diff --git a/app/assets/javascripts/components/ApplicationView.tsx b/app/assets/javascripts/components/ApplicationView.tsx
index 4c7fc910897..821be89779c 100644
--- a/app/assets/javascripts/components/ApplicationView.tsx
+++ b/app/assets/javascripts/components/ApplicationView.tsx
@@ -27,6 +27,7 @@ import { PremiumModalProvider } from './Premium';
 import { ConfirmSignoutContainer } from './ConfirmSignoutModal';
 import { TagsContextMenu } from './Tags/TagContextMenu';
 import { ToastContainer } from '@standardnotes/stylekit';
+import { FilePreviewModalProvider } from './Files/FilePreviewModalProvider';
 
 type Props = {
   application: WebApplication;
@@ -175,88 +176,78 @@ export class ApplicationView extends PureComponent<Props, State> {
     const renderAppContents = !this.state.needsUnlock && this.state.launched;
 
     return (
-      <PremiumModalProvider
-        application={this.application}
-        appState={this.appState}
-      >
-        <div className={this.platformString + ' main-ui-view sn-component'}>
-          {renderAppContents && (
-            <div
-              id="app"
-              className={this.state.appClass + ' app app-column-container'}
-            >
-              <Navigation application={this.application} />
-
-              <NotesView
-                application={this.application}
-                appState={this.appState}
-              />
-
-              <NoteGroupView application={this.application} />
-            </div>
-          )}
-
-          {renderAppContents && (
-            <>
-              <Footer
-                application={this.application}
-                applicationGroup={this.props.mainApplicationGroup}
-              />
-
-              <SessionsModal
-                application={this.application}
-                appState={this.appState}
-              />
-
-              <PreferencesViewWrapper
-                appState={this.appState}
-                application={this.application}
-              />
-
-              <RevisionHistoryModalWrapper
-                application={this.application}
-                appState={this.appState}
-              />
-            </>
-          )}
-
-          {this.state.challenges.map((challenge) => {
-            return (
-              <div className="sk-modal">
-                <ChallengeModal
-                  key={challenge.id}
+      <FilePreviewModalProvider application={this.application}>
+        <PremiumModalProvider
+          application={this.application}
+          appState={this.appState}
+        >
+          <div className={this.platformString + ' main-ui-view sn-component'}>
+            {renderAppContents && (
+              <div
+                id="app"
+                className={this.state.appClass + ' app app-column-container'}
+              >
+                <Navigation application={this.application} />
+                <NotesView
                   application={this.application}
-                  challenge={challenge}
-                  onDismiss={this.removeChallenge}
+                  appState={this.appState}
                 />
+                <NoteGroupView application={this.application} />
               </div>
-            );
-          })}
-
-          {renderAppContents && (
-            <>
-              <NotesContextMenu
-                application={this.application}
-                appState={this.appState}
-              />
-
-              <TagsContextMenu appState={this.appState} />
-
-              <PurchaseFlowWrapper
-                application={this.application}
-                appState={this.appState}
-              />
-
-              <ConfirmSignoutContainer
-                appState={this.appState}
-                application={this.application}
-              />
-
-              <ToastContainer />
-            </>
-          )}
-        </div>
-      </PremiumModalProvider>
+            )}
+            {renderAppContents && (
+              <>
+                <Footer
+                  application={this.application}
+                  applicationGroup={this.props.mainApplicationGroup}
+                />
+                <SessionsModal
+                  application={this.application}
+                  appState={this.appState}
+                />
+                <PreferencesViewWrapper
+                  appState={this.appState}
+                  application={this.application}
+                />
+                <RevisionHistoryModalWrapper
+                  application={this.application}
+                  appState={this.appState}
+                />
+              </>
+            )}
+            {this.state.challenges.map((challenge) => {
+              return (
+                <div className="sk-modal">
+                  <ChallengeModal
+                    key={challenge.id}
+                    application={this.application}
+                    challenge={challenge}
+                    onDismiss={this.removeChallenge}
+                  />
+                </div>
+              );
+            })}
+            {renderAppContents && (
+              <>
+                <NotesContextMenu
+                  application={this.application}
+                  appState={this.appState}
+                />
+                <TagsContextMenu appState={this.appState} />
+                <PurchaseFlowWrapper
+                  application={this.application}
+                  appState={this.appState}
+                />
+                <ConfirmSignoutContainer
+                  appState={this.appState}
+                  application={this.application}
+                />
+                <ToastContainer />
+              </>
+            )}
+          </div>
+        </PremiumModalProvider>
+      </FilePreviewModalProvider>
     );
   }
 }
diff --git a/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx b/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx
index 61d85f73750..aeac0c6bdc9 100644
--- a/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx
+++ b/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileItem.tsx
@@ -10,10 +10,10 @@ import {
 } from './PopoverFileItemAction';
 import { PopoverFileSubmenu } from './PopoverFileSubmenu';
 
-const getFileIconComponent = (iconType: string) => {
+export const getFileIconComponent = (iconType: string, className: string) => {
   const IconComponent = ICONS[iconType as keyof typeof ICONS];
 
-  return <IconComponent className="w-8 h-8 flex-shrink-0" />;
+  return <IconComponent className={className} />;
 };
 
 export type PopoverFileItemProps = {
@@ -69,7 +69,10 @@ export const PopoverFileItem: FunctionComponent<PopoverFileItemProps> = ({
   return (
     <div className="flex items-center justify-between p-3">
       <div className="flex items-center">
-        {getFileIconComponent(getIconType(file.mimeType))}
+        {getFileIconComponent(
+          getIconType(file.mimeType),
+          'w-8 h-8 flex-shrink-0'
+        )}
         <div className="flex flex-col mx-4">
           {isRenamingFile ? (
             <input
@@ -82,7 +85,7 @@ export const PopoverFileItem: FunctionComponent<PopoverFileItemProps> = ({
               onBlur={handleFileNameInputBlur}
             />
           ) : (
-            <div className="text-sm mb-1">{file.name}</div>
+            <div className="text-sm mb-1 break-word">{file.name}</div>
           )}
           <div className="text-xs color-grey-0">
             {file.created_at.toLocaleString()} ·{' '}
diff --git a/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileSubmenu.tsx b/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileSubmenu.tsx
index 9e82b996896..d9183779d4c 100644
--- a/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileSubmenu.tsx
+++ b/app/assets/javascripts/components/AttachedFilesPopover/PopoverFileSubmenu.tsx
@@ -19,6 +19,7 @@ import {
 import { Icon } from '../Icon';
 import { Switch } from '../Switch';
 import { useCloseOnBlur } from '../utils';
+import { useFilePreviewModal } from '../Files/FilePreviewModalProvider';
 import { PopoverFileItemProps } from './PopoverFileItem';
 import { PopoverFileItemActionType } from './PopoverFileItemAction';
 
@@ -32,6 +33,8 @@ export const PopoverFileSubmenu: FunctionComponent<Props> = ({
   handleFileAction,
   setIsRenamingFile,
 }) => {
+  const filePreviewModal = useFilePreviewModal();
+
   const menuContainerRef = useRef<HTMLDivElement>(null);
   const menuButtonRef = useRef<HTMLButtonElement>(null);
   const menuRef = useRef<HTMLDivElement>(null);
@@ -99,6 +102,17 @@ export const PopoverFileSubmenu: FunctionComponent<Props> = ({
         >
           {isMenuOpen && (
             <>
+              <button
+                onBlur={closeOnBlur}
+                className="sn-dropdown-item focus:bg-info-backdrop"
+                onClick={() => {
+                  filePreviewModal.activate(file);
+                  closeMenu();
+                }}
+              >
+                <Icon type="file" className="mr-2 color-neutral" />
+                Preview file
+              </button>
               {isAttachedToNote ? (
                 <button
                   onBlur={closeOnBlur}
diff --git a/app/assets/javascripts/components/Files/FilePreviewModal.tsx b/app/assets/javascripts/components/Files/FilePreviewModal.tsx
new file mode 100644
index 00000000000..92e1128d569
--- /dev/null
+++ b/app/assets/javascripts/components/Files/FilePreviewModal.tsx
@@ -0,0 +1,194 @@
+import { WebApplication } from '@/ui_models/application';
+import { concatenateUint8Arrays } from '@/utils/concatenateUint8Arrays';
+import { DialogContent, DialogOverlay } from '@reach/dialog';
+import { SNFile } from '@standardnotes/snjs';
+import { NoPreviewIllustration } from '@standardnotes/stylekit';
+import { FunctionComponent } from 'preact';
+import { useCallback, useEffect, useRef, useState } from 'preact/hooks';
+import { getFileIconComponent } from '../AttachedFilesPopover/PopoverFileItem';
+import { Button } from '../Button';
+import { Icon } from '../Icon';
+import { isFileTypePreviewable } from './isFilePreviewable';
+
+type Props = {
+  application: WebApplication;
+  file: SNFile;
+  onDismiss: () => void;
+};
+
+const getPreviewComponentForFile = (file: SNFile, objectUrl: string) => {
+  if (file.mimeType.startsWith('image/')) {
+    return <img src={objectUrl} />;
+  }
+
+  if (file.mimeType.startsWith('video/')) {
+    return <video className="w-full h-full" src={objectUrl} controls />;
+  }
+
+  if (file.mimeType.startsWith('audio/')) {
+    return <audio src={objectUrl} controls />;
+  }
+
+  return <object className="w-full h-full" data={objectUrl} />;
+};
+
+export const FilePreviewModal: FunctionComponent<Props> = ({
+  application,
+  file,
+  onDismiss,
+}) => {
+  const [objectUrl, setObjectUrl] = useState<string>();
+  const [isFilePreviewable, setIsFilePreviewable] = useState(false);
+  const [isLoadingFile, setIsLoadingFile] = useState(false);
+  const closeButtonRef = useRef<HTMLButtonElement>(null);
+
+  const getObjectUrl = useCallback(async () => {
+    setIsLoadingFile(true);
+    try {
+      const chunks: Uint8Array[] = [];
+      await application.files.downloadFile(
+        file,
+        async (decryptedChunk: Uint8Array) => {
+          chunks.push(decryptedChunk);
+        }
+      );
+      const finalDecryptedBytes = concatenateUint8Arrays(chunks);
+      setObjectUrl(
+        URL.createObjectURL(
+          new Blob([finalDecryptedBytes], {
+            type: file.mimeType,
+          })
+        )
+      );
+    } catch (error) {
+      console.error(error);
+    } finally {
+      setIsLoadingFile(false);
+    }
+  }, [application.files, file]);
+
+  useEffect(() => {
+    const isPreviewable = isFileTypePreviewable(file.mimeType);
+    setIsFilePreviewable(isPreviewable);
+
+    if (!objectUrl && isPreviewable) {
+      getObjectUrl();
+    }
+
+    return () => {
+      if (objectUrl) {
+        URL.revokeObjectURL(objectUrl);
+      }
+    };
+  }, [file.mimeType, getObjectUrl, objectUrl]);
+
+  return (
+    <DialogOverlay
+      className="sn-component"
+      aria-label="File preview modal"
+      onDismiss={onDismiss}
+      initialFocusRef={closeButtonRef}
+    >
+      <DialogContent
+        className="flex flex-col rounded shadow-overlay"
+        style={{
+          width: '90%',
+          maxWidth: '90%',
+          minHeight: '90%',
+          background: 'var(--sn-stylekit-background-color)',
+        }}
+      >
+        <div className="flex flex-shrink-0 justify-between items-center min-h-6 px-4 py-3 border-0 border-b-1 border-solid border-main">
+          <div className="flex items-center">
+            <div className="w-6 h-6">
+              {getFileIconComponent(
+                application.iconsController.getIconForFileType(file.mimeType),
+                'w-6 h-6 flex-shrink-0'
+              )}
+            </div>
+            <span className="ml-3 font-medium">{file.name}</span>
+          </div>
+          <div className="flex items-center">
+            {objectUrl && (
+              <Button
+                type="primary"
+                className="mr-4"
+                onClick={() => {
+                  application
+                    .getArchiveService()
+                    .downloadData(objectUrl, file.name);
+                }}
+              >
+                Download
+              </Button>
+            )}
+            <button
+              ref={closeButtonRef}
+              onClick={onDismiss}
+              aria-label="Close modal"
+              className="flex p-1 bg-transparent border-0 cursor-pointer"
+            >
+              <Icon type="close" className="color-neutral" />
+            </button>
+          </div>
+        </div>
+        <div className="flex flex-grow items-center justify-center min-h-0 overflow-auto">
+          {objectUrl ? (
+            getPreviewComponentForFile(file, objectUrl)
+          ) : isLoadingFile ? (
+            <div className="sk-spinner w-5 h-5 spinner-info"></div>
+          ) : (
+            <div className="flex flex-col items-center">
+              <NoPreviewIllustration className="w-30 h-30 mb-4" />
+              <div className="font-bold text-base mb-2">
+                This file can't be previewed.
+              </div>
+              {isFilePreviewable ? (
+                <>
+                  <div className="text-sm text-center color-grey-0 mb-4 max-w-35ch">
+                    There was an error loading the file. Try again, or download
+                    it and open it using another application.
+                  </div>
+                  <div className="flex items-center">
+                    <Button
+                      type="primary"
+                      className="mr-3"
+                      onClick={() => {
+                        getObjectUrl();
+                      }}
+                    >
+                      Try again
+                    </Button>
+                    <Button
+                      type="normal"
+                      onClick={() => {
+                        application.getAppState().files.downloadFile(file);
+                      }}
+                    >
+                      Download
+                    </Button>
+                  </div>
+                </>
+              ) : (
+                <>
+                  <div className="text-sm text-center color-grey-0 mb-4 max-w-35ch">
+                    To view this file, download it and open it using another
+                    application.
+                  </div>
+                  <Button
+                    type="primary"
+                    onClick={() => {
+                      application.getAppState().files.downloadFile(file);
+                    }}
+                  >
+                    Download
+                  </Button>
+                </>
+              )}
+            </div>
+          )}
+        </div>
+      </DialogContent>
+    </DialogOverlay>
+  );
+};
diff --git a/app/assets/javascripts/components/Files/FilePreviewModalProvider.tsx b/app/assets/javascripts/components/Files/FilePreviewModalProvider.tsx
new file mode 100644
index 00000000000..02aa3157ad3
--- /dev/null
+++ b/app/assets/javascripts/components/Files/FilePreviewModalProvider.tsx
@@ -0,0 +1,53 @@
+import { WebApplication } from '@/ui_models/application';
+import { SNFile } from '@standardnotes/snjs';
+import { createContext, FunctionComponent } from 'preact';
+import { useContext, useState } from 'preact/hooks';
+import { FilePreviewModal } from './FilePreviewModal';
+
+type FilePreviewModalContextData = {
+  activate: (file: SNFile) => void;
+};
+
+const FilePreviewModalContext =
+  createContext<FilePreviewModalContextData | null>(null);
+
+export const useFilePreviewModal = (): FilePreviewModalContextData => {
+  const value = useContext(FilePreviewModalContext);
+
+  if (!value) {
+    throw new Error('FilePreviewModalProvider not found.');
+  }
+
+  return value;
+};
+
+export const FilePreviewModalProvider: FunctionComponent<{
+  application: WebApplication;
+}> = ({ application, children }) => {
+  const [isOpen, setIsOpen] = useState(false);
+  const [file, setFile] = useState<SNFile>();
+
+  const activate = (file: SNFile) => {
+    setFile(file);
+    setIsOpen(true);
+  };
+
+  const close = () => {
+    setIsOpen(false);
+  };
+
+  return (
+    <>
+      {isOpen && file && (
+        <FilePreviewModal
+          application={application}
+          file={file}
+          onDismiss={close}
+        />
+      )}
+      <FilePreviewModalContext.Provider value={{ activate }}>
+        {children}
+      </FilePreviewModalContext.Provider>
+    </>
+  );
+};
diff --git a/app/assets/javascripts/components/Files/isFilePreviewable.ts b/app/assets/javascripts/components/Files/isFilePreviewable.ts
new file mode 100644
index 00000000000..8813d9884b4
--- /dev/null
+++ b/app/assets/javascripts/components/Files/isFilePreviewable.ts
@@ -0,0 +1,12 @@
+export const isFileTypePreviewable = (fileType: string) => {
+  const isImage = fileType.startsWith('image/');
+  const isVideo = fileType.startsWith('video/');
+  const isAudio = fileType.startsWith('audio/');
+  const isPdf = fileType === 'application/pdf';
+
+  if (isImage || isVideo || isAudio || isPdf) {
+    return true;
+  }
+
+  return false;
+};
diff --git a/app/assets/javascripts/components/Icon.tsx b/app/assets/javascripts/components/Icon.tsx
index ecd115fa22e..e8adb1ff4f9 100644
--- a/app/assets/javascripts/components/Icon.tsx
+++ b/app/assets/javascripts/components/Icon.tsx
@@ -27,9 +27,8 @@ import {
   EmailIcon,
   EyeIcon,
   EyeOffIcon,
-  FileIcon,
-  FolderIcon,
   FileDocIcon,
+  FileIcon,
   FileImageIcon,
   FileMovIcon,
   FileMusicIcon,
@@ -38,6 +37,7 @@ import {
   FilePptIcon,
   FileXlsIcon,
   FileZipIcon,
+  FolderIcon,
   HashtagIcon,
   HashtagOffIcon,
   HelpIcon,
@@ -165,7 +165,6 @@ export const ICONS = {
   settings: SettingsIcon,
   signIn: SignInIcon,
   signOut: SignOutIcon,
-  spellcheck: NotesIcon,
   spreadsheets: SpreadsheetsIcon,
   star: StarIcon,
   sync: SyncIcon,
diff --git a/app/assets/javascripts/components/NotesOptions/NotesOptions.tsx b/app/assets/javascripts/components/NotesOptions/NotesOptions.tsx
index e9db3eb9a48..3fb22b7a063 100644
--- a/app/assets/javascripts/components/NotesOptions/NotesOptions.tsx
+++ b/app/assets/javascripts/components/NotesOptions/NotesOptions.tsx
@@ -161,7 +161,7 @@ const SpellcheckOptions: FunctionComponent<{
         disabled={!spellcheckControllable}
       >
         <span className="flex items-center">
-          <Icon type="spellcheck" className={iconClass} />
+          <Icon type="notes" className={iconClass} />
           Spellcheck
         </span>
         <Switch
diff --git a/app/assets/javascripts/components/RevisionHistoryModal/RevisionHistoryModalWrapper.tsx b/app/assets/javascripts/components/RevisionHistoryModal/RevisionHistoryModalWrapper.tsx
index 41ff9664543..3c866cc516c 100644
--- a/app/assets/javascripts/components/RevisionHistoryModal/RevisionHistoryModalWrapper.tsx
+++ b/app/assets/javascripts/components/RevisionHistoryModal/RevisionHistoryModalWrapper.tsx
@@ -3,13 +3,7 @@ import { STRING_RESTORE_LOCKED_ATTEMPT } from '@/strings';
 import { WebApplication } from '@/ui_models/application';
 import { AppState } from '@/ui_models/app_state';
 import { getPlatformString } from '@/utils';
-import {
-  AlertDialogContent,
-  AlertDialogDescription,
-  AlertDialogLabel,
-  AlertDialogOverlay,
-} from '@reach/alert-dialog';
-import VisuallyHidden from '@reach/visually-hidden';
+import { DialogContent, DialogOverlay } from '@reach/dialog';
 import {
   ButtonType,
   ContentType,
@@ -240,24 +234,22 @@ export const RevisionHistoryModal: FunctionComponent<RevisionHistoryModalProps>
     };
 
     return (
-      <AlertDialogOverlay
+      <DialogOverlay
         className={`sn-component ${getPlatformString()}`}
         onDismiss={dismissModal}
-        leastDestructiveRef={closeButtonRef}
+        initialFocusRef={closeButtonRef}
+        aria-label="Note revision history"
       >
-        <AlertDialogContent
+        <DialogContent
           className="rounded shadow-overlay"
           style={{
             width: '90%',
             maxWidth: '90%',
             minHeight: '90%',
-            background: '#fff',
+            background: 'var(--sn-stylekit-background-color)',
           }}
         >
-          <AlertDialogLabel>
-            <VisuallyHidden>Note revision history</VisuallyHidden>
-          </AlertDialogLabel>
-          <AlertDialogDescription
+          <div
             className={`bg-default flex flex-col h-full overflow-hidden ${
               isDeletingRevision ? 'pointer-events-none cursor-not-allowed' : ''
             }`}
@@ -333,9 +325,9 @@ export const RevisionHistoryModal: FunctionComponent<RevisionHistoryModalProps>
                 </div>
               )}
             </div>
-          </AlertDialogDescription>
-        </AlertDialogContent>
-      </AlertDialogOverlay>
+          </div>
+        </DialogContent>
+      </DialogOverlay>
     );
   });
 
diff --git a/app/assets/javascripts/services/archiveManager.ts b/app/assets/javascripts/services/archiveManager.ts
index 7737e818483..f97530fbd02 100644
--- a/app/assets/javascripts/services/archiveManager.ts
+++ b/app/assets/javascripts/services/archiveManager.ts
@@ -24,6 +24,8 @@ type ZippableData = {
   content: Blob;
 }[];
 
+type ObjectURL = string;
+
 export class ArchiveManager {
   private readonly application: WebApplication;
   private textFile?: string;
@@ -32,6 +34,10 @@ export class ArchiveManager {
     this.application = application;
   }
 
+  public async getMimeType(ext: string) {
+    return (await import('@zip.js/zip.js')).getMimeType(ext);
+  }
+
   public async downloadBackup(encrypted: boolean): Promise<void> {
     const intent = encrypted
       ? EncryptionIntent.FileEncrypted
@@ -150,10 +156,10 @@ export class ArchiveManager {
     return this.textFile;
   }
 
-  downloadData(data: Blob, fileName: string) {
+  downloadData(data: Blob | ObjectURL, fileName: string) {
     const link = document.createElement('a');
     link.setAttribute('download', fileName);
-    link.href = this.hrefForData(data);
+    link.href = typeof data === 'string' ? data : this.hrefForData(data);
     document.body.appendChild(link);
     link.click();
     link.remove();
diff --git a/app/assets/javascripts/ui_models/app_state/files_state.ts b/app/assets/javascripts/ui_models/app_state/files_state.ts
index 85cc77803e1..89d92472f3b 100644
--- a/app/assets/javascripts/ui_models/app_state/files_state.ts
+++ b/app/assets/javascripts/ui_models/app_state/files_state.ts
@@ -1,8 +1,10 @@
+import { concatenateUint8Arrays } from '@/utils/concatenateUint8Arrays';
 import {
   ClassicFileReader,
   StreamingFileReader,
   StreamingFileSaver,
   ClassicFileSaver,
+  parseFileName,
 } from '@standardnotes/filepicker';
 import { ClientDisplayableError, SNFile } from '@standardnotes/snjs';
 import { addToast, dismissToast, ToastType } from '@standardnotes/stylekit';
@@ -31,19 +33,24 @@ export class FilesState {
         message: `Downloading file...`,
       });
 
+      const decryptedBytesArray: Uint8Array[] = [];
+
       await this.application.files.downloadFile(
         file,
         async (decryptedBytes: Uint8Array) => {
           if (isUsingStreamingSaver) {
             await saver.pushBytes(decryptedBytes);
           } else {
-            saver.saveFile(file.name, decryptedBytes);
+            decryptedBytesArray.push(decryptedBytes);
           }
         }
       );
 
       if (isUsingStreamingSaver) {
         await saver.finish();
+      } else {
+        const finalBytes = concatenateUint8Arrays(decryptedBytesArray);
+        saver.saveFile(file.name, finalBytes);
       }
 
       addToast({
@@ -85,6 +92,11 @@ export class FilesState {
       const uploadedFiles: SNFile[] = [];
 
       for (const file of selectedFiles) {
+        toastId = addToast({
+          type: ToastType.Loading,
+          message: `Uploading file "${file.name}"...`,
+        });
+
         const operation = await this.application.files.beginNewFileUpload();
 
         if (operation instanceof ClientDisplayableError) {
@@ -92,8 +104,7 @@ export class FilesState {
             type: ToastType.Error,
             message: `Unable to start upload session`,
           });
-
-          return;
+          throw new Error(`Unable to start upload session`);
         }
 
         const onChunk = async (
@@ -109,20 +120,22 @@ export class FilesState {
           );
         };
 
-        toastId = addToast({
-          type: ToastType.Loading,
-          message: `Uploading file "${file.name}"...`,
-        });
-
         const fileResult = await picker.readFile(
           file,
           minimumChunkSize,
           onChunk
         );
 
+        if (!fileResult.mimeType) {
+          const { ext } = parseFileName(file.name);
+          fileResult.mimeType = await this.application
+            .getArchiveService()
+            .getMimeType(ext);
+        }
+
         const uploadedFile = await this.application.files.finishUpload(
           operation,
-          { name: fileResult.name, mimeType: fileResult.mimeType }
+          fileResult
         );
 
         if (uploadedFile instanceof ClientDisplayableError) {
@@ -130,8 +143,7 @@ export class FilesState {
             type: ToastType.Error,
             message: `Unable to close upload session`,
           });
-
-          return;
+          throw new Error(`Unable to close upload session`);
         }
 
         uploadedFiles.push(uploadedFile);
diff --git a/app/assets/javascripts/utils/concatenateUint8Arrays.ts b/app/assets/javascripts/utils/concatenateUint8Arrays.ts
new file mode 100644
index 00000000000..a52a09820cf
--- /dev/null
+++ b/app/assets/javascripts/utils/concatenateUint8Arrays.ts
@@ -0,0 +1,14 @@
+export const concatenateUint8Arrays = (arrays: Uint8Array[]) => {
+  const totalLength = arrays
+    .map((array) => array.length)
+    .reduce((prev, next) => prev + next, 0);
+
+  const concatenatedArray = new Uint8Array(totalLength);
+  let offset = 0;
+  arrays.forEach((array) => {
+    concatenatedArray.set(array, offset);
+    offset += array.length;
+  });
+
+  return concatenatedArray;
+};
diff --git a/app/assets/stylesheets/_sn.scss b/app/assets/stylesheets/_sn.scss
index eafd24cd51e..629e8de9132 100644
--- a/app/assets/stylesheets/_sn.scss
+++ b/app/assets/stylesheets/_sn.scss
@@ -16,6 +16,10 @@
   width: 6.5rem;
 }
 
+.h-30 {
+  width: 7.5rem;
+}
+
 .h-33 {
   height: 8.25rem;
 }
@@ -318,6 +322,10 @@
   max-width: 22.25rem;
 }
 
+.max-w-35ch {
+  max-width: 35ch;
+}
+
 .mb-4 {
   margin-bottom: 1rem;
 }
@@ -333,6 +341,10 @@
   width: 0.75rem;
 }
 
+.w-6 {
+  width: 1.5rem;
+}
+
 .w-18 {
   width: 4.5rem;
 }
@@ -341,8 +353,8 @@
   width: 6.5rem;
 }
 
-.max-w-200 {
-  max-width: 50rem;
+.w-30 {
+  width: 7.5rem;
 }
 
 .w-92 {
@@ -405,6 +417,10 @@
   min-width: 22.5rem;
 }
 
+.max-w-200 {
+  max-width: 50rem;
+}
+
 .min-h-1px {
   min-height: 1px;
 }
@@ -989,6 +1005,10 @@
   color: var(--sn-stylekit-neutral-contrast-color);
 }
 
+.break-word {
+  word-break: break-word;
+}
+
 .transition {
   transition-property: color, background-color, border-color,
     text-decoration-color, fill, stroke, opacity, box-shadow, transform, filter,
diff --git a/package.json b/package.json
index 618430a72c6..b4556ec059e 100644
--- a/package.json
+++ b/package.json
@@ -33,7 +33,7 @@
     "@standardnotes/stylekit": "5.17.0",
     "@svgr/webpack": "^6.2.1",
     "@types/jest": "^27.4.1",
-    "@types/react": "^17.0.41",
+    "@types/react": "^17.0.42",
     "@types/wicg-file-system-access": "^2020.9.5",
     "@typescript-eslint/eslint-plugin": "^5.16.0",
     "@typescript-eslint/parser": "^5.16.0",
@@ -73,10 +73,10 @@
     "@reach/tooltip": "^0.16.2",
     "@standardnotes/components": "1.7.12",
     "@standardnotes/features": "1.35.4",
-    "@standardnotes/filepicker": "1.10.1",
+    "@standardnotes/filepicker": "1.10.2",
     "@standardnotes/settings": "1.13.1",
     "@standardnotes/sncrypto-web": "1.8.0",
-    "@standardnotes/snjs": "2.90.0",
+    "@standardnotes/snjs": "2.91.0",
     "@zip.js/zip.js": "^2.4.7",
     "mobx": "^6.5.0",
     "mobx-react-lite": "^3.3.0",
diff --git a/yarn.lock b/yarn.lock
index f607b5b4c20..6936ed62329 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2430,10 +2430,10 @@
     "@standardnotes/auth" "^3.17.11"
     "@standardnotes/common" "^1.17.0"
 
-"@standardnotes/filepicker@1.10.1":
-  version "1.10.1"
-  resolved "https://registry.yarnpkg.com/@standardnotes/filepicker/-/filepicker-1.10.1.tgz#451e8b80a670c35f4de5a1a17535b26876d4b92b"
-  integrity sha512-7q535TdXT0vKaIPvFDRPgcACrPAEs6Rgbw4pi8jLGY/Rodfty0zCN3z4NeDb/IdOGPpM8QYhKMLpYoZcKDjIMQ==
+"@standardnotes/filepicker@1.10.2":
+  version "1.10.2"
+  resolved "https://registry.yarnpkg.com/@standardnotes/filepicker/-/filepicker-1.10.2.tgz#4e2d76a327e61c5d864ce6e0597786caa83f2e20"
+  integrity sha512-+3LCaU7CH5gzZJBd6mXajx4ztdIVax8fqk49poHXRQd/mMIc36cOfCwbLlJeT4X6GL7UMLktieZZQqtG7hmRdw==
 
 "@standardnotes/payloads@^1.4.18":
   version "1.4.18"
@@ -2484,10 +2484,10 @@
     buffer "^6.0.3"
     libsodium-wrappers "^0.7.9"
 
-"@standardnotes/snjs@2.90.0":
-  version "2.90.0"
-  resolved "https://registry.yarnpkg.com/@standardnotes/snjs/-/snjs-2.90.0.tgz#87f11c52d8511ee7c0939f021b5ce96f47748222"
-  integrity sha512-3AilDSB7FdqxPP25zf41PoHZ0iqd6dcuzT4qtYkLTGnAz/WaCLzJy0sS/e5x9tHW3sltoVRhXJsRRmQV5JZFCQ==
+"@standardnotes/snjs@2.91.0":
+  version "2.91.0"
+  resolved "https://registry.yarnpkg.com/@standardnotes/snjs/-/snjs-2.91.0.tgz#53ab1100b6f4cacbdc4f3f779511ec0ed8cebe32"
+  integrity sha512-dt4K22eq1f/dNawto1hkiYrnTrV7wFu+QKlg18/TUAUnsdgpwMs+fznFB5UrKpW2BLzYPQPfjrVFKAsvkR91nQ==
   dependencies:
     "@standardnotes/applications" "^1.2.6"
     "@standardnotes/auth" "^3.17.11"
@@ -2858,10 +2858,10 @@
   resolved "https://registry.yarnpkg.com/@types/range-parser/-/range-parser-1.2.4.tgz#cd667bcfdd025213aafb7ca5915a932590acdcdc"
   integrity sha512-EEhsLsD6UsDM1yFhAvy0Cjr6VwmpMWqFBCb9w07wVugF7w9nfajxLuVmngTIpgS6svCnm6Vaw+MZhoDCKnOfsw==
 
-"@types/react@^17.0.41":
-  version "17.0.41"
-  resolved "https://registry.yarnpkg.com/@types/react/-/react-17.0.41.tgz#6e179590d276394de1e357b3f89d05d7d3da8b85"
-  integrity sha512-chYZ9ogWUodyC7VUTRBfblysKLjnohhFY9bGLwvnUFFy48+vB9DikmB3lW0qTFmBcKSzmdglcvkHK71IioOlDA==
+"@types/react@^17.0.42":
+  version "17.0.42"
+  resolved "https://registry.yarnpkg.com/@types/react/-/react-17.0.42.tgz#8242b9219bf8a911c47f248e327206fea3f4ee5a"
+  integrity sha512-nuab3x3CpJ7VFeNA+3HTUuEkvClYHXqWtWd7Ud6AZYW7Z3NH9WKtgU+tFB0ZLcHq+niB/HnzLcaZPqMJ95+k5Q==
   dependencies:
     "@types/prop-types" "*"
     "@types/scheduler" "*"