diff --git a/server/queues/tasks/ExportDocumentTreeTask.ts b/server/queues/tasks/ExportDocumentTreeTask.ts
index 5bc018963..556bee033 100644
--- a/server/queues/tasks/ExportDocumentTreeTask.ts
+++ b/server/queues/tasks/ExportDocumentTreeTask.ts
@@ -34,6 +34,7 @@ export default abstract class ExportDocumentTreeTask extends ExportTask {
     format: FileOperationFormat;
     pathMap: Map<string, string>;
   }) {
+    Logger.debug("task", `Adding document to archive`, { documentId });
     const document = await Document.findByPk(documentId);
     if (!document) {
       return;
@@ -43,18 +44,27 @@ export default abstract class ExportDocumentTreeTask extends ExportTask {
       format === FileOperationFormat.HTMLZip
         ? await DocumentHelper.toHTML(document, { centered: true })
         : await DocumentHelper.toMarkdown(document);
-    const attachments = await Attachment.findAll({
-      where: {
-        teamId: document.teamId,
-        id: parseAttachmentIds(document.text),
-      },
-    });
+
+    const attachmentIds = parseAttachmentIds(document.text);
+    const attachments = attachmentIds.length
+      ? await Attachment.findAll({
+          where: {
+            teamId: document.teamId,
+            id: attachmentIds,
+          },
+        })
+      : [];
 
     // Add any referenced attachments to the zip file and replace the
     // reference in the document with the path to the attachment in the zip
     await Promise.all(
       attachments.map(async (attachment) => {
         try {
+          Logger.debug("task", `Adding attachment to archive`, {
+            documentId,
+            key: attachment.key,
+          });
+
           const stream = getFileByKey(attachment.key);
           const dir = path.dirname(pathInZip);
           if (stream) {
@@ -119,6 +129,10 @@ export default abstract class ExportDocumentTreeTask extends ExportTask {
     format: FileOperationFormat
   ) {
     const pathMap = this.createPathMap(collections, format);
+    Logger.debug(
+      "task",
+      `Start adding ${Object.values(pathMap).length} documents to archive`
+    );
 
     for (const path of pathMap) {
       const documentId = path[0].replace("/doc/", "");
@@ -133,7 +147,9 @@ export default abstract class ExportDocumentTreeTask extends ExportTask {
       });
     }
 
-    return ZipHelper.toTmpFile(zip);
+    Logger.debug("task", "Completed adding documents to archive");
+
+    return await ZipHelper.toTmpFile(zip);
   }
 
   /**
diff --git a/server/utils/ZipHelper.ts b/server/utils/ZipHelper.ts
index f8bf3e95d..e516cf939 100644
--- a/server/utils/ZipHelper.ts
+++ b/server/utils/ZipHelper.ts
@@ -4,6 +4,7 @@ import JSZip from "jszip";
 import { find } from "lodash";
 import tmp from "tmp";
 import { ValidationError } from "@server/errors";
+import Logger from "@server/logging/Logger";
 import { trace } from "@server/logging/tracing";
 import { deserializeFilename } from "./fs";
 
@@ -83,6 +84,7 @@ export default class ZipHelper {
    * @returns pathname of the temporary file where the zip was written to disk
    */
   public static async toTmpFile(zip: JSZip): Promise<string> {
+    Logger.debug("utils", "Creating tmp file…");
     return new Promise((resolve, reject) => {
       tmp.file(
         {
@@ -93,13 +95,38 @@ export default class ZipHelper {
           if (err) {
             return reject(err);
           }
+
+          let previousMetadata: JSZip.JSZipMetadata = {
+            percent: 0,
+            currentFile: null,
+          };
+
           zip
-            .generateNodeStream({
-              type: "nodebuffer",
-              streamFiles: true,
-            })
+            .generateNodeStream(
+              {
+                type: "nodebuffer",
+                streamFiles: true,
+              },
+              (metadata) => {
+                const percent = Math.round(metadata.percent);
+                if (percent !== previousMetadata.percent) {
+                  previousMetadata = {
+                    currentFile: metadata.currentFile,
+                    percent,
+                  };
+                  Logger.debug(
+                    "utils",
+                    `Writing zip file progress… %${percent}`,
+                    { currentFile: metadata.currentFile }
+                  );
+                }
+              }
+            )
             .pipe(fs.createWriteStream(path))
-            .on("finish", () => resolve(path))
+            .on("finish", () => {
+              Logger.debug("utils", "Writing zip complete", { path });
+              return resolve(path);
+            })
             .on("error", reject);
         }
       );