diff --git a/components/sidebar/sidebar_category/sidebar_category_menu/__snapshots__/sidebar_category_menu.test.tsx.snap b/components/sidebar/sidebar_category/sidebar_category_menu/__snapshots__/sidebar_category_menu.test.tsx.snap
index 2fa2970526d0..4c2265e877f3 100644
--- a/components/sidebar/sidebar_category/sidebar_category_menu/__snapshots__/sidebar_category_menu.test.tsx.snap
+++ b/components/sidebar/sidebar_category/sidebar_category_menu/__snapshots__/sidebar_category_menu.test.tsx.snap
@@ -8,6 +8,7 @@ exports[`components/sidebar/sidebar_category/sidebar_category_menu should match
     id="SidebarCategoryMenu-category1"
     isMenuOpen={false}
     onToggleMenu={[Function]}
+    refCallback={[Function]}
     tooltipText="Category options"
   >
     <MenuGroup>
@@ -46,6 +47,45 @@ exports[`components/sidebar/sidebar_category/sidebar_category_menu should match
         text="Delete Category"
       />
     </MenuGroup>
+    <MenuGroup>
+      <SubMenuItem
+        direction="right"
+        icon={
+          <i
+            className="icon-sort-alphabetical-ascending"
+          />
+        }
+        id="sortChannels"
+        openUp={false}
+        selectedValueText="Alphabetically"
+        show={true}
+        styleSelectableItem={true}
+        subMenu={
+          Array [
+            Object {
+              "action": [Function],
+              "direction": "right",
+              "id": "sortAlphabetical",
+              "text": "Alphabetically",
+            },
+            Object {
+              "action": [Function],
+              "direction": "right",
+              "id": "sortByMostRecent",
+              "text": "Recent Activity",
+            },
+            Object {
+              "action": [Function],
+              "direction": "right",
+              "id": "sortManual",
+              "text": "Manually",
+            },
+          ]
+        }
+        text="Sort"
+        xOffset={0}
+      />
+    </MenuGroup>
     <MenuGroup>
       <MenuItemAction
         icon={
@@ -71,6 +111,7 @@ exports[`components/sidebar/sidebar_category/sidebar_category_menu should match
     id="SidebarCategoryMenu-category1"
     isMenuOpen={false}
     onToggleMenu={[Function]}
+    refCallback={[Function]}
     tooltipText="Category options"
   >
     <MenuGroup>
@@ -86,6 +127,45 @@ exports[`components/sidebar/sidebar_category/sidebar_category_menu should match
         text="Mute Category"
       />
     </MenuGroup>
+    <MenuGroup>
+      <SubMenuItem
+        direction="right"
+        icon={
+          <i
+            className="icon-sort-alphabetical-ascending"
+          />
+        }
+        id="sortChannels"
+        openUp={false}
+        selectedValueText="Alphabetically"
+        show={true}
+        styleSelectableItem={true}
+        subMenu={
+          Array [
+            Object {
+              "action": [Function],
+              "direction": "right",
+              "id": "sortAlphabetical",
+              "text": "Alphabetically",
+            },
+            Object {
+              "action": [Function],
+              "direction": "right",
+              "id": "sortByMostRecent",
+              "text": "Recent Activity",
+            },
+            Object {
+              "action": [Function],
+              "direction": "right",
+              "id": "sortManual",
+              "text": "Manually",
+            },
+          ]
+        }
+        text="Sort"
+        xOffset={0}
+      />
+    </MenuGroup>
     <MenuGroup>
       <MenuItemAction
         icon={
diff --git a/components/sidebar/sidebar_category/sidebar_category_menu/index.ts b/components/sidebar/sidebar_category/sidebar_category_menu/index.ts
index 5893ea7f211e..fda859d56d07 100644
--- a/components/sidebar/sidebar_category/sidebar_category_menu/index.ts
+++ b/components/sidebar/sidebar_category/sidebar_category_menu/index.ts
@@ -4,9 +4,10 @@
 import {connect} from 'react-redux';
 import {Dispatch, bindActionCreators, ActionCreatorsMapObject} from 'redux';
 
-import {setCategoryMuted} from 'mattermost-redux/actions/channel_categories';
+import {setCategoryMuted, setCategorySorting} from 'mattermost-redux/actions/channel_categories';
 import {getCurrentTeam} from 'mattermost-redux/selectors/entities/teams';
 import {ActionFunc} from 'mattermost-redux/types/actions';
+import {CategorySorting} from 'mattermost-redux/types/channel_categories';
 import {GlobalState} from 'mattermost-redux/types/store';
 
 import {openModal} from 'actions/views/modals';
@@ -28,6 +29,7 @@ type Actions = {
         data: boolean;
     }>;
     setCategoryMuted: (categoryId: string, muted: boolean) => Promise<void>;
+    setCategorySorting: (categoryId: string, sorting: CategorySorting) => void;
 }
 
 function mapDispatchToProps(dispatch: Dispatch) {
@@ -35,6 +37,7 @@ function mapDispatchToProps(dispatch: Dispatch) {
         actions: bindActionCreators<ActionCreatorsMapObject<ActionFunc>, Actions>({
             openModal,
             setCategoryMuted,
+            setCategorySorting,
         }, dispatch),
     };
 }
diff --git a/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.test.tsx b/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.test.tsx
index 98635b45d5af..1588290f6c23 100644
--- a/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.test.tsx
+++ b/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.test.tsx
@@ -29,6 +29,7 @@ describe('components/sidebar/sidebar_category/sidebar_category_menu', () => {
         actions: {
             openModal: jest.fn(),
             setCategoryMuted: jest.fn(),
+            setCategorySorting: jest.fn(),
         },
     };
 
diff --git a/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.tsx b/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.tsx
index 15f2c895f6d0..6d952461b287 100644
--- a/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.tsx
+++ b/components/sidebar/sidebar_category/sidebar_category_menu/sidebar_category_menu.tsx
@@ -5,14 +5,16 @@ import React from 'react';
 import {IntlShape, injectIntl} from 'react-intl';
 
 import {CategoryTypes} from 'mattermost-redux/constants/channel_categories';
-import {ChannelCategory} from 'mattermost-redux/types/channel_categories';
+import {ChannelCategory, CategorySorting} from 'mattermost-redux/types/channel_categories';
 
 import {trackEvent} from 'actions/telemetry_actions';
 import DeleteCategoryModal from 'components/delete_category_modal';
 import EditCategoryModal from 'components/edit_category_modal';
 import SidebarMenu from 'components/sidebar/sidebar_menu';
+import SidebarMenuType from 'components/sidebar/sidebar_menu/sidebar_menu';
 import Menu from 'components/widgets/menu/menu';
 import {ModalIdentifiers} from 'utils/constants';
+import {Props as SubmenuItemProps} from 'components/widgets/menu/menu_items/submenu_item';
 
 type Props = {
     currentTeamId: string;
@@ -25,11 +27,14 @@ type Props = {
             data: boolean;
         }>;
         setCategoryMuted: (categoryId: string, muted: boolean) => Promise<void>;
+        setCategorySorting: (categoryId: string, sorting: CategorySorting) => void;
     };
 };
 
 type State = {
     showDeleteCategoryModal: boolean;
+    openUp: boolean;
+    width: number;
 }
 
 class SidebarCategoryMenu extends React.PureComponent<Props, State> {
@@ -38,6 +43,8 @@ class SidebarCategoryMenu extends React.PureComponent<Props, State> {
 
         this.state = {
             showDeleteCategoryModal: false,
+            openUp: false,
+            width: 0,
         };
     }
 
@@ -74,6 +81,13 @@ class SidebarCategoryMenu extends React.PureComponent<Props, State> {
         trackEvent('ui', 'ui_sidebar_category_menu_createCategory');
     }
 
+    handleSortChannels = (sorting: CategorySorting) => {
+        const {category} = this.props;
+
+        this.props.actions.setCategorySorting(category.id, sorting);
+        trackEvent('ui', `ui_sidebar_sort_dm_${sorting}`);
+    }
+
     onToggleMenu = (open: boolean) => {
         this.props.onToggleMenu(open);
 
@@ -104,6 +118,25 @@ class SidebarCategoryMenu extends React.PureComponent<Props, State> {
             );
         }
 
+        const sortMenuItems: SubmenuItemProps[] = [{
+            id: 'sortAlphabetical',
+            direction: 'right' as any,
+            text: intl.formatMessage({id: 'user.settings.sidebar.sortAlpha', defaultMessage: 'Alphabetically'}),
+            action: () => this.handleSortChannels(CategorySorting.Alphabetical),
+        },
+        {
+            id: 'sortByMostRecent',
+            direction: 'right' as any,
+            text: intl.formatMessage({id: 'sidebar.sortedByRecencyLabel', defaultMessage: 'Recent Activity'}),
+            action: () => this.handleSortChannels(CategorySorting.Recency),
+        },
+        {
+            id: 'sortManual',
+            direction: 'right' as any,
+            text: intl.formatMessage({id: 'sidebar.sortedManually', defaultMessage: 'Manually'}),
+            action: () => this.handleSortChannels(CategorySorting.Manual),
+        }];
+
         let deleteCategory;
         let renameCategory;
         if (category.type === CategoryTypes.CUSTOM) {
@@ -127,6 +160,32 @@ class SidebarCategoryMenu extends React.PureComponent<Props, State> {
             );
         }
 
+        let selectedValueText;
+
+        switch (category.sorting) {
+        case CategorySorting.Alphabetical:
+            selectedValueText = intl.formatMessage({id: 'user.settings.sidebar.sortAlpha', defaultMessage: 'Alphabetically'});
+            break;
+        case CategorySorting.Recency:
+            selectedValueText = intl.formatMessage({id: 'user.settings.sidebar.recent', defaultMessage: 'Recent Activity'});
+            break;
+        default:
+            selectedValueText = intl.formatMessage({id: 'sidebar.sortedManually', defaultMessage: 'Manually'});
+        }
+
+        let icon;
+
+        switch (category.sorting) {
+        case CategorySorting.Alphabetical:
+            icon = <i className='icon-sort-alphabetical-ascending'/>;
+            break;
+        case CategorySorting.Recency:
+            icon = <i className='icon-clock-outline'/>;
+            break;
+        default:
+            icon = <i className='icon-format-list-bulleted'/>;
+        }
+
         return (
             <React.Fragment>
                 <Menu.Group>
@@ -134,6 +193,19 @@ class SidebarCategoryMenu extends React.PureComponent<Props, State> {
                     {renameCategory}
                     {deleteCategory}
                 </Menu.Group>
+                <Menu.Group>
+                    <Menu.ItemSubMenu
+                        id={'sortChannels'}
+                        subMenu={sortMenuItems}
+                        text={intl.formatMessage({id: 'sidebar.sort', defaultMessage: 'Sort'})}
+                        selectedValueText={selectedValueText}
+                        icon={icon}
+                        direction={'right' as any}
+                        openUp={this.state.openUp}
+                        xOffset={this.state.width}
+                        styleSelectableItem={true}
+                    />
+                </Menu.Group>
                 <Menu.Group>
                     <Menu.ItemAction
                         id={`create-${category.id}`}
@@ -146,12 +218,22 @@ class SidebarCategoryMenu extends React.PureComponent<Props, State> {
         );
     }
 
+    refCallback = (ref: SidebarMenuType) => {
+        if (ref) {
+            this.setState({
+                openUp: ref.state.openUp,
+                width: ref.state.width,
+            });
+        }
+    }
+
     render() {
         const {intl, category} = this.props;
 
         return (
             <React.Fragment>
                 <SidebarMenu
+                    refCallback={this.refCallback}
                     id={`SidebarCategoryMenu-${category.id}`}
                     ariaLabel={intl.formatMessage({id: 'sidebar_left.sidebar_category_menu.dropdownAriaLabel', defaultMessage: 'Category Menu'})}
                     buttonAriaLabel={intl.formatMessage({id: 'sidebar_left.sidebar_category_menu.dropdownAriaLabel', defaultMessage: 'Category Menu'})}
diff --git a/i18n/en.json b/i18n/en.json
index 677bf7794411..9a098110960f 100644
--- a/i18n/en.json
+++ b/i18n/en.json
@@ -3815,6 +3815,7 @@
   "sidebar.show": "Show",
   "sidebar.sort": "Sort",
   "sidebar.sortedByRecencyLabel": "Recent activity",
+  "sidebar.sortedManually": "Manually",
   "sidebar.team_select": "{siteName} - Join a team",
   "sidebar.tutorialScreen1.body": "**Channels** organize conversations across different topics. They're open to everyone on your team. To send private communications use **Direct Messages** for a single person or **Private Channels** for multiple people.",
   "sidebar.tutorialScreen1.title": "Channels",
diff --git a/package-lock.json b/package-lock.json
index b60c54a37dca..c7893ae91248 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -12815,7 +12815,10 @@
       "version": "1.3.1",
       "resolved": "https://registry.npmjs.org/full-icu/-/full-icu-1.3.1.tgz",
       "integrity": "sha512-VMtK//85QJomhk3cXOCksNwOYaw1KWnYTS37GYGgyf7A3ajdBoPGhaJuJWAH2S2kq8GZeXkdKn+3Mfmgy11cVw==",
-      "dev": true
+      "dev": true,
+      "requires": {
+        "icu4c-data": "0.64.2"
+      }
     },
     "function-bind": {
       "version": "1.1.1",
@@ -13740,6 +13743,12 @@
         "postcss": "^7.0.14"
       }
     },
+    "icu4c-data": {
+      "version": "0.64.2",
+      "resolved": "https://registry.npmjs.org/icu4c-data/-/icu4c-data-0.64.2.tgz",
+      "integrity": "sha512-BPuTfkRTkplmK1pNrqgyOLJ0qB2UcQ12EotVLwiWh4ErtZR1tEYoRZk/LBLmlDfK5v574/lQYLB4jT9vApBiBQ==",
+      "dev": true
+    },
     "identity-obj-proxy": {
       "version": "3.0.0",
       "resolved": "https://registry.npmjs.org/identity-obj-proxy/-/identity-obj-proxy-3.0.0.tgz",
diff --git a/sass/layout/_sidebar-left.scss b/sass/layout/_sidebar-left.scss
index 85c441764bb7..85d036dd49c6 100644
--- a/sass/layout/_sidebar-left.scss
+++ b/sass/layout/_sidebar-left.scss
@@ -415,6 +415,7 @@
                 color: rgba(var(--center-channel-color-rgb), 0.56);
                 width: 60%;
                 text-align: right;
+                margin-top: 1px;
             }
         }
     }