diff --git a/images/icons/v2/trash-outline-24.svg b/images/icons/v2/trash-outline-24.svg
new file mode 100644
index 0000000000..cf8f68d817
--- /dev/null
+++ b/images/icons/v2/trash-outline-24.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="24" height="24" viewBox="0 0 24 24"><title>trash-outline-24</title><path d="M22,4.5H16.35a4.45,4.45,0,0,0-8.7,0H2V6H3.5L4.86,20A2.25,2.25,0,0,0,7.1,22h9.8a2.25,2.25,0,0,0,2.24-2L20.5,6H22Zm-10-2a3,3,0,0,1,2.82,2H9.18A3,3,0,0,1,12,2.5Zm5.65,17.33a.76.76,0,0,1-.75.67H7.1a.76.76,0,0,1-.75-.67L5,6H19ZM11.25,18V8h1.5V18Zm3.25,0L15,8h1.5L16,18ZM8,18,7.5,8H9l.5,10Z"/></svg>
\ No newline at end of file
diff --git a/images/icons/v2/trash-solid-24.svg b/images/icons/v2/trash-solid-24.svg
new file mode 100644
index 0000000000..3d74ebb95e
--- /dev/null
+++ b/images/icons/v2/trash-solid-24.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="24" height="24" viewBox="0 0 24 24"><title>trash-solid-24</title><path d="M16.38,4.5a4.49,4.49,0,0,0-8.76,0H2V6H3.5L4.86,20A2.25,2.25,0,0,0,7.1,22h9.8a2.25,2.25,0,0,0,2.24-2L20.5,6H22V4.5ZM12,2.5a3,3,0,0,1,2.82,2H9.18A3,3,0,0,1,12,2.5ZM8,18,7.5,8H9l.5,10Zm4.75,0h-1.5V8h1.5ZM16,18H14.5L15,8h1.5Z"/></svg>
\ No newline at end of file
diff --git a/stylesheets/_modules.scss b/stylesheets/_modules.scss
index a327f62812..fcb0aa6321 100644
--- a/stylesheets/_modules.scss
+++ b/stylesheets/_modules.scss
@@ -9638,22 +9638,20 @@ button.module-image__border-overlay:focus {
 /* Third-party module: react-contextmenu*/
 
 .react-contextmenu {
+  @include popper-shadow();
+
   outline: none;
   border-radius: 4px;
-  min-width: 160px;
-  padding: 0px;
-  padding-top: 8px;
-  padding-bottom: 8px;
+  min-width: 220px;
+  padding: 6px 0;
   opacity: 0;
   user-select: none;
 
   @include light-theme {
-    background-color: $color-gray-02;
-    border: 1px solid $color-gray-02;
+    background-color: $color-white;
   }
   @include dark-theme {
-    background-color: $color-gray-90;
-    border: 1px solid $color-gray-60;
+    background-color: $color-gray-75;
   }
 }
 
@@ -9669,10 +9667,7 @@ button.module-image__border-overlay:focus {
 
   @include font-body-2;
 
-  padding-left: 16px;
-  padding-top: 3px;
-  padding-bottom: 2px;
-  padding-right: 16px;
+  padding: 7px 12px;
 
   @include light-theme {
     color: $color-gray-90;
@@ -9680,6 +9675,19 @@ button.module-image__border-overlay:focus {
   @include dark-theme {
     color: $color-gray-02;
   }
+
+  &--divider {
+    height: 1px;
+    margin: 6px 0;
+    padding: 0;
+
+    @include light-theme {
+      background-color: $color-gray-15;
+    }
+    @include dark-theme {
+      background-color: $color-gray-60;
+    }
+  }
 }
 
 .react-contextmenu-item--checked:before {
@@ -9706,15 +9714,25 @@ button.module-image__border-overlay:focus {
 
 .react-contextmenu-item.react-contextmenu-submenu
   > .react-contextmenu-item:after {
-  content: '\25B6';
+  content: ' ';
   display: inline-block;
+  height: 18px;
   position: absolute;
   right: 7px;
+  width: 12px;
 
   @include light-theme {
+    @include color-svg(
+      '../images/icons/v2/chevron-right-16.svg',
+      $color-gray-75
+    );
     color: $color-gray-90;
   }
   @include dark-theme {
+    @include color-svg(
+      '../images/icons/v2/chevron-right-16.svg',
+      $color-gray-15
+    );
     color: $color-gray-02;
   }
 }
@@ -9726,7 +9744,7 @@ button.module-image__border-overlay:focus {
     background-color: $color-gray-15;
   }
   @include dark-theme {
-    background-color: $color-gray-75;
+    background-color: $color-gray-60;
     color: $color-white;
   }
 }
@@ -9777,6 +9795,123 @@ button.module-image__border-overlay:focus {
   }
 }
 
+.module-message__context {
+  &--icon::before {
+    content: ' ';
+    display: inline-block;
+    height: 14px;
+    margin-right: 8px;
+    width: 14px;
+    vertical-align: middle;
+  }
+
+  &__download::before {
+    @include light-theme {
+      @include color-svg(
+        '../images/icons/v2/save-outline-24.svg',
+        $color-black
+      );
+    }
+
+    @include dark-theme {
+      @include color-svg(
+        '../images/icons/v2/save-solid-24.svg',
+        $color-gray-15
+      );
+    }
+  }
+
+  &__reply::before {
+    @include light-theme {
+      @include color-svg(
+        '../images/icons/v2/reply-outline-24.svg',
+        $color-black
+      );
+    }
+
+    @include dark-theme {
+      @include color-svg(
+        '../images/icons/v2/reply-solid-24.svg',
+        $color-gray-15
+      );
+    }
+  }
+
+  &__react::before {
+    @include light-theme {
+      @include color-svg(
+        '../images/icons/v2/add-emoji-outline-24.svg',
+        $color-black
+      );
+    }
+
+    @include dark-theme {
+      @include color-svg(
+        '../images/icons/v2/add-emoji-outline-24.svg',
+        $color-gray-15
+      );
+    }
+  }
+
+  &__more-info::before {
+    @include light-theme {
+      @include color-svg(
+        '../images/icons/v2/info-outline-24.svg',
+        $color-black
+      );
+    }
+
+    @include dark-theme {
+      @include color-svg(
+        '../images/icons/v2/info-outline-24.svg',
+        $color-gray-15
+      );
+    }
+  }
+
+  &__retry-send::before {
+    @include light-theme {
+      @include color-svg('../images/icons/v2/send-24.svg', $color-black);
+    }
+
+    @include dark-theme {
+      @include color-svg('../images/icons/v2/send-24.svg', $color-gray-15);
+    }
+  }
+
+  &__delete-message::before {
+    @include light-theme {
+      @include color-svg(
+        '../images/icons/v2/trash-outline-24.svg',
+        $color-black
+      );
+    }
+
+    @include dark-theme {
+      @include color-svg(
+        '../images/icons/v2/trash-solid-24.svg',
+        $color-gray-15
+      );
+    }
+  }
+
+  &__delete-message-for-everyone::before {
+    @include light-theme {
+      @include color-svg(
+        '../images/icons/v2/trash-outline-24.svg',
+        $color-black
+      );
+    }
+
+    @include dark-theme {
+      @include color-svg(
+        '../images/icons/v2/trash-solid-24.svg',
+        $color-gray-15
+      );
+    }
+  }
+}
+
 /* Spec: container > 438px and container < 593px */
 @media (min-width: 800px) and (max-width: 925px) {
   .module-message {
diff --git a/ts/components/conversation/ConversationHeader.tsx b/ts/components/conversation/ConversationHeader.tsx
index 38835156f1..fbfb41d6f5 100644
--- a/ts/components/conversation/ConversationHeader.tsx
+++ b/ts/components/conversation/ConversationHeader.tsx
@@ -350,6 +350,28 @@ export class ConversationHeader extends React.Component<PropsType> {
 
     return (
       <ContextMenu id={triggerId}>
+        <SubMenu title={muteTitle}>
+          {muteOptions.map(item => (
+            <MenuItem
+              key={item.name}
+              disabled={item.disabled}
+              onClick={() => {
+                onSetMuteNotifications(item.value);
+              }}
+            >
+              {item.name}
+            </MenuItem>
+          ))}
+        </SubMenu>
+        {isPinned ? (
+          <MenuItem onClick={() => onSetPin(false)}>
+            {i18n('unpinConversation')}
+          </MenuItem>
+        ) : (
+          <MenuItem onClick={() => onSetPin(true)}>
+            {i18n('pinConversation')}
+          </MenuItem>
+        )}
         {disableTimerChanges ? null : (
           <SubMenu title={disappearingTitle}>
             {(timerOptions || []).map(item => (
@@ -364,19 +386,6 @@ export class ConversationHeader extends React.Component<PropsType> {
             ))}
           </SubMenu>
         )}
-        <SubMenu title={muteTitle}>
-          {muteOptions.map(item => (
-            <MenuItem
-              key={item.name}
-              disabled={item.disabled}
-              onClick={() => {
-                onSetMuteNotifications(item.value);
-              }}
-            >
-              {item.name}
-            </MenuItem>
-          ))}
-        </SubMenu>
         <MenuItem onClick={onShowAllMedia}>{i18n('viewRecentMedia')}</MenuItem>
         {isGroup ? (
           <MenuItem onClick={onShowGroupMembers}>
@@ -388,6 +397,7 @@ export class ConversationHeader extends React.Component<PropsType> {
             {i18n('showSafetyNumber')}
           </MenuItem>
         ) : null}
+        <MenuItem divider />
         {!isGroup && acceptedMessageRequest ? (
           <MenuItem onClick={onResetSession}>{i18n('resetSession')}</MenuItem>
         ) : null}
@@ -398,15 +408,6 @@ export class ConversationHeader extends React.Component<PropsType> {
         ) : (
           <MenuItem onClick={onArchive}>{i18n('archiveConversation')}</MenuItem>
         )}
-        {isPinned ? (
-          <MenuItem onClick={() => onSetPin(false)}>
-            {i18n('unpinConversation')}
-          </MenuItem>
-        ) : (
-          <MenuItem onClick={() => onSetPin(true)}>
-            {i18n('pinConversation')}
-          </MenuItem>
-        )}
         <MenuItem onClick={onDeleteMessages}>{i18n('deleteMessages')}</MenuItem>
       </ContextMenu>
     );
diff --git a/ts/components/conversation/Message.stories.tsx b/ts/components/conversation/Message.stories.tsx
index fe015136c6..b7392c22da 100644
--- a/ts/components/conversation/Message.stories.tsx
+++ b/ts/components/conversation/Message.stories.tsx
@@ -796,3 +796,21 @@ story.add('@Mentions', () => {
 
   return renderBothDirections(props);
 });
+
+story.add('All the context menus', () => {
+  const props = createProps({
+    attachments: [
+      {
+        url: '/fixtures/tina-rolf-269345-unsplash.jpg',
+        fileName: 'tina-rolf-269345-unsplash.jpg',
+        contentType: IMAGE_JPEG,
+        width: 128,
+        height: 128,
+      },
+    ],
+    status: 'partial-sent',
+    canDeleteForEveryone: true,
+  });
+
+  return <Message {...props} direction="outgoing" />;
+});
diff --git a/ts/components/conversation/Message.tsx b/ts/components/conversation/Message.tsx
index 0a4f39620d..0b4f64fe23 100644
--- a/ts/components/conversation/Message.tsx
+++ b/ts/components/conversation/Message.tsx
@@ -1347,7 +1347,9 @@ export class Message extends React.PureComponent<Props, State> {
 
     const { canDeleteForEveryone } = this.state;
 
-    const showRetry = status === 'error' && direction === 'outgoing';
+    const showRetry =
+      (status === 'error' || status === 'partial-sent') &&
+      direction === 'outgoing';
     const multipleAttachments = attachments && attachments.length > 1;
 
     const menu = (
@@ -1360,7 +1362,8 @@ export class Message extends React.PureComponent<Props, State> {
         attachments[0] ? (
           <MenuItem
             attributes={{
-              className: 'module-message__context__download',
+              className:
+                'module-message__context--icon module-message__context__download',
             }}
             onClick={this.openGenericAttachment}
           >
@@ -1371,20 +1374,8 @@ export class Message extends React.PureComponent<Props, State> {
           <>
             <MenuItem
               attributes={{
-                className: 'module-message__context__react',
-              }}
-              onClick={(event: React.MouseEvent) => {
-                event.stopPropagation();
-                event.preventDefault();
-
-                this.toggleReactionPicker();
-              }}
-            >
-              {i18n('reactToMessage')}
-            </MenuItem>
-            <MenuItem
-              attributes={{
-                className: 'module-message__context__reply',
+                className:
+                  'module-message__context--icon module-message__context__reply',
               }}
               onClick={(event: React.MouseEvent) => {
                 event.stopPropagation();
@@ -1395,11 +1386,26 @@ export class Message extends React.PureComponent<Props, State> {
             >
               {i18n('replyToMessage')}
             </MenuItem>
+            <MenuItem
+              attributes={{
+                className:
+                  'module-message__context--icon module-message__context__react',
+              }}
+              onClick={(event: React.MouseEvent) => {
+                event.stopPropagation();
+                event.preventDefault();
+
+                this.toggleReactionPicker();
+              }}
+            >
+              {i18n('reactToMessage')}
+            </MenuItem>
           </>
         ) : null}
         <MenuItem
           attributes={{
-            className: 'module-message__context__more-info',
+            className:
+              'module-message__context--icon module-message__context__more-info',
           }}
           onClick={(event: React.MouseEvent) => {
             event.stopPropagation();
@@ -1413,7 +1419,8 @@ export class Message extends React.PureComponent<Props, State> {
         {showRetry ? (
           <MenuItem
             attributes={{
-              className: 'module-message__context__retry-send',
+              className:
+                'module-message__context--icon module-message__context__retry-send',
             }}
             onClick={(event: React.MouseEvent) => {
               event.stopPropagation();
@@ -1427,7 +1434,8 @@ export class Message extends React.PureComponent<Props, State> {
         ) : null}
         <MenuItem
           attributes={{
-            className: 'module-message__context__delete-message',
+            className:
+              'module-message__context--icon module-message__context__delete-message',
           }}
           onClick={(event: React.MouseEvent) => {
             event.stopPropagation();
@@ -1441,7 +1449,8 @@ export class Message extends React.PureComponent<Props, State> {
         {canDeleteForEveryone ? (
           <MenuItem
             attributes={{
-              className: 'module-message__context__delete-message-for-everyone',
+              className:
+                'module-message__context--icon module-message__context__delete-message-for-everyone',
             }}
             onClick={(event: React.MouseEvent) => {
               event.stopPropagation();