diff --git a/js/models/messages.js b/js/models/messages.js
index 5b55a7317..27f307739 100644
--- a/js/models/messages.js
+++ b/js/models/messages.js
@@ -571,7 +571,6 @@
       const isGroup = !!conversation && !conversation.isPrivate();
 
       const attachments = this.get('attachments') || [];
-      const firstAttachment = attachments[0];
 
       return {
         text: this.createNonBreakingLastSeparator(this.get('body')),
@@ -987,6 +986,13 @@
         attachments: attachmentsWithData,
         now: this.get('sent_at'),
       });
+      const filenameOverridenAttachments = finalAttachments.map(attachment => ({
+        ...attachment,
+        fileName: Signal.Types.Attachment.getSuggestedFilenameSending({
+          attachment,
+          timestamp: Date.now(),
+        }),
+      }));
 
       const quoteWithData = await loadQuoteData(this.get('quote'));
       const previewWithData = await loadPreviewData(this.get('preview'));
@@ -996,7 +1002,10 @@
 
       const { AttachmentUtils } = libsession.Utils;
       const [attachments, preview, quote] = await Promise.all([
-        AttachmentUtils.uploadAttachments(finalAttachments, openGroup),
+        AttachmentUtils.uploadAttachments(
+          filenameOverridenAttachments,
+          openGroup
+        ),
         AttachmentUtils.uploadLinkPreviews(previewWithData, openGroup),
         AttachmentUtils.uploadQuoteThumbnails(quoteWithData, openGroup),
       ]);
diff --git a/js/modules/types/attachment.js b/js/modules/types/attachment.js
index 1aaa1e0b0..26e91b16a 100644
--- a/js/modules/types/attachment.js
+++ b/js/modules/types/attachment.js
@@ -214,6 +214,7 @@ exports.deleteData = deleteOnDisk => {
 exports.isVoiceMessage = AttachmentTS.isVoiceMessage;
 exports.save = AttachmentTS.save;
 exports.getFileExtension = AttachmentTS.getFileExtension;
+exports.getSuggestedFilenameSending = AttachmentTS.getSuggestedFilenameSending;
 
 const THUMBNAIL_SIZE = 150;
 const THUMBNAIL_CONTENT_TYPE = 'image/png';
diff --git a/stylesheets/_session.scss b/stylesheets/_session.scss
index 38569d474..6b4b9c5de 100644
--- a/stylesheets/_session.scss
+++ b/stylesheets/_session.scss
@@ -1340,6 +1340,7 @@ input {
   position: absolute;
   bottom: 15px;
   right: 25px;
+  z-index: 2;
 
   .session-icon-button {
     display: flex;
diff --git a/ts/components/conversation/Message.tsx b/ts/components/conversation/Message.tsx
index 84ce4361a..525821323 100644
--- a/ts/components/conversation/Message.tsx
+++ b/ts/components/conversation/Message.tsx
@@ -181,7 +181,6 @@ export class Message extends React.PureComponent<Props, State> {
     this.checkExpired();
   }
 
-
   public checkExpired() {
     const now = Date.now();
     const { isExpired, expirationTimestamp, expirationLength } = this.props;
@@ -956,7 +955,6 @@ export class Message extends React.PureComponent<Props, State> {
     } = this.props;
     const { expired, expiring } = this.state;
 
-
     if (expired) {
       return null;
     }
@@ -988,7 +986,11 @@ export class Message extends React.PureComponent<Props, State> {
     }
 
     return (
-      <div id={id} className={classNames(divClasses)} onContextMenu={this.handleContextMenu}>
+      <div
+        id={id}
+        className={classNames(divClasses)}
+        onContextMenu={this.handleContextMenu}
+      >
         {this.renderAvatar()}
         <div
           className={classNames(
@@ -1006,7 +1008,10 @@ export class Message extends React.PureComponent<Props, State> {
 
             // User clicked on message body
             const target = event.target as HTMLDivElement;
-            if (!multiSelectMode && target.className === 'text-selectable' || window.contextMenuShown) {
+            if (
+              (!multiSelectMode && target.className === 'text-selectable') ||
+              window.contextMenuShown
+            ) {
               return;
             }
 
@@ -1035,7 +1040,10 @@ export class Message extends React.PureComponent<Props, State> {
 
               // User clicked on message body
               const target = event.target as HTMLDivElement;
-              if (target.className === 'text-selectable'  || window.contextMenuShown) {
+              if (
+                target.className === 'text-selectable' ||
+                window.contextMenuShown
+              ) {
                 return;
               }
 
@@ -1062,11 +1070,7 @@ export class Message extends React.PureComponent<Props, State> {
   private handleContextMenu(e: any) {
     e.preventDefault();
     e.stopPropagation();
-    const {
-      isRss,
-      multiSelectMode,
-      isKickedFromGroup,
-    } = this.props;
+    const { isRss, multiSelectMode, isKickedFromGroup } = this.props;
     const enableContextMenu = !isRss && !multiSelectMode && !isKickedFromGroup;
 
     if (enableContextMenu) {
diff --git a/ts/components/session/conversation/SessionConversationMessagesList.tsx b/ts/components/session/conversation/SessionConversationMessagesList.tsx
index ee29bd734..392701b15 100644
--- a/ts/components/session/conversation/SessionConversationMessagesList.tsx
+++ b/ts/components/session/conversation/SessionConversationMessagesList.tsx
@@ -33,7 +33,7 @@ interface Props {
   ) => Promise<{ previousTopMessage: string }>;
   replyToMessage: (messageId: number) => Promise<void>;
   onClickAttachment: (attachment: any, message: any) => void;
-  onDownloadAttachment: ({ attachment }: { attachment: any}) => void;
+  onDownloadAttachment: ({ attachment }: { attachment: any }) => void;
 }
 
 export class SessionConversationMessagesList extends React.Component<
@@ -181,7 +181,7 @@ export class SessionConversationMessagesList extends React.Component<
       this.props.onClickAttachment(attachment, messageProps);
     };
     messageProps.onDownload = (attachment: AttachmentType) => {
-      this.props.onDownloadAttachment({attachment});
+      this.props.onDownloadAttachment({ attachment });
     };
 
     return <Message {...messageProps} />;
diff --git a/ts/session/utils/Attachments.ts b/ts/session/utils/Attachments.ts
index bcb22e458..10345d500 100644
--- a/ts/session/utils/Attachments.ts
+++ b/ts/session/utils/Attachments.ts
@@ -67,7 +67,6 @@ export class AttachmentUtils {
       }
       server = openGroupServer;
     }
-
     const pointer: AttachmentPointer = {
       contentType: attachment.contentType
         ? (attachment.contentType as string)
diff --git a/ts/test/types/Attachment_test.ts b/ts/test/types/Attachment_test.ts
index e3c18b2c8..6d2c15ff3 100644
--- a/ts/test/types/Attachment_test.ts
+++ b/ts/test/types/Attachment_test.ts
@@ -48,7 +48,6 @@ describe('Attachment', () => {
           contentType: MIME.VIDEO_QUICKTIME,
           url: 'funny-cat.mov',
           fileName: 'funny-cat.mov',
-
         };
         const timestamp = moment('2000-01-01').toDate();
         const actual = Attachment.getSuggestedFilename({
@@ -64,7 +63,8 @@ describe('Attachment', () => {
         const attachment: Attachment.AttachmentType = {
           fileName: 'funny-cat.mov',
           url: 'funny-cat.mov',
-          contentType: MIME.VIDEO_QUICKTIME,        };
+          contentType: MIME.VIDEO_QUICKTIME,
+        };
         const timestamp = new Date(new Date(0).getTimezoneOffset() * 60 * 1000);
         const actual = Attachment.getSuggestedFilename({
           attachment,
diff --git a/ts/types/Attachment.ts b/ts/types/Attachment.ts
index 09f6af521..a4fb4ffa0 100644
--- a/ts/types/Attachment.ts
+++ b/ts/types/Attachment.ts
@@ -369,6 +369,24 @@ export const getSuggestedFilename = ({
   return `${prefix}${suffix}${indexSuffix}${extension}`;
 };
 
+// Used for overriden the sent filename of an attachment, but keeping the file extension the same
+export const getSuggestedFilenameSending = ({
+  attachment,
+  timestamp,
+}: {
+  attachment: AttachmentType;
+  timestamp?: number | Date;
+}): string => {
+  const prefix = 'session-attachment';
+  const suffix = timestamp
+    ? moment(timestamp).format('-YYYY-MM-DD-HHmmss')
+    : '';
+  const fileType = getFileExtension(attachment);
+  const extension = fileType ? `.${fileType}` : '';
+
+  return `${prefix}${suffix}${extension}`;
+};
+
 export const getFileExtension = (
   attachment: AttachmentType
 ): string | undefined => {