
   "trustedDependencies": [
+    "@sentry/cli",
     "@tailwindcss/oxide",
     "extension",
     "docs",
-    "@sentry/cli",
+    "inngest-cli",
   ],
   "overrides": {
     "@types/react": "19.1.13",
@@ -3304,6 +3307,8 @@
 
     "inngest": ["inngest@3.49.3", "", { "dependencies": { "@bufbuild/protobuf": "^2.2.3", "@inngest/ai": "^0.1.3", "@jpwilliams/waitgroup": "^2.1.1", "@opentelemetry/api": "^1.9.0", "@opentelemetry/auto-instrumentations-node": ">=0.66.0 <1.0.0", "@opentelemetry/context-async-hooks": ">=2.0.0 <3.0.0", "@opentelemetry/exporter-trace-otlp-http": ">=0.200.0 <0.300.0", "@opentelemetry/instrumentation": ">=0.200.0 <0.300.0", "@opentelemetry/resources": ">=2.0.0 <3.0.0", "@opentelemetry/sdk-trace-base": ">=2.0.0 <3.0.0", "@standard-schema/spec": "^1.0.0", "@types/debug": "^4.1.12", "@types/ms": "~2.1.0", "canonicalize": "^1.0.8", "chalk": "^4.1.2", "cross-fetch": "^4.0.0", "debug": "^4.3.4", "hash.js": "^1.1.7", "json-stringify-safe": "^5.0.1", "ms": "^2.1.3", "serialize-error-cjs": "^0.1.3", "strip-ansi": "^5.2.0", "temporal-polyfill": "^0.2.5", "ulid": "^2.3.0", "zod": "^3.25.0" }, "peerDependencies": { "@sveltejs/kit": ">=1.27.3", "@vercel/node": ">=2.15.9", "aws-lambda": ">=1.0.7", "express": ">=4.19.2", "fastify": ">=4.21.0", "h3": ">=1.8.1", "hono": ">=4.2.7", "koa": ">=2.14.2", "next": ">=12.0.0", "typescript": ">=5.8.0" }, "optionalPeers": ["@sveltejs/kit", "@vercel/node", "aws-lambda", "express", "fastify", "h3", "hono", "koa", "next", "typescript"] }, "sha512-JH4VBcxmBh7J0QIk28yYNSlBs1q2wnlds20Sj4a1m8RXRSfDh+z6+Lq+WVpaHH0XolsPYwkRwUA9Gf540AcBmg=="],
 
+    "inngest-cli": ["inngest-cli@1.40.0", "", { "dependencies": { "adm-zip": "^0.5.10", "debug": "^4.3.4", "node-fetch": "^2.6.7", "tar": "^7.5.3" }, "bin": { "inngest-cli": "bin/inngest", "inngest": "bin/inngest" } }, "sha512-65dtJcvxq/XR9PuVab4gNC0ZdyAeyNf7mYe5A/L1WV2SgbqEaqQz3cd9ukOSWSlEP8684C1vwCM/wlZp7/eD5g=="],
+
     "input-otp": ["input-otp@1.4.2", "", { "peerDependencies": { "react": "^16.8 || ^17.0 || ^18.0 || ^19.0.0 || ^19.0.0-rc", "react-dom": "^16.8 || ^17.0 || ^18.0 || ^19.0.0 || ^19.0.0-rc" } }, "sha512-l3jWwYNvrEa6NTCt7BECfCm48GvwuZzkoeG3gBL2w4CHeOXW3eKFmf9UNYkNfYc3mxMrthMnxjIE07MT0zLBQA=="],
 
     "internmap": ["internmap@2.0.3", "", {}, "sha512-5Hh7Y1wQbvY5ooGgPbDaL5iYLAPzMTUrjMulskHLH6wnv/A+1q5rgEaiuqEjB+oxGXIVZs1FF+R/KPN3ZSQYYg=="],
@@ -3966,6 +3971,8 @@
 
     "pngjs": ["pngjs@3.4.0", "", {}, "sha512-NCrCHhWmnQklfH4MtJMRjZ2a8c80qXeMlQMv2uVp9ISJMTt562SbGd6n2oq0PaPgKm7Z6pL9E2UlLIhC+SHL3w=="],
 
+    "portless": ["portless@0.15.5", "", { "os": [ "linux", "win32", "darwin", ], "bin": { "portless": "dist/cli.js" } }, "sha512-zmJu4Q8/fY54oVUT/5NnmF4Ih8wTdCvCf6JCN783dRYl9mXkJBzXSckX2lztGCLIbM70varDjCudAbGKT73XPg=="],
+
     "postcss": ["postcss@8.5.23", "", { "dependencies": { "nanoid": "^3.3.16", "picocolors": "^1.1.1", "source-map-js": "^1.2.1" } }, "sha512-g50586zr4bZmwFiTlflMu8E0bDTb5I5gertgwAKmsdUlTQIhZtunzUlD1WSzwcVWPoAVpsrA6vlfCD7oXvRwgg=="],
 
     "postcss-nested": ["postcss-nested@6.2.0", "", { "dependencies": { "postcss-selector-parser": "^6.1.1" }, "peerDependencies": { "postcss": "^8.2.14" } }, "sha512-HQbt28KulC5AJzG+cZtj9kvKB93CFCdLvog1WFLf1D+xmMvPGlBstkpTEZfK5+AN9hfJocyBFCNiqyS48bpgzQ=="],
@@ -4750,7 +4757,7 @@
 
     "y18n": ["y18n@5.0.8", "", {}, "sha512-0pfFzegeDWJHJIAmTLRP2DwHjdF5s7jo9tuztdQxAhINCdvS+3nGINqPd00AphqJR/0LhANUS6/+7SCb98YOfA=="],
 
-    "yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+    "yallist": ["yallist@5.0.0", "", {}, "sha512-YgvUTfwqyc7UXVMrB+SImsVYSmTS8X/tSrtdNZMImM+n7+QTriRXyXim0mBrTXNeqzVF0KWGgHPeiyViFFrNDw=="],
 
     "yaml": ["yaml@2.9.0", "", { "bin": { "yaml": "bin.mjs" } }, "sha512-2AvhNX3mb8zd6Zy7INTtSpl1F15HW6Wnqj0srWlkKLcpYl/gMIMJiyuGq2KeI2YFxUPjdlB+3Lc10seMLtL4cA=="],
 
@@ -5756,8 +5763,6 @@
 
     "tar/minipass": ["minipass@7.1.2", "", {}, "sha512-qOOzS1cBTWYF4BH8fVePDBOO9iptMnGUEZwNc/cMWnTV2nVLZ7VoNWEPHkYczZA0pdoA7dl6e7FL659nX9S2aw=="],
 
-    "tar/yallist": ["yallist@5.0.0", "", {}, "sha512-YgvUTfwqyc7UXVMrB+SImsVYSmTS8X/tSrtdNZMImM+n7+QTriRXyXim0mBrTXNeqzVF0KWGgHPeiyViFFrNDw=="],
-
     "terser/acorn": ["acorn@8.15.0", "", { "bin": { "acorn": "bin/acorn" } }, "sha512-NZyJarBfL7nWwIq+FDL6Zp/yHEhePMNnnJ0y3qfieCrmNvYct8uvtiV41UvlSe6apAfk0fY1FbWx+NwfmpvtTg=="],
 
     "terser/commander": ["commander@2.20.3", "", {}, "sha512-GpVkmM8vF2vQUkj2LvZmD35JxeJOLCwJ9cUkugyk2nuhbv3+mJvpLYYt+0+USMxE+oj+ey/lJEnhZw75x/OMcQ=="],
@@ -5856,6 +5861,8 @@
 
     "@babel/helper-annotate-as-pure/@babel/types/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
+    "@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@babel/helper-create-class-features-plugin/@babel/traverse/@babel/code-frame": ["@babel/code-frame@7.28.6", "", { "dependencies": { "@babel/helper-validator-identifier": "^7.28.5", "js-tokens": "^4.0.0", "picocolors": "^1.1.1" } }, "sha512-JYgintcMjRiCvS8mMECzaEn+m3PfoQiyqukOMCCVQtoJGYJw8j/8LBJEiqkHLkfwCcs74E3pbAUFNg7d9VNJ+Q=="],
 
     "@babel/helper-create-class-features-plugin/@babel/traverse/@babel/generator": ["@babel/generator@7.28.6", "", { "dependencies": { "@babel/parser": "^7.28.6", "@babel/types": "^7.28.6", "@jridgewell/gen-mapping": "^0.3.12", "@jridgewell/trace-mapping": "^0.3.28", "jsesc": "^3.0.2" } }, "sha512-lOoVRwADj8hjf7al89tvQ2a1lf53Z+7tiXMgpZJL3maQPDxh0DgLMN62B2MKUOFcoodBHLMbDM6WAbKgNy5Suw=="],
@@ -7032,6 +7039,8 @@
 
     "@babel/helper-create-class-features-plugin/@babel/traverse/@babel/types/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
+    "@babel/helper-define-polyfill-provider/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@babel/helper-member-expression-to-functions/@babel/traverse/@babel/code-frame/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
     "@babel/helper-module-imports/@babel/traverse/@babel/code-frame/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
@@ -7064,6 +7073,8 @@
 
     "@babel/plugin-transform-async-generator-functions/@babel/traverse/@babel/types/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
+    "@babel/plugin-transform-classes/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@babel/plugin-transform-classes/@babel/traverse/@babel/code-frame/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
     "@babel/plugin-transform-classes/@babel/traverse/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.27.1", "", {}, "sha512-qMlSxKbpRlAridDExk92nSobyDdpPijUq2DW6oDnUqd0iOGxmQjyqhMIihI9+zv4LPyZdRje2cavWPbCbWm3eA=="],
@@ -7082,6 +7093,8 @@
 
     "@babel/plugin-transform-destructuring/@babel/traverse/@babel/types/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
+    "@babel/plugin-transform-function-name/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@babel/plugin-transform-function-name/@babel/traverse/@babel/code-frame/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
     "@babel/plugin-transform-function-name/@babel/traverse/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.27.1", "", {}, "sha512-qMlSxKbpRlAridDExk92nSobyDdpPijUq2DW6oDnUqd0iOGxmQjyqhMIihI9+zv4LPyZdRje2cavWPbCbWm3eA=="],
@@ -7100,6 +7113,8 @@
 
     "@babel/plugin-transform-modules-commonjs/@babel/helper-module-transforms/@babel/traverse/@babel/types": ["@babel/types@7.28.6", "", { "dependencies": { "@babel/helper-string-parser": "^7.27.1", "@babel/helper-validator-identifier": "^7.28.5" } }, "sha512-0ZrskXVEHSWIqZM/sQZ4EV3jZJXRkio/WCxaqKZP1g//CEWEPSfeZFcms4XeKBCHU0ZKnIkdJeU/kF+eRp5lBg=="],
 
+    "@babel/plugin-transform-object-rest-spread/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@babel/plugin-transform-object-rest-spread/@babel/traverse/@babel/code-frame/@babel/helper-validator-identifier": ["@babel/helper-validator-identifier@7.28.5", "", {}, "sha512-qSs4ifwzKJSV39ucNjsvc6WVHs6b7S03sOh2OcHF9UHfVPqWWALUsNUVzhSBiItjRZoLHx7nIarVjqKVusUZ1Q=="],
 
     "@babel/plugin-transform-object-rest-spread/@babel/traverse/@babel/types/@babel/helper-string-parser": ["@babel/helper-string-parser@7.27.1", "", {}, "sha512-qMlSxKbpRlAridDExk92nSobyDdpPijUq2DW6oDnUqd0iOGxmQjyqhMIihI9+zv4LPyZdRje2cavWPbCbWm3eA=="],
@@ -7450,6 +7465,8 @@
 
     "@expo/cli/ora/cli-cursor/restore-cursor/signal-exit": ["signal-exit@3.0.7", "", {}, "sha512-wnD2ZE+l+SPC/uoS0vXeE9L1+0wuaMqKlfz9AMUo38JsyLSBWSFcHR1Rri62LZc12vLr1gb3jl7iwQhgwpAbGQ=="],
 
+    "@expo/metro-config/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@expo/package-manager/ora/chalk/ansi-styles/color-convert": ["color-convert@1.9.3", "", { "dependencies": { "color-name": "1.1.3" } }, "sha512-QfAUtd+vFdAtFQcC8CCyYt1fYWxSqAiK2cSD6zDB8N3cpsEBAvRxp9zOGg6G/SHHJYAT88/az/IuDGALsNVbGg=="],
 
     "@expo/package-manager/ora/chalk/supports-color/has-flag": ["has-flag@3.0.0", "", {}, "sha512-sKJf1+ceQBr4SMkvQnBDNDtf4TXpVhVGateu0t918bl30FnbE2m4vNLX+VWe/dpjlb+HugGYzW7uQXH98HPEYw=="],
@@ -7462,6 +7479,12 @@
 
     "@istanbuljs/load-nyc-config/find-up/locate-path/p-locate/p-limit": ["p-limit@2.3.0", "", { "dependencies": { "p-try": "^2.0.0" } }, "sha512-//88mFWSJx8lxCzwdAABTJL2MyWB12+eIY7MDL2SqLmAkeKU9qxRvWuSyTjm3FUmpBEMuFfckAIqEaVGUDxb6w=="],
 
+    "@jest/transform/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "@react-native/babel-preset/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "@react-native/codegen/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "@react-native/codegen/yargs/cliui/wrap-ansi/ansi-styles": ["ansi-styles@4.3.0", "", { "dependencies": { "color-convert": "^2.0.1" } }, "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg=="],
 
     "@react-native/dev-middleware/chrome-launcher/lighthouse-logger/debug/ms": ["ms@2.0.0", "", {}, "sha512-Tpp60P6IUJDTuOq/5Z8cdskzJujfwqfOTkrwIwj7IRISpnkJnT6SyJ4PCPnGMoFjC9ddhal5KVIYtAt97ix05A=="],
@@ -7470,10 +7493,24 @@
 
     "addons-linter/yargs/cliui/wrap-ansi/ansi-styles": ["ansi-styles@4.3.0", "", { "dependencies": { "color-convert": "^2.0.1" } }, "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg=="],
 
+    "babel-dead-code-elimination/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "istanbul-lib-instrument/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "metro-babel-transformer/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "metro-transform-plugins/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "metro-transform-worker/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
+    "metro/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "metro/yargs/cliui/wrap-ansi/ansi-styles": ["ansi-styles@4.3.0", "", { "dependencies": { "color-convert": "^2.0.1" } }, "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg=="],
 
     "react-native/yargs/cliui/wrap-ansi/ansi-styles": ["ansi-styles@4.3.0", "", { "dependencies": { "color-convert": "^2.0.1" } }, "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg=="],
 
+    "shadcn/@babel/core/@babel/helper-compilation-targets/lru-cache/yallist": ["yallist@3.1.1", "", {}, "sha512-a4UGQaWPH59mOXUYnAG2ewncQS4i4F43Tv3JoAM+s2VDAmS9NsK8GpDMLrCHPksFT7h3K6TOoUNn2pb7RoXx4g=="],
+
     "web-ext/yargs/cliui/wrap-ansi/ansi-styles": ["ansi-styles@4.3.0", "", { "dependencies": { "color-convert": "^2.0.1" } }, "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg=="],
 
     "@expo/cli/ora/chalk/ansi-styles/color-convert/color-name": ["color-name@1.1.3", "", {}, "sha512-72fSenhMw2HZMTVHeCA9KCmpEIbzWiQsjN+BHcBbS9vr1mtt+vJjPdksIBNUmKAW8TFUDPJK5SUU3QhE9NEXDw=="],
diff --git a/docs/development.md b/docs/development.md
index bd012e2b..fddba9c5 100644
--- a/docs/development.md
+++ b/docs/development.md
@@ -11,20 +11,20 @@ See `docs/getting-started.md` for the authoritative versions. In short:
 
 These match the root `package.json` scripts.
 
-| Command                | Description                                  |
-| ---------------------- | -------------------------------------------- |
-| `bun run dev`          | Start all workspaces in development mode     |
-| `bun run dev:apps`     | Start app workspaces in development mode     |
-| `bun run dev:packages` | Start package workspaces in development mode |
-| `bun run build`        | Build all workspaces                         |
-| `bun run clean`        | Clean build artifacts                        |
-| `bun run check`        | Run Adamantite checks                        |
-| `bun run fix`          | Auto-fix issues with Adamantite              |
-| `bun run format`       | Format code with Adamantite                  |
-| `bun run test`         | Run the test suite                           |
-| `bun run docker:up`    | Start local services                         |
-| `bun run docker:down`  | Stop local services                          |
-| `bun run boundaries`   | Generate dependency boundaries report        |
+| Command                | Description                                |
+| ---------------------- | ------------------------------------------ |
+| `bun run dev`          | Start all workspaces with named HTTPS URLs |
+| `bun run dev:apps`     | Start application workspaces with Portless |
+| `bun run dev:packages` | Start package workspaces with Portless     |
+| `bun run build`        | Build all workspaces                       |
+| `bun run clean`        | Clean build artifacts                      |
+| `bun run check`        | Run Adamantite checks                      |
+| `bun run fix`          | Auto-fix issues with Adamantite            |
+| `bun run format`       | Format code with Adamantite                |
+| `bun run test`         | Run the test suite                         |
+| `bun run docker:up`    | Start local services                       |
+| `bun run docker:down`  | Stop local services                        |
+| `bun run boundaries`   | Generate dependency boundaries report      |
 
 If you want to run a command for a specific workspace, you can use the following syntax:
 
@@ -32,6 +32,35 @@ If you want to run a command for a specific workspace, you can use the following
 bun run <command> --filter <workspace>
 ```
 
+## Portless
+
+Every HTTP-serving workspace uses `portless` as its `dev` script and keeps its
+underlying framework command in `dev:app`, following Portless's
+[recommended Turborepo configuration](https://portless.sh/configuration). This means
+both root commands such as `bun run dev` and workspace-local commands such as
+`cd apps/api && bun run dev` use named HTTPS URLs. The normalized npm scope owns the
+hostname suffix. For a scope named `example`, the App uses
+`https://example.localhost`, the API uses `https://api.example.localhost`, and other
+HTTP development servers follow the same `<workspace>.example.localhost` convention.
+
+Each HTTP-serving workspace's package-local `portless` object is the source of truth
+for its project-qualified name and `dev:app` script. Portless assigns an available
+upstream port at runtime, so multiple projects can run concurrently without sharing
+application ports. Separate projects still need distinct npm scopes—and therefore
+distinct Portless names—while Git worktrees receive automatic route prefixes.
+
+Drizzle Studio, React Email, and the Inngest dev server use the same package-local
+pattern. Inngest runs from `packages/workflows`; Docker Compose is reserved for data
+infrastructure.
+
+The first run may request administrator access to trust Portless's local certificate
+authority and bind port 443. Use `portless doctor` to inspect proxy, certificate, DNS,
+and route health.
+
+Portless routes Mobile, Desktop, and Extension development servers, but it does not
+replace Expo, Tauri, or browser-extension launch behavior. `.localhost` resolves only
+on the development machine; physical devices require Portless LAN mode and `.local`.
+
 ## Managing Dependencies
 
 - `bun run bump:deps` - Update dependencies interactively
diff --git a/docs/generators.md b/docs/generators.md
index 77a7016b..d609496f 100644
--- a/docs/generators.md
+++ b/docs/generators.md
@@ -136,8 +136,8 @@ Generate the optional client in an app that consumes the API:
 
 ```bash
 bun run generate files-client
-bun run generate files-client --args app http://localhost:3000/files
-bun run generate files-client --args web http://localhost:3000/files
+bun run generate files-client --args app https://api.init.localhost/files
+bun run generate files-client --args web https://api.init.localhost/files
 ```
 
 The generator can target any workspace under `apps/`. It creates
diff --git a/docs/getting-started.md b/docs/getting-started.md
index beeeda58..dd3092e9 100644
--- a/docs/getting-started.md
+++ b/docs/getting-started.md
@@ -78,50 +78,60 @@ bun run codegen
 bun run docker:up
 ```
 
-5. Start the development server:
+5. Start the development servers through Portless:
 
 ```bash
-bun run dev # or bun run dev --filter <workspace> to start a specific workspace
+bun run dev
 ```
 
+Portless serves local HTTP development servers over named HTTPS URLs. On first use it
+creates a local certificate authority, asks the operating system to trust it, and
+starts its proxy on port 443. The project scope determines the hostname suffix; the
+default template uses:
+
+- App: `https://init.localhost`
+- API: `https://api.init.localhost`
+- Web: `https://web.init.localhost`
+- Docs: `https://docs.init.localhost`
+- Mobile server: `https://mobile.init.localhost`
+- Desktop frontend: `https://desktop.init.localhost`
+- Extension server: `https://extension.init.localhost`
+- Drizzle Studio: `https://db.init.localhost`
+- Email preview: `https://email.init.localhost`
+- Inngest: `https://workflows.init.localhost`
+
+Running `bun template setup` or a root `bun template rename` changes `init` in these
+hostnames to the normalized project scope. The App owns the bare project hostname.
+
+Every HTTP-serving workspace uses `portless` as its `dev` script and keeps its
+framework command in `dev:app`. Running `bun run dev` inside `apps/api`, for example,
+serves `https://api.init.localhost`. At the repository root, the same command runs all
+workspaces through Turbo. Package-local Portless configuration keeps both entry points
+on the same names.
+
 ### First Run Checklist
 
 - Run `bun template setup`
 - Generate source files and types with `bun run codegen`
 - Start services with `bun run docker:up`
-- Start a workspace with `bun run dev --filter <workspace>`
-
-### Ports
-
-#### Apps
-
-Apps run in the 3000-3999 range.
-
-- API: `3000`
-- App: `3001`
-- Mobile: `3002`
-- Desktop: `3003`
-- Docs: `3004`
-- Extension: `3005`
-- Web: `3006`
-
-#### Packages
+- Start the named HTTPS development topology with `bun run dev`
+- Run `portless doctor` if a local URL or certificate is unavailable
 
-Packages run in the 4000-4999 range.
+### Port Allocation
 
-- Email: `4000`
-- Convex: `4001`
-- Convex site: `4002`
-- Desktop HMR: `4003`
+Portless assigns an available upstream port to each application and package UI when it
+starts. The public HTTPS names stay stable even when two projects run simultaneously.
+Separate projects must use different npm scopes so their public names do not collide;
+Git worktrees receive automatic route prefixes. Use `portless list` to inspect the
+current assignments.
 
-#### Infra
+#### Infrastructure Ports
 
-Infra runs in the 8000-8999 range.
+Docker infrastructure retains fixed host ports and can still conflict across projects:
 
 - Redis: `8000`
 - Database: `8001`
 - Minio: `8002` (S3), `8003` (console)
-- Workflows (Inngest): `8004`
 
 ### Troubleshooting
 
@@ -129,3 +139,7 @@ Infra runs in the 8000-8999 range.
 - Node version mismatch: install Node.js `>=24` with your version manager.
 - Docker services not running: check `docker ps`, then run `bun run docker:up`.
 - Missing env variables: compare `.env.local` with each `.env.template`.
+- Portless trust or DNS problems: run `portless doctor`, then follow its suggested
+  `portless trust` or `portless hosts sync` command.
+- `.localhost` is available only on the development machine. Expo on a physical device
+  requires Portless LAN mode and a `.local` hostname.
diff --git a/docs/template-commands.md b/docs/template-commands.md
index c5b93459..6f850eac 100644
--- a/docs/template-commands.md
+++ b/docs/template-commands.md
@@ -11,6 +11,7 @@ Configure a newly created project. This command:
 - Prompts for the apps and packages to keep
 - Sets the project name, which is also used as the package scope
 - Rewrites `@init/` references with the project name
+- Sets package-local Portless route names from the normalized package scope
 - Stamps `.template.json` with the source template, commit, and creation time
 
 ```bash
@@ -19,7 +20,8 @@ bun template setup
 
 ### `bun template rename`
 
-Rename the project and rewrite its `@init/` package scope references.
+Rename the project, rewrite its package scope references, and update its Portless
+hostnames.
 
 ```bash
 bun template rename --name <name> [--scope <scope>]
@@ -27,7 +29,8 @@ bun template rename --name <name> [--scope <scope>]
 
 ### `bun template add app <name>`
 
-Copy an app workspace from the template using Turbo generators, then apply the project's package scope.
+Copy an app workspace from the template using Turbo generators, apply the project's
+package scope, and restore its Portless route configuration.
 
 ```bash
 bun template add app web
@@ -35,7 +38,8 @@ bun template add app web
 
 ### `bun template add package <name>`
 
-Copy a package workspace from the template using Turbo generators, then apply the project's package scope.
+Copy a package workspace from the template using Turbo generators, apply the project's
+package scope, and restore its Portless route configuration when it owns a local UI.
 
 ```bash
 bun template add package auth
diff --git a/infra/local/docker-compose.yml b/infra/local/docker-compose.yml
index 8171e279..32bb595d 100644
--- a/infra/local/docker-compose.yml
+++ b/infra/local/docker-compose.yml
@@ -57,14 +57,3 @@ services:
       - >
         mc alias set local http://minio:9000 minioadmin minioadmin &&
         mc mb --ignore-existing local/assets
-
-  inngest:
-    image: inngest/inngest:v1.16.0
-    command: "inngest dev -u http://host.docker.internal:3000/workflows --poll-interval 60" # Check for new workflows every 60 seconds
-    ports:
-      - "8004:8288"
-    healthcheck:
-      test: ["CMD", "curl", "--fail", "--silent", "http://localhost:8288/health"]
-      interval: 5s
-      timeout: 3s
-      retries: 20
diff --git a/package.json b/package.json
index acedb85f..da272b30 100644
--- a/package.json
+++ b/package.json
@@ -25,7 +25,7 @@
     "dev:apps": "turbo run dev --filter=!@init/*",
     "dev:packages": "turbo run dev --filter=@init/*",
     "docker:down": "docker compose -f infra/local/docker-compose.yml down",
-    "docker:up": "docker compose -f infra/local/docker-compose.yml up -d",
+    "docker:up": "docker compose -f infra/local/docker-compose.yml up -d --remove-orphans",
     "fix": "adamantite fix",
     "fix:monorepo": "adamantite monorepo --fix",
     "format": "adamantite format",
@@ -48,6 +48,7 @@
     "oxfmt": "0.60.0",
     "oxlint": "1.75.0",
     "oxlint-tsgolint": "7.0.2001",
+    "portless": "0.15.5",
     "sherif": "1.13.0",
     "turbo": "2.10.7",
     "typescript": "7.0.2",
@@ -80,6 +81,7 @@
     "@sentry/cli",
     "@tailwindcss/oxide",
     "docs",
-    "extension"
+    "extension",
+    "inngest-cli"
   ]
 }
diff --git a/packages/db/package.json b/packages/db/package.json
index be75b0b3..930b1de2 100644
--- a/packages/db/package.json
+++ b/packages/db/package.json
@@ -15,7 +15,8 @@
   "scripts": {
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
-    "dev": "bun --bun drizzle-kit studio",
+    "dev": "portless",
+    "dev:app": "bun --bun drizzle-kit studio --port ${PORT:-4983}",
     "generate": "bun --bun drizzle-kit generate",
     "migrate": "bun --bun drizzle-kit migrate",
     "push": "bun --bun drizzle-kit push",
@@ -35,5 +36,9 @@
     "drizzle-seed": "0.3.1",
     "postgres": "3.4.8",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "db.init",
+    "script": "dev:app"
   }
 }
diff --git a/packages/email/package.json b/packages/email/package.json
index ac717a9a..8e6cb4f7 100644
--- a/packages/email/package.json
+++ b/packages/email/package.json
@@ -11,7 +11,8 @@
     "build": "email build --dir src/templates",
     "bump:deps": "bun update --interactive",
     "clean": "git clean -xdf .cache .turbo dist node_modules",
-    "dev": "email dev --dir src/templates --port 4000",
+    "dev": "portless",
+    "dev:app": "email dev --dir src/templates --port ${PORT:-4000}",
     "export": "email export --dir src/templates"
   },
   "dependencies": {
@@ -32,5 +33,9 @@
     "react": "19.1.0",
     "react-email": "6.9.1",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "email.init",
+    "script": "dev:app"
   }
 }
diff --git a/packages/env/src/presets.ts b/packages/env/src/presets.ts
index f0f5a85a..b951bdb4 100644
--- a/packages/env/src/presets.ts
+++ b/packages/env/src/presets.ts
@@ -114,6 +114,15 @@ export const kv = () =>
     skipValidation: isCI,
   })
 
+export const portless = () =>
+  createEnv({
+    runtimeEnv: env,
+    server: {
+      PORTLESS_URL: z.url().optional(),
+    },
+    skipValidation: isCI,
+  })
+
 export const resend = () =>
   createEnv({
     runtimeEnv: env,
diff --git a/packages/workflows/package.json b/packages/workflows/package.json
index 6ff05261..1ee06872 100644
--- a/packages/workflows/package.json
+++ b/packages/workflows/package.json
@@ -14,7 +14,9 @@
   },
   "scripts": {
     "bump:deps": "bun update --interactive",
-    "clean": "git clean -xdf .cache .turbo dist node_modules"
+    "clean": "git clean -xdf .cache .turbo dist node_modules",
+    "dev": "portless",
+    "dev:app": "inngest dev --port ${PORT:-8288} --connect-executor-grpc-port $(( ${PORT:-8288} + 10000 )) --connect-gateway-grpc-port $(( ${PORT:-8288} + 11000 )) --connect-gateway-port $(( ${PORT:-8288} + 12000 )) -u ${INNGEST_API_URL:-https://api.init.localhost/workflows} --poll-interval 60"
   },
   "dependencies": {
     "@init/observability": "workspace:*",
@@ -23,6 +25,11 @@
   },
   "devDependencies": {
     "@tooling/tsconfig": "workspace:*",
+    "inngest-cli": "1.40.0",
     "typescript": "7.0.2"
+  },
+  "portless": {
+    "name": "workflows.init",
+    "script": "dev:app"
   }
 }
diff --git a/scripts/template/add.ts b/scripts/template/add.ts
index ac7f6877..d4183c0d 100644
--- a/scripts/template/add.ts
+++ b/scripts/template/add.ts
@@ -2,6 +2,7 @@ import { join } from "node:path"
 import consola from "consola"
 
 import { defineCommand } from "../utils"
+import { restorePortlessWorkspaces } from "./portless"
 import { renameProject } from "./rename"
 import {
   getDependencyNames,
@@ -159,6 +160,7 @@ export default defineCommand({
     }
 
     const copiedPaths = await addWorkspaces(rootDir, scope, [target], new Set([targetPath]))
+    await restorePortlessWorkspaces(rootDir, copiedPaths, scope)
     consola.success(`Added ${copiedPaths.join(", ")}. Run bun install to link the new workspaces.`)
   },
 })
diff --git a/scripts/template/portless.ts b/scripts/template/portless.ts
new file mode 100644
index 00000000..5726b438
--- /dev/null
+++ b/scripts/template/portless.ts
@@ -0,0 +1,66 @@
+import { join, relative } from "node:path"
+
+import { getWorkspaces, readJson, writeJson } from "./shared"
+
+export function getWorkspaceRouteName(workspacePath: string, projectName: string) {
+  const normalizedWorkspacePath = workspacePath.replaceAll("\\", "/")
+  if (normalizedWorkspacePath === "apps/app") return projectName
+
+  const workspaceName = normalizedWorkspacePath.split("/").at(-1)
+  return workspaceName ? `${workspaceName}.${projectName}` : projectName
+}
+
+async function updateWorkspacePackageName(
+  rootDir: string,
+  workspacePath: string,
+  projectName: string
+) {
+  const packageJsonPath = join(rootDir, workspacePath, "package.json")
+  if (!(await Bun.file(packageJsonPath).exists())) return null
+
+  const packageJson = await readJson(packageJsonPath)
+  const portless = packageJson.portless as { name?: string } | undefined
+  if (!portless) return null
+
+  const routeName = getWorkspaceRouteName(workspacePath, projectName)
+  if (portless.name === routeName) return null
+
+  portless.name = routeName
+  await writeJson(packageJsonPath, packageJson)
+
+  return packageJsonPath
+}
+
+async function updateWorkspaceNames(
+  rootDir: string,
+  workspacePaths: string[],
+  projectName: string
+) {
+  const changedFiles = await Promise.all(
+    workspacePaths.map((workspacePath) =>
+      updateWorkspacePackageName(rootDir, workspacePath, projectName)
+    )
+  )
+
+  return changedFiles.filter((path): path is string => path !== null)
+}
+
+export async function updatePortlessProjectName(rootDir: string, projectName: string) {
+  const workspaces = await Promise.all([
+    getWorkspaces(rootDir, "app"),
+    getWorkspaces(rootDir, "package"),
+  ])
+  const workspacePaths = workspaces
+    .flat()
+    .map((workspace) => relative(rootDir, workspace.directory))
+
+  return updateWorkspaceNames(rootDir, workspacePaths, projectName)
+}
+
+export async function restorePortlessWorkspaces(
+  rootDir: string,
+  workspacePaths: string[],
+  projectName: string
+) {
+  return updateWorkspaceNames(rootDir, workspacePaths, projectName)
+}
diff --git a/scripts/template/rename.ts b/scripts/template/rename.ts
index e3df3e06..ab6f07ef 100644
--- a/scripts/template/rename.ts
+++ b/scripts/template/rename.ts
@@ -2,6 +2,7 @@ import { join, resolve } from "node:path"
 import consola from "consola"
 
 import { defineCommand } from "../utils"
+import { updatePortlessProjectName } from "./portless"
 import {
   checkIsPathWithinRoot,
   getProjectScope,
@@ -32,23 +33,35 @@ export async function renameProject({
 }: RenameOptions): Promise<RenameResult> {
   const normalizedScope = normalizeScope(scope)
   const normalizedSourceScope = normalizeScope(sourceScope)
-  const changedFiles = await replaceTextInFiles(
-    rootDir,
-    getScopePrefix(normalizedSourceScope),
-    getScopePrefix(normalizedScope)
+  const changedFiles = new Set(
+    await replaceTextInFiles(
+      rootDir,
+      getScopePrefix(normalizedSourceScope),
+      getScopePrefix(normalizedScope)
+    )
   )
 
-  if (!projectName) return { changedFiles }
+  for (const path of await replaceTextInFiles(
+    rootDir,
+    `${normalizedSourceScope}.localhost`,
+    `${normalizedScope}.localhost`
+  ))
+    changedFiles.add(path)
+
+  if (!projectName) return { changedFiles: [...changedFiles] }
+
+  for (const path of await updatePortlessProjectName(rootDir, normalizedScope))
+    changedFiles.add(path)
 
   const packageJsonPath = join(rootDir, "package.json")
   const packageJson = await readJson(packageJsonPath)
-  if (packageJson.name === projectName) return { changedFiles }
-
-  packageJson.name = projectName
-  await writeJson(packageJsonPath, packageJson)
-  changedFiles.push(packageJsonPath)
+  if (packageJson.name !== projectName) {
+    packageJson.name = projectName
+    await writeJson(packageJsonPath, packageJson)
+    changedFiles.add(packageJsonPath)
+  }
 
-  return { changedFiles }
+  return { changedFiles: [...changedFiles] }
 }
 
 export default defineCommand({
diff --git a/turbo/generators/commands/files-client.ts b/turbo/generators/commands/files-client.ts
index 8c55f83b..91260781 100644
--- a/turbo/generators/commands/files-client.ts
+++ b/turbo/generators/commands/files-client.ts
@@ -103,7 +103,7 @@ export function registerFilesClientGenerator(plop: PlopTypes.NodePlopAPI): void
         type: "list",
       },
       {
-        default: "http://localhost:3000/files",
+        default: "https://api.init.localhost/files",
         message: "What is the Files SDK endpoint?",
         name: "endpoint",
         type: "input",
diff --git a/turbo/generators/templates/backend-clients/hono/app/env.hbs b/turbo/generators/templates/backend-clients/hono/app/env.hbs
index 32bb380d..9e4d7bb1 100644
--- a/turbo/generators/templates/backend-clients/hono/app/env.hbs
+++ b/turbo/generators/templates/backend-clients/hono/app/env.hbs
@@ -1,2 +1,2 @@
 # --- Hono API ---
-PUBLIC_API_URL="http://localhost:3000"
+PUBLIC_API_URL="https://api.init.localhost"
diff --git a/turbo/generators/templates/backend-clients/hono/desktop/env.hbs b/turbo/generators/templates/backend-clients/hono/desktop/env.hbs
index 32bb380d..9e4d7bb1 100644
--- a/turbo/generators/templates/backend-clients/hono/desktop/env.hbs
+++ b/turbo/generators/templates/backend-clients/hono/desktop/env.hbs
@@ -1,2 +1,2 @@
 # --- Hono API ---
-PUBLIC_API_URL="http://localhost:3000"
+PUBLIC_API_URL="https://api.init.localhost"
diff --git a/turbo/generators/templates/backend-clients/hono/mobile/env.hbs b/turbo/generators/templates/backend-clients/hono/mobile/env.hbs
index fd08f176..b0cfa272 100644
--- a/turbo/generators/templates/backend-clients/hono/mobile/env.hbs
+++ b/turbo/generators/templates/backend-clients/hono/mobile/env.hbs
@@ -1,2 +1,2 @@
 # --- Hono API ---
-EXPO_PUBLIC_API_URL="http://localhost:3000"
+EXPO_PUBLIC_API_URL="https://api.init.localhost"