diff --git a/.changeset/quiet-cloud-session-timeouts.md b/.changeset/quiet-cloud-session-timeouts.md
new file mode 100644
index 0000000000..eaa5659e08
--- /dev/null
+++ b/.changeset/quiet-cloud-session-timeouts.md
@@ -0,0 +1,7 @@
+---
+"@kilocode/cli": patch
+"@kilocode/kilo-gateway": patch
+"kilo-code": patch
+---
+
+Restore Cloud Agent transcripts in VS Code session previews and stop cloud session previews or continuation from loading indefinitely when a request stalls.
diff --git a/packages/kilo-gateway/src/cloud-sessions.ts b/packages/kilo-gateway/src/cloud-sessions.ts
index fd5e9d4c99..2752073db1 100644
--- a/packages/kilo-gateway/src/cloud-sessions.ts
+++ b/packages/kilo-gateway/src/cloud-sessions.ts
@@ -7,6 +7,7 @@ export interface DrizzleDb {
 }
 
 const INGEST_BASE = process.env.KILO_SESSION_INGEST_URL ?? "https://ingest.kilosessions.ai"
+const TIMEOUT = 30_000
 
 function exportUrl(sessionId: string) {
   return UUID_RE.test(sessionId)
@@ -18,6 +19,7 @@ export type FetchResult = { ok: true; data: any } | { ok: false; status: number;
 
 export async function fetchCloudSession(token: string, sessionId: string): Promise<FetchResult> {
   const response = await fetch(exportUrl(sessionId), {
+    signal: AbortSignal.timeout(TIMEOUT),
     headers: {
       Authorization: `Bearer ${token}`,
       ...buildKiloHeaders(),
@@ -33,6 +35,7 @@ export async function fetchCloudSession(token: string, sessionId: string): Promi
 
 export async function fetchCloudSessionForImport(token: string, sessionId: string): Promise<FetchResult> {
   const response = await fetch(exportUrl(sessionId), {
+    signal: AbortSignal.timeout(TIMEOUT),
     headers: {
       Authorization: `Bearer ${token}`,
       ...buildKiloHeaders(),
diff --git a/packages/kilo-gateway/test/cloud-sessions.test.ts b/packages/kilo-gateway/test/cloud-sessions.test.ts
new file mode 100644
index 0000000000..2c292bb5ef
--- /dev/null
+++ b/packages/kilo-gateway/test/cloud-sessions.test.ts
@@ -0,0 +1,48 @@
+import { describe, expect, test } from "bun:test"
+import { fetchCloudSession, fetchCloudSessionForImport } from "../src/cloud-sessions"
+
+async function expectStalledFetchToTimeOut(run: () => Promise<unknown>) {
+  const fetch = globalThis.fetch
+  const timeout = AbortSignal.timeout
+  let delay: number | undefined
+
+  AbortSignal.timeout = (ms) => {
+    delay = ms
+    const controller = new AbortController()
+    queueMicrotask(() => controller.abort(new DOMException("The operation timed out", "TimeoutError")))
+    return controller.signal
+  }
+  globalThis.fetch = ((_input: RequestInfo | URL, init?: RequestInit) =>
+    new Promise<Response>((_resolve, reject) => {
+      init?.signal?.addEventListener("abort", () => reject(init.signal?.reason), { once: true })
+    })) as typeof globalThis.fetch
+
+  try {
+    const outcome = await Promise.race([
+      run().then(
+        () => "resolved" as const,
+        (err) => {
+          if (err instanceof DOMException && err.name === "TimeoutError") return "timed-out" as const
+          throw err
+        },
+      ),
+      Bun.sleep(50).then(() => "still-pending" as const),
+    ])
+
+    expect(outcome).toBe("timed-out")
+    expect(delay).toBe(30_000)
+  } finally {
+    globalThis.fetch = fetch
+    AbortSignal.timeout = timeout
+  }
+}
+
+describe("cloud session export requests", () => {
+  test("times out a stalled preview request", async () => {
+    await expectStalledFetchToTimeOut(() => fetchCloudSession("token", "session-id"))
+  })
+
+  test("times out a stalled import request", async () => {
+    await expectStalledFetchToTimeOut(() => fetchCloudSessionForImport("token", "session-id"))
+  })
+})
diff --git a/packages/kilo-vscode/script/local-bin.ts b/packages/kilo-vscode/script/local-bin.ts
index 951d0f8ce4..51c50e7c9b 100644
--- a/packages/kilo-vscode/script/local-bin.ts
+++ b/packages/kilo-vscode/script/local-bin.ts
@@ -23,6 +23,7 @@ const kiloVscodeDir = join(import.meta.dir, "..")
 const packagesDir = join(kiloVscodeDir, "..")
 const opencodeDir = join(packagesDir, "opencode")
 const coreDir = join(packagesDir, "core")
+const gatewayDir = join(packagesDir, "kilo-gateway")
 const indexingDir = join(packagesDir, "kilo-indexing")
 
 const targetBinDir = join(kiloVscodeDir, "bin")
@@ -38,8 +39,12 @@ async function cliSourceHash(): Promise<string | null> {
   try {
     const opencodeResult = await $`git log -1 --format=%H -- .`.cwd(opencodeDir).quiet()
     const coreResult = await $`git log -1 --format=%H -- .`.cwd(coreDir).quiet()
+    const gatewayResult = await $`git log -1 --format=%H -- .`.cwd(gatewayDir).quiet()
     const indexingResult = await $`git log -1 --format=%H -- .`.cwd(indexingDir).quiet()
-    return `${opencodeResult.text().trim()}-${coreResult.text().trim()}-${indexingResult.text().trim()}` || null
+    return (
+      `${opencodeResult.text().trim()}-${coreResult.text().trim()}-${gatewayResult.text().trim()}-${indexingResult.text().trim()}` ||
+      null
+    )
   } catch {
     return null
   }
@@ -49,10 +54,12 @@ async function isDirty(): Promise<boolean> {
   try {
     const opencodeResult = await $`git status --porcelain -- .`.cwd(opencodeDir).quiet()
     const coreResult = await $`git status --porcelain -- .`.cwd(coreDir).quiet()
+    const gatewayResult = await $`git status --porcelain -- .`.cwd(gatewayDir).quiet()
     const indexingResult = await $`git status --porcelain -- .`.cwd(indexingDir).quiet()
     return (
       opencodeResult.text().trim().length > 0 ||
       coreResult.text().trim().length > 0 ||
+      gatewayResult.text().trim().length > 0 ||
       indexingResult.text().trim().length > 0
     )
   } catch {
diff --git a/packages/kilo-vscode/src/kilo-provider/handlers/cloud-session.ts b/packages/kilo-vscode/src/kilo-provider/handlers/cloud-session.ts
index 29ce097953..f2cab56fab 100644
--- a/packages/kilo-vscode/src/kilo-provider/handlers/cloud-session.ts
+++ b/packages/kilo-vscode/src/kilo-provider/handlers/cloud-session.ts
@@ -10,6 +10,8 @@ import type { CloudSessionData, EditorContext } from "../../services/cli-backend
 import { getErrorMessage, sessionToWebview, mapCloudSessionMessageToWebviewMessage } from "../../kilo-provider-utils"
 import type { MessageFile } from "../message-files"
 
+const TIMEOUT = 30_000
+
 export interface CloudSessionContext {
   readonly client: KiloClient | null
   currentSession: Session | null
@@ -73,7 +75,7 @@ export async function handleRequestCloudSessionData(ctx: CloudSessionContext, se
   }
 
   try {
-    const result = await ctx.client.kilo.cloud.session.get({ id: sessionId })
+    const result = await ctx.client.kilo.cloud.session.get({ id: sessionId }, { signal: AbortSignal.timeout(TIMEOUT) })
     const data = result.data as CloudSessionData | undefined
     if (!data) {
       ctx.postMessage({
@@ -135,10 +137,13 @@ export async function handleImportAndSend(
   // Step 1: Import the cloud session with fresh IDs
   let session: Session | undefined
   try {
-    const result = await ctx.client.kilo.cloud.session.import({
-      sessionId: cloudSessionId,
-      directory: dir,
-    })
+    const result = await ctx.client.kilo.cloud.session.import(
+      {
+        sessionId: cloudSessionId,
+        directory: dir,
+      },
+      { signal: AbortSignal.timeout(TIMEOUT) },
+    )
     session = result.data as Session | undefined
   } catch (error) {
     console.error("[Kilo New] KiloProvider: ❌ Cloud session import failed:", error)
diff --git a/packages/kilo-vscode/tests/unit/cloud-session-handler.test.ts b/packages/kilo-vscode/tests/unit/cloud-session-handler.test.ts
new file mode 100644
index 0000000000..accf86ee0a
--- /dev/null
+++ b/packages/kilo-vscode/tests/unit/cloud-session-handler.test.ts
@@ -0,0 +1,92 @@
+import { describe, expect, it } from "bun:test"
+import {
+  handleImportAndSend,
+  handleRequestCloudSessionData,
+  type CloudSessionContext,
+} from "../../src/kilo-provider/handlers/cloud-session"
+
+function stalled(options?: { signal?: AbortSignal }) {
+  return new Promise<never>((_resolve, reject) => {
+    options?.signal?.addEventListener("abort", () => reject(options.signal?.reason), { once: true })
+  })
+}
+
+function context(sent: unknown[]) {
+  return {
+    client: {
+      kilo: {
+        cloud: {
+          session: {
+            get: (_params: { id: string }, options?: { signal?: AbortSignal }) => stalled(options),
+            import: (_params: { sessionId: string; directory: string }, options?: { signal?: AbortSignal }) =>
+              stalled(options),
+          },
+        },
+      },
+    },
+    currentSession: null,
+    trackedSessionIds: new Set<string>(),
+    connectionService: { recordMessageSessionId: () => undefined },
+    postMessage: (message: unknown) => sent.push(message),
+    getWorkspaceDirectory: () => "/repo",
+    gatherEditorContext: async () => ({}),
+  } as unknown as CloudSessionContext
+}
+
+describe("cloud session preview handler", () => {
+  it("reports a failure when the CLI preview request stalls", async () => {
+    const timeout = AbortSignal.timeout
+    AbortSignal.timeout = () => {
+      const controller = new AbortController()
+      queueMicrotask(() => controller.abort(new DOMException("The operation timed out", "TimeoutError")))
+      return controller.signal
+    }
+
+    try {
+      const sent: unknown[] = []
+      const outcome = await Promise.race([
+        handleRequestCloudSessionData(context(sent), "cloud-session").then(() => "resolved" as const),
+        Bun.sleep(50).then(() => "still-pending" as const),
+      ])
+
+      expect(outcome).toBe("resolved")
+      expect(sent).toEqual([
+        {
+          type: "cloudSessionImportFailed",
+          cloudSessionId: "cloud-session",
+          error: "The operation timed out",
+        },
+      ])
+    } finally {
+      AbortSignal.timeout = timeout
+    }
+  })
+
+  it("reports a failure when the CLI import request stalls", async () => {
+    const timeout = AbortSignal.timeout
+    AbortSignal.timeout = () => {
+      const controller = new AbortController()
+      queueMicrotask(() => controller.abort(new DOMException("The operation timed out", "TimeoutError")))
+      return controller.signal
+    }
+
+    try {
+      const sent: unknown[] = []
+      const outcome = await Promise.race([
+        handleImportAndSend(context(sent), "cloud-session", "Continue").then(() => "resolved" as const),
+        Bun.sleep(50).then(() => "still-pending" as const),
+      ])
+
+      expect(outcome).toBe("resolved")
+      expect(sent).toEqual([
+        {
+          type: "cloudSessionImportFailed",
+          cloudSessionId: "cloud-session",
+          error: "The operation timed out",
+        },
+      ])
+    } finally {
+      AbortSignal.timeout = timeout
+    }
+  })
+})
diff --git a/packages/opencode/src/kilocode/server/httpapi/groups/kilo-gateway.ts b/packages/opencode/src/kilocode/server/httpapi/groups/kilo-gateway.ts
index 79112d93b2..92012557e8 100644
--- a/packages/opencode/src/kilocode/server/httpapi/groups/kilo-gateway.ts
+++ b/packages/opencode/src/kilocode/server/httpapi/groups/kilo-gateway.ts
@@ -188,35 +188,49 @@ export const TranscriptionResponse = Schema.Struct({
   usage: Schema.optional(Schema.Unknown),
 })
 
-export const CloudMessage = Schema.Struct({
-  info: Schema.Struct({
-    id: Schema.String,
-    sessionID: Schema.String,
-    role: Schema.Literals(["user", "assistant"]),
-    time: Schema.Struct({
-      created: Schema.Finite,
-      completed: Schema.optional(Schema.Finite),
-    }),
+const UnknownRecord = Schema.Record(Schema.String, Schema.Unknown)
+
+export const CloudMessage = Schema.StructWithRest(
+  Schema.Struct({
+    info: Schema.StructWithRest(
+      Schema.Struct({
+        id: Schema.String,
+        sessionID: Schema.String,
+        role: Schema.Literals(["user", "assistant"]),
+        time: Schema.Struct({
+          created: Schema.Finite,
+          completed: Schema.optional(Schema.Finite),
+        }),
+      }),
+      [UnknownRecord],
+    ),
+    parts: Schema.Array(
+      Schema.StructWithRest(
+        Schema.Struct({
+          id: Schema.String,
+          sessionID: Schema.String,
+          messageID: Schema.String,
+          type: Schema.String,
+        }),
+        [UnknownRecord],
+      ),
+    ),
   }),
-  parts: Schema.Array(
-    Schema.Struct({
-      id: Schema.String,
-      sessionID: Schema.String,
-      messageID: Schema.String,
-      type: Schema.String,
-    }),
-  ),
-})
+  [UnknownRecord],
+)
 
 export const CloudSessionData = Schema.Struct({
-  info: Schema.Struct({
-    id: Schema.String,
-    title: Schema.String,
-    time: Schema.Struct({
-      created: Schema.Finite,
-      updated: Schema.Finite,
+  info: Schema.StructWithRest(
+    Schema.Struct({
+      id: Schema.String,
+      title: Schema.String,
+      time: Schema.Struct({
+        created: Schema.Finite,
+        updated: Schema.Finite,
+      }),
     }),
-  }),
+    [UnknownRecord],
+  ),
   messages: Schema.Array(CloudMessage),
 })
 
diff --git a/packages/opencode/test/kilocode/cloud-session-schema.test.ts b/packages/opencode/test/kilocode/cloud-session-schema.test.ts
new file mode 100644
index 0000000000..c45642af9e
--- /dev/null
+++ b/packages/opencode/test/kilocode/cloud-session-schema.test.ts
@@ -0,0 +1,38 @@
+import { describe, expect, test } from "bun:test"
+import { Schema } from "effect"
+import { CloudSessionData } from "../../src/kilocode/server/httpapi/groups/kilo-gateway"
+
+describe("cloud session HTTP schema", () => {
+  test("preserves transcript fields needed by the VS Code preview", () => {
+    const input = {
+      info: {
+        id: "ses_cloud",
+        title: "Cloud transcript",
+        slug: "cloud-transcript",
+        time: { created: 1, updated: 2 },
+      },
+      messages: [
+        {
+          info: {
+            id: "msg_user",
+            sessionID: "ses_cloud",
+            role: "user" as const,
+            agent: "code",
+            time: { created: 3 },
+          },
+          parts: [
+            {
+              id: "prt_text",
+              sessionID: "ses_cloud",
+              messageID: "msg_user",
+              type: "text",
+              text: "Show this cloud message",
+            },
+          ],
+        },
+      ],
+    }
+
+    expect(Schema.encodeUnknownSync(CloudSessionData)(input)).toEqual(input)
+  })
+})
diff --git a/packages/sdk/openapi.json b/packages/sdk/openapi.json
index 6f845c28f5..66750773bf 100644
--- a/packages/sdk/openapi.json
+++ b/packages/sdk/openapi.json
@@ -12025,8 +12025,7 @@
                           "additionalProperties": false
                         }
                       },
-                      "required": ["id", "title", "time"],
-                      "additionalProperties": false
+                      "required": ["id", "title", "time"]
                     },
                     "messages": {
                       "type": "array",
@@ -12060,8 +12059,7 @@
                                 "additionalProperties": false
                               }
                             },
-                            "required": ["id", "sessionID", "role", "time"],
-                            "additionalProperties": false
+                            "required": ["id", "sessionID", "role", "time"]
                           },
                           "parts": {
                             "type": "array",
@@ -12081,13 +12079,11 @@
                                   "type": "string"
                                 }
                               },
-                              "required": ["id", "sessionID", "messageID", "type"],
-                              "additionalProperties": false
+                              "required": ["id", "sessionID", "messageID", "type"]
                             }
                           }
                         },
-                        "required": ["info", "parts"],
-                        "additionalProperties": false
+                        "required": ["info", "parts"]
                       }
                     }
                   },
@@ -12170,7 +12166,6 @@
                     }
                   },
                   "required": ["id", "title", "time"],
-                  "additionalProperties": false,
                   "description": "Imported session info"
                 }
               }