diff --git a/.yarn/cache/@types-wicg-file-system-access-npm-2020.9.6-97b11f6f2d-2dbf33ee55.zip b/.yarn/cache/@types-wicg-file-system-access-npm-2020.9.6-97b11f6f2d-2dbf33ee55.zip
deleted file mode 100644
index 5cdc98ab6..000000000
Binary files a/.yarn/cache/@types-wicg-file-system-access-npm-2020.9.6-97b11f6f2d-2dbf33ee55.zip and /dev/null differ
diff --git a/.yarn/cache/@types-wicg-file-system-access-npm-2023.10.4-96a8d75efc-bfbadfbddc.zip b/.yarn/cache/@types-wicg-file-system-access-npm-2023.10.4-96a8d75efc-bfbadfbddc.zip
new file mode 100644
index 000000000..6b2591c5e
Binary files /dev/null and b/.yarn/cache/@types-wicg-file-system-access-npm-2023.10.4-96a8d75efc-bfbadfbddc.zip differ
diff --git a/packages/filepicker/package.json b/packages/filepicker/package.json
index 277e1e955..9c6ecd6c1 100644
--- a/packages/filepicker/package.json
+++ b/packages/filepicker/package.json
@@ -29,7 +29,7 @@
     "@standardnotes/common": "^1.50.0",
     "@standardnotes/files": "workspace:*",
     "@standardnotes/utils": "workspace:*",
-    "@types/wicg-file-system-access": "^2020.9.5",
+    "@types/wicg-file-system-access": "^2023.10.4",
     "reflect-metadata": "^0.1.13"
   }
 }
diff --git a/packages/filepicker/src/Streaming/StreamingSaver.ts b/packages/filepicker/src/Streaming/StreamingSaver.ts
index 2036ce2d1..d7cf2f2d4 100644
--- a/packages/filepicker/src/Streaming/StreamingSaver.ts
+++ b/packages/filepicker/src/Streaming/StreamingSaver.ts
@@ -22,12 +22,14 @@ export class StreamingFileSaver {
   }
 
   /** This function must be called in response to a user interaction, otherwise, it will be rejected by the browser. */
-  async selectFileToSaveTo(): Promise<void> {
+  async selectFileToSaveTo(handle?: FileSystemFileHandle): Promise<void> {
     this.log('Showing save file picker')
 
-    const downloadHandle = await window.showSaveFilePicker({
-      suggestedName: this.name,
-    })
+    const downloadHandle = handle
+      ? handle
+      : await window.showSaveFilePicker({
+          suggestedName: this.name,
+        })
 
     this.writableStream = await downloadHandle.createWritable()
   }
diff --git a/packages/web/package.json b/packages/web/package.json
index 4d854f43c..d5ad6cd71 100644
--- a/packages/web/package.json
+++ b/packages/web/package.json
@@ -59,7 +59,7 @@
     "@types/jest": "^29.2.4",
     "@types/react": "^18.2.39",
     "@types/react-dom": "^18.2.17",
-    "@types/wicg-file-system-access": "^2020.9.5",
+    "@types/wicg-file-system-access": "^2023.10.4",
     "@zip.js/zip.js": "^2.6.60",
     "autoprefixer": "^10.4.13",
     "babel-loader": "^9.1.2",
diff --git a/packages/web/src/javascripts/Components/AttachedFilesPopover/PopoverFileItemAction.tsx b/packages/web/src/javascripts/Components/AttachedFilesPopover/PopoverFileItemAction.tsx
index f2a4a94e7..0ea3d33ee 100644
--- a/packages/web/src/javascripts/Components/AttachedFilesPopover/PopoverFileItemAction.tsx
+++ b/packages/web/src/javascripts/Components/AttachedFilesPopover/PopoverFileItemAction.tsx
@@ -18,6 +18,7 @@ export type FileItemAction =
       >
       payload: {
         file: FileItem
+        directoryHandle?: FileSystemDirectoryHandle
       }
     }
   | {
diff --git a/packages/web/src/javascripts/Controllers/FilesController.ts b/packages/web/src/javascripts/Controllers/FilesController.ts
index d1d8c51db..4be70f7ee 100644
--- a/packages/web/src/javascripts/Controllers/FilesController.ts
+++ b/packages/web/src/javascripts/Controllers/FilesController.ts
@@ -67,8 +67,8 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
   showProtectedOverlay = false
   fileContextMenuLocation: FileContextMenuLocation = { x: 0, y: 0 }
 
-  shouldUseStreamingReader = StreamingFileSaver.available()
-  reader = this.shouldUseStreamingReader ? StreamingFileReader : ClassicFileReader
+  shouldUseStreamingAPI = StreamingFileSaver.available()
+  reader = this.shouldUseStreamingAPI ? StreamingFileReader : ClassicFileReader
   maxFileSize = this.reader.maximumFileSize()
 
   override deinit(): void {
@@ -251,7 +251,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
         await this.deleteFile(file)
         break
       case FileItemActionType.DownloadFile:
-        await this.downloadFile(file)
+        await this.downloadFile(file, action.payload.directoryHandle)
         break
       case FileItemActionType.ToggleFileProtection: {
         const isProtected = await this.toggleFileProtection(file)
@@ -289,7 +289,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     })
   }
 
-  private async downloadFile(file: FileItem): Promise<void> {
+  private async downloadFile(file: FileItem, directoryHandle?: FileSystemDirectoryHandle): Promise<void> {
     let downloadingToastId = ''
     let canShowProgressNotification = false
 
@@ -298,12 +298,15 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     }
 
     try {
-      const saver = StreamingFileSaver.available() ? new StreamingFileSaver(file.name) : new ClassicFileSaver()
+      const saver = this.shouldUseStreamingAPI ? new StreamingFileSaver(file.name) : new ClassicFileSaver()
 
       const isUsingStreamingSaver = saver instanceof StreamingFileSaver
 
       if (isUsingStreamingSaver) {
-        await saver.selectFileToSaveTo()
+        const fileHandle = directoryHandle
+          ? await directoryHandle.getFileHandle(file.name, { create: true })
+          : undefined
+        await saver.selectFileToSaveTo(fileHandle)
       }
 
       if (this.mobileDevice && canShowProgressNotification) {
@@ -413,7 +416,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
   }
 
   alertIfFileExceedsSizeLimit = (file: File): boolean => {
-    if (!this.shouldUseStreamingReader && this.maxFileSize && file.size >= this.maxFileSize) {
+    if (!this.shouldUseStreamingAPI && this.maxFileSize && file.size >= this.maxFileSize) {
       this.alerts
         .alert(
           `This file exceeds the limits supported in this browser. To upload files greater than ${
@@ -465,7 +468,7 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
       const fileToUpload =
         fileOrHandle instanceof File
           ? fileOrHandle
-          : fileOrHandle instanceof FileSystemFileHandle && this.shouldUseStreamingReader
+          : fileOrHandle instanceof FileSystemFileHandle && this.shouldUseStreamingAPI
           ? await fileOrHandle.getFile()
           : undefined
 
@@ -661,15 +664,41 @@ export class FilesController extends AbstractViewController<FilesControllerEvent
     void this.sync.sync()
   }
 
+  getDirectoryHandleForDownloads = async () => {
+    if (!this.shouldUseStreamingAPI) {
+      return
+    }
+
+    const directoryHandle = await window.showDirectoryPicker({
+      startIn: 'downloads',
+    })
+
+    return directoryHandle
+  }
+
   downloadFiles = async (files: FileItem[]) => {
     // macOS doesn't allow multiple calls to the filepicker at the
     // same time, so we need to iterate one by one
     if (this.platform === Platform.MacDesktop || this.platform === Platform.MacWeb) {
+      let directoryHandle: FileSystemDirectoryHandle | undefined
+
+      if (files.length > 1) {
+        try {
+          directoryHandle = await this.getDirectoryHandleForDownloads()
+        } catch (error) {
+          if (error instanceof DOMException && error.name === 'AbortError') {
+            return
+          }
+          console.error(error)
+        }
+      }
+
       for (const file of files) {
         await this.handleFileAction({
           type: FileItemActionType.DownloadFile,
           payload: {
             file,
+            directoryHandle,
           },
         })
       }
diff --git a/yarn.lock b/yarn.lock
index a7debbcd5..a5d050fd9 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6753,7 +6753,7 @@ __metadata:
     "@standardnotes/files": "workspace:*"
     "@standardnotes/utils": "workspace:*"
     "@types/jest": ^29.2.3
-    "@types/wicg-file-system-access": ^2020.9.5
+    "@types/wicg-file-system-access": ^2023.10.4
     "@typescript-eslint/eslint-plugin": "*"
     eslint: "*"
     eslint-plugin-prettier: "*"
@@ -7519,7 +7519,7 @@ __metadata:
     "@types/jest": ^29.2.4
     "@types/react": ^18.2.39
     "@types/react-dom": ^18.2.17
-    "@types/wicg-file-system-access": ^2020.9.5
+    "@types/wicg-file-system-access": ^2023.10.4
     "@zip.js/zip.js": ^2.6.60
     autoprefixer: ^10.4.13
     babel-loader: ^9.1.2
@@ -8457,10 +8457,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/wicg-file-system-access@npm:^2020.9.5":
-  version: 2020.9.6
-  resolution: "@types/wicg-file-system-access@npm:2020.9.6"
-  checksum: 2dbf33ee55684d4ed0607ae4b470e0147806b15ec047563c59d94e6ac13be7bed904cc7eece5e4be7c0d58a4de0b0635089f7cd5b7738372e436c760b0719241
+"@types/wicg-file-system-access@npm:^2023.10.4":
+  version: 2023.10.4
+  resolution: "@types/wicg-file-system-access@npm:2023.10.4"
+  checksum: bfbadfbddcdf04f600e0bb1b3dfe8dd79661c987ded487c2ac03670932e4ab9cd277c8b98d6229d10a910cb149c1bf956f43f189c4349f1c1a97cff310154aeb
   languageName: node
   linkType: hard