diff --git a/server/commands/documentBatchImporter.js b/server/commands/documentBatchImporter.js
index d0ba6aecc..aa1f12096 100644
--- a/server/commands/documentBatchImporter.js
+++ b/server/commands/documentBatchImporter.js
@@ -4,7 +4,8 @@ import path from "path";
 import File from "formidable/lib/file";
 import invariant from "invariant";
 import JSZip from "jszip";
-import { Collection, User } from "../models";
+import { values, keys } from "lodash";
+import { Attachment, Document, Collection, User } from "../models";
 import attachmentCreator from "./attachmentCreator";
 import documentCreator from "./documentCreator";
 import documentImporter from "./documentImporter";
@@ -25,9 +26,9 @@ export default async function documentBatchImporter({
   const zip = await JSZip.loadAsync(zipData);
 
   // store progress and pointers
-  let attachments = {};
-  let collections = {};
-  let documents = {};
+  let collections: { string: Collection } = {};
+  let documents: { string: Document } = {};
+  let attachments: { string: Attachment } = {};
 
   // this is so we can use async / await a little easier
   let folders = [];
@@ -46,9 +47,6 @@ export default async function documentBatchImporter({
       continue;
     }
 
-    // all top level items must be directories representing collections
-    console.log("iterating over", itemPath, depth);
-
     if (depth === 0 && item.dir && name) {
       // check if collection with name exists
       let [collection, isCreated] = await Collection.findOrCreate({
@@ -79,8 +77,9 @@ export default async function documentBatchImporter({
     }
 
     if (depth > 0 && !item.dir && item.name.endsWith(".md")) {
-      const collection = collections[itemDir];
-      invariant(collection, "Collection must exist for document", itemDir);
+      const collectionDir = itemDir.split("/")[0];
+      const collection = collections[collectionDir];
+      invariant(collection, `Collection must exist for document ${itemDir}`);
 
       // we have a document
       const content = await item.async("string");
@@ -98,9 +97,12 @@ export default async function documentBatchImporter({
         ip,
       });
 
-      // must be a nested document, find the parent
+      // must be a nested document, find and reference the parent document
+      let parentDocumentId;
       if (depth > 1) {
-        console.log("nested doc", itemDir);
+        const parentDocument = documents[`${itemDir}.md`] || documents[itemDir];
+        invariant(parentDocument, `Document must exist for parent ${itemDir}`);
+        parentDocumentId = parentDocument.id;
       }
 
       const document = await documentCreator({
@@ -108,7 +110,7 @@ export default async function documentBatchImporter({
         text,
         publish: true,
         collectionId: collection.id,
-        parentDocumentId: undefined,
+        parentDocumentId,
         user,
         ip,
       });
@@ -117,11 +119,6 @@ export default async function documentBatchImporter({
       continue;
     }
 
-    if (depth > 0 && item.dir && name !== "uploads") {
-      // we have a nested document, create if it doesn't exist based on title
-      continue;
-    }
-
     if (depth > 0 && !item.dir && itemPath.includes("uploads")) {
       // we have an attachment
       const buffer = await item.async("nodebuffer");
@@ -139,6 +136,21 @@ export default async function documentBatchImporter({
     console.log(`Skipped ${itemPath}`);
   }
 
+  // All collections, documents, and attachments have been created – time to
+  // update the documents to point to newly uploaded attachments where possible
+  for (const attachmentPath of keys(attachments)) {
+    const attachment = attachments[attachmentPath];
+
+    for (const document of values(documents)) {
+      document.text = document.text
+        .replace(attachmentPath, attachment.redirectUrl)
+        .replace(`/${attachmentPath}`, attachment.redirectUrl);
+
+      // does nothing if the document text is unchanged
+      await document.save();
+    }
+  }
+
   return {
     documents,
     collections,
diff --git a/server/commands/documentBatchImporter.test.js b/server/commands/documentBatchImporter.test.js
index cf97c71a4..53b94d963 100644
--- a/server/commands/documentBatchImporter.test.js
+++ b/server/commands/documentBatchImporter.test.js
@@ -29,7 +29,7 @@ describe("documentBatchImporter", () => {
     });
 
     expect(Object.keys(response.collections).length).toEqual(1);
-    expect(Object.keys(response.documents).length).toEqual(15);
+    expect(Object.keys(response.documents).length).toEqual(8);
     expect(Object.keys(response.attachments).length).toEqual(6);
   });
 });
diff --git a/server/policies/document.js b/server/policies/document.js
index 06356c8b3..203d80551 100644
--- a/server/policies/document.js
+++ b/server/policies/document.js
@@ -8,7 +8,7 @@ const { allow, cannot } = policy;
 
 allow(User, "create", Document);
 
-allow(User, "batchImport", Document, actor => {
+allow(User, "batchImport", Document, (actor) => {
   if (actor.isAdmin) return true;
   throw new AdminRequiredError();
 });
diff --git a/server/test/fixtures/outline.zip b/server/test/fixtures/outline.zip
index bc361a7ad..030598dcb 100644
Binary files a/server/test/fixtures/outline.zip and b/server/test/fixtures/outline.zip differ