From 49b85262c5a1944d7fdb50e43900a4adb13aba6c Mon Sep 17 00:00:00 2001
From: Dennis Tang <dennis@dennistang.net>
Date: Thu, 19 Apr 2018 14:43:20 +0000
Subject: Resolve "Improve tooltips of collapsed sidebars"

---
 app/assets/javascripts/due_date_select.js          |  9 ++-
 app/assets/javascripts/labels_select.js            |  5 +-
 app/assets/javascripts/milestone_select.js         | 14 +++-
 app/assets/javascripts/right_sidebar.js            | 12 ++-
 .../sidebar/components/assignees/assignees.vue     | 20 ++++-
 .../components/assignees/sidebar_assignees.vue     | 12 ++-
 .../confidential/confidential_issue_sidebar.vue    | 19 ++++-
 .../sidebar/components/lock/lock_issue_sidebar.vue | 21 ++++-
 .../components/participants/participants.vue       | 18 ++++-
 .../components/time_tracking/collapsed_state.vue   | 32 +++++++-
 app/assets/javascripts/sidebar/mount_sidebar.js    |  1 +
 app/assets/javascripts/users_select.js             |  7 +-
 .../components/sidebar/toggle_sidebar.vue          | 39 +++++++---
 app/assets/stylesheets/framework/variables.scss    |  3 +
 app/assets/stylesheets/pages/issuable.scss         | 28 ++++++-
 app/assets/stylesheets/pages/milestone.scss        | 14 +++-
 app/helpers/issuables_helper.rb                    | 38 ++++++++-
 app/helpers/milestones_helper.rb                   | 91 ++++++++++++++++++----
 app/models/concerns/milestoneish.rb                |  4 +-
 app/serializers/entity_date_helper.rb              | 27 +++++++
 app/views/projects/issues/_issue.html.haml         |  2 +-
 .../merge_requests/_merge_request.html.haml        |  2 +-
 app/views/shared/issuable/_sidebar.html.haml       | 11 ++-
 .../shared/issuable/_sidebar_assignees.html.haml   |  2 +-
 app/views/shared/issuable/_sidebar_todo.html.haml  |  6 +-
 .../form/_merge_request_assignee.html.haml         |  2 +-
 app/views/shared/milestones/_sidebar.html.haml     | 35 +++++----
 .../25010-collapsed-sidebar-tooltips.yml           |  5 ++
 doc/user/project/issues/issues_functionalities.md  |  2 +-
 doc/workflow/todos.md                              |  4 +-
 spec/features/issues/todo_spec.rb                  |  4 +-
 spec/helpers/issuables_helper_spec.rb              |  8 +-
 spec/helpers/milestones_helper_spec.rb             | 54 -------------
 spec/javascripts/collapsed_sidebar_todo_spec.js    | 10 +--
 spec/models/milestone_spec.rb                      | 12 ++-
 spec/serializers/entity_date_helper_spec.rb        | 55 +++++++++++++
 36 files changed, 458 insertions(+), 170 deletions(-)
 create mode 100644 changelogs/unreleased/25010-collapsed-sidebar-tooltips.yml

diff --git a/app/assets/javascripts/due_date_select.js b/app/assets/javascripts/due_date_select.js
index 842a4255f08..4164149dd06 100644
--- a/app/assets/javascripts/due_date_select.js
+++ b/app/assets/javascripts/due_date_select.js
@@ -2,7 +2,9 @@
 
 import $ from 'jquery';
 import Pikaday from 'pikaday';
+import { __ } from '~/locale';
 import axios from './lib/utils/axios_utils';
+import { timeFor } from './lib/utils/datetime_utility';
 import { parsePikadayDate, pikadayToString } from './lib/utils/datefix';
 
 class DueDateSelect {
@@ -14,6 +16,7 @@ class DueDateSelect {
     this.$dropdownParent = $dropdownParent;
     this.$datePicker = $dropdownParent.find('.js-due-date-calendar');
     this.$block = $block;
+    this.$sidebarCollapsedValue = $block.find('.sidebar-collapsed-icon');
     this.$selectbox = $dropdown.closest('.selectbox');
     this.$value = $block.find('.value');
     this.$valueContent = $block.find('.value-content');
@@ -128,7 +131,8 @@ class DueDateSelect {
 
   submitSelectedDate(isDropdown) {
     const selectedDateValue = this.datePayload[this.abilityName].due_date;
-    const displayedDateStyle = this.displayedDate !== 'No due date' ? 'bold' : 'no-value';
+    const hasDueDate = this.displayedDate !== 'No due date';
+    const displayedDateStyle = hasDueDate ? 'bold' : 'no-value';
 
     this.$loading.removeClass('hidden').fadeIn();
 
@@ -145,10 +149,13 @@ class DueDateSelect {
 
     return axios.put(this.issueUpdateURL, this.datePayload)
       .then(() => {
+        const tooltipText = hasDueDate ? `${__('Due date')}<br />${selectedDateValue} (${timeFor(selectedDateValue)})` : __('Due date');
         if (isDropdown) {
           this.$dropdown.trigger('loaded.gl.dropdown');
           this.$dropdown.dropdown('toggle');
         }
+        this.$sidebarCollapsedValue.attr('data-original-title', tooltipText);
+
         return this.$loading.fadeOut();
       });
   }
diff --git a/app/assets/javascripts/labels_select.js b/app/assets/javascripts/labels_select.js
index d0050abb8e9..9b62cfb8206 100644
--- a/app/assets/javascripts/labels_select.js
+++ b/app/assets/javascripts/labels_select.js
@@ -83,7 +83,7 @@ export default class LabelsSelect {
         $dropdown.trigger('loading.gl.dropdown');
         axios.put(issueUpdateURL, data)
           .then(({ data }) => {
-            var labelCount, template, labelTooltipTitle, labelTitles;
+            var labelCount, template, labelTooltipTitle, labelTitles, formattedLabels;
             $loading.fadeOut();
             $dropdown.trigger('loaded.gl.dropdown');
             $selectbox.hide();
@@ -115,8 +115,7 @@ export default class LabelsSelect {
               labelTooltipTitle = labelTitles.join(', ');
             }
             else {
-              labelTooltipTitle = '';
-              $sidebarLabelTooltip.tooltip('destroy');
+              labelTooltipTitle = __('Labels');
             }
 
             $sidebarLabelTooltip
diff --git a/app/assets/javascripts/milestone_select.js b/app/assets/javascripts/milestone_select.js
index d0a2b27b0e6..7e9a50a885d 100644
--- a/app/assets/javascripts/milestone_select.js
+++ b/app/assets/javascripts/milestone_select.js
@@ -4,6 +4,7 @@
 
 import $ from 'jquery';
 import _ from 'underscore';
+import { __ } from '~/locale';
 import axios from './lib/utils/axios_utils';
 import { timeFor } from './lib/utils/datetime_utility';
 import ModalStore from './boards/stores/modal_store';
@@ -25,7 +26,7 @@ export default class MilestoneSelect {
     }
 
     $els.each((i, dropdown) => {
-      let collapsedSidebarLabelTemplate, milestoneLinkNoneTemplate, milestoneLinkTemplate, selectedMilestone, selectedMilestoneDefault;
+      let milestoneLinkNoneTemplate, milestoneLinkTemplate, selectedMilestone, selectedMilestoneDefault;
       const $dropdown = $(dropdown);
       const projectId = $dropdown.data('projectId');
       const milestonesUrl = $dropdown.data('milestones');
@@ -52,7 +53,6 @@ export default class MilestoneSelect {
       if (issueUpdateURL) {
         milestoneLinkTemplate = _.template('<a href="/<%- full_path %>/milestones/<%- iid %>" class="bold has-tooltip" data-container="body" title="<%- remaining %>"><%- title %></a>');
         milestoneLinkNoneTemplate = '<span class="no-value">None</span>';
-        collapsedSidebarLabelTemplate = _.template('<span class="has-tooltip" data-container="body" title="<%- name %><br /><%- remaining %>" data-placement="left" data-html="true"> <%- title %> </span>');
       }
       return $dropdown.glDropdown({
         showMenuAbove: showMenuAbove,
@@ -214,10 +214,16 @@ export default class MilestoneSelect {
                   data.milestone.remaining = timeFor(data.milestone.due_date);
                   data.milestone.name = data.milestone.title;
                   $value.html(milestoneLinkTemplate(data.milestone));
-                  return $sidebarCollapsedValue.find('span').html(collapsedSidebarLabelTemplate(data.milestone));
+                  return $sidebarCollapsedValue
+                    .attr('data-original-title', `${data.milestone.name}<br />${data.milestone.remaining}`)
+                    .find('span')
+                    .text(data.milestone.title);
                 } else {
                   $value.html(milestoneLinkNoneTemplate);
-                  return $sidebarCollapsedValue.find('span').text('No');
+                  return $sidebarCollapsedValue
+                    .attr('data-original-title', __('Milestone'))
+                    .find('span')
+                    .text(__('None'));
                 }
               })
               .catch(() => {
diff --git a/app/assets/javascripts/right_sidebar.js b/app/assets/javascripts/right_sidebar.js
index 2088a49590a..6eb0b62fa1c 100644
--- a/app/assets/javascripts/right_sidebar.js
+++ b/app/assets/javascripts/right_sidebar.js
@@ -5,6 +5,7 @@ import _ from 'underscore';
 import Cookies from 'js-cookie';
 import flash from './flash';
 import axios from './lib/utils/axios_utils';
+import { __ } from './locale';
 
 function Sidebar(currentUser) {
   this.toggleTodo = this.toggleTodo.bind(this);
@@ -41,12 +42,14 @@ Sidebar.prototype.addEventListeners = function() {
 };
 
 Sidebar.prototype.sidebarToggleClicked = function (e, triggered) {
-  var $allGutterToggleIcons, $this, $thisIcon;
+  var $allGutterToggleIcons, $this, isExpanded, tooltipLabel;
   e.preventDefault();
   $this = $(this);
-  $thisIcon = $this.find('i');
+  isExpanded = $this.find('i').hasClass('fa-angle-double-right');
+  tooltipLabel = isExpanded ? __('Expand sidebar') : __('Collapse sidebar');
   $allGutterToggleIcons = $('.js-sidebar-toggle i');
-  if ($thisIcon.hasClass('fa-angle-double-right')) {
+
+  if (isExpanded) {
     $allGutterToggleIcons.removeClass('fa-angle-double-right').addClass('fa-angle-double-left');
     $('aside.right-sidebar').removeClass('right-sidebar-expanded').addClass('right-sidebar-collapsed');
     $('.layout-page').removeClass('right-sidebar-expanded').addClass('right-sidebar-collapsed');
@@ -57,6 +60,9 @@ Sidebar.prototype.sidebarToggleClicked = function (e, triggered) {
 
     if (gl.lazyLoader) gl.lazyLoader.loadCheck();
   }
+
+  $this.attr('data-original-title', tooltipLabel);
+
   if (!triggered) {
     Cookies.set("collapsed_gutter", $('.right-sidebar').hasClass('right-sidebar-collapsed'));
   }
diff --git a/app/assets/javascripts/sidebar/components/assignees/assignees.vue b/app/assets/javascripts/sidebar/components/assignees/assignees.vue
index 1e7f46454bf..2d00e8ac7e0 100644
--- a/app/assets/javascripts/sidebar/components/assignees/assignees.vue
+++ b/app/assets/javascripts/sidebar/components/assignees/assignees.vue
@@ -1,6 +1,12 @@
 <script>
+import { __ } from '~/locale';
+import tooltip from '~/vue_shared/directives/tooltip';
+
 export default {
   name: 'Assignees',
+  directives: {
+    tooltip,
+  },
   props: {
     rootPath: {
       type: String,
@@ -14,6 +20,11 @@ export default {
       type: Boolean,
       required: true,
     },
+    issuableType: {
+      type: String,
+      require: true,
+      default: 'issue',
+    },
   },
   data() {
     return {
@@ -62,6 +73,12 @@ export default {
         names.push(`+ ${this.users.length - maxRender} more`);
       }
 
+      if (!this.users.length) {
+        const emptyTooltipLabel = this.issuableType === 'issue' ?
+          __('Assignee(s)') : __('Assignee');
+        names.push(emptyTooltipLabel);
+      }
+
       return names.join(', ');
     },
     sidebarAvatarCounter() {
@@ -109,7 +126,8 @@ export default {
   <div>
     <div
       class="sidebar-collapsed-icon sidebar-collapsed-user"
-      :class="{ 'multiple-users': hasMoreThanOneAssignee, 'has-tooltip': hasAssignees }"
+      :class="{ 'multiple-users': hasMoreThanOneAssignee }"
+      v-tooltip
       data-container="body"
       data-placement="left"
       :title="collapsedTooltipTitle"
diff --git a/app/assets/javascripts/sidebar/components/assignees/sidebar_assignees.vue b/app/assets/javascripts/sidebar/components/assignees/sidebar_assignees.vue
index 3c6b9c27814..b04a2eff798 100644
--- a/app/assets/javascripts/sidebar/components/assignees/sidebar_assignees.vue
+++ b/app/assets/javascripts/sidebar/components/assignees/sidebar_assignees.vue
@@ -1,9 +1,9 @@
 <script>
-import Flash from '../../../flash';
+import Flash from '~/flash';
+import eventHub from '~/sidebar/event_hub';
+import Store from '~/sidebar/stores/sidebar_store';
 import AssigneeTitle from './assignee_title.vue';
 import Assignees from './assignees.vue';
-import Store from '../../stores/sidebar_store';
-import eventHub from '../../event_hub';
 
 export default {
   name: 'SidebarAssignees',
@@ -25,6 +25,11 @@ export default {
       required: false,
       default: false,
     },
+    issuableType: {
+      type: String,
+      require: true,
+      default: 'issue',
+    },
   },
   data() {
     return {
@@ -90,6 +95,7 @@ export default {
       :users="store.assignees"
       :editable="store.editable"
       @assign-self="assignSelf"
+      :issuable-type="issuableType"
     />
   </div>
 </template>
diff --git a/app/assets/javascripts/sidebar/components/confidential/confidential_issue_sidebar.vue b/app/assets/javascripts/sidebar/components/confidential/confidential_issue_sidebar.vue
index ceb02309959..7f0de722f61 100644
--- a/app/assets/javascripts/sidebar/components/confidential/confidential_issue_sidebar.vue
+++ b/app/assets/javascripts/sidebar/components/confidential/confidential_issue_sidebar.vue
@@ -1,15 +1,19 @@
 <script>
-import Flash from '../../../flash';
+import { __ } from '~/locale';
+import Flash from '~/flash';
+import tooltip from '~/vue_shared/directives/tooltip';
+import Icon from '~/vue_shared/components/icon.vue';
+import eventHub from '~/sidebar/event_hub';
 import editForm from './edit_form.vue';
-import Icon from '../../../vue_shared/components/icon.vue';
-import { __ } from '../../../locale';
-import eventHub from '../../event_hub';
 
 export default {
   components: {
     editForm,
     Icon,
   },
+  directives: {
+    tooltip,
+  },
   props: {
     isConfidential: {
       required: true,
@@ -33,6 +37,9 @@ export default {
     confidentialityIcon() {
       return this.isConfidential ? 'eye-slash' : 'eye';
     },
+    tooltipLabel() {
+      return this.isConfidential ? __('Confidential') : __('Not confidential');
+    },
   },
   created() {
     eventHub.$on('closeConfidentialityForm', this.toggleForm);
@@ -65,6 +72,10 @@ export default {
     <div
       class="sidebar-collapsed-icon"
       @click="toggleForm"
+      v-tooltip
+      data-container="body"
+      data-placement="left"
+      :title="tooltipLabel"
     >
       <icon
         :name="confidentialityIcon"
diff --git a/app/assets/javascripts/sidebar/components/lock/lock_issue_sidebar.vue b/app/assets/javascripts/sidebar/components/lock/lock_issue_sidebar.vue
index e4893451af3..1a5e7b67eca 100644
--- a/app/assets/javascripts/sidebar/components/lock/lock_issue_sidebar.vue
+++ b/app/assets/javascripts/sidebar/components/lock/lock_issue_sidebar.vue
@@ -1,15 +1,22 @@
 <script>
+import { __ } from '~/locale';
 import Flash from '~/flash';
+import tooltip from '~/vue_shared/directives/tooltip';
+import issuableMixin from '~/vue_shared/mixins/issuable';
+import Icon from '~/vue_shared/components/icon.vue';
+import eventHub from '~/sidebar/event_hub';
 import editForm from './edit_form.vue';
-import issuableMixin from '../../../vue_shared/mixins/issuable';
-import Icon from '../../../vue_shared/components/icon.vue';
-import eventHub from '../../event_hub';
 
 export default {
   components: {
     editForm,
     Icon,
   },
+
+  directives: {
+    tooltip,
+  },
+
   mixins: [issuableMixin],
 
   props: {
@@ -44,6 +51,10 @@ export default {
     isLockDialogOpen() {
       return this.mediator.store.isLockDialogOpen;
     },
+
+    tooltipLabel() {
+      return this.isLocked ? __('Locked') : __('Unlocked');
+    },
   },
 
   created() {
@@ -85,6 +96,10 @@ export default {
     <div
       class="sidebar-collapsed-icon"
       @click="toggleForm"
+      v-tooltip
+      data-container="body"
+      data-placement="left"
+      :title="tooltipLabel"
     >
       <icon
         :name="lockIcon"
diff --git a/app/assets/javascripts/sidebar/components/participants/participants.vue b/app/assets/javascripts/sidebar/components/participants/participants.vue
index 006a6d2905d..6d95153af28 100644
--- a/app/assets/javascripts/sidebar/components/participants/participants.vue
+++ b/app/assets/javascripts/sidebar/components/participants/participants.vue
@@ -1,9 +1,13 @@
 <script>
-  import { __, n__, sprintf } from '../../../locale';
-  import loadingIcon from '../../../vue_shared/components/loading_icon.vue';
-  import userAvatarImage from '../../../vue_shared/components/user_avatar/user_avatar_image.vue';
+  import { __, n__, sprintf } from '~/locale';
+  import tooltip from '~/vue_shared/directives/tooltip';
+  import loadingIcon from '~/vue_shared/components/loading_icon.vue';
+  import userAvatarImage from '~/vue_shared/components/user_avatar/user_avatar_image.vue';
 
   export default {
+    directives: {
+      tooltip,
+    },
     components: {
       loadingIcon,
       userAvatarImage,
@@ -72,7 +76,13 @@
 
 <template>
   <div>
-    <div class="sidebar-collapsed-icon">
+    <div
+      class="sidebar-collapsed-icon"
+      v-tooltip
+      data-container="body"
+      data-placement="left"
+      :title="participantLabel"
+    >
       <i
         class="fa fa-users"
         aria-hidden="true"
diff --git a/app/assets/javascripts/sidebar/components/time_tracking/collapsed_state.vue b/app/assets/javascripts/sidebar/components/time_tracking/collapsed_state.vue
index 3b86f1145d1..9d9ee9dea4d 100644
--- a/app/assets/javascripts/sidebar/components/time_tracking/collapsed_state.vue
+++ b/app/assets/javascripts/sidebar/components/time_tracking/collapsed_state.vue
@@ -1,12 +1,17 @@
 <script>
-  import icon from '../../../vue_shared/components/icon.vue';
-  import { abbreviateTime } from '../../../lib/utils/pretty_time';
+  import { __, sprintf } from '~/locale';
+  import { abbreviateTime } from '~/lib/utils/pretty_time';
+  import icon from '~/vue_shared/components/icon.vue';
+  import tooltip from '~/vue_shared/directives/tooltip';
 
   export default {
     name: 'TimeTrackingCollapsedState',
     components: {
       icon,
     },
+    directives: {
+      tooltip,
+    },
     props: {
       showComparisonState: {
         type: Boolean,
@@ -79,6 +84,21 @@
 
         return '';
       },
+      timeTrackedTooltipText() {
+        let title;
+        if (this.showComparisonState) {
+          title = __('Time remaining');
+        } else if (this.showEstimateOnlyState) {
+          title = __('Estimated');
+        } else if (this.showSpentOnlyState) {
+          title = __('Time spent');
+        }
+
+        return sprintf('%{title}: %{text}', ({ title, text: this.text }));
+      },
+      tooltipText() {
+        return this.showNoTimeTrackingState ? __('Time tracking') : this.timeTrackedTooltipText;
+      },
     },
     methods: {
       abbreviateTime(timeStr) {
@@ -89,7 +109,13 @@
 </script>
 
 <template>
-  <div class="sidebar-collapsed-icon">
+  <div
+    class="sidebar-collapsed-icon"
+    v-tooltip
+    data-container="body"
+    data-placement="left"
+    :title="tooltipText"
+  >
     <icon name="timer" />
     <div class="time-tracking-collapsed-summary">
       <div :class="divClass">
diff --git a/app/assets/javascripts/sidebar/mount_sidebar.js b/app/assets/javascripts/sidebar/mount_sidebar.js
index 9f5d852260e..26eb4cffba3 100644
--- a/app/assets/javascripts/sidebar/mount_sidebar.js
+++ b/app/assets/javascripts/sidebar/mount_sidebar.js
@@ -27,6 +27,7 @@ function mountAssigneesComponent(mediator) {
         mediator,
         field: el.dataset.field,
         signedIn: el.hasAttribute('data-signed-in'),
+        issuableType: gl.utils.isInIssuePage() ? 'issue' : 'merge_request',
       },
     }),
   });
diff --git a/app/assets/javascripts/users_select.js b/app/assets/javascripts/users_select.js
index 520a0b3f424..8486019897d 100644
--- a/app/assets/javascripts/users_select.js
+++ b/app/assets/javascripts/users_select.js
@@ -5,6 +5,7 @@
 import $ from 'jquery';
 import _ from 'underscore';
 import axios from './lib/utils/axios_utils';
+import { __ } from './locale';
 import ModalStore from './boards/stores/modal_store';
 
 // TODO: remove eventHub hack after code splitting refactor
@@ -182,7 +183,7 @@ function UsersSelect(currentUser, els, options = {}) {
 
         return axios.put(issueURL, data)
           .then(({ data }) => {
-            var user;
+            var user, tooltipTitle;
             $dropdown.trigger('loaded.gl.dropdown');
             $loading.fadeOut();
             if (data.assignee) {
@@ -191,15 +192,17 @@ function UsersSelect(currentUser, els, options = {}) {
                 username: data.assignee.username,
                 avatar: data.assignee.avatar_url
               };
+              tooltipTitle = _.escape(user.name);
             } else {
               user = {
                 name: 'Unassigned',
                 username: '',
                 avatar: ''
               };
+              tooltipTitle = __('Assignee');
             }
             $value.html(assigneeTemplate(user));
-            $collapsedSidebar.attr('title', _.escape(user.name)).tooltip('fixTitle');
+            $collapsedSidebar.attr('title', tooltipTitle).tooltip('fixTitle');
             return $collapsedSidebar.html(collapsedAssigneeTemplate(user));
           });
       };
diff --git a/app/assets/javascripts/vue_shared/components/sidebar/toggle_sidebar.vue b/app/assets/javascripts/vue_shared/components/sidebar/toggle_sidebar.vue
index 8211d425b1f..de6f8c32e74 100644
--- a/app/assets/javascripts/vue_shared/components/sidebar/toggle_sidebar.vue
+++ b/app/assets/javascripts/vue_shared/components/sidebar/toggle_sidebar.vue
@@ -1,18 +1,29 @@
 <script>
-  export default {
-    name: 'ToggleSidebar',
-    props: {
-      collapsed: {
-        type: Boolean,
-        required: true,
-      },
+import { __ } from '~/locale';
+import tooltip from '~/vue_shared/directives/tooltip';
+
+export default {
+  name: 'ToggleSidebar',
+  directives: {
+    tooltip,
+  },
+  props: {
+    collapsed: {
+      type: Boolean,
+      required: true,
+    },
+  },
+  computed: {
+    tooltipLabel() {
+      return this.collapsed ? __('Expand sidebar') : __('Collapse sidebar');
     },
-    methods: {
-      toggle() {
-        this.$emit('toggle');
-      },
+  },
+  methods: {
+    toggle() {
+      this.$emit('toggle');
     },
-  };
+  },
+};
 </script>
 
 <template>
@@ -20,6 +31,10 @@
     type="button"
     class="btn btn-blank gutter-toggle btn-sidebar-action"
     @click="toggle"
+    v-tooltip
+    data-container="body"
+    data-placement="left"
+    :title="tooltipLabel"
   >
     <i
       aria-label="toggle collapse"
diff --git a/app/assets/stylesheets/framework/variables.scss b/app/assets/stylesheets/framework/variables.scss
index 37223175199..8c44ebc85ef 100644
--- a/app/assets/stylesheets/framework/variables.scss
+++ b/app/assets/stylesheets/framework/variables.scss
@@ -247,6 +247,7 @@ $btn-sm-side-margin: 7px;
 $btn-xs-side-margin: 5px;
 $issue-status-expired: $orange-500;
 $issuable-sidebar-color: $gl-text-color-secondary;
+$sidebar-block-hover-color: #ebebeb;
 $group-path-color: #999;
 $namespace-kind-color: #aaa;
 $panel-heading-link-color: #777;
@@ -373,6 +374,8 @@ $dropdown-hover-color: $blue-400;
 $link-active-background: rgba(0, 0, 0, 0.04);
 $link-hover-background: rgba(0, 0, 0, 0.06);
 $inactive-badge-background: rgba(0, 0, 0, 0.08);
+$sidebar-toggle-height: 60px;
+$sidebar-milestone-toggle-bottom-margin: 10px;
 
 /*
 * Buttons
diff --git a/app/assets/stylesheets/pages/issuable.scss b/app/assets/stylesheets/pages/issuable.scss
index 2c0ed976301..b2dad4a358a 100644
--- a/app/assets/stylesheets/pages/issuable.scss
+++ b/app/assets/stylesheets/pages/issuable.scss
@@ -187,7 +187,12 @@
       padding-left: 10px;
 
       &:hover {
-        color: $gray-darkest;
+        color: $gl-text-color;
+      }
+
+      &:hover,
+      &:focus {
+        text-decoration: none;
       }
     }
 
@@ -368,6 +373,14 @@
       padding: 15px 0 0;
       border-bottom: 0;
       overflow: hidden;
+
+      &:hover {
+        background-color: $sidebar-block-hover-color;
+      }
+
+      &.issuable-sidebar-header {
+        padding-top: 0;
+      }
     }
 
     .participants {
@@ -380,8 +393,17 @@
 
     .gutter-toggle {
       width: 100%;
+      height: $sidebar-toggle-height;
       margin-left: 0;
-      padding-left: 25px;
+      padding-left: 0;
+      border-bottom: 1px solid $border-gray-dark;
+    }
+
+    a.gutter-toggle {
+      display: flex;
+      justify-content: center;
+      flex-direction: column;
+      text-align: center;
     }
 
     .sidebar-collapsed-icon {
@@ -428,10 +450,10 @@
 
       .btn-clipboard {
         border: 0;
+        background: transparent;
         color: $issuable-sidebar-color;
 
         &:hover {
-          background: transparent;
           color: $gl-text-color;
         }
       }
diff --git a/app/assets/stylesheets/pages/milestone.scss b/app/assets/stylesheets/pages/milestone.scss
index 3af8d80daab..bac3b70c734 100644
--- a/app/assets/stylesheets/pages/milestone.scss
+++ b/app/assets/stylesheets/pages/milestone.scss
@@ -53,10 +53,6 @@
 }
 
 .milestone-sidebar {
-  .gutter-toggle {
-    margin-bottom: 10px;
-  }
-
   .milestone-progress {
     .title {
       padding-top: 5px;
@@ -102,7 +98,17 @@
     margin-right: 0;
   }
 
+  .right-sidebar-expanded & {
+    .gutter-toggle {
+      margin-bottom: $sidebar-milestone-toggle-bottom-margin;
+    }
+  }
+
   .right-sidebar-collapsed & {
+    .milestone-progress {
+      padding-top: 0;
+    }
+
     .reference {
       border-top: 1px solid $border-gray-normal;
     }
diff --git a/app/helpers/issuables_helper.rb b/app/helpers/issuables_helper.rb
index 06c3e569c84..f39a62bccc8 100644
--- a/app/helpers/issuables_helper.rb
+++ b/app/helpers/issuables_helper.rb
@@ -9,6 +9,32 @@ module IssuablesHelper
     "right-sidebar-#{sidebar_gutter_collapsed? ? 'collapsed' : 'expanded'}"
   end
 
+  def sidebar_gutter_tooltip_text
+    sidebar_gutter_collapsed? ? _('Expand sidebar') : _('Collapse sidebar')
+  end
+
+  def sidebar_assignee_tooltip_label(issuable)
+    if issuable.assignee
+      issuable.assignee.name
+    else
+      issuable.allows_multiple_assignees? ? _('Assignee(s)') : _('Assignee')
+    end
+  end
+
+  def sidebar_due_date_tooltip_label(issuable)
+    if issuable.due_date
+      "#{_('Due date')}<br />#{due_date_remaining_days(issuable)}"
+    else
+      _('Due date')
+    end
+  end
+
+  def due_date_remaining_days(issuable)
+    remaining_days_in_words = remaining_days_in_words(issuable)
+
+    "#{issuable.due_date.to_s(:medium)} (#{remaining_days_in_words})"
+  end
+
   def multi_label_name(current_labels, default_label)
     if current_labels && current_labels.any?
       title = current_labels.first.try(:title)
@@ -153,10 +179,14 @@ module IssuablesHelper
   def issuable_labels_tooltip(labels, limit: 5)
     first, last = labels.partition.with_index { |_, i| i < limit  }
 
-    label_names = first.collect(&:name)
-    label_names << "and #{last.size} more" unless last.empty?
+    if labels && labels.any?
+      label_names = first.collect(&:name)
+      label_names << "and #{last.size} more" unless last.empty?
 
-    label_names.join(', ')
+      label_names.join(', ')
+    else
+      _("Labels")
+    end
   end
 
   def issuables_state_counter_text(issuable_type, state, display_count)
@@ -321,7 +351,7 @@ module IssuablesHelper
   def issuable_todo_button_data(issuable, todo, is_collapsed)
     {
       todo_text: "Add todo",
-      mark_text: "Mark done",
+      mark_text: "Mark todo as done",
       todo_icon: (is_collapsed ? icon('plus-square') : nil),
       mark_icon: (is_collapsed ? icon('check-square', class: 'todo-undone') : nil),
       issuable_id: issuable.id,
diff --git a/app/helpers/milestones_helper.rb b/app/helpers/milestones_helper.rb
index be8cb358de2..e8caab3e50c 100644
--- a/app/helpers/milestones_helper.rb
+++ b/app/helpers/milestones_helper.rb
@@ -1,4 +1,6 @@
 module MilestonesHelper
+  include EntityDateHelper
+
   def milestones_filter_path(opts = {})
     if @project
       project_milestones_path(@project, opts)
@@ -72,6 +74,19 @@ module MilestonesHelper
     end
   end
 
+  def milestone_progress_tooltip_text(milestone)
+    has_issues = milestone.total_issues_count(current_user) > 0
+
+    if has_issues
+      [
+        _('Progress'),
+        _("%{percent}%% complete") % { percent: milestone.percent_complete(current_user) }
+      ].join('<br />')
+    else
+      _('Progress')
+    end
+  end
+
   def milestone_progress_bar(milestone)
     options = {
       class: 'progress-bar progress-bar-success',
@@ -95,27 +110,69 @@ module MilestonesHelper
   end
 
   def milestone_tooltip_title(milestone)
-    if milestone.due_date
-      [milestone.due_date.to_s(:medium), "(#{milestone_remaining_days(milestone)})"].join(' ')
+    if milestone
+      "#{milestone.title}<br />#{milestone_tooltip_due_date(milestone)}"
+    else
+      _('Milestone')
     end
   end
 
-  def milestone_remaining_days(milestone)
-    if milestone.expired?
-      content_tag(:strong, 'Past due')
-    elsif milestone.upcoming?
-      content_tag(:strong, 'Upcoming')
-    elsif milestone.due_date
-      time_ago = time_ago_in_words(milestone.due_date)
-      content = time_ago.gsub(/\d+/) { |match| "<strong>#{match}</strong>" }
-      content.slice!("about ")
-      content << " remaining"
-      content.html_safe
-    elsif milestone.start_date && milestone.start_date.past?
-      days    = milestone.elapsed_days
-      content = content_tag(:strong, days)
-      content << " #{'day'.pluralize(days)} elapsed"
+  def milestone_time_for(date, date_type)
+    title = date_type == :start ? "Start date" : "End date"
+
+    if date
+      time_ago = time_ago_in_words(date)
+      time_ago.slice!("about ")
+
+      time_ago << if date.past?
+                    " ago"
+                  else
+                    " remaining"
+                  end
+
+      content = [
+        title,
+        "<br />",
+        date.to_s(:medium),
+        "(#{time_ago})"
+      ].join(" ")
+
       content.html_safe
+    else
+      title
+    end
+  end
+
+  def milestone_issues_tooltip_text(milestone)
+    issues = milestone.count_issues_by_state(current_user)
+
+    return _("Issues") if issues.empty?
+
+    content = []
+
+    content << n_("1 open issue", "%d open issues", issues["opened"]) % issues["opened"] if issues["opened"]
+    content << n_("1 closed issue", "%d closed issues", issues["closed"]) % issues["closed"] if issues["closed"]
+
+    content.join('<br />').html_safe
+  end
+
+  def milestone_merge_requests_tooltip_text(milestone)
+    merge_requests = milestone.merge_requests
+
+    return _("Merge requests") if merge_requests.empty?
+
+    content = []
+
+    content << n_("1 open merge request", "%d open merge requests", merge_requests.opened.count) % merge_requests.opened.count if merge_requests.opened.any?
+    content << n_("1 closed merge request", "%d closed merge requests", merge_requests.closed.count) % merge_requests.closed.count if merge_requests.closed.any?
+    content << n_("1 merged merge request", "%d merged merge requests", merge_requests.merged.count) % merge_requests.merged.count if merge_requests.merged.any?
+
+    content.join('<br />').html_safe
+  end
+
+  def milestone_tooltip_due_date(milestone)
+    if milestone.due_date
+      "#{milestone.due_date.to_s(:medium)} (#{remaining_days_in_words(milestone)})"
     end
   end
 
diff --git a/app/models/concerns/milestoneish.rb b/app/models/concerns/milestoneish.rb
index 5130ecec472..967fd9c5eea 100644
--- a/app/models/concerns/milestoneish.rb
+++ b/app/models/concerns/milestoneish.rb
@@ -102,14 +102,14 @@ module Milestoneish
     Gitlab::TimeTrackingFormatter.output(total_issue_time_estimate)
   end
 
-  private
-
   def count_issues_by_state(user)
     memoize_per_user(user, :count_issues_by_state) do
       issues_visible_to_user(user).reorder(nil).group(:state).count
     end
   end
 
+  private
+
   def memoize_per_user(user, method_name)
     memoized_users[method_name][user&.id] ||= yield
   end
diff --git a/app/serializers/entity_date_helper.rb b/app/serializers/entity_date_helper.rb
index 71d9a65fb58..464217123b4 100644
--- a/app/serializers/entity_date_helper.rb
+++ b/app/serializers/entity_date_helper.rb
@@ -1,5 +1,6 @@
 module EntityDateHelper
   include ActionView::Helpers::DateHelper
+  include ActionView::Helpers::TagHelper
 
   def interval_in_words(diff)
     return 'Not started' unless diff
@@ -34,4 +35,30 @@ module EntityDateHelper
 
     duration_hash
   end
+
+  # Generates an HTML-formatted string for remaining dates based on start_date and due_date
+  #
+  # It returns "Past due" for expired entities
+  # It returns "Upcoming" for upcoming entities
+  # If due date is provided, it returns "# days|weeks|months remaining|ago"
+  # If start date is provided and elapsed, with no due date, it returns "# days elapsed"
+  def remaining_days_in_words(entity)
+    if entity.try(:expired?)
+      content_tag(:strong, 'Past due')
+    elsif entity.try(:upcoming?)
+      content_tag(:strong, 'Upcoming')
+    elsif entity.due_date
+      is_upcoming = (entity.due_date - Date.today).to_i > 0
+      time_ago = time_ago_in_words(entity.due_date)
+      content = time_ago.gsub(/\d+/) { |match| "<strong>#{match}</strong>" }
+      content.slice!("about ")
+      content << " " + (is_upcoming ? _("remaining") : _("ago"))
+      content.html_safe
+    elsif entity.start_date && entity.start_date.past?
+      days    = entity.elapsed_days
+      content = content_tag(:strong, days)
+      content << " #{'day'.pluralize(days)} elapsed"
+      content.html_safe
+    end
+  end
 end
diff --git a/app/views/projects/issues/_issue.html.haml b/app/views/projects/issues/_issue.html.haml
index 0c58dd60e2c..e27f5658e87 100644
--- a/app/views/projects/issues/_issue.html.haml
+++ b/app/views/projects/issues/_issue.html.haml
@@ -26,7 +26,7 @@
           - if issue.milestone
             %span.issuable-milestone.hidden-xs
               &nbsp;
-              = link_to project_issues_path(issue.project, milestone_title: issue.milestone.title), data: { html: 1, toggle: 'tooltip', title: issuable_milestone_tooltip_title(issue) } do
+              = link_to project_issues_path(issue.project, milestone_title: issue.milestone.title), data: { html: 1, toggle: 'tooltip', title: milestone_tooltip_due_date(issue.milestone) } do
                 = icon('clock-o')
                 = issue.milestone.title
           - if issue.due_date
diff --git a/app/views/projects/merge_requests/_merge_request.html.haml b/app/views/projects/merge_requests/_merge_request.html.haml
index a94267deeb2..027a9ff1416 100644
--- a/app/views/projects/merge_requests/_merge_request.html.haml
+++ b/app/views/projects/merge_requests/_merge_request.html.haml
@@ -23,7 +23,7 @@
         - if merge_request.milestone
           %span.issuable-milestone.hidden-xs
             &nbsp;
-            = link_to project_merge_requests_path(merge_request.project, milestone_title: merge_request.milestone.title), data: { html: 1, toggle: 'tooltip', title: issuable_milestone_tooltip_title(merge_request) } do
+            = link_to project_merge_requests_path(merge_request.project, milestone_title: merge_request.milestone.title), data: { html: 1, toggle: 'tooltip', title: milestone_tooltip_due_date(merge_request.milestone) } do
               = icon('clock-o')
               = merge_request.milestone.title
         - if merge_request.target_project.default_branch != merge_request.target_branch
diff --git a/app/views/shared/issuable/_sidebar.html.haml b/app/views/shared/issuable/_sidebar.html.haml
index aa883b9b1fa..093033775a9 100644
--- a/app/views/shared/issuable/_sidebar.html.haml
+++ b/app/views/shared/issuable/_sidebar.html.haml
@@ -7,7 +7,7 @@
       - if current_user
         %span.issuable-header-text.hide-collapsed.pull-left
           = _('Todo')
-      %a.gutter-toggle.pull-right.js-sidebar-toggle{ role: "button", href: "#", "aria-label" => "Toggle sidebar" }
+      %a.gutter-toggle.pull-right.js-sidebar-toggle.has-tooltip{ role: "button", href: "#", "aria-label" => "Toggle sidebar", title: sidebar_gutter_tooltip_text, data: { container: 'body', placement: 'left' } }
         = sidebar_gutter_toggle_icon
       - if current_user
         = render "shared/issuable/sidebar_todo", todo: todo, issuable: issuable
@@ -19,12 +19,11 @@
       .block.assignee
         = render "shared/issuable/sidebar_assignees", issuable: issuable, can_edit_issuable: can_edit_issuable, signed_in: current_user.present?
       .block.milestone
-        .sidebar-collapsed-icon
+        .sidebar-collapsed-icon.has-tooltip{ title: milestone_tooltip_title(issuable.milestone), data: { container: 'body', html: 1, placement: 'left' } }
           = icon('clock-o', 'aria-hidden': 'true')
           %span.milestone-title
             - if issuable.milestone
-              %span.has-tooltip{ title: "#{issuable.milestone.title}<br>#{milestone_tooltip_title(issuable.milestone)}", data: { container: 'body', html: 1, placement: 'left' } }
-                = issuable.milestone.title
+              = issuable.milestone.title
             - else
               = _('None')
         .title.hide-collapsed
@@ -34,7 +33,7 @@
             = link_to _('Edit'), '#', class: 'js-sidebar-dropdown-toggle edit-link pull-right'
         .value.hide-collapsed
           - if issuable.milestone
-            = link_to issuable.milestone.title, milestone_path(issuable.milestone), class: "bold has-tooltip", title: milestone_tooltip_title(issuable.milestone), data: { container: "body", html: 1 }
+            = link_to issuable.milestone.title, milestone_path(issuable.milestone), class: "bold has-tooltip", title: milestone_tooltip_due_date(issuable.milestone), data: { container: "body", html: 1 }
           - else
             %span.no-value
               = _('None')
@@ -50,7 +49,7 @@
             = icon('spinner spin', 'aria-hidden': 'true')
       - if issuable.has_attribute?(:due_date)
         .block.due_date
-          .sidebar-collapsed-icon
+          .sidebar-collapsed-icon.has-tooltip{ data: { placement: 'left', container: 'body', html: 1 }, title: sidebar_due_date_tooltip_label(issuable) }
             = icon('calendar', 'aria-hidden': 'true')
             %span.js-due-date-sidebar-value
               = issuable.due_date.try(:to_s, :medium) || 'None'
diff --git a/app/views/shared/issuable/_sidebar_assignees.html.haml b/app/views/shared/issuable/_sidebar_assignees.html.haml
index 304df38a096..21006a76b28 100644
--- a/app/views/shared/issuable/_sidebar_assignees.html.haml
+++ b/app/views/shared/issuable/_sidebar_assignees.html.haml
@@ -4,7 +4,7 @@
       = _('Assignee')
       = icon('spinner spin')
 - else
-  .sidebar-collapsed-icon.sidebar-collapsed-user{ data: { toggle: "tooltip", placement: "left", container: "body" }, title: (issuable.assignee.name if issuable.assignee) }
+  .sidebar-collapsed-icon.sidebar-collapsed-user{ data: { toggle: "tooltip", placement: "left", container: "body" }, title: sidebar_assignee_tooltip_label(issuable) }
     - if issuable.assignee
       = link_to_member(@project, issuable.assignee, size: 24)
     - else
diff --git a/app/views/shared/issuable/_sidebar_todo.html.haml b/app/views/shared/issuable/_sidebar_todo.html.haml
index b77e104c072..74327fb1ba8 100644
--- a/app/views/shared/issuable/_sidebar_todo.html.haml
+++ b/app/views/shared/issuable/_sidebar_todo.html.haml
@@ -1,11 +1,11 @@
 - is_collapsed = local_assigns.fetch(:is_collapsed, false)
-- mark_content = is_collapsed ? icon('check-square', class: 'todo-undone') : _('Mark done')
+- mark_content = is_collapsed ? icon('check-square', class: 'todo-undone') : _('Mark todo as done')
 - todo_content = is_collapsed ? icon('plus-square') : _('Add todo')
 
 %button.issuable-todo-btn.js-issuable-todo{ type: 'button',
   class: (is_collapsed ? 'btn-blank sidebar-collapsed-icon dont-change-state has-tooltip' : 'btn btn-default issuable-header-btn pull-right'),
-  title: (todo.nil? ? _('Add todo') : _('Mark done')),
-  'aria-label' => (todo.nil? ? _('Add todo') : _('Mark done')),
+  title: (todo.nil? ? _('Add todo') : _('Mark todo as done')),
+  'aria-label' => (todo.nil? ? _('Add todo') : _('Mark todo as done')),
   data: issuable_todo_button_data(issuable, todo, is_collapsed) }
   %span.issuable-todo-inner.js-issuable-todo-inner<
     - if todo
diff --git a/app/views/shared/issuable/form/_merge_request_assignee.html.haml b/app/views/shared/issuable/form/_merge_request_assignee.html.haml
index bf8613b0f0d..d7740eddcca 100644
--- a/app/views/shared/issuable/form/_merge_request_assignee.html.haml
+++ b/app/views/shared/issuable/form/_merge_request_assignee.html.haml
@@ -1,6 +1,6 @@
 - merge_request = issuable
 .block.assignee
-  .sidebar-collapsed-icon.sidebar-collapsed-user{ data: { toggle: "tooltip", placement: "left", container: "body" }, title: (merge_request.assignee.name if merge_request.assignee) }
+  .sidebar-collapsed-icon.sidebar-collapsed-user{ data: { toggle: "tooltip", placement: "left", container: "body" }, title: sidebar_assignee_tooltip_label(issuable) }
     - if merge_request.assignee
       = link_to_member(@project, merge_request.assignee, size: 24)
     - else
diff --git a/app/views/shared/milestones/_sidebar.html.haml b/app/views/shared/milestones/_sidebar.html.haml
index ee134480705..8e9a1b56bb8 100644
--- a/app/views/shared/milestones/_sidebar.html.haml
+++ b/app/views/shared/milestones/_sidebar.html.haml
@@ -4,12 +4,8 @@
 %aside.right-sidebar.js-right-sidebar{ data: { "offset-top" => affix_offset, "spy" => "affix", "always-show-toggle" => true }, class: sidebar_gutter_collapsed_class, 'aria-live' => 'polite' }
   .issuable-sidebar.milestone-sidebar
     .block.milestone-progress.issuable-sidebar-header
-      %a.gutter-toggle.pull-right.js-sidebar-toggle{ role: "button", href: "#", "aria-label" => "Toggle sidebar" }
+      %a.gutter-toggle.pull-right.js-sidebar-toggle.has-tooltip{ role: "button", href: "#", "aria-label" => "Toggle sidebar", title: sidebar_gutter_tooltip_text, data: { container: 'body', placement: 'left' } }
         = sidebar_gutter_toggle_icon
-
-      .sidebar-collapsed-icon
-        %span== #{milestone.percent_complete(current_user)}%
-        = milestone_progress_bar(milestone)
       .title.hide-collapsed
         %strong.bold== #{milestone.percent_complete(current_user)}%
         %span.hide-collapsed
@@ -17,6 +13,11 @@
       .value.hide-collapsed
         = milestone_progress_bar(milestone)
 
+    .block.milestone-progress.hide-expanded
+      .sidebar-collapsed-icon.has-tooltip{ title: milestone_progress_tooltip_text(milestone), data: { container: 'body', html: 1, placement: 'left' } }
+        %span== #{milestone.percent_complete(current_user)}%
+        = milestone_progress_bar(milestone)
+
     .block.start_date.hide-collapsed
       .title
         Start date
@@ -35,19 +36,25 @@
         %span.collapsed-milestone-date
           - if milestone.start_date && milestone.due_date
             - if milestone.start_date.year == milestone.due_date.year
-              .milestone-date= milestone.start_date.strftime('%b %-d')
+              .milestone-date.has-tooltip{ title: milestone_time_for(milestone.start_date, :start), data: { container: 'body', html: 1, placement: 'left' } }
+                = milestone.start_date.strftime('%b %-d')
             - else
-              .milestone-date= milestone.start_date.strftime('%b %-d %Y')
+              .milestone-date.has-tooltip{ title: milestone_time_for(milestone.start_date, :start), data: { container: 'body', html: 1, placement: 'left' } }
+                = milestone.start_date.strftime('%b %-d %Y')
             .date-separator -
-            .due_date= milestone.due_date.strftime('%b %-d %Y')
+            .due_date.has-tooltip{ title: milestone_time_for(milestone.due_date, :end), data: { container: 'body', html: 1, placement: 'left' } }
+              = milestone.due_date.strftime('%b %-d %Y')
           - elsif milestone.start_date
             From
-            .milestone-date= milestone.start_date.strftime('%b %-d %Y')
+            .milestone-date.has-tooltip{ title: milestone_time_for(milestone.start_date, :start), data: { container: 'body', html: 1, placement: 'left' } }
+              = milestone.start_date.strftime('%b %-d %Y')
           - elsif milestone.due_date
             Until
-            .milestone-date= milestone.due_date.strftime('%b %-d %Y')
+            .milestone-date.has-tooltip{ title: milestone_time_for(milestone.due_date, :end), data: { container: 'body', html: 1, placement: 'left' } }
+              = milestone.due_date.strftime('%b %-d %Y')
           - else
-            None
+            .has-tooltip{ title: milestone_time_for(milestone.start_date, :start), data: { container: 'body', html: 1, placement: 'left' } }
+              None
       .title.hide-collapsed
         Due date
         - if @project && can?(current_user, :admin_milestone, @project)
@@ -58,14 +65,14 @@
             %span.bold= milestone.due_date.to_s(:medium)
           - else
             %span.no-value No due date
-        - remaining_days = milestone_remaining_days(milestone)
+        - remaining_days = remaining_days_in_words(milestone)
         - if remaining_days.present?
           = surround '(', ')' do
             %span.remaining-days= remaining_days
 
     - if !project || can?(current_user, :read_issue, project)
       .block.issues
-        .sidebar-collapsed-icon
+        .sidebar-collapsed-icon.has-tooltip{ title: milestone_issues_tooltip_text(milestone), data: { container: 'body', html: 1, placement: 'left' } }
           %strong
             = custom_icon('issues')
           %span= milestone.issues_visible_to_user(current_user).count
@@ -93,7 +100,7 @@
           = icon('spinner spin')
 
     .block.merge-requests
-      .sidebar-collapsed-icon
+      .sidebar-collapsed-icon.has-tooltip{ title: milestone_merge_requests_tooltip_text(milestone), data: { container: 'body', html: 1, placement: 'left' } }
         %strong
           = custom_icon('mr_bold')
         %span= milestone.merge_requests.count
diff --git a/changelogs/unreleased/25010-collapsed-sidebar-tooltips.yml b/changelogs/unreleased/25010-collapsed-sidebar-tooltips.yml
new file mode 100644
index 00000000000..1226fb4eefd
--- /dev/null
+++ b/changelogs/unreleased/25010-collapsed-sidebar-tooltips.yml
@@ -0,0 +1,5 @@
+---
+title: Improve tooltips in collapsed right sidebar
+merge_request: 17714
+author:
+type: changed
diff --git a/doc/user/project/issues/issues_functionalities.md b/doc/user/project/issues/issues_functionalities.md
index 6bcf7686a71..cf5cf1794ee 100644
--- a/doc/user/project/issues/issues_functionalities.md
+++ b/doc/user/project/issues/issues_functionalities.md
@@ -28,7 +28,7 @@ Comments and system notes also appear automatically in response to various actio
 #### 2. Todos
 
 - Add todo: add that issue to your [GitLab Todo](../../../workflow/todos.html) list
-- Mark done: mark that issue as done (reflects on the Todo list)
+- Mark todo as done: mark that issue as done (reflects on the Todo list)
 
 #### 3. Assignee
 
diff --git a/doc/workflow/todos.md b/doc/workflow/todos.md
index e612646cfbc..f13d29884d4 100644
--- a/doc/workflow/todos.md
+++ b/doc/workflow/todos.md
@@ -92,9 +92,9 @@ corresponding **Done** button, and it will disappear from your Todo list.
 ![A Todo in the Todos dashboard](img/todo_list_item.png)
 
 A Todo can also be marked as done from the issue or merge request sidebar using
-the "Mark done" button.
+the "Mark todo as done" button.
 
-![Mark Done from the issuable sidebar](img/todos_mark_done_sidebar.png)
+![Mark todo as done from the issuable sidebar](img/todos_mark_done_sidebar.png)
 
 You can mark all your Todos as done at once by clicking on the **Mark all as
 done** button.
diff --git a/spec/features/issues/todo_spec.rb b/spec/features/issues/todo_spec.rb
index 8e6493bbd93..4a44ec302fc 100644
--- a/spec/features/issues/todo_spec.rb
+++ b/spec/features/issues/todo_spec.rb
@@ -14,7 +14,7 @@ feature 'Manually create a todo item from issue', :js do
   it 'creates todo when clicking button' do
     page.within '.issuable-sidebar' do
       click_button 'Add todo'
-      expect(page).to have_content 'Mark done'
+      expect(page).to have_content 'Mark todo as done'
     end
 
     page.within '.header-content .todos-count' do
@@ -31,7 +31,7 @@ feature 'Manually create a todo item from issue', :js do
   it 'marks a todo as done' do
     page.within '.issuable-sidebar' do
       click_button 'Add todo'
-      click_button 'Mark done'
+      click_button 'Mark todo as done'
     end
 
     expect(page).to have_selector('.todos-count', visible: false)
diff --git a/spec/helpers/issuables_helper_spec.rb b/spec/helpers/issuables_helper_spec.rb
index 4224cea4652..7b59fde999d 100644
--- a/spec/helpers/issuables_helper_spec.rb
+++ b/spec/helpers/issuables_helper_spec.rb
@@ -22,11 +22,15 @@ describe IssuablesHelper do
   end
 
   describe '#issuable_labels_tooltip' do
-    it 'returns label text' do
+    it 'returns label text with no labels' do
+      expect(issuable_labels_tooltip([])).to eq("Labels")
+    end
+
+    it 'returns label text with labels within max limit' do
       expect(issuable_labels_tooltip([label])).to eq(label.title)
     end
 
-    it 'returns label text' do
+    it 'returns label text with labels exceeding max limit' do
       expect(issuable_labels_tooltip([label, label2], limit: 1)).to eq("#{label.title}, and 1 more")
     end
   end
diff --git a/spec/helpers/milestones_helper_spec.rb b/spec/helpers/milestones_helper_spec.rb
index 70b4a89cb86..f5185cb2857 100644
--- a/spec/helpers/milestones_helper_spec.rb
+++ b/spec/helpers/milestones_helper_spec.rb
@@ -83,58 +83,4 @@ describe MilestonesHelper do
       end
     end
   end
-
-  describe '#milestone_remaining_days' do
-    around do |example|
-      Timecop.freeze(Time.utc(2017, 3, 17)) { example.run }
-    end
-
-    context 'when less than 31 days remaining' do
-      let(:milestone_remaining) { milestone_remaining_days(build_stubbed(:milestone, due_date: 12.days.from_now.utc)) }
-
-      it 'returns days remaining' do
-        expect(milestone_remaining).to eq("<strong>12</strong> days remaining")
-      end
-    end
-
-    context 'when less than 1 year and more than 30 days remaining' do
-      let(:milestone_remaining) { milestone_remaining_days(build_stubbed(:milestone, due_date: 2.months.from_now.utc)) }
-
-      it 'returns months remaining' do
-        expect(milestone_remaining).to eq("<strong>2</strong> months remaining")
-      end
-    end
-
-    context 'when more than 1 year remaining' do
-      let(:milestone_remaining) { milestone_remaining_days(build_stubbed(:milestone, due_date: (1.year.from_now + 2.days).utc)) }
-
-      it 'returns years remaining' do
-        expect(milestone_remaining).to eq("<strong>1</strong> year remaining")
-      end
-    end
-
-    context 'when milestone is expired' do
-      let(:milestone_remaining) { milestone_remaining_days(build_stubbed(:milestone, due_date: 2.days.ago.utc)) }
-
-      it 'returns "Past due"' do
-        expect(milestone_remaining).to eq("<strong>Past due</strong>")
-      end
-    end
-
-    context 'when milestone has start_date in the future' do
-      let(:milestone_remaining) { milestone_remaining_days(build_stubbed(:milestone, start_date: 2.days.from_now.utc)) }
-
-      it 'returns "Upcoming"' do
-        expect(milestone_remaining).to eq("<strong>Upcoming</strong>")
-      end
-    end
-
-    context 'when milestone has start_date in the past' do
-      let(:milestone_remaining) { milestone_remaining_days(build_stubbed(:milestone, start_date: 2.days.ago.utc)) }
-
-      it 'returns days elapsed' do
-        expect(milestone_remaining).to eq("<strong>2</strong> days elapsed")
-      end
-    end
-  end
 end
diff --git a/spec/javascripts/collapsed_sidebar_todo_spec.js b/spec/javascripts/collapsed_sidebar_todo_spec.js
index 2abf52a1676..8427e8a0ba7 100644
--- a/spec/javascripts/collapsed_sidebar_todo_spec.js
+++ b/spec/javascripts/collapsed_sidebar_todo_spec.js
@@ -85,7 +85,7 @@ describe('Issuable right sidebar collapsed todo toggle', () => {
     setTimeout(() => {
       expect(
         document.querySelector('.issuable-sidebar-header .js-issuable-todo').textContent.trim(),
-      ).toBe('Mark done');
+      ).toBe('Mark todo as done');
 
       done();
     });
@@ -97,7 +97,7 @@ describe('Issuable right sidebar collapsed todo toggle', () => {
     setTimeout(() => {
       expect(
         document.querySelector('.js-issuable-todo.sidebar-collapsed-icon').getAttribute('data-original-title'),
-      ).toBe('Mark done');
+      ).toBe('Mark todo as done');
 
       done();
     });
@@ -128,13 +128,13 @@ describe('Issuable right sidebar collapsed todo toggle', () => {
       .catch(done.fail);
   });
 
-  it('updates aria-label to mark done', (done) => {
+  it('updates aria-label to mark todo as done', (done) => {
     document.querySelector('.js-issuable-todo.sidebar-collapsed-icon').click();
 
     setTimeout(() => {
       expect(
         document.querySelector('.js-issuable-todo.sidebar-collapsed-icon').getAttribute('aria-label'),
-      ).toBe('Mark done');
+      ).toBe('Mark todo as done');
 
       done();
     });
@@ -147,7 +147,7 @@ describe('Issuable right sidebar collapsed todo toggle', () => {
       .then(() => {
         expect(
           document.querySelector('.js-issuable-todo.sidebar-collapsed-icon').getAttribute('aria-label'),
-        ).toBe('Mark done');
+        ).toBe('Mark todo as done');
 
         document.querySelector('.js-issuable-todo.sidebar-collapsed-icon').click();
       })
diff --git a/spec/models/milestone_spec.rb b/spec/models/milestone_spec.rb
index 47f4a792e5c..c7460981a32 100644
--- a/spec/models/milestone_spec.rb
+++ b/spec/models/milestone_spec.rb
@@ -96,7 +96,9 @@ describe Milestone do
         allow(milestone).to receive(:due_date).and_return(Date.today.prev_year)
       end
 
-      it { expect(milestone.expired?).to be_truthy }
+      it 'returns true when due_date is in the past' do
+        expect(milestone.expired?).to be_truthy
+      end
     end
 
     context "not expired" do
@@ -104,17 +106,19 @@ describe Milestone do
         allow(milestone).to receive(:due_date).and_return(Date.today.next_year)
       end
 
-      it { expect(milestone.expired?).to be_falsey }
+      it 'returns false when due_date is in the future' do
+        expect(milestone.expired?).to be_falsey
+      end
     end
   end
 
   describe '#upcoming?' do
-    it 'returns true' do
+    it 'returns true when start_date is in the future' do
       milestone = build(:milestone, start_date: Time.now + 1.month)
       expect(milestone.upcoming?).to be_truthy
     end
 
-    it 'returns false' do
+    it 'returns false when start_date is in the past' do
       milestone = build(:milestone, start_date: Date.today.prev_year)
       expect(milestone.upcoming?).to be_falsey
     end
diff --git a/spec/serializers/entity_date_helper_spec.rb b/spec/serializers/entity_date_helper_spec.rb
index b9cc2f64831..36da8d33a44 100644
--- a/spec/serializers/entity_date_helper_spec.rb
+++ b/spec/serializers/entity_date_helper_spec.rb
@@ -32,6 +32,7 @@ describe EntityDateHelper do
   end
 
   it 'converts 86560 seconds' do
+    Rails.logger.debug date_helper_class.inspect
     expect(date_helper_class.distance_of_time_as_hash(86560)).to eq(days: 1, mins: 2, seconds: 40)
   end
 
@@ -42,4 +43,58 @@ describe EntityDateHelper do
   it 'converts 986760 seconds' do
     expect(date_helper_class.distance_of_time_as_hash(986760)).to eq(days: 11, hours: 10, mins: 6)
   end
+
+  describe '#remaining_days_in_words' do
+    around do |example|
+      Timecop.freeze(Time.utc(2017, 3, 17)) { example.run }
+    end
+
+    context 'when less than 31 days remaining' do
+      let(:milestone_remaining) { date_helper_class.remaining_days_in_words(build_stubbed(:milestone, due_date: 12.days.from_now.utc)) }
+
+      it 'returns days remaining' do
+        expect(milestone_remaining).to eq("<strong>12</strong> days remaining")
+      end
+    end
+
+    context 'when less than 1 year and more than 30 days remaining' do
+      let(:milestone_remaining) { date_helper_class.remaining_days_in_words(build_stubbed(:milestone, due_date: 2.months.from_now.utc)) }
+
+      it 'returns months remaining' do
+        expect(milestone_remaining).to eq("<strong>2</strong> months remaining")
+      end
+    end
+
+    context 'when more than 1 year remaining' do
+      let(:milestone_remaining) { date_helper_class.remaining_days_in_words(build_stubbed(:milestone, due_date: (1.year.from_now + 2.days).utc)) }
+
+      it 'returns years remaining' do
+        expect(milestone_remaining).to eq("<strong>1</strong> year remaining")
+      end
+    end
+
+    context 'when milestone is expired' do
+      let(:milestone_remaining) { date_helper_class.remaining_days_in_words(build_stubbed(:milestone, due_date: 2.days.ago.utc)) }
+
+      it 'returns "Past due"' do
+        expect(milestone_remaining).to eq("<strong>Past due</strong>")
+      end
+    end
+
+    context 'when milestone has start_date in the future' do
+      let(:milestone_remaining) { date_helper_class.remaining_days_in_words(build_stubbed(:milestone, start_date: 2.days.from_now.utc)) }
+
+      it 'returns "Upcoming"' do
+        expect(milestone_remaining).to eq("<strong>Upcoming</strong>")
+      end
+    end
+
+    context 'when milestone has start_date in the past' do
+      let(:milestone_remaining) { date_helper_class.remaining_days_in_words(build_stubbed(:milestone, start_date: 2.days.ago.utc)) }
+
+      it 'returns days elapsed' do
+        expect(milestone_remaining).to eq("<strong>2</strong> days elapsed")
+      end
+    end
+  end
 end
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