diff --git a/Signal.xcodeproj/project.pbxproj b/Signal.xcodeproj/project.pbxproj
index ba6958e90..1b858cb17 100644
--- a/Signal.xcodeproj/project.pbxproj
+++ b/Signal.xcodeproj/project.pbxproj
@@ -1665,6 +1665,9 @@
 							com.apple.VPNLite = {
 								enabled = 0;
 							};
+							com.apple.iCloud = {
+								enabled = 1;
+							};
 						};
 					};
 					D221A0A9169C9E5F00537ABF = {
diff --git a/Signal/Signal.entitlements b/Signal/Signal.entitlements
index 903def2af..dfec421ea 100644
--- a/Signal/Signal.entitlements
+++ b/Signal/Signal.entitlements
@@ -4,5 +4,17 @@
 <dict>
 	<key>aps-environment</key>
 	<string>development</string>
+	<key>com.apple.developer.icloud-container-identifiers</key>
+	<array>
+		<string>iCloud.$(CFBundleIdentifier)</string>
+	</array>
+	<key>com.apple.developer.icloud-services</key>
+	<array>
+		<string>CloudDocuments</string>
+	</array>
+	<key>com.apple.developer.ubiquity-container-identifiers</key>
+	<array>
+		<string>iCloud.$(CFBundleIdentifier)</string>
+	</array>
 </dict>
 </plist>
diff --git a/Signal/src/ViewControllers/MessagesViewController.m b/Signal/src/ViewControllers/MessagesViewController.m
index dcecdee09..72d7aa9fb 100644
--- a/Signal/src/ViewControllers/MessagesViewController.m
+++ b/Signal/src/ViewControllers/MessagesViewController.m
@@ -186,7 +186,10 @@ typedef enum : NSUInteger {
 
 #pragma mark -
 
-@interface MessagesViewController () <JSQMessagesComposerTextViewPasteDelegate, OWSTextViewPasteDelegate> {
+@interface MessagesViewController () <JSQMessagesComposerTextViewPasteDelegate,
+    OWSTextViewPasteDelegate,
+    UIDocumentMenuDelegate,
+    UIDocumentPickerDelegate> {
     UIImage *tappedImage;
     BOOL isGroupConversation;
 }
@@ -2182,6 +2185,87 @@ typedef enum : NSUInteger {
     [self presentViewController:actionSheetController animated:YES completion:nil];
 }
 
+
+#pragma mark - Attachment Picking: Documents
+
+- (void)showAttachmentDocumentPicker
+{
+    NSString *allItems = (__bridge NSString *)kUTTypeData;
+    NSArray<NSString *> *documentTypes = @[ allItems ];
+    // UIDocumentPickerModeImport copies to a temp file within our container.
+    // It uses more memory than "open" but let's us avoid working with security scoped URLs.
+    UIDocumentPickerMode pickerMode = UIDocumentPickerModeImport;
+    UIDocumentMenuViewController *menuController =
+        [[UIDocumentMenuViewController alloc] initWithDocumentTypes:documentTypes inMode:pickerMode];
+    menuController.delegate = self;
+    [self presentViewController:menuController animated:YES completion:nil];
+}
+
+#pragma mark UIDocumentMenuDelegate
+
+- (void)documentMenu:(UIDocumentMenuViewController *)documentMenu
+    didPickDocumentPicker:(UIDocumentPickerViewController *)documentPicker
+{
+    documentPicker.delegate = self;
+    [self presentViewController:documentPicker animated:YES completion:nil];
+}
+
+#pragma mark UIDocumentPickerDelegate
+- (void)documentPicker:(UIDocumentPickerViewController *)controller didPickDocumentAtURL:(NSURL *)url
+{
+    DDLogDebug(@"%@ Picked document at url: %@", self.tag, url);
+    NSData *attachmentData = [NSData dataWithContentsOfURL:url];
+
+    NSString *type;
+    NSError *error;
+    [url getResourceValue:&type forKey:NSURLTypeIdentifierKey error:&error];
+    if (error) {
+        DDLogError(@"%@ Determining type of picked document at url: %@ failed with error: %@", self.tag, url, error);
+        OWSAssert(NO);
+    }
+
+    if (!type) {
+        DDLogDebug(@"%@ falling back to default filetype for picked document at url: %@", self.tag, url);
+        OWSAssert(NO);
+        type = (__bridge NSString *)kUTTypeData;
+    }
+
+    NSString *filename = url.lastPathComponent;
+    if (!filename) {
+        DDLogDebug(@"%@ Unable to determine filename from url: %@", self.tag, url);
+        OWSAssert(NO);
+        filename = NSLocalizedString(
+            @"ATTACHMENT_DEFAULT_FILENAME", @"Generic filename for an attachment with no known name");
+    }
+
+    if (!attachmentData || attachmentData.length == 0) {
+        DDLogError(@"%@ attachment data was unexpectedly empty for picked document url: %@", self.tag, url);
+        OWSAssert(NO);
+        UIAlertController *alertController = [UIAlertController
+            alertControllerWithTitle:NSLocalizedString(@"ATTACHMENT_PICKER_DOCUMENTS_FAILED_ALERT_TITLE",
+                                         @"Alert title when picking a document fails for an unknown reason")
+                             message:nil
+                      preferredStyle:UIAlertControllerStyleAlert];
+
+        UIAlertAction *dismissAction = [UIAlertAction actionWithTitle:NSLocalizedString(@"DISMISS_BUTTON_TEXT", nil)
+                                                                style:UIAlertActionStyleCancel
+                                                              handler:nil];
+        [alertController addAction:dismissAction];
+
+        dispatch_async(dispatch_get_main_queue(), ^{
+            [self presentViewController:alertController animated:YES completion:nil];
+        });
+        return;
+    }
+
+    OWSAssert(attachmentData);
+    OWSAssert(type);
+    OWSAssert(filename);
+    SignalAttachment *attachment =
+        [[SignalAttachment alloc] initWithData:attachmentData dataUTI:type filename:filename];
+    [ThreadUtil sendMessageWithAttachment:attachment inThread:self.thread messageSender:self.messageSender];
+}
+
 #pragma mark - UIImagePickerController
 
 /*
@@ -2680,7 +2764,16 @@ typedef enum : NSUInteger {
                                              [self chooseFromLibrary];
                                          }];
     [actionSheetController addAction:chooseMediaAction];
-    
+
+    UIAlertAction *chooseDocumentAction =
+        [UIAlertAction actionWithTitle:NSLocalizedString(@"MEDIA_FROM_DOCUMENT_PICKER_BUTTON",
+                                           @"action sheet button title when choosing attachment type")
+                                 style:UIAlertActionStyleDefault
+                               handler:^(UIAlertAction *_Nonnull action) {
+                                   [self showAttachmentDocumentPicker];
+                               }];
+    [actionSheetController addAction:chooseDocumentAction];
+
     [self presentViewController:actionSheetController animated:true completion:nil];
 }
 
diff --git a/Signal/src/views/AttachmentPointerView.swift b/Signal/src/views/AttachmentPointerView.swift
index f5c03ed6f..931797f29 100644
--- a/Signal/src/views/AttachmentPointerView.swift
+++ b/Signal/src/views/AttachmentPointerView.swift
@@ -14,7 +14,7 @@ class AttachmentPointerView: UIView {
     let isIncoming: Bool
     let filename: String
     let attachmentPointer: TSAttachmentPointer
-    let genericFilename = NSLocalizedString("ATTACHMENT_DOWNLOADING_DEFAULT_ATTACHMENT_LABEL", comment: "Generic name label when downloading an attachment with no known name.")
+    let genericFilename = NSLocalizedString("ATTACHMENT_DEFAULT_FILENAME", comment: "Generic filename for an attachment with no known name")
 
     var progress: CGFloat = 0 {
         didSet {
diff --git a/Signal/translations/en.lproj/Localizable.strings b/Signal/translations/en.lproj/Localizable.strings
index 142ef2af8..0cdff1500 100644
--- a/Signal/translations/en.lproj/Localizable.strings
+++ b/Signal/translations/en.lproj/Localizable.strings
@@ -61,8 +61,8 @@
 /* Label for 'send' button in the 'attachment approval' dialog. */
 "ATTACHMENT_APPROVAL_SEND_BUTTON" = "Send";
 
-/* Generic name label when downloading an attachment with no known name. */
-"ATTACHMENT_DOWNLOADING_DEFAULT_ATTACHMENT_LABEL" = "Attachment";
+/* Generic filename for an attachment with no known name */
+"ATTACHMENT_DEFAULT_FILENAME" = "Attachment";
 
 /* Status label when an attachment download has failed. */
 "ATTACHMENT_DOWNLOADING_STATUS_FAILED" = "Failed. Tap to retry.";
@@ -100,6 +100,9 @@
 /* Accessibility label for attaching photos */
 "ATTACHMENT_LABEL" = "Attachment";
 
+/* Alert title when picking a document fails for an unknown reason */
+"ATTACHMENT_PICKER_DOCUMENTS_FAILED_ALERT_TITLE" = "Failed to choose document.";
+
 /* An explanation of the consequences of blocking another user. */
 "BLOCK_BEHAVIOR_EXPLANATION" = "Blocked users will not be able to call you or send you messages.";
 
@@ -589,6 +592,9 @@
 /* media picker option to take photo or video */
 "MEDIA_FROM_CAMERA_BUTTON" = "Camera";
 
+/* action sheet button title when choosing attachment type */
+"MEDIA_FROM_DOCUMENT_PICKER_BUTTON" = "Document";
+
 /* media picker option to choose from library */
 "MEDIA_FROM_LIBRARY_BUTTON" = "Photo Library";