diff --git a/packages/client/src/generated/types.ts b/packages/client/src/generated/types.ts
index 21ee2cffddb..4873a9c4559 100644
--- a/packages/client/src/generated/types.ts
+++ b/packages/client/src/generated/types.ts
@@ -664,6 +664,7 @@ export type SessionContextOutput = {
         readonly time: { readonly created: number }
         readonly sessionID: string
         readonly text: string
+        readonly description?: string
         readonly type: "synthetic"
       }
     | {
@@ -932,6 +933,7 @@ export type SessionHistoryOutput = {
           readonly sessionID: string
           readonly messageID: string
           readonly text: string
+          readonly description?: string
         }
       }
     | {
@@ -1425,6 +1427,7 @@ export type SessionEventsOutput =
         readonly sessionID: string
         readonly messageID: string
         readonly text: string
+        readonly description?: string
       }
     }
   | {
@@ -1824,6 +1827,7 @@ export type SessionMessageOutput = {
         readonly time: { readonly created: number }
         readonly sessionID: string
         readonly text: string
+        readonly description?: string
         readonly type: "synthetic"
       }
     | {
@@ -2004,6 +2008,7 @@ export type MessageListOutput = {
         readonly time: { readonly created: number }
         readonly sessionID: string
         readonly text: string
+        readonly description?: string
         readonly type: "synthetic"
       }
     | {
@@ -3523,6 +3528,7 @@ export type EventSubscribeOutput =
         readonly sessionID: string
         readonly messageID: string
         readonly text: string
+        readonly description?: string
       }
     }
   | {
@@ -3983,6 +3989,14 @@ export type EventSubscribeOutput =
       readonly location?: { readonly directory: string; readonly workspaceID?: string }
       readonly data: { readonly projectID: string }
     }
+  | {
+      readonly id: string
+      readonly metadata?: { readonly [x: string]: unknown }
+      readonly type: "skill.updated"
+      readonly durable?: { readonly aggregateID: string; readonly seq: number; readonly version: number }
+      readonly location?: { readonly directory: string; readonly workspaceID?: string }
+      readonly data: {}
+    }
   | {
       readonly id: string
       readonly metadata?: { readonly [x: string]: unknown }
diff --git a/packages/core/src/filesystem/watcher.ts b/packages/core/src/filesystem/watcher.ts
index 6d4bb1c3262..e4f3bce2851 100644
--- a/packages/core/src/filesystem/watcher.ts
+++ b/packages/core/src/filesystem/watcher.ts
@@ -6,6 +6,7 @@ import type ParcelWatcher from "@parcel/watcher"
 import { makeLocationNode } from "../effect/app-node"
 import { Cause, Context, Effect, Layer } from "effect"
 import { FileSystemWatcher } from "@opencode-ai/schema/filesystem-watcher"
+import os from "os"
 import path from "path"
 import { Config } from "../config"
 import { EventV2 } from "../event"
@@ -57,10 +58,14 @@ export class Service extends Context.Service<Service, Interface>()("@opencode/v2
 export const layer = Layer.effect(
   Service,
   Effect.gen(function* () {
-    if (yield* Flag.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER) return Service.of({})
+    if (Flag.OPENCODE_DISABLE_FILEWATCHER) return Service.of({})
 
     const backend = getBackend()
     const location = yield* Location.Service
+    if (path.resolve(location.directory) === path.resolve(os.homedir())) {
+      yield* Effect.logInfo("watcher skipped home directory", { directory: location.directory })
+      return Service.of({})
+    }
     if (!backend) {
       yield* Effect.logError("watcher backend not supported", {
         directory: location.directory,
@@ -84,6 +89,7 @@ export const layer = Layer.effect(
     )
 
     const callback: ParcelWatcher.SubscribeCallback = (_error, updates) => {
+      if (_error) runFork(Effect.logError("watcher callback failed", { error: _error }))
       for (const update of updates) {
         if (update.type === "create") runFork(events.publish(Event.Updated, { file: update.path, event: "add" }))
         if (update.type === "update") runFork(events.publish(Event.Updated, { file: update.path, event: "change" }))
@@ -94,7 +100,11 @@ export const layer = Layer.effect(
     const subscribe = (directory: string, ignore: string[]) => {
       const pending = w.subscribe(directory, callback, { ignore, backend })
       return Effect.promise(() => pending).pipe(
-        Effect.tap((subscription) => Effect.sync(() => subscriptions.push(subscription))),
+        Effect.tap((subscription) =>
+          Effect.sync(() => subscriptions.push(subscription)).pipe(
+            Effect.andThen(Effect.logInfo("watcher subscribed", { directory, backend, ignores: ignore.length })),
+          ),
+        ),
         Effect.timeout(SUBSCRIBE_TIMEOUT_MS),
         Effect.catchCause((cause) => {
           pending.then((subscription) => subscription.unsubscribe()).catch(() => {})
@@ -106,11 +116,9 @@ export const layer = Layer.effect(
     const config = (yield* (yield* Config.Service).entries())
       .filter((entry): entry is Config.Document => entry.type === "document")
       .flatMap((item) => item.info.watcher?.ignore ?? [])
-    if (yield* Flag.OPENCODE_EXPERIMENTAL_FILEWATCHER) {
-      yield* Effect.forkScoped(
-        subscribe(location.directory, [...Ignore.PATTERNS, ...config, ...protecteds(location.directory)]),
-      )
-    }
+    yield* Effect.forkScoped(
+      subscribe(location.directory, [...Ignore.PATTERNS, ...config, ...protecteds(location.directory)]),
+    )
 
     if (location.vcs?.type === "git") {
       const resolved = (yield* git.repo.discover(location.directory))?.gitDirectory
diff --git a/packages/core/src/flag/flag.ts b/packages/core/src/flag/flag.ts
index a0eb78a13e2..1c975040dc6 100644
--- a/packages/core/src/flag/flag.ts
+++ b/packages/core/src/flag/flag.ts
@@ -32,14 +32,9 @@ export const Flag = {
   OPENCODE_SERVER_PASSWORD: process.env["OPENCODE_SERVER_PASSWORD"],
   OPENCODE_SERVER_USERNAME: process.env["OPENCODE_SERVER_USERNAME"],
   OPENCODE_DISABLE_FFF: fff === undefined ? process.platform === "win32" : truthy("OPENCODE_DISABLE_FFF"),
+  OPENCODE_DISABLE_FILEWATCHER: truthy("OPENCODE_DISABLE_FILEWATCHER"),
 
   // Experimental
-  OPENCODE_EXPERIMENTAL_FILEWATCHER: Config.boolean("OPENCODE_EXPERIMENTAL_FILEWATCHER").pipe(
-    Config.withDefault(false),
-  ),
-  OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER: Config.boolean("OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER").pipe(
-    Config.withDefault(false),
-  ),
   OPENCODE_EXPERIMENTAL_DISABLE_COPY_ON_SELECT:
     copy === undefined ? process.platform === "win32" : truthy("OPENCODE_EXPERIMENTAL_DISABLE_COPY_ON_SELECT"),
   OPENCODE_MODELS_URL: process.env["OPENCODE_MODELS_URL"],
diff --git a/packages/core/src/session.ts b/packages/core/src/session.ts
index 252f9ca0b22..d5e139bc590 100644
--- a/packages/core/src/session.ts
+++ b/packages/core/src/session.ts
@@ -39,6 +39,7 @@ import { Revert } from "@opencode-ai/schema/revert"
 import { FSUtil } from "./fs-util"
 import { SessionDurable } from "@opencode-ai/schema/durable-event-manifest"
 import { SkillV2 } from "./skill"
+import { Job } from "./job"
 
 export const RevertState = Revert.State
 export type RevertState = Revert.State
@@ -191,9 +192,14 @@ export interface Interface {
   ) => Effect.Effect<void, NotFoundError | BusyError | MessageDecodeError | OperationUnavailableError>
   readonly wait: (id: SessionSchema.ID) => Effect.Effect<void, NotFoundError>
   readonly active: Effect.Effect<ReadonlySet<SessionSchema.ID>>
+  readonly background: (sessionID: SessionSchema.ID) => Effect.Effect<void, NotFoundError>
   readonly resume: (sessionID: SessionSchema.ID) => Effect.Effect<void, NotFoundError | SessionRunner.RunError>
   readonly interrupt: (sessionID: SessionSchema.ID) => Effect.Effect<void>
-  readonly synthetic: (input: { sessionID: SessionSchema.ID; text: string }) => Effect.Effect<void, NotFoundError>
+  readonly synthetic: (input: {
+    sessionID: SessionSchema.ID
+    text: string
+    description?: string
+  }) => Effect.Effect<void, NotFoundError>
   readonly revert: {
     readonly stage: (input: {
       sessionID: SessionSchema.ID
@@ -217,6 +223,7 @@ export const layer = Layer.effect(
     const execution = yield* SessionExecution.Service
     const store = yield* SessionStore.Service
     const locations = yield* LocationServiceMap.Service
+    const jobs = yield* Job.Service
     const scope = yield* Scope.Scope
     const decodeMessage = Schema.decodeUnknownEffect(SessionMessage.Message)
     const isDurableSessionEvent = Schema.is(SessionEvent.Durable)
@@ -512,6 +519,22 @@ export const layer = Layer.effect(
         yield* execution.awaitIdle(sessionID)
       }),
       active: execution.active,
+      background: Effect.fn("V2Session.background")(function* (sessionID) {
+        yield* result.get(sessionID)
+        const backgrounded = yield* jobs.backgroundAll({ sessionID })
+        if (backgrounded.length === 0) return
+        yield* result.synthetic({
+          sessionID,
+          text: [
+            "User requested that active blocking work be moved to the background.",
+            "",
+            "Backgrounded work:",
+            ...backgrounded.map((job) => `- ${job.type}: ${job.title && job.title.length > 0 ? job.title : job.id}`),
+            "",
+            "The backgrounded work is still unfinished. Move on to other work if you can. If there is nothing else useful to do, finish your response. Do not wait, sleep, poll, or report the backgrounded work as complete until a later completion notification is added to the conversation.",
+          ].join("\n"),
+        })
+      }),
       resume: Effect.fn("V2Session.resume")(function* (sessionID) {
         yield* result.get(sessionID)
         yield* execution.resume(sessionID)
@@ -523,6 +546,7 @@ export const layer = Layer.effect(
           messageID: SessionMessage.ID.create(),
           timestamp: yield* DateTime.now,
           text: input.text,
+          description: input.description,
         })
         yield* execution.resume(input.sessionID).pipe(Effect.ignore, Effect.forkIn(scope, { startImmediately: true }), Effect.asVoid)
       }),
@@ -587,6 +611,7 @@ export const node = makeGlobalNode({
   service: Service,
   layer: layer.pipe(Layer.orDie),
   deps: [
+    Job.node,
     Database.node,
     EventV2.node,
     ProjectV2.node,
diff --git a/packages/core/src/session/message-updater.ts b/packages/core/src/session/message-updater.ts
index 1e124980478..5b63031c959 100644
--- a/packages/core/src/session/message-updater.ts
+++ b/packages/core/src/session/message-updater.ts
@@ -153,6 +153,7 @@ export function update(adapter: Adapter, event: SessionEvent.Event) {
           SessionMessage.Synthetic.make({
             sessionID: event.data.sessionID,
             text: event.data.text,
+            description: event.data.description,
             id: event.data.messageID,
             type: "synthetic",
             time: { created: event.data.timestamp },
diff --git a/packages/core/src/skill.ts b/packages/core/src/skill.ts
index cb8ce271c59..eeafe608856 100644
--- a/packages/core/src/skill.ts
+++ b/packages/core/src/skill.ts
@@ -2,10 +2,12 @@ export * as SkillV2 from "./skill"
 
 import { makeLocationNode } from "./effect/app-node"
 import path from "path"
-import { Context, Effect, Layer, Schema, Types } from "effect"
+import { Context, Effect, Layer, Schema, Stream, Types } from "effect"
+import { FileSystemWatcher } from "@opencode-ai/schema/filesystem-watcher"
 import { Skill } from "@opencode-ai/schema/skill"
 import { AgentV2 } from "./agent"
 import { ConfigMarkdown } from "./config/markdown"
+import { EventV2 } from "./event"
 import { FSUtil } from "./fs-util"
 import { PermissionV2 } from "./permission"
 import { AbsolutePath } from "./schema"
@@ -27,6 +29,8 @@ export type Source = typeof Source.Type
 export const Info = Skill.Info
 export type Info = Skill.Info
 
+export const Event = Skill.Event
+
 export const available = (skills: ReadonlyArray<Info>, agent: AgentV2.Info) =>
   skills.filter((skill) => PermissionV2.evaluate("skill", skill.name, agent.permissions).effect !== "deny")
 
@@ -58,6 +62,7 @@ export const layer = Layer.effect(
   Effect.gen(function* () {
     const discovery = yield* SkillDiscovery.Service
     const fs = yield* FSUtil.Service
+    const events = yield* EventV2.Service
 
     const state = State.create<Data, Draft>({
       initial: () => ({ sources: [] }),
@@ -72,7 +77,15 @@ export const layer = Layer.effect(
 
     const load = Effect.fn("SkillV2.load")(function* (source: Source) {
       const skills: Info[] = []
-      if (source.type === "embedded") return [source.skill]
+      if (source.type === "embedded") {
+        yield* Effect.logDebug("skill source loaded", {
+          source: Source.key(source),
+          type: source.type,
+          directories: [],
+          skills: [source.skill.name],
+        })
+        return { skills: [source.skill], directories: [] }
+      }
       const directories = source.type === "directory" ? [source.path] : yield* discovery.pull(source.url)
       for (const directory of directories) {
         const files = yield* fs
@@ -101,19 +114,42 @@ export const layer = Layer.effect(
           })
         }
       }
-      return skills
+      yield* Effect.logDebug("skill source loaded", {
+        source: Source.key(source),
+        type: source.type,
+        directories,
+        skills: skills.map((skill) => skill.name),
+      })
+      return { skills, directories }
     })
 
-    // QUESTION(Dax): Should local skill sources invalidate on filesystem watch
-    // events, following the reload policy chosen for other context sources?
-    const cache = new Map<string, Info[]>()
+    const cache = new Map<string, { skills: Info[]; directories: readonly string[] }>()
+    const invalidate = Effect.fn("SkillV2.invalidateFromWatcher")(function* (file: string) {
+      const invalidated = Array.from(cache.entries()).filter(([, loaded]) =>
+        loaded.directories.some((directory) => FSUtil.contains(directory, file)),
+      )
+      if (invalidated.length === 0) return
+      for (const [key] of invalidated) cache.delete(key)
+      yield* Effect.logInfo("skill cache invalidated", {
+        file,
+        sources: invalidated.map(([key]) => key),
+        skills: invalidated.flatMap(([, loaded]) => loaded.skills.map((skill) => skill.name)),
+      })
+      yield* events.publish(Event.Updated, {}).pipe(Effect.asVoid)
+    })
+
+    yield* events.subscribe(FileSystemWatcher.Event.Updated).pipe(
+      Stream.runForEach((event) => invalidate(event.data.file)),
+      Effect.forkScoped({ startImmediately: true }),
+    )
+
     const list = Effect.fn("SkillV2.list")(function* () {
       const skills = new Map<string, Info>()
       for (const source of state.get().sources) {
         const key = Source.key(source)
         const loaded = cache.get(key) ?? (yield* load(source))
         cache.set(key, loaded)
-        for (const skill of loaded) skills.set(skill.name, skill)
+        for (const skill of loaded.skills) skills.set(skill.name, skill)
       }
       return Array.from(skills.values())
     })
@@ -131,4 +167,4 @@ export const layer = Layer.effect(
 
 export const locationLayer = layer.pipe(Layer.provide(SkillDiscovery.defaultLayer))
 
-export const node = makeLocationNode({ service: Service, layer, deps: [SkillDiscovery.node, FSUtil.node] })
+export const node = makeLocationNode({ service: Service, layer, deps: [SkillDiscovery.node, FSUtil.node, EventV2.node] })
diff --git a/packages/core/test/filesystem/watcher.test.ts b/packages/core/test/filesystem/watcher.test.ts
index a189442e8b1..118f099dad7 100644
--- a/packages/core/test/filesystem/watcher.test.ts
+++ b/packages/core/test/filesystem/watcher.test.ts
@@ -2,7 +2,7 @@ import { $ } from "bun"
 import { describe, expect } from "bun:test"
 import fs from "fs/promises"
 import path from "path"
-import { ConfigProvider, Deferred, Duration, Effect, Fiber, Layer, Option, Stream } from "effect"
+import { Deferred, Duration, Effect, Fiber, Layer, Option, Stream } from "effect"
 import { Config } from "@opencode-ai/core/config"
 import { EventV2 } from "@opencode-ai/core/event"
 import { FSUtil } from "@opencode-ai/core/fs-util"
@@ -27,13 +27,6 @@ const configLayer = Layer.succeed(
   }),
 )
 
-const flagsLayer = ConfigProvider.layer(
-  ConfigProvider.fromUnknown({
-    OPENCODE_EXPERIMENTAL_FILEWATCHER: "true",
-    OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER: "false",
-  }),
-)
-
 function provide(directory: string, vcs?: Location.Interface["vcs"]) {
   const locationLayer = Layer.succeed(
     Location.Service,
@@ -44,7 +37,6 @@ function provide(directory: string, vcs?: Location.Interface["vcs"]) {
       Layer.provide(configLayer),
       Layer.provide(Git.defaultLayer),
       Layer.provide(locationLayer),
-      Layer.provide(flagsLayer),
     ),
   )
 }
diff --git a/packages/core/test/move-session.test.ts b/packages/core/test/move-session.test.ts
index 07f1459335a..b70bcd8f406 100644
--- a/packages/core/test/move-session.test.ts
+++ b/packages/core/test/move-session.test.ts
@@ -9,6 +9,7 @@ import { Database } from "@opencode-ai/core/database/database"
 import { FSUtil } from "@opencode-ai/core/fs-util"
 import { Git } from "@opencode-ai/core/git"
 import { EventV2 } from "@opencode-ai/core/event"
+import { Job } from "@opencode-ai/core/job"
 import { Project } from "@opencode-ai/core/project"
 import { ProjectTable } from "@opencode-ai/core/project/sql"
 import { ProjectDirectories } from "@opencode-ai/core/project/directories"
@@ -29,6 +30,7 @@ const project = Project.layer.pipe(
   Layer.provide(ProjectDirectories.defaultLayer),
 )
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(Database.defaultLayer),
   Layer.provide(EventV2.defaultLayer),
diff --git a/packages/core/test/permission.test.ts b/packages/core/test/permission.test.ts
index dca9f8ead4b..b63bdef8883 100644
--- a/packages/core/test/permission.test.ts
+++ b/packages/core/test/permission.test.ts
@@ -3,6 +3,7 @@ import { Deferred, Effect, Fiber, Layer } from "effect"
 import { AgentV2 } from "@opencode-ai/core/agent"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
+import { Job } from "@opencode-ai/core/job"
 import { Location } from "@opencode-ai/core/location"
 import { PermissionV2 } from "@opencode-ai/core/permission"
 import { PermissionTable } from "@opencode-ai/core/permission/sql"
@@ -24,6 +25,7 @@ const current = Layer.succeed(
   Location.Service.of(location({ directory: AbsolutePath.make("/project") })),
 )
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
diff --git a/packages/core/test/session-compact.test.ts b/packages/core/test/session-compact.test.ts
index a877624906c..35db267d8a8 100644
--- a/packages/core/test/session-compact.test.ts
+++ b/packages/core/test/session-compact.test.ts
@@ -4,6 +4,7 @@ import { OpenAIChat } from "@opencode-ai/llm/protocols"
 import { Config } from "@opencode-ai/core/config"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
+import { Job } from "@opencode-ai/core/job"
 import { Location } from "@opencode-ai/core/location"
 import { LocationServiceMap } from "@opencode-ai/core/location-service-map"
 import type { LocationServices } from "@opencode-ai/core/location-services"
@@ -60,6 +61,7 @@ const locations = Layer.effect(
   ),
 )
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locations),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
diff --git a/packages/core/test/session-create.test.ts b/packages/core/test/session-create.test.ts
index aaff515d12f..aff3fa1b0e5 100644
--- a/packages/core/test/session-create.test.ts
+++ b/packages/core/test/session-create.test.ts
@@ -6,6 +6,7 @@ import { asc, eq } from "drizzle-orm"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
 import { EventTable } from "@opencode-ai/core/event/sql"
+import { Job } from "@opencode-ai/core/job"
 import { Location } from "@opencode-ai/core/location"
 import { ModelV2 } from "@opencode-ai/core/model"
 import { ProjectV2 } from "@opencode-ai/core/project"
@@ -36,6 +37,7 @@ const projects = Layer.succeed(
   }),
 )
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
@@ -182,11 +184,9 @@ describe("SessionV2.create", () => {
       expect((yield* session.context(parent.id)).map((message) => message.type)).toEqual(["user", "synthetic", "user"])
       expect((yield* session.context(forked.id)).map((message) => message.type)).toEqual(["user", "synthetic", "user"])
       expect((yield* session.context(forked.id)).at(-1)).toMatchObject({ text: "Child continues" })
-      expect((yield* session.history({ sessionID: forked.id, limit: 10 })).events.map((event) => event.durable?.seq)).toEqual([
-        0,
-        4,
-        5,
-      ])
+      expect(
+        (yield* session.history({ sessionID: forked.id, limit: 10 })).events.map((event) => event.durable?.seq),
+      ).toEqual([0, 4, 5])
       expect(yield* SessionInput.find(db, admitted.id)).toMatchObject({ sessionID: parent.id })
     }),
   )
diff --git a/packages/core/test/session-history.test.ts b/packages/core/test/session-history.test.ts
index 9fbfb786d3b..1323ed5fc5a 100644
--- a/packages/core/test/session-history.test.ts
+++ b/packages/core/test/session-history.test.ts
@@ -2,6 +2,7 @@ import { describe, expect } from "bun:test"
 import { Effect, Layer, Schema } from "effect"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
+import { Job } from "@opencode-ai/core/job"
 import { Location } from "@opencode-ai/core/location"
 import { locationServiceMapLayer } from "@opencode-ai/core/location-services"
 import { ProjectV2 } from "@opencode-ai/core/project"
@@ -23,6 +24,7 @@ const projects = Layer.succeed(
   }),
 )
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
diff --git a/packages/core/test/session-prompt.test.ts b/packages/core/test/session-prompt.test.ts
index 666e9d2fde5..86558f728ab 100644
--- a/packages/core/test/session-prompt.test.ts
+++ b/packages/core/test/session-prompt.test.ts
@@ -4,6 +4,7 @@ import { eq } from "drizzle-orm"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
 import { EventTable } from "@opencode-ai/core/event/sql"
+import { Job } from "@opencode-ai/core/job"
 import { SessionEvent } from "@opencode-ai/core/session/event"
 import { ModelV2 } from "@opencode-ai/core/model"
 import { ProviderV2 } from "@opencode-ai/core/provider"
@@ -45,6 +46,7 @@ const execution = Layer.succeed(
   }),
 )
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
@@ -114,7 +116,11 @@ const eventCount = (type: string) =>
 
 const encodeMessage = Schema.encodeSync(SessionMessage.Message)
 const assistantRow = (id: SessionMessage.ID, seq: number) => {
-  const { id: _, type, ...data } = encodeMessage(
+  const {
+    id: _,
+    type,
+    ...data
+  } = encodeMessage(
     SessionMessage.Assistant.make({
       id,
       type: "assistant",
diff --git a/packages/core/test/session-runner-recorded.test.ts b/packages/core/test/session-runner-recorded.test.ts
index 82be33fcc70..74f325207c7 100644
--- a/packages/core/test/session-runner-recorded.test.ts
+++ b/packages/core/test/session-runner-recorded.test.ts
@@ -5,6 +5,7 @@ import { Auth, LLMClient, RequestExecutor } from "@opencode-ai/llm/route"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
 import { EventTable } from "@opencode-ai/core/event/sql"
+import { Job } from "@opencode-ai/core/job"
 import { PermissionV2 } from "@opencode-ai/core/permission"
 import { AgentV2 } from "@opencode-ai/core/agent"
 import { Config } from "@opencode-ai/core/config"
@@ -111,6 +112,7 @@ const execution = Layer.effect(
   }),
 ).pipe(Layer.provide(runner))
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
diff --git a/packages/core/test/session-runner.test.ts b/packages/core/test/session-runner.test.ts
index 23c2e5099dc..5ba16da802b 100644
--- a/packages/core/test/session-runner.test.ts
+++ b/packages/core/test/session-runner.test.ts
@@ -12,6 +12,7 @@ import {
 import * as OpenAIChat from "@opencode-ai/llm/protocols/openai-chat"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
+import { Job } from "@opencode-ai/core/job"
 import { PermissionV2 } from "@opencode-ai/core/permission"
 import { EventTable } from "@opencode-ai/core/event/sql"
 import { Project } from "@opencode-ai/core/project"
@@ -266,6 +267,7 @@ const execution = Layer.effect(
   }),
 ).pipe(Layer.provide(runner))
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
diff --git a/packages/core/test/session-wait.test.ts b/packages/core/test/session-wait.test.ts
index cd8399a534c..b2d0b545f95 100644
--- a/packages/core/test/session-wait.test.ts
+++ b/packages/core/test/session-wait.test.ts
@@ -2,6 +2,7 @@ import { describe, expect } from "bun:test"
 import { Effect, Layer } from "effect"
 import { Database } from "@opencode-ai/core/database/database"
 import { EventV2 } from "@opencode-ai/core/event"
+import { Job } from "@opencode-ai/core/job"
 import { Location } from "@opencode-ai/core/location"
 import { ProjectV2 } from "@opencode-ai/core/project"
 import { AbsolutePath } from "@opencode-ai/core/schema"
@@ -21,6 +22,7 @@ const execution = Layer.mock(SessionExecution.Service, {
   awaitIdle: (sessionID) => Effect.sync(() => awaited.push(sessionID)),
 })
 const sessions = SessionV2.layer.pipe(
+  Layer.provide(Job.layer),
   Layer.provide(locationServiceMapLayer),
   Layer.provide(EventV2.defaultLayer),
   Layer.provide(Database.defaultLayer),
diff --git a/packages/core/test/skill.test.ts b/packages/core/test/skill.test.ts
index 94196fd3bda..7b662b388db 100644
--- a/packages/core/test/skill.test.ts
+++ b/packages/core/test/skill.test.ts
@@ -1,14 +1,16 @@
 import fs from "fs/promises"
 import path from "path"
 import { describe, expect } from "bun:test"
-import { Effect, Layer } from "effect"
+import { Deferred, Effect, Fiber, Layer, Stream } from "effect"
 import { AgentV2 } from "@opencode-ai/core/agent"
 import { AppNodeBuilder } from "@opencode-ai/core/effect/app-node-builder"
 import { LayerNode } from "@opencode-ai/core/effect/layer-node"
+import { EventV2 } from "@opencode-ai/core/event"
 import { FSUtil } from "@opencode-ai/core/fs-util"
 import { AbsolutePath } from "@opencode-ai/core/schema"
 import { SkillV2 } from "@opencode-ai/core/skill"
 import { SkillDiscovery } from "@opencode-ai/core/skill/discovery"
+import { FileSystemWatcher } from "@opencode-ai/schema/filesystem-watcher"
 import { tmpdir } from "./fixture/tmpdir"
 import { testEffect } from "./lib/effect"
 
@@ -24,7 +26,7 @@ const discovery = Layer.succeed(
   }),
 )
 const it = testEffect(
-  AppNodeBuilder.build(LayerNode.group([SkillV2.node, AgentV2.node]), [
+  AppNodeBuilder.build(LayerNode.group([SkillV2.node, AgentV2.node, EventV2.node]), [
     LayerNode.replace(SkillDiscovery.layer, discovery),
   ]),
 )
@@ -40,6 +42,19 @@ description: ${description}
   )
 }
 
+function waitForSkillUpdate() {
+  return Effect.gen(function* () {
+    const events = yield* EventV2.Service
+    const deferred = yield* Deferred.make<void>()
+    const fiber = yield* events.subscribe(SkillV2.Event.Updated).pipe(
+      Stream.runForEach(() => Deferred.succeed(deferred, undefined).pipe(Effect.asVoid)),
+      Effect.forkScoped,
+    )
+    yield* Effect.yieldNow
+    return { deferred, fiber }
+  })
+}
+
 describe("SkillV2", () => {
   it.live("registers sources and resolves later source precedence", () =>
     Effect.acquireRelease(
@@ -124,4 +139,41 @@ describe("SkillV2", () => {
       ),
     ),
   )
+
+  it.live("invalidates cached skills and publishes updates for watcher changes", () =>
+    Effect.acquireRelease(
+      Effect.promise(() => tmpdir()),
+      (tmp) => Effect.promise(() => tmp[Symbol.asyncDispose]()),
+    ).pipe(
+      Effect.flatMap((tmp) =>
+        Effect.gen(function* () {
+          yield* Effect.promise(async () => {
+            await fs.mkdir(path.join(tmp.path, "deploy"), { recursive: true })
+            await write(tmp.path, "deploy", "Initial deploy")
+          })
+
+          const events = yield* EventV2.Service
+          const skill = yield* SkillV2.Service
+          yield* skill.transform((editor) => editor.source({ type: "directory", path: AbsolutePath.make(tmp.path) }))
+
+          expect((yield* skill.list()).find((item) => item.name === "deploy")?.description).toBe("Initial deploy")
+
+          const file = path.join(tmp.path, "deploy", "SKILL.md")
+          yield* Effect.promise(() => write(tmp.path, "deploy", "Updated deploy"))
+          expect((yield* skill.list()).find((item) => item.name === "deploy")?.description).toBe("Initial deploy")
+
+          yield* Effect.acquireUseRelease(
+            waitForSkillUpdate(),
+            ({ deferred }) =>
+              events
+                .publish(FileSystemWatcher.Event.Updated, { file, event: "change" })
+                .pipe(Effect.andThen(Deferred.await(deferred)), Effect.timeout("1 second")),
+            ({ fiber }) => Fiber.interrupt(fiber),
+          )
+
+          expect((yield* skill.list()).find((item) => item.name === "deploy")?.description).toBe("Updated deploy")
+        }),
+      ),
+    ),
+  )
 })
diff --git a/packages/desktop/src/main/server.ts b/packages/desktop/src/main/server.ts
index b213dbc82a2..75ff5029287 100644
--- a/packages/desktop/src/main/server.ts
+++ b/packages/desktop/src/main/server.ts
@@ -46,7 +46,6 @@ export function preferAppEnv(userDataPath: string) {
   Object.assign(process.env, {
     ...(shell ? loadShellEnv(shell, getLogger()) : null),
     OPENCODE_EXPERIMENTAL_ICON_DISCOVERY: "true",
-    OPENCODE_EXPERIMENTAL_FILEWATCHER: "true",
     OPENCODE_CLIENT: "desktop",
     XDG_STATE_HOME: process.env.XDG_STATE_HOME ?? userDataPath,
   })
diff --git a/packages/desktop/src/main/wsl/sidecar.ts b/packages/desktop/src/main/wsl/sidecar.ts
index 522e575a47e..850b6494791 100644
--- a/packages/desktop/src/main/wsl/sidecar.ts
+++ b/packages/desktop/src/main/wsl/sidecar.ts
@@ -29,7 +29,7 @@ export async function spawnWslSidecar(
     'PATH=$(awk -v RS=: -v ORS=: \'$0 !~ /^\\/mnt\\//\' <<<"$PATH" | sed "s/:$//")',
     "export PATH",
     "export WSLENV=",
-    "export OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER=true",
+    "export OPENCODE_DISABLE_FILEWATCHER=true",
     "export OPENCODE_CLIENT=desktop",
     `export OPENCODE_SERVER_USERNAME=${shellEscape(username)}`,
     `export OPENCODE_SERVER_PASSWORD=${shellEscape(password)}`,
diff --git a/packages/schema/src/event-manifest.ts b/packages/schema/src/event-manifest.ts
index 1adfba0290b..5e8a2871f34 100644
--- a/packages/schema/src/event-manifest.ts
+++ b/packages/schema/src/event-manifest.ts
@@ -23,6 +23,7 @@ import { QuestionV1 } from "./question-v1.js"
 import { Reference } from "./reference.js"
 import { ServerEvent } from "./server-event.js"
 import { Shell } from "./shell.js"
+import { Skill } from "./skill.js"
 import { SessionCompactionEvent } from "./session-compaction-event.js"
 import { SessionEvent } from "./session-event.js"
 import { SessionStatusEvent } from "./session-status-event.js"
@@ -52,6 +53,7 @@ const featureDefinitions = Event.inventory(
   ...Permission.Event.Definitions,
   ...Plugin.Event.Definitions,
   ...ProjectDirectories.Event.Definitions,
+  ...Skill.Event.Definitions,
   ...FileSystemWatcher.Event.Definitions,
   ...Pty.Event.Definitions,
   ...Shell.Event.Definitions,
diff --git a/packages/schema/src/session-event.ts b/packages/schema/src/session-event.ts
index ae955f47695..fde5dd60142 100644
--- a/packages/schema/src/session-event.ts
+++ b/packages/schema/src/session-event.ts
@@ -137,6 +137,7 @@ export const Synthetic = Event.define({
     ...Base,
     messageID: SessionMessage.ID,
     text: Schema.String,
+    description: Schema.String.pipe(optional),
   },
 })
 export type Synthetic = typeof Synthetic.Type
diff --git a/packages/schema/src/session-message.ts b/packages/schema/src/session-message.ts
index 318dbfa9c7e..457cf872063 100644
--- a/packages/schema/src/session-message.ts
+++ b/packages/schema/src/session-message.ts
@@ -55,6 +55,7 @@ export const Synthetic = Schema.Struct({
   ...Base,
   sessionID: SessionID,
   text: Schema.String,
+  description: Schema.String.pipe(optional),
   type: Schema.Literal("synthetic"),
 }).annotate({ identifier: "Session.Message.Synthetic" })
 
diff --git a/packages/schema/src/skill.ts b/packages/schema/src/skill.ts
index ec654bff217..30099b7a901 100644
--- a/packages/schema/src/skill.ts
+++ b/packages/schema/src/skill.ts
@@ -3,6 +3,7 @@ export * as Skill from "./skill.js"
 import { Schema } from "effect"
 import { optional } from "./schema.js"
 import { AbsolutePath } from "./schema.js"
+import { define, inventory } from "./event.js"
 
 export interface DirectorySource extends Schema.Schema.Type<typeof DirectorySource> {}
 export const DirectorySource = Schema.Struct({
@@ -25,6 +26,9 @@ export const Info = Schema.Struct({
   content: Schema.String,
 }).annotate({ identifier: "SkillV2.Info" })
 
+const Updated = define({ type: "skill.updated", schema: {} })
+export const Event = { Updated, Definitions: inventory(Updated) }
+
 export interface EmbeddedSource extends Schema.Schema.Type<typeof EmbeddedSource> {}
 export const EmbeddedSource = Schema.Struct({
   type: Schema.Literal("embedded"),
diff --git a/packages/sdk/js/src/v2/gen/types.gen.ts b/packages/sdk/js/src/v2/gen/types.gen.ts
index 938f916ca2c..7da625990d3 100644
--- a/packages/sdk/js/src/v2/gen/types.gen.ts
+++ b/packages/sdk/js/src/v2/gen/types.gen.ts
@@ -63,6 +63,7 @@ export type Event =
   | EventPermissionV2Replied
   | EventPluginAdded
   | EventProjectDirectoriesUpdated
+  | EventSkillUpdated
   | EventFileWatcherUpdated
   | EventPtyCreated
   | EventPtyUpdated
@@ -940,6 +941,7 @@ export type GlobalEvent = {
           sessionID: string
           messageID: string
           text: string
+          description?: string
         }
       }
     | {
@@ -1354,6 +1356,13 @@ export type GlobalEvent = {
           projectID: string
         }
       }
+    | {
+        id: string
+        type: "skill.updated"
+        properties: {
+          [key: string]: unknown
+        }
+      }
     | {
         id: string
         type: "file.watcher.updated"
@@ -3037,6 +3046,7 @@ export type V2Event =
   | PermissionV2Replied
   | PluginAdded
   | ProjectDirectoriesUpdated
+  | SkillUpdated
   | FileWatcherUpdated
   | PtyCreated
   | PtyUpdated
@@ -3607,6 +3617,7 @@ export type SyncEventSessionNextSynthetic = {
       sessionID: string
       messageID: string
       text: string
+      description?: string
     }
   }
 }
@@ -4210,6 +4221,7 @@ export type SessionMessageSynthetic = {
   }
   sessionID: string
   text: string
+  description?: string
   type: "synthetic"
 }
 
@@ -4570,6 +4582,7 @@ export type SessionNextSynthetic = {
     sessionID: string
     messageID: string
     text: string
+    description?: string
   }
 }
 
@@ -5861,6 +5874,23 @@ export type ProjectDirectoriesUpdated = {
   }
 }
 
+export type SkillUpdated = {
+  id: string
+  metadata?: {
+    [key: string]: unknown
+  }
+  type: "skill.updated"
+  durable?: {
+    aggregateID: string
+    seq: number
+    version: number
+  }
+  location?: LocationRef
+  data: {
+    [key: string]: unknown
+  }
+}
+
 export type FileWatcherUpdated = {
   id: string
   metadata?: {
@@ -6774,6 +6804,7 @@ export type EventSessionNextSynthetic = {
     sessionID: string
     messageID: string
     text: string
+    description?: string
   }
 }
 
@@ -7226,6 +7257,14 @@ export type EventProjectDirectoriesUpdated = {
   }
 }
 
+export type EventSkillUpdated = {
+  id: string
+  type: "skill.updated"
+  properties: {
+    [key: string]: unknown
+  }
+}
+
 export type EventFileWatcherUpdated = {
   id: string
   type: "file.watcher.updated"
diff --git a/packages/server/src/handlers/session.ts b/packages/server/src/handlers/session.ts
index c41374522bc..15788fd6ece 100644
--- a/packages/server/src/handlers/session.ts
+++ b/packages/server/src/handlers/session.ts
@@ -3,7 +3,6 @@ import { DateTime, Effect, Stream } from "effect"
 import { HttpApiBuilder, HttpApiSchema } from "effect/unstable/httpapi"
 import { Api } from "../api"
 import { SessionsCursor } from "@opencode-ai/protocol/groups/session"
-import { Job } from "@opencode-ai/core/job"
 import {
   ConflictError,
   InvalidCursorError,
@@ -22,7 +21,6 @@ const DefaultSessionHistoryLimit = 50
 export const SessionHandler = HttpApiBuilder.group(Api, "server.session", (handlers) =>
   Effect.gen(function* () {
     const session = yield* SessionV2.Service
-    const jobs = yield* Job.Service
 
     return handlers
       .handle(
@@ -486,7 +484,7 @@ export const SessionHandler = HttpApiBuilder.group(Api, "server.session", (handl
       .handle(
         "session.background",
         Effect.fn(function* (ctx) {
-          yield* session.get(ctx.params.sessionID).pipe(
+          yield* session.background(ctx.params.sessionID).pipe(
             Effect.catchTag("Session.NotFoundError", (error) =>
               Effect.fail(
                 new SessionNotFoundError({
@@ -496,32 +494,6 @@ export const SessionHandler = HttpApiBuilder.group(Api, "server.session", (handl
               ),
             ),
           )
-          const backgrounded = yield* jobs.backgroundAll({ sessionID: ctx.params.sessionID })
-          if (backgrounded.length > 0)
-            yield* session
-              .synthetic({
-                sessionID: ctx.params.sessionID,
-                text: [
-                  "User requested that active blocking work be moved to the background.",
-                  "",
-                  "Backgrounded work:",
-                  ...backgrounded.map(
-                    (job) => `- ${job.type}: ${job.title && job.title.length > 0 ? job.title : job.id}`,
-                  ),
-                  "",
-                  "The backgrounded work is still unfinished. Move on to other work if you can. If there is nothing else useful to do, finish your response. Do not wait, sleep, poll, or report the backgrounded work as complete until a later completion notification is added to the conversation.",
-                ].join("\n"),
-              })
-              .pipe(
-                Effect.catchTag("Session.NotFoundError", (error) =>
-                  Effect.fail(
-                    new SessionNotFoundError({
-                      sessionID: error.sessionID,
-                      message: `Session not found: ${error.sessionID}`,
-                    }),
-                  ),
-                ),
-              )
           return HttpApiSchema.NoContent.make()
         }),
       )
diff --git a/packages/tui/src/context/data.tsx b/packages/tui/src/context/data.tsx
index 1589e93f92f..f8e89931426 100644
--- a/packages/tui/src/context/data.tsx
+++ b/packages/tui/src/context/data.tsx
@@ -163,6 +163,9 @@ export const { use: useData, provider: DataProvider } = createSimpleContext({
         case "agent.updated":
           void result.location.agent.refresh(event.location)
           break
+        case "skill.updated":
+          void result.location.skill.refresh(event.location)
+          break
         case "session.next.agent.switched":
           if (store.session.info[event.data.sessionID])
             setStore("session", "info", event.data.sessionID, "agent", event.data.agent)
@@ -248,6 +251,7 @@ export const { use: useData, provider: DataProvider } = createSimpleContext({
               type: "synthetic",
               sessionID: event.data.sessionID,
               text: event.data.text,
+              description: event.data.description,
               time: { created: event.data.timestamp },
             })
           })
diff --git a/packages/tui/src/routes/session/index.tsx b/packages/tui/src/routes/session/index.tsx
index 459c48553ba..17c4d76cb4f 100644
--- a/packages/tui/src/routes/session/index.tsx
+++ b/packages/tui/src/routes/session/index.tsx
@@ -1250,13 +1250,14 @@ function SessionSwitchMessageV2(props: { message: SessionMessage }) {
 function SessionNoticeMessageV2(props: { message: SessionMessage }) {
   const { theme } = useTheme()
   const text = () => {
-    if (props.message.type === "system" || props.message.type === "synthetic") return props.message.text
+    if (props.message.type === "system") return "Instructions updated"
+    if (props.message.type === "synthetic") return props.message.description ?? ""
     return ""
   }
   return (
-    <box paddingLeft={3}>
-      <text fg={theme.textMuted}>{text()}</text>
-    </box>
+    <InlineToolRow icon="◈" color={theme.textMuted} pending="Notice" complete={true}>
+      {text()}
+    </InlineToolRow>
   )
 }
 
diff --git a/packages/tui/src/routes/session/rows.ts b/packages/tui/src/routes/session/rows.ts
index 3b21eec0cfd..b489404f4fa 100644
--- a/packages/tui/src/routes/session/rows.ts
+++ b/packages/tui/src/routes/session/rows.ts
@@ -119,7 +119,9 @@ export function createSessionRows(sessionID: Accessor<string>) {
     data.on("session.next.prompt.admitted", message),
     data.on("session.next.prompted", message),
     data.on("session.next.context.updated", message),
-    data.on("session.next.synthetic", message),
+    data.on("session.next.synthetic", (event) => {
+      if (event.data.sessionID === sessionID() && event.data.description?.trim()) appendMessage(event.data.messageID)
+    }),
     data.on("session.next.shell.started", message),
     data.on("session.next.agent.switched", message),
     data.on("session.next.model.switched", message),
@@ -160,6 +162,7 @@ export function createSessionRows(sessionID: Accessor<string>) {
 export function reduceSessionRows(messages: SessionMessage[]) {
   return messages.reduce<SessionRow[]>((rows, message) => {
     if (message.type !== "assistant") {
+      if (message.type === "synthetic" && !message.description?.trim()) return rows
       completePrevious(rows)
       rows.push({ type: "message", messageID: message.id })
       return rows
diff --git a/packages/tui/test/cli/tui/session-rows.test.ts b/packages/tui/test/cli/tui/session-rows.test.ts
index d6a804625f1..fec6f5eb871 100644
--- a/packages/tui/test/cli/tui/session-rows.test.ts
+++ b/packages/tui/test/cli/tui/session-rows.test.ts
@@ -122,6 +122,66 @@ test("completes exploration groups when another row follows", () => {
   ])
 })
 
+test("hides synthetic messages without descriptions", () => {
+  const messages: SessionMessage[] = [
+    assistant("assistant-1", [{ type: "tool", id: "read-1", name: "read", state: pending(), time: { created: 1 } }]),
+    {
+      type: "synthetic",
+      id: "synthetic-1",
+      sessionID: "session-1",
+      text: "internal context",
+      time: { created: 2 },
+    },
+    assistant("assistant-2", [{ type: "tool", id: "grep-1", name: "grep", state: pending(), time: { created: 3 } }]),
+  ]
+
+  expect(reduceSessionRows(messages)).toEqual([
+    {
+      type: "group",
+      kind: "exploration",
+      pending: [],
+      completed: false,
+      refs: [
+        { messageID: "assistant-1", partID: "read-1" },
+        { messageID: "assistant-2", partID: "grep-1" },
+      ],
+    },
+  ])
+})
+
+test("renders synthetic messages with descriptions", () => {
+  const messages: SessionMessage[] = [
+    assistant("assistant-1", [{ type: "tool", id: "read-1", name: "read", state: pending(), time: { created: 1 } }]),
+    {
+      type: "synthetic",
+      id: "synthetic-1",
+      sessionID: "session-1",
+      text: "internal context",
+      description: "Explicit notice",
+      time: { created: 2 },
+    },
+    assistant("assistant-2", [{ type: "tool", id: "grep-1", name: "grep", state: pending(), time: { created: 3 } }]),
+  ]
+
+  expect(reduceSessionRows(messages)).toEqual([
+    {
+      type: "group",
+      kind: "exploration",
+      pending: [],
+      completed: true,
+      refs: [{ messageID: "assistant-1", partID: "read-1" }],
+    },
+    { type: "message", messageID: "synthetic-1" },
+    {
+      type: "group",
+      kind: "exploration",
+      pending: [],
+      completed: false,
+      refs: [{ messageID: "assistant-2", partID: "grep-1" }],
+    },
+  ])
+})
+
 function assistant(id: string, content: SessionMessageAssistant["content"]): SessionMessageAssistant {
   return {
     type: "assistant",