diff --git a/ui/src/lib/company-export-selection.test.ts b/ui/src/lib/company-export-selection.test.ts
new file mode 100644
index 000000000..91828e4aa
--- /dev/null
+++ b/ui/src/lib/company-export-selection.test.ts
@@ -0,0 +1,41 @@
+import { describe, expect, it } from "vitest";
+import { buildInitialExportCheckedFiles } from "./company-export-selection";
+
+describe("buildInitialExportCheckedFiles", () => {
+  it("checks non-task files and recurring task packages by default", () => {
+    const checked = buildInitialExportCheckedFiles(
+      [
+        "README.md",
+        ".paperclip.yaml",
+        "tasks/one-off/TASK.md",
+        "tasks/recurring/TASK.md",
+        "tasks/recurring/notes.md",
+      ],
+      [
+        { path: "tasks/one-off/TASK.md", recurring: false },
+        { path: "tasks/recurring/TASK.md", recurring: true },
+      ],
+      new Set<string>(),
+    );
+
+    expect(Array.from(checked).sort()).toEqual([
+      ".paperclip.yaml",
+      "README.md",
+      "tasks/recurring/TASK.md",
+      "tasks/recurring/notes.md",
+    ]);
+  });
+
+  it("preserves previous manual selections for one-time tasks", () => {
+    const checked = buildInitialExportCheckedFiles(
+      ["README.md", "tasks/one-off/TASK.md"],
+      [{ path: "tasks/one-off/TASK.md", recurring: false }],
+      new Set(["tasks/one-off/TASK.md"]),
+    );
+
+    expect(Array.from(checked).sort()).toEqual([
+      "README.md",
+      "tasks/one-off/TASK.md",
+    ]);
+  });
+});
diff --git a/ui/src/lib/company-export-selection.ts b/ui/src/lib/company-export-selection.ts
new file mode 100644
index 000000000..2b4d59be8
--- /dev/null
+++ b/ui/src/lib/company-export-selection.ts
@@ -0,0 +1,56 @@
+import type { CompanyPortabilityIssueManifestEntry } from "@paperclipai/shared";
+
+function isTaskPath(filePath: string): boolean {
+  return /(?:^|\/)tasks\//.test(filePath);
+}
+
+function buildRecurringTaskPrefixes(
+  issues: Array<Pick<CompanyPortabilityIssueManifestEntry, "path" | "recurring">>,
+): Set<string> {
+  const prefixes = new Set<string>();
+
+  for (const issue of issues) {
+    if (!issue.recurring) continue;
+
+    const filePath = issue.path.trim();
+    if (!filePath) continue;
+
+    prefixes.add(filePath);
+
+    const lastSlash = filePath.lastIndexOf("/");
+    if (lastSlash >= 0) {
+      prefixes.add(`${filePath.slice(0, lastSlash + 1)}`);
+    }
+  }
+
+  return prefixes;
+}
+
+function isRecurringTaskFile(filePath: string, recurringTaskPrefixes: Set<string>): boolean {
+  for (const prefix of recurringTaskPrefixes) {
+    if (filePath === prefix || filePath.startsWith(prefix)) return true;
+  }
+  return false;
+}
+
+export function buildInitialExportCheckedFiles(
+  filePaths: string[],
+  issues: Array<Pick<CompanyPortabilityIssueManifestEntry, "path" | "recurring">>,
+  previousCheckedFiles: Set<string>,
+): Set<string> {
+  const next = new Set<string>();
+  const recurringTaskPrefixes = buildRecurringTaskPrefixes(issues);
+
+  for (const filePath of filePaths) {
+    if (previousCheckedFiles.has(filePath)) {
+      next.add(filePath);
+      continue;
+    }
+
+    if (!isTaskPath(filePath) || isRecurringTaskFile(filePath, recurringTaskPrefixes)) {
+      next.add(filePath);
+    }
+  }
+
+  return next;
+}
diff --git a/ui/src/pages/CompanyExport.tsx b/ui/src/pages/CompanyExport.tsx
index e0a3f4e7f..298785d9d 100644
--- a/ui/src/pages/CompanyExport.tsx
+++ b/ui/src/pages/CompanyExport.tsx
@@ -17,6 +17,7 @@ import { PageSkeleton } from "../components/PageSkeleton";
 import { MarkdownBody } from "../components/MarkdownBody";
 import { cn } from "../lib/utils";
 import { createZipArchive } from "../lib/zip";
+import { buildInitialExportCheckedFiles } from "../lib/company-export-selection";
 import { getPortableFileDataUrl, getPortableFileText, isPortableImageFile } from "../lib/portable-files";
 import {
   Download,
@@ -34,11 +35,6 @@ import {
   PackageFileTree,
 } from "../components/PackageFileTree";
 
-/** Returns true if the path looks like a task file (e.g. tasks/slug/TASK.md or projects/x/tasks/slug/TASK.md) */
-function isTaskPath(filePath: string): boolean {
-  return /(?:^|\/)tasks\//.test(filePath);
-}
-
 /**
  * Extract the set of agent/project/task slugs that are "checked" based on
  * which file paths are in the checked set.
@@ -588,14 +584,13 @@ export function CompanyExport() {
       }),
     onSuccess: (result) => {
       setExportData(result);
-      setCheckedFiles((prev) => {
-        const next = new Set<string>();
-        for (const filePath of Object.keys(result.files)) {
-          if (prev.has(filePath)) next.add(filePath);
-          else if (!isTaskPath(filePath)) next.add(filePath);
-        }
-        return next;
-      });
+      setCheckedFiles((prev) =>
+        buildInitialExportCheckedFiles(
+          Object.keys(result.files),
+          result.manifest.issues,
+          prev,
+        ),
+      );
       // Expand top-level dirs (except tasks — collapsed by default)
       const tree = buildFileTree(result.files);
       const topDirs = new Set<string>();