diff --git a/cli/src/__tests__/cloud.test.ts b/cli/src/__tests__/cloud.test.ts
index 0c5aeae8b6d..a863978df21 100644
--- a/cli/src/__tests__/cloud.test.ts
+++ b/cli/src/__tests__/cloud.test.ts
@@ -14,7 +14,7 @@ import {
   normalizedContentHash,
   type LocalUpstreamExportBundle,
 } from "../commands/client/cloud-transfer.js";
-import { getCloudConnection } from "../commands/client/cloud-store.js";
+import { getCloudConnection, resolveCloudConnectionStorePath } from "../commands/client/cloud-store.js";
 
 const originalEnv = { ...process.env };
 const originalFetch = globalThis.fetch;
@@ -75,6 +75,11 @@ describe("cloud CLI helpers", () => {
 
     expect(connection.accessToken).toBe("upt_test");
     expect(getCloudConnection("https://cloud.example.test")?.token.id).toBe("token-1");
+    const rawStore = fs.readFileSync(resolveCloudConnectionStorePath(), "utf8");
+    expect(rawStore).not.toContain("upt_test");
+    expect(rawStore).not.toContain("PRIVATE KEY");
+    expect(rawStore).toContain("accessTokenMaterial");
+    expect(rawStore).toContain("privateKeyMaterial");
   });
 
   it("hard-blocks incompatible transfer schema versions with the stable schema exit code", () => {
@@ -116,6 +121,31 @@ describe("cloud CLI helpers", () => {
     expect(chunkBodies[0]).toEqual(chunkBodies[2]);
     expect(chunkBodies[1]).toEqual(chunkBodies[3]);
   });
+
+  it("uses the manifest-only request shape for CLI previews", async () => {
+    const bundle = await buildTestBundle();
+    const calls: Array<{ path: string; body: unknown }> = [];
+    const coordinator = new LocalUpstreamPushCoordinator({
+      targetOrigin: "https://cloud.example.test",
+      paperclipCompanyId: "target-company-1",
+      fetch: async (url, init) => {
+        const parsed = new URL(String(url));
+        calls.push({ path: parsed.pathname, body: init?.body ? JSON.parse(String(init.body)) as unknown : {} });
+        return jsonResponse({ warnings: [], conflicts: [] });
+      },
+    });
+
+    await coordinator.preview(bundle);
+
+    expect(calls).toHaveLength(1);
+    expect(calls[0]?.path).toBe("/api/companies/target-company-1/upstream-imports/preview");
+    expect(calls[0]?.body).toMatchObject({
+      manifest: bundle.manifest,
+      previewShape: "manifest_only",
+      conflictKeysBySource: {},
+    });
+    expect(calls[0]?.body).not.toHaveProperty("entities");
+  });
 });
 
 async function buildTestBundle(): Promise<LocalUpstreamExportBundle> {
diff --git a/cli/src/commands/client/cloud-store.ts b/cli/src/commands/client/cloud-store.ts
index fa63c7133b0..9d18151d0f8 100644
--- a/cli/src/commands/client/cloud-store.ts
+++ b/cli/src/commands/client/cloud-store.ts
@@ -1,3 +1,4 @@
+import { createCipheriv, createDecipheriv, randomBytes } from "node:crypto";
 import fs from "node:fs";
 import path from "node:path";
 import { resolvePaperclipInstanceRoot } from "../../config/home.js";
@@ -39,6 +40,13 @@ interface CloudConnectionStore {
   currentConnectionId?: string;
 }
 
+interface EncryptedCloudCredential {
+  scheme: "local_encrypted_v1";
+  iv: string;
+  tag: string;
+  ciphertext: string;
+}
+
 function defaultStore(): CloudConnectionStore {
   return {
     version: 1,
@@ -76,7 +84,7 @@ export function writeCloudConnectionStore(
   storePath = resolveCloudConnectionStorePath(),
 ): void {
   fs.mkdirSync(path.dirname(storePath), { recursive: true });
-  fs.writeFileSync(storePath, `${JSON.stringify(store, null, 2)}\n`, { mode: 0o600 });
+  fs.writeFileSync(storePath, `${JSON.stringify(serializeStore(store), null, 2)}\n`, { mode: 0o600 });
 }
 
 export function upsertCloudConnection(
@@ -130,11 +138,11 @@ function normalizeConnection(value: unknown): CloudConnection | null {
   const targetHost = stringValue(record.targetHost);
   const stackId = stringValue(record.stackId);
   const targetCompanyId = stringValue(record.targetCompanyId);
-  const accessToken = stringValue(record.accessToken);
+  const accessToken = readCredential(record, "accessToken", "accessTokenMaterial");
   const token = typeof record.token === "object" && record.token !== null && !Array.isArray(record.token)
     ? record.token as CloudConnectionTokenRecord
     : null;
-  const privateKeyPem = stringValue(record.privateKeyPem);
+  const privateKeyPem = readCredential(record, "privateKeyPem", "privateKeyMaterial");
   const sourcePublicKey = stringValue(record.sourcePublicKey);
   const sourceInstanceId = stringValue(record.sourceInstanceId);
   const sourceInstanceFingerprint = stringValue(record.sourceInstanceFingerprint);
@@ -175,3 +183,117 @@ function stringValue(value: unknown): string | null {
 function stringArray(value: unknown): string[] {
   return Array.isArray(value) ? value.filter((entry): entry is string => typeof entry === "string") : [];
 }
+
+function readCredential(record: Record<string, unknown>, plaintextKey: string, materialKey: string): string | null {
+  const material = record[materialKey];
+  if (material && typeof material === "object" && !Array.isArray(material)) {
+    try {
+      return decryptCredential(material as Record<string, unknown>);
+    } catch {
+      return null;
+    }
+  }
+  return stringValue(record[plaintextKey]);
+}
+
+function serializeStore(store: CloudConnectionStore): Record<string, unknown> {
+  const connections: Record<string, unknown> = {};
+  for (const [id, connection] of Object.entries(store.connections)) {
+    connections[id] = serializeConnection(connection);
+  }
+  return {
+    version: 1,
+    connections,
+    ...(store.currentConnectionId ? { currentConnectionId: store.currentConnectionId } : {}),
+  };
+}
+
+function serializeConnection(connection: CloudConnection): Record<string, unknown> {
+  const { accessToken, privateKeyPem, ...rest } = connection;
+  return {
+    ...rest,
+    accessTokenMaterial: encryptCredential(accessToken),
+    privateKeyMaterial: encryptCredential(privateKeyPem),
+  };
+}
+
+function encryptCredential(value: string): EncryptedCloudCredential {
+  const iv = randomBytes(12);
+  const key = loadOrCreateCredentialKey();
+  const cipher = createCipheriv("aes-256-gcm", key, iv);
+  const ciphertext = Buffer.concat([cipher.update(value, "utf8"), cipher.final()]);
+  return {
+    scheme: "local_encrypted_v1",
+    iv: iv.toString("base64"),
+    tag: cipher.getAuthTag().toString("base64"),
+    ciphertext: ciphertext.toString("base64"),
+  };
+}
+
+function decryptCredential(material: Record<string, unknown>): string {
+  if (
+    material.scheme !== "local_encrypted_v1" ||
+    typeof material.iv !== "string" ||
+    typeof material.tag !== "string" ||
+    typeof material.ciphertext !== "string"
+  ) {
+    throw new Error("Invalid encrypted cloud credential material");
+  }
+  const decipher = createDecipheriv(
+    "aes-256-gcm",
+    loadOrCreateCredentialKey(),
+    Buffer.from(material.iv, "base64"),
+  );
+  decipher.setAuthTag(Buffer.from(material.tag, "base64"));
+  const plain = Buffer.concat([
+    decipher.update(Buffer.from(material.ciphertext, "base64")),
+    decipher.final(),
+  ]);
+  return plain.toString("utf8");
+}
+
+function loadOrCreateCredentialKey(): Buffer {
+  const envKey = process.env.PAPERCLIP_SECRETS_MASTER_KEY;
+  if (envKey?.trim()) {
+    const decoded = decodeCredentialKey(envKey);
+    if (!decoded) throw new Error("Invalid PAPERCLIP_SECRETS_MASTER_KEY");
+    return decoded;
+  }
+
+  const keyPath = path.resolve(
+    process.env.PAPERCLIP_SECRETS_MASTER_KEY_FILE?.trim() ||
+      path.join(resolvePaperclipInstanceRoot(), "secrets", "master.key"),
+  );
+  if (fs.existsSync(keyPath)) {
+    const decoded = decodeCredentialKey(fs.readFileSync(keyPath, "utf8"));
+    if (!decoded) throw new Error(`Invalid secrets master key at ${keyPath}`);
+    return decoded;
+  }
+
+  fs.mkdirSync(path.dirname(keyPath), { recursive: true });
+  const generated = randomBytes(32);
+  fs.writeFileSync(keyPath, generated.toString("base64"), { encoding: "utf8", mode: 0o600 });
+  try {
+    fs.chmodSync(keyPath, 0o600);
+  } catch {
+    // Best effort; the credential store itself is also written 0600.
+  }
+  return generated;
+}
+
+function decodeCredentialKey(raw: string): Buffer | null {
+  const trimmed = raw.trim();
+  if (/^[A-Fa-f0-9]{64}$/.test(trimmed)) {
+    return Buffer.from(trimmed, "hex");
+  }
+  try {
+    const decoded = Buffer.from(trimmed, "base64");
+    if (decoded.length === 32) return decoded;
+  } catch {
+    // ignored
+  }
+  if (Buffer.byteLength(trimmed, "utf8") === 32) {
+    return Buffer.from(trimmed, "utf8");
+  }
+  return null;
+}
diff --git a/cli/src/commands/client/cloud-transfer.ts b/cli/src/commands/client/cloud-transfer.ts
index 9cd1ccbe74a..1c2d41f23e1 100644
--- a/cli/src/commands/client/cloud-transfer.ts
+++ b/cli/src/commands/client/cloud-transfer.ts
@@ -144,7 +144,8 @@ export class LocalUpstreamPushCoordinator {
   async preview(bundle: LocalUpstreamExportBundle): Promise<unknown> {
     return this.post(`/api/companies/${encodeURIComponent(this.#paperclipCompanyId)}/upstream-imports/preview`, {
       manifest: bundle.manifest,
-      entities: bundle.entities,
+      previewShape: "manifest_only",
+      conflictKeysBySource: conflictKeysBySource(bundle.entities),
     });
   }
 
@@ -191,6 +192,21 @@ export class LocalUpstreamPushCoordinator {
   }
 }
 
+function conflictKeysBySource(entities: LocalUpstreamExportEntity[]): Record<string, string[]> {
+  const output: Record<string, string[]> = {};
+  for (const entity of entities) {
+    if (!entity.conflictKeys?.length) continue;
+    output[sourceEntityKeyString(entity.record.key)] = [...entity.conflictKeys];
+  }
+  return output;
+}
+
+function sourceEntityKeyString(key: SourceEntityKey): string {
+  return [key.sourceInstanceId, key.sourceCompanyId, key.sourceEntityType, key.sourceEntityId]
+    .map((part) => encodeURIComponent(part))
+    .join("/");
+}
+
 export function buildLocalUpstreamExportBundle(
   input: BuildLocalUpstreamExportBundleInput,
 ): LocalUpstreamExportBundle {
diff --git a/server/src/services/cloud-upstreams.ts b/server/src/services/cloud-upstreams.ts
index 4043b61e1d3..cf192f9e94e 100644
--- a/server/src/services/cloud-upstreams.ts
+++ b/server/src/services/cloud-upstreams.ts
@@ -340,7 +340,7 @@ export function cloudUpstreamService(db: Db, options: { instanceId?: string } =
       }
       return updateRun(row.id, {
         status: "cancelled",
-        activeStep: "push",
+        activeStep: row.activeStep,
         progressPercent: 100,
         completedAt: new Date(),
         events: [
@@ -500,6 +500,8 @@ export function cloudUpstreamService(db: Db, options: { instanceId?: string } =
       const completedAt = new Date();
       const finalEvents = [
         ...input.initialEvents,
+        event(completedAt.toISOString(), "scan", "completed", "Scanned the local company inventory."),
+        event(completedAt.toISOString(), "preview", "completed", "Generated the transfer manifest."),
         event(completedAt.toISOString(), "push", "completed", "Pushed mapped objects without duplicate creation."),
         event(completedAt.toISOString(), "verify", "completed", "Verified the cloud import ledger and generated a run report."),
         event(completedAt.toISOString(), "activate", "completed", "Activation checklist is ready for manual unpause decisions."),