diff --git a/website/client/src/assets/scss/form.scss b/website/client/src/assets/scss/form.scss
index 2e5934f5d5..edfb99245e 100644
--- a/website/client/src/assets/scss/form.scss
+++ b/website/client/src/assets/scss/form.scss
@@ -23,7 +23,7 @@ input, textarea, input.form-control, textarea.form-control {
   border-radius: 2px;
   font-size: 14px;
   line-height: 1.43;
-  color: $gray-200;
+  color: $gray-50;
   border: 1px solid $gray-400;
 
   &:hover:not(:disabled) {
@@ -32,7 +32,6 @@ input, textarea, input.form-control, textarea.form-control {
 
   &:active:not(:disabled), &:focus:not(:disabled) {
     border-color: $purple-500;
-    color: $gray-50;
     outline: 0;
     box-shadow: none;
   }
diff --git a/website/client/src/components/header/userDropdown.vue b/website/client/src/components/header/userDropdown.vue
index fc0ae7edb5..093868c844 100644
--- a/website/client/src/components/header/userDropdown.vue
+++ b/website/client/src/components/header/userDropdown.vue
@@ -133,13 +133,12 @@
 </style>
 
 <script>
-import axios from 'axios';
 import { mapState } from '@/libs/store';
 import * as Analytics from '@/libs/analytics';
 import userIcon from '@/assets/svg/user.svg';
 import MenuDropdown from '../ui/customMenuDropdown';
-import markPMSRead from '@/../../common/script/ops/markPMSRead';
 import MessageCount from './messageCount';
+import { EVENTS } from '@/libs/events';
 
 export default {
   components: {
@@ -164,11 +163,8 @@ export default {
       this.$root.$emit('bv::show::modal', 'avatar-modal');
     },
     showPrivateMessages () {
-      markPMSRead(this.user);
-      axios.post('/api/v4/user/mark-pms-read');
-
       if (this.$router.history.current.name === 'privateMessages') {
-        this.$root.$emit('pm::refresh');
+        this.$root.$emit(EVENTS.PM_REFRESH);
       } else {
         this.$router.push('/private-messages');
       }
diff --git a/website/client/src/components/messages/conversationItem.vue b/website/client/src/components/messages/conversationItem.vue
index f4d70df722..982145c0c1 100644
--- a/website/client/src/components/messages/conversationItem.vue
+++ b/website/client/src/components/messages/conversationItem.vue
@@ -10,21 +10,7 @@
         :backer="backer"
         :contributor="contributor"
         :name="displayName"
-      /><span
-        v-if="username"
-        class="username"
-      >@{{ username }}</span>
-      <div
-        v-if="lastMessageDate"
-        class="time"
-      >
-        {{ lastMessageDate | timeAgo }}
-      </div>
-    </div>
-    <div class="preview-row">
-      <div class="messagePreview">
-        {{ lastMessageText }}
-      </div>
+      />
       <div
         v-if="userLoggedIn.id !== uuid"
         class="actions"
@@ -44,16 +30,34 @@
               v-html="icons.dots"
             ></div>
           </template>
-          <b-dropdown-item @click="block()">
+          <b-dropdown-item @click="toggleBlock()">
             <span class="dropdown-icon-item">
               <div
                 class="svg-icon inline"
                 v-html="icons.remove"
-              ></div><span class="text">{{ $t('block') }}</span></span>
+              ></div><span class="text">{{ $t(isBlocked ? 'unblock' : 'block') }}</span></span>
           </b-dropdown-item>
         </b-dropdown>
       </div>
     </div>
+    <span class="username-row">
+      <span
+        v-if="username"
+        class="username"
+      >@{{ username }}</span> <span
+      v-if="lastMessageDate"
+      class="time"
+    >•
+        {{ lastMessageDate | timeAgo }}
+      </span>
+    </span>
+
+    <div class="preview-row">
+      <div class="messagePreview">
+        {{ lastMessageText }}
+      </div>
+
+    </div>
   </div>
 </template>
 
@@ -79,6 +83,9 @@ export default {
     ...mapState({
       userLoggedIn: 'user.data',
     }),
+    isBlocked () {
+      return this.userLoggedIn.inbox.blocks.includes(this.uuid);
+    },
   },
   data () {
     return {
@@ -101,8 +108,8 @@ export default {
         dropdown.hide();
       }
     },
-    block () {
-      this.$store.dispatch('user:block', {
+    toggleBlock () {
+      this.$store.dispatch(this.isBlocked ? 'user:unblock' : 'user:block', {
         uuid: this.uuid,
       });
     },
@@ -133,6 +140,12 @@ export default {
       height: 16px;
       width: 4px;
 
+      &:not(:hover) {
+        svg path {
+          fill: $gray-200;
+        }
+      }
+
       svg path {
         fill: $purple-300
       }
@@ -144,7 +157,7 @@ export default {
   @import '~@/assets/scss/colors.scss';
 
   .conversation {
-    padding: 1.5rem;
+    padding: 1rem 1.5rem;
     border-bottom: 1px solid $gray-500;
 
     &:hover {
@@ -164,6 +177,7 @@ export default {
       display: flex;
       flex-direction: row;
       height: 20px;
+      position: relative;
 
       .user-label {
         flex: 1;
@@ -172,11 +186,6 @@ export default {
         white-space: nowrap;
       }
 
-      .username {
-        flex: 1;
-        flex-grow: 0;
-      }
-
       .time {
         flex: 2;
         text-align: end;
@@ -187,10 +196,15 @@ export default {
       }
     }
 
+    .username-row {
+      flex: 1;
+      flex-grow: 0;
+      font-size: 12px;
+      color: $gray-200;
+    }
+
     .messagePreview {
-      //width: 100%;
-      height: 30px;
-      margin-right: 40px;
+      max-height: 30px;
       margin-top: 4px;
       font-size: 12px;
       font-weight: normal;
@@ -221,7 +235,6 @@ export default {
     right: 0;
     display: none;
     width: 16px;
-    margin-top: 4px;
 
     .dots {
       height: 16px;
diff --git a/website/client/src/components/messages/messageList.vue b/website/client/src/components/messages/messageList.vue
index 5270ee7b6c..b59bbdcd25 100644
--- a/website/client/src/components/messages/messageList.vue
+++ b/website/client/src/components/messages/messageList.vue
@@ -34,10 +34,9 @@
         class="d-flex flex-grow-1"
       >
         <avatar
-          v-if="msg.userStyles || (cachedProfileData[msg.uuid]
-            && !cachedProfileData[msg.uuid].rejected)"
+          v-if="conversationOpponentUser"
           class="avatar-left"
-          :member="msg.userStyles || cachedProfileData[msg.uuid]"
+          :member="conversationOpponentUser"
           :avatar-only="true"
           :override-top-padding="'14px'"
           :hide-class-badge="true"
@@ -65,10 +64,9 @@
           />
         </div>
         <avatar
-          v-if="msg.userStyles
-            || (cachedProfileData[msg.uuid] && !cachedProfileData[msg.uuid].rejected)"
+          v-if="user"
           class="avatar-right"
-          :member="msg.userStyles || cachedProfileData[msg.uuid]"
+          :member="user"
           :avatar-only="true"
           :hide-class-badge="true"
           :override-top-padding="'14px'"
@@ -88,18 +86,18 @@
   }
 
   .avatar {
-    width: 15%;
+    width: 170px;
     min-width: 8rem;
     height: 120px;
     padding-top: 0 !important;
   }
 
-  .avatar-left {
-    margin-left: -1rem;
-  }
-
   .avatar-right {
     margin-left: -1rem;
+
+    ::v-deep .character-sprites {
+      margin-right: 1rem !important;
+    }
   }
 
   .card {
@@ -201,7 +199,6 @@
 
 <script>
 import moment from 'moment';
-import axios from 'axios';
 import debounce from 'lodash/debounce';
 import { PerfectScrollbar } from 'vue2-perfect-scrollbar';
 import { mapState } from '@/libs/store';
@@ -219,13 +216,11 @@ export default {
     chat: {},
     isLoading: Boolean,
     canLoadMore: Boolean,
+    conversationOpponentUser: {},
   },
   data () {
     return {
       currentDayDividerDisplay: moment().day(),
-      cachedProfileData: {},
-      currentProfileLoadedCount: 0,
-      currentProfileLoadedEnd: 10,
       loading: false,
       handleScrollBack: false,
       lastOffset: -1,
@@ -233,8 +228,6 @@ export default {
     };
   },
   mounted () {
-    this.loadProfileCache();
-
     this.$el.addEventListener('selectstart', () => this.handleSelectStart());
     this.$el.addEventListener('mouseup', () => this.handleSelectChange());
   },
@@ -253,7 +246,6 @@ export default {
     // @TODO: We need a different lazy load mechnism.
     // But honestly, adding a paging route to chat would solve this
     messages () {
-      this.loadProfileCache();
       return this.chat;
     },
     psOptions () {
@@ -263,9 +255,6 @@ export default {
     },
   },
   methods: {
-    handleScroll () {
-      this.loadProfileCache(window.scrollY / 1000);
-    },
     async triggerLoad () {
       const container = this.$refs.container.$el;
 
@@ -284,62 +273,6 @@ export default {
         this.handleScrollBack = true;
       }
     },
-    loadProfileCache: debounce(function loadProfileCache (screenPosition) {
-      this._loadProfileCache(screenPosition);
-    }, 1000),
-    async _loadProfileCache (screenPosition) {
-      if (this.loading) return;
-      this.loading = true;
-
-      const promises = [];
-      const noProfilesLoaded = Object.keys(this.cachedProfileData).length === 0;
-
-      // @TODO: write an explination
-      // @TODO: Remove this after enough messages are cached
-      if (!noProfilesLoaded && screenPosition
-        && Math.floor(screenPosition) + 1 > this.currentProfileLoadedEnd / 10) {
-        this.currentProfileLoadedEnd = 10 * (Math.floor(screenPosition) + 1);
-      } else if (!noProfilesLoaded && screenPosition) {
-        return;
-      }
-
-      const aboutToCache = {};
-      this.messages.forEach(message => {
-        const { uuid } = message;
-
-        if (message.userStyles) {
-          this.$set(this.cachedProfileData, uuid, message.userStyles);
-        }
-
-        if (Boolean(uuid) && !this.cachedProfileData[uuid] && !aboutToCache[uuid]) {
-          if (uuid === 'system' || this.currentProfileLoadedCount === this.currentProfileLoadedEnd) return;
-          aboutToCache[uuid] = {};
-          promises.push(axios.get(`/api/v4/members/${uuid}`));
-          this.currentProfileLoadedCount += 1;
-        }
-      });
-
-      const results = await Promise.all(promises);
-      results.forEach(result => {
-        // We could not load the user. Maybe they were deleted.
-        // So, let's cache empty so we don't try again
-        if (!result || !result.data || result.status >= 400) {
-          return;
-        }
-
-        const userData = result.data.data;
-        this.$set(this.cachedProfileData, userData._id, userData);
-      });
-
-      // Merge in any attempts that were rejected so we don't attempt again
-      for (const uuid in aboutToCache) {
-        if (!this.cachedProfileData[uuid]) {
-          this.$set(this.cachedProfileData, uuid, { rejected: true });
-        }
-      }
-
-      this.loading = false;
-    },
     displayDivider (message) {
       if (this.currentDayDividerDisplay !== moment(message.timestamp).day()) {
         this.currentDayDividerDisplay = moment(message.timestamp).day();
@@ -348,29 +281,8 @@ export default {
 
       return false;
     },
-    async showMemberModal (memberId) {
-      let profile = this.cachedProfileData[memberId];
-
-      if (!profile._id) {
-        const result = await this.$store.dispatch('members:fetchMember', { memberId });
-        if (result.response && result.response.status === 404) {
-          return this.$store.dispatch('snackbars:add', {
-            title: 'Habitica',
-            text: this.$t('messageDeletedUser'),
-            type: 'error',
-            timeout: false,
-          });
-        }
-        this.cachedProfileData[memberId] = result.data.data;
-        profile = result.data.data;
-      }
-
-      // Open the modal only if the data is available
-      if (profile && !profile.rejected) {
-        this.$router.push({ name: 'userProfile', params: { userId: profile._id } });
-      }
-
-      return null;
+    showMemberModal (memberId) {
+      this.$router.push({ name: 'userProfile', params: { userId: memberId } });
     },
     itemWasMounted: debounce(function itemWasMounted () {
       if (this.handleScrollBack) {
diff --git a/website/client/src/components/settings/usernameForm.vue b/website/client/src/components/settings/usernameForm.vue
index 1b7ce0e41d..1d680302c2 100644
--- a/website/client/src/components/settings/usernameForm.vue
+++ b/website/client/src/components/settings/usernameForm.vue
@@ -157,6 +157,7 @@
 import axios from 'axios';
 import debounce from 'lodash/debounce';
 import { mapState } from '@/libs/store';
+import { EVENTS } from '@/libs/events';
 
 export default {
   props: {
@@ -218,9 +219,9 @@ export default {
   },
   methods: {
     async close () {
-      this.$root.$emit('habitica::resync-requested');
+      this.$root.$emit(EVENTS.RESYNC_REQUESTED);
       await this.$store.dispatch('user:fetch', { forceLoad: true });
-      this.$root.$emit('habitica::resync-completed');
+      this.$root.$emit(EVENTS.RESYNC_COMPLETED);
       if (this.avatarIntro) {
         this.$emit('usernameConfirmed');
       } else {
diff --git a/website/client/src/components/tasks/column.vue b/website/client/src/components/tasks/column.vue
index 4ed515fde4..c9262c2186 100644
--- a/website/client/src/components/tasks/column.vue
+++ b/website/client/src/components/tasks/column.vue
@@ -348,6 +348,7 @@ import habitIcon from '@/assets/svg/habit.svg';
 import dailyIcon from '@/assets/svg/daily.svg';
 import todoIcon from '@/assets/svg/todo.svg';
 import rewardIcon from '@/assets/svg/reward.svg';
+import { EVENTS } from '@/libs/events';
 
 export default {
   components: {
@@ -500,7 +501,7 @@ export default {
     });
 
     if (this.type !== 'todo') return;
-    this.$root.$on('habitica::resync-completed', () => {
+    this.$root.$on(EVENTS.RESYNC_COMPLETED, () => {
       if (this.activeFilter.label !== 'complete2') return;
       this.loadCompletedTodos();
     });
@@ -508,7 +509,7 @@ export default {
   destroyed () {
     this.$root.$off('buyModal::boughtItem');
     if (this.type !== 'todo') return;
-    this.$root.$off('habitica::resync-requested');
+    this.$root.$off(EVENTS.RESYNC_COMPLETED);
   },
   methods: {
     ...mapActions({
diff --git a/website/client/src/components/ui/textarea.stories.js b/website/client/src/components/ui/textarea.stories.js
index 7fd0d205a4..34f76eae00 100644
--- a/website/client/src/components/ui/textarea.stories.js
+++ b/website/client/src/components/ui/textarea.stories.js
@@ -2,7 +2,7 @@
 import { storiesOf } from '@storybook/vue';
 import { text, withKnobs } from '@storybook/addon-knobs';
 
-const stories = storiesOf('Textare', module);
+const stories = storiesOf('Textarea', module);
 
 stories.addDecorator(withKnobs);
 
@@ -11,7 +11,11 @@ stories
     components: { },
     template: `
       <div style="position: absolute; margin: 20px">
-        <textarea autofocus ref="area">Normal {{text}}</textarea>  <button @click="$refs.area.focus()">Focus</button>
+        <textarea autofocus ref="area">Normal {{text}}</textarea>
+        <br />
+        <button class="btn btn-dark" @click="$refs.area.focus()">Focus ^</button>
+        <br />
+        <textarea placeholder="placeholder"></textarea>
         <br />
 
         <textarea disabled>Disabled {{text}}</textarea><br />
diff --git a/website/client/src/components/userLink.vue b/website/client/src/components/userLink.vue
index 258266d11c..0026f492fc 100644
--- a/website/client/src/components/userLink.vue
+++ b/website/client/src/components/userLink.vue
@@ -2,7 +2,7 @@
   <router-link
     v-if="displayName"
     v-b-tooltip.hover.top="tierTitle"
-    class="leader"
+    class="leader user-link"
     :to="{'name': 'userProfile', 'params': {'userId': id}}"
     :class="levelStyle()"
   >
@@ -56,7 +56,7 @@ import tierNPC from '@/assets/svg/tier-npc.svg';
 
 export default {
   mixins: [styleHelper],
-  props: ['user', 'userId', 'name', 'backer', 'contributor'],
+  props: ['user', 'userId', 'name', 'backer', 'contributor', 'hideTooltip'],
   data () {
     return {
       icons: Object.freeze({
@@ -111,7 +111,7 @@ export default {
       return this.icons[`tier${this.level}`];
     },
     tierTitle () {
-      return achievementsLib.getContribText(this.contributor, this.isNPC) || '';
+      return this.hideTooltip ? '' : achievementsLib.getContribText(this.contributor, this.isNPC) || '';
     },
     levelStyle () {
       return this.userLevelStyleFromLevel(this.level, this.isNPC);
diff --git a/website/client/src/libs/events.js b/website/client/src/libs/events.js
new file mode 100644
index 0000000000..bfe17e3fa1
--- /dev/null
+++ b/website/client/src/libs/events.js
@@ -0,0 +1,6 @@
+export const EVENTS = {
+  RESYNC_REQUESTED: 'habitica::resync-requested',
+  RESYNC_COMPLETED: 'habitica::resync-completed',
+
+  PM_REFRESH: 'pm::refresh',
+};
diff --git a/website/client/src/mixins/sync.js b/website/client/src/mixins/sync.js
index 40b5a051ce..d1e574670e 100644
--- a/website/client/src/mixins/sync.js
+++ b/website/client/src/mixins/sync.js
@@ -1,12 +1,14 @@
+import { EVENTS } from '@/libs/events';
+
 export default {
   methods: {
     async sync () {
-      this.$root.$emit('habitica::resync-requested');
+      this.$root.$emit(EVENTS.RESYNC_REQUESTED);
       await Promise.all([
         this.$store.dispatch('user:fetch', { forceLoad: true }),
         this.$store.dispatch('tasks:fetchUserTasks', { forceLoad: true }),
       ]);
-      this.$root.$emit('habitica::resync-completed');
+      this.$root.$emit(EVENTS.RESYNC_COMPLETED);
     },
   },
 };
diff --git a/website/client/src/pages/private-messages.vue b/website/client/src/pages/private-messages.vue
index d351f20494..9b47801b1c 100644
--- a/website/client/src/pages/private-messages.vue
+++ b/website/client/src/pages/private-messages.vue
@@ -3,7 +3,7 @@
     <div class="floating-header-shadow"></div>
     <div class="header-bar d-flex w-100">
       <!-- changing w-25 would also need changes in .left-header.w-25 -->
-      <div class="d-flex w-25 left-header">
+      <div class="d-flex left-header">
         <div
           v-once
           class="mail-icon svg-icon"
@@ -19,22 +19,28 @@
           <!-- placeholder -->
         </div>
       </div>
-      <div class="d-flex w-75 selected-conversion">
-        <face-avatar
-          v-if="selectedConversation.userStyles"
-          :member="selectedConversation.userStyles"
-          :class="selectedConversationFaceAvatarClass"
-        />
-        <user-label
+      <div class="d-flex selected-conversion">
+        <router-link
+          :to="{'name': 'userProfile', 'params': {'userId': selectedConversation.key}}"
+        >
+          <face-avatar
+            v-if="selectedConversation.userStyles"
+            :member="selectedConversation.userStyles"
+            :class="selectedConversationFaceAvatarClass"
+          />
+        </router-link>
+        <user-link
           :backer="selectedConversation.backer"
           :contributor="selectedConversation.contributor"
           :name="selectedConversation.name"
+          :user="selectedConversation"
+          :userId="selectedConversation.key"
           :hide-tooltip="true"
         />
       </div>
     </div>
     <div class="d-flex content">
-      <div class="w-25 sidebar d-flex flex-column">
+      <div class="sidebar d-flex flex-column">
         <div class="disable-background">
           <toggle-switch
             :label="optTextSet.switchDescription"
@@ -50,24 +56,6 @@
             :placeholder="$t('search')"
           />
         </div>
-        <div
-          v-if="filtersConversations.length === 0"
-          class="empty-messages m-auto text-center empty-sidebar"
-        >
-          <div>
-            <div
-              v-once
-              class="svg-icon envelope"
-              v-html="icons.messageIcon"
-            ></div>
-            <h4 v-once>
-              {{ $t('emptyMessagesLine1') }}
-            </h4>
-            <p v-if="!user.flags.chatRevoked">
-              {{ $t('emptyMessagesLine2') }}
-            </p>
-          </div>
-        </div>
         <div
           v-if="filtersConversations.length > 0"
           class="conversations"
@@ -88,18 +76,39 @@
           />
         </div>
       </div>
-      <div class="w-75 messages-column d-flex flex-column align-items-center">
+      <div class="messages-column d-flex flex-column align-items-center">
         <div
-          v-if="!selectedConversation.key"
+          v-if="filtersConversations.length === 0
+            && (!selectedConversation || !selectedConversation.key)"
+          class="empty-messages m-auto text-center empty-sidebar"
+        >
+          <div class="no-messages-box">
+            <div
+              v-once
+              class="svg-icon envelope"
+              v-html="icons.messageIcon"
+            ></div>
+            <h2 v-once>
+              {{ $t('emptyMessagesLine1') }}
+            </h2>
+            <p v-if="!user.flags.chatRevoked">
+              {{ $t('emptyMessagesLine2') }}
+            </p>
+          </div>
+        </div>
+        <div
+          v-if="filtersConversations.length !== 0 && !selectedConversation.key"
           class="empty-messages full-height m-auto text-center"
         >
-          <div
-            v-once
-            class="svg-icon envelope"
-            v-html="icons.messageIcon"
-          ></div>
-          <h4>{{ placeholderTexts.title }}</h4>
-          <p v-html="placeholderTexts.description"></p>
+          <div class="no-messages-box">
+            <div
+              v-once
+              class="svg-icon envelope"
+              v-html="icons.messageIcon"
+            ></div>
+            <h2>{{ placeholderTexts.title }}</h2>
+            <p v-html="placeholderTexts.description"></p>
+          </div>
         </div>
         <div
           v-if="selectedConversation.key && selectedConversationMessages.length === 0"
@@ -120,34 +129,37 @@
           ref="chatscroll"
           class="message-scroll"
           :chat="selectedConversationMessages"
+          :conversationOpponentUser="selectedConversation.userStyles"
           :can-load-more="canLoadMore"
           :is-loading="messagesLoading"
           @message-removed="messageRemoved"
           @triggerLoad="infiniteScrollTrigger"
         />
         <div
-          v-if="user.inbox.optOut"
+          v-if="disabledTexts"
           class="pm-disabled-caption text-center"
         >
-          <h4>{{ $t('PMDisabledCaptionTitle') }}</h4>
-          <p>{{ $t('PMDisabledCaptionText') }}</p>
+          <h4>{{ disabledTexts.title }}</h4>
+          <p>{{ disabledTexts.description }}</p>
         </div>
         <div>
           <div
-            v-if="selectedConversation.key && !user.flags.chatRevoked"
             class="new-message-row d-flex align-items-center"
           >
             <textarea
+              ref="textarea"
               v-model="newMessage"
               class="flex-fill"
               :placeholder="$t('needsTextPlaceholder')"
               :maxlength="MAX_MESSAGE_LENGTH"
-              :class="{'has-content': newMessage !== ''}"
+              :class="{'has-content': newMessage !== '', 'disabled': newMessageDisabled}"
+              :style="{'--textarea-auto-height': textareaAutoHeight}"
               @keyup.ctrl.enter="sendPrivateMessage()"
-            ></textarea>
+              @input="autoSize()"
+            >
+            </textarea>
           </div>
           <div
-            v-if="selectedConversation.key && !user.flags.chatRevoked"
             class="sub-new-message-row d-flex"
           >
             <div
@@ -157,7 +169,7 @@
             ></div>
             <button
               class="btn btn-primary"
-              :class="{'disabled':newMessage === ''}"
+              :class="{'disabled':newMessageDisabled || newMessage === ''}"
               @click="sendPrivateMessage()"
             >
               {{ $t('send') }}
@@ -268,10 +280,6 @@
     .placeholder.svg-icon {
       width: 32px;
     }
-
-    .left-header.w-25 {
-      width: calc(25% - 2rem) !important;
-    }
   }
 
   .full-height {
@@ -281,7 +289,7 @@
     justify-content: center;
   }
 
-  .user-label {
+  .user-link {
     margin-left: 12px;
   }
 
@@ -292,10 +300,13 @@
     background-image: url(~@/assets/svg/for-css/search_gray.svg) !important;
     padding-left: 40px;
 
-    color: $gray-200 !important;
     height: 40px;
   }
 
+  .input-search::placeholder {
+    color: $gray-200 !important;
+  }
+
   .selected-conversion {
     justify-content: center;
     align-items: center;
@@ -314,32 +325,42 @@
 
 
   .conversations {
-    max-height: 35rem;
     overflow-x: hidden;
     overflow-y: auto;
     height: 100%;
   }
 
   .empty-messages {
-    h3, h4, p {
-      color: $gray-400;
+    h3, p {
+      color: $gray-200;
       margin: 0rem;
     }
 
+    h2 {
+      color: $gray-200;
+      margin-bottom: 1rem;
+    }
+
     p {
       font-size: 12px;
     }
 
-    .envelope {
-      width: 30px;
-      margin: 0 auto 0.5rem;
+    .no-messages-box {
+      display: flex;
+      flex-direction: column;
+      align-items: center;
+      width: 330px;
     }
-  }
 
-  .envelope {
-    color: $gray-500 !important;
-    margin: 0rem;
-    max-width: 2rem;
+    .envelope {
+      color: $gray-400 !important;
+      margin-bottom: 1.5rem;
+
+      ::v-deep svg {
+        width: 64px;
+        height: 48px;
+      }
+    }
   }
 
   h3 {
@@ -371,7 +392,12 @@
     word-break: break-word;
   }
 
+  .selected-conversion {
+    flex: 1;
+  }
+
   .messages-column {
+    flex: 1;
     padding: 0rem;
     display: flex;
     flex-direction: column;
@@ -398,16 +424,24 @@
     padding-right: 1.5rem;
 
     textarea {
-      height: 5.5rem;
       display: inline-block;
       vertical-align: bottom;
       border-radius: 2px;
       z-index: 5;
+
+      &.disabled {
+        pointer-events: none;
+        opacity: 0.64;
+        background-color: $gray-500;
+      }
+
+      min-height: var(--textarea-auto-height, 40px);
+      max-height: var(--textarea-auto-height, 40px);
     }
   }
 
   .sub-new-message-row {
-    padding: 1rem 1.5rem 1.5rem;
+    padding: 1.5rem;
 
     .guidelines {
       height: 32px;
@@ -433,17 +467,17 @@
         pointer-events: none;
         opacity: 0.64;
         background-color: $gray-500;
+        color: $gray-100;
       }
     }
   }
 
   .pm-disabled-caption {
     padding-top: 1em;
-    background-color: $gray-700;
     z-index: 2;
 
     h4, p {
-      color: $gray-300;
+      color: $gray-200;
     }
 
     h4 {
@@ -457,10 +491,14 @@
     }
   }
 
+  .left-header {
+    max-width: calc(330px - 2rem); // minus the left padding
+    flex: 1;
+  }
+
   .sidebar {
+    width: 330px;
     background-color: $gray-700;
-    min-height: 540px;
-    max-width: 330px;
     padding: 0;
     border-bottom-left-radius: 8px;
 
@@ -468,6 +506,10 @@
       padding: 1rem 1.5rem;
       border-bottom: 1px solid $gray-500;
     }
+
+    @media only screen and (max-width: 768px) {
+      width: 280px;
+    }
   }
 
   .time {
@@ -522,7 +564,7 @@ import { MAX_MESSAGE_LENGTH } from '@/../../common/script/constants';
 import { mapState } from '@/libs/store';
 import styleHelper from '@/mixins/styleHelper';
 import toggleSwitch from '@/components/ui/toggleSwitch';
-import userLabel from '@/components/userLabel';
+import userLink from '@/components/userLink';
 
 import messageList from '@/components/messages/messageList';
 import messageIcon from '@/assets/svg/message.svg';
@@ -530,6 +572,9 @@ import mail from '@/assets/svg/mail.svg';
 import conversationItem from '@/components/messages/conversationItem';
 import faceAvatar from '@/components/faceAvatar';
 import Avatar from '@/components/avatar';
+import { EVENTS } from '@/libs/events';
+
+const MAX_TEXTAREA_HEIGHT = 80;
 
 export default {
   components: {
@@ -537,7 +582,7 @@ export default {
     messageList,
     toggleSwitch,
     conversationItem,
-    userLabel,
+    userLink,
     faceAvatar,
   },
   filters: {
@@ -564,14 +609,23 @@ export default {
       messagesLoading: false,
       initiatedConversation: null,
       updateConversationsCounter: 0,
+      textareaAutoHeight: undefined,
       MAX_MESSAGE_LENGTH: MAX_MESSAGE_LENGTH.toString(),
     };
   },
   async mounted () {
-    this.$root.$on('pm::refresh', async () => {
+    // notification click to refresh
+    this.$root.$on(EVENTS.PM_REFRESH, async () => {
       await this.reload();
 
-      this.selectConversation(this.loadedConversations[0].uuid, true);
+      this.selectFirstConversation();
+    });
+
+    // header sync button
+    this.$root.$on(EVENTS.RESYNC_COMPLETED, async () => {
+      await this.reload();
+
+      this.selectFirstConversation();
     });
 
     await this.reload();
@@ -594,7 +648,7 @@ export default {
     }
   },
   destroyed () {
-    this.$root.$off('habitica::new-private-message');
+    this.$root.$off(EVENTS.RESYNC_COMPLETED);
   },
   computed: {
     ...mapState({ user: 'user.data' }),
@@ -616,6 +670,7 @@ export default {
           id: '',
           text: '',
           timestamp: new Date(),
+          canReceive: true,
         }];
       }
       // Create conversation objects
@@ -635,6 +690,7 @@ export default {
             contributor: recentMessage.contributor,
             userStyles: recentMessage.userStyles,
             backer: recentMessage.backer,
+            canReceive: recentMessage.canReceive,
             canLoadMore: false,
             page: 0,
           };
@@ -693,6 +749,39 @@ export default {
         description: this.$t('PMPlaceholderDescription'),
       };
     },
+    disabledTexts () {
+      if (this.user.flags.chatRevoked) {
+        return {
+          title: this.$t('PMPlaceholderTitleRevoked'),
+          description: this.$t('chatPrivilegesRevoked'),
+        };
+      }
+
+      if (this.user.inbox.optOut) {
+        return {
+          title: this.$t('PMDisabledCaptionTitle'),
+          description: this.$t('PMDisabledCaptionText'),
+        };
+      }
+
+      if (this.selectedConversation && this.selectedConversation.key) {
+        if (this.user.inbox.blocks.includes(this.selectedConversation.key)) {
+          return {
+            title: this.$t('PMDisabledCaptionTitle'),
+            description: this.$t('PMUnblockUserToSendMessages'),
+          };
+        }
+
+        if (!this.selectedConversation.canReceive) {
+          return {
+            title: this.$t('PMCanNotReply'),
+            description: this.$t('PMUserDoesNotReceiveMessages'),
+          };
+        }
+      }
+
+      return null;
+    },
     optTextSet () {
       if (!this.user.inbox.optOut) {
         return {
@@ -711,6 +800,10 @@ export default {
       }
       return '';
     },
+    newMessageDisabled () {
+      return !this.selectedConversation || !this.selectedConversation.key
+        || this.disabledTexts !== null;
+    },
   },
 
   methods: {
@@ -721,6 +814,8 @@ export default {
       this.loadedConversations = conversationRes.data.data;
       this.selectedConversation = {};
 
+      await this.$store.dispatch('user:markPrivMessagesRead');
+
       this.loaded = true;
     },
     messageRemoved (message) {
@@ -813,6 +908,7 @@ export default {
       });
 
       this.newMessage = '';
+      this.autoSize();
     },
     removeTags (html) {
       const tmp = document.createElement('DIV');
@@ -856,6 +952,27 @@ export default {
       this.selectedConversation.canLoadMore = loadedMessages.length === 10;
       this.messagesLoading = false;
     },
+    autoSize () {
+      const { textarea } = this.$refs;
+      // weird issue: browser only removing the scrollHeight / clientHeight per key event - 56-54-52
+      let { scrollHeight } = textarea;
+
+      if (this.newMessage === '') {
+        // reset height when the message was removed again
+        scrollHeight = 40;
+      }
+
+      if (scrollHeight > MAX_TEXTAREA_HEIGHT) {
+        scrollHeight = MAX_TEXTAREA_HEIGHT;
+      }
+
+      this.textareaAutoHeight = `${scrollHeight}px`;
+    },
+    selectFirstConversation () {
+      if (this.loadedConversations.length > 0) {
+        this.selectConversation(this.loadedConversations[0].uuid, true);
+      }
+    },
   },
 };
 </script>
diff --git a/website/client/src/store/actions/user.js b/website/client/src/store/actions/user.js
index 3a98137fed..fa1de5dcc7 100644
--- a/website/client/src/store/actions/user.js
+++ b/website/client/src/store/actions/user.js
@@ -6,6 +6,7 @@ import { togglePinnedItem as togglePinnedItemOp } from '@/../../common/script/op
 import changeClassOp from '@/../../common/script/ops/changeClass';
 import disableClassesOp from '@/../../common/script/ops/disableClasses';
 import openMysteryItemOp from '@/../../common/script/ops/openMysteryItem';
+import markPMSRead from '../../../../common/script/ops/markPMSRead';
 
 export function fetch (store, options = {}) { // eslint-disable-line no-shadow
   return loadAsyncResource({
@@ -172,6 +173,11 @@ export function unblock (store, params) {
   return axios.post(`/api/v4/user/block/${params.uuid}`);
 }
 
+export function markPrivMessagesRead (store) {
+  markPMSRead(store.state.user.data);
+  return axios.post('/api/v4/user/mark-pms-read');
+}
+
 export function newPrivateMessageTo (store, params) {
   const { member } = params;
 
diff --git a/website/common/locales/en/generic.json b/website/common/locales/en/generic.json
index 0a10811c2a..ac5b9c5555 100644
--- a/website/common/locales/en/generic.json
+++ b/website/common/locales/en/generic.json
@@ -296,7 +296,7 @@
   "dismissAll": "Dismiss All",
   "messages": "Messages",
   "emptyMessagesLine1": "You don't have any messages",
-  "emptyMessagesLine2": "Send a message to start a conversation!",
+  "emptyMessagesLine2": "You can send a new message to a user by visiting their profile and clicking the \"Message\" button.",
   "userSentMessage": "<span class=\"notification-bold\"><%= user %></span> sent you a message",
   "letsgo": "Let's Go!",
   "selected": "Selected",
diff --git a/website/common/locales/en/groups.json b/website/common/locales/en/groups.json
index ee7280939d..31c8edff5f 100644
--- a/website/common/locales/en/groups.json
+++ b/website/common/locales/en/groups.json
@@ -143,6 +143,9 @@
   "PMDisabledOptPopoverText": "Private Messages are disabled. Enable this option to allow users to contact you via your profile.",
   "PMDisabledCaptionTitle": "Private Messages are disabled",
   "PMDisabledCaptionText": "You can still send messages, but no one can send them to you.",
+  "PMCanNotReply": "You can not reply to this conversation",
+  "PMUserDoesNotReceiveMessages": "This user is no longer receiving private messages",
+  "PMUnblockUserToSendMessages": "Unblock this user to continue sending and receiving messages.",
   "block": "Block",
   "unblock": "Un-block",
   "blockWarning": "Block - This will have no effect if the player is a moderator now or becomes a moderator in future.",
diff --git a/website/server/controllers/api-v4/inbox.js b/website/server/controllers/api-v4/inbox.js
index be5cca6a4d..28843f93e9 100644
--- a/website/server/controllers/api-v4/inbox.js
+++ b/website/server/controllers/api-v4/inbox.js
@@ -93,6 +93,7 @@ api.clearMessages = {
  *       "text":"last message of conversation",
  *       "userStyles": {},
  *       "contributor": {},
+ *       "canReceive": true,
  *       "count":1
  *    }
  * }
diff --git a/website/server/libs/inbox/conversation.methods.js b/website/server/libs/inbox/conversation.methods.js
index b1f20d53fe..72a50111e3 100644
--- a/website/server/libs/inbox/conversation.methods.js
+++ b/website/server/libs/inbox/conversation.methods.js
@@ -2,70 +2,40 @@ import { inboxModel as Inbox, setUserStyles } from '../../models/message';
 import { model as User } from '../../models/user';
 
 /**
- * Get the users for conversations
- * 1. Get the user data of last sent message by conversation
- * 2. If the target user hasn't replied yet ( 'sent:true' ) , list user data by users directly
- * @param owner
+ * Get the current user (avatar/setting etc) for conversations
  * @param users
  * @returns {Promise<void>}
  */
-async function usersMapByConversations (owner, users) {
-  const query = Inbox
-    .aggregate([
-      {
-        $match: {
-          ownerId: owner._id,
-          uuid: { $in: users },
-          sent: false, // only messages the other user sent to you
-        },
-      },
-      {
-        $group: {
-          _id: '$uuid',
-          userStyles: { $last: '$userStyles' },
-          contributor: { $last: '$contributor' },
-          backer: { $last: '$backer' },
-        },
-      },
-    ]);
-
-
-  const usersAr = await query.exec();
+async function usersMapByConversations (users) {
   const usersMap = {};
 
-  for (const usr of usersAr) {
-    usersMap[usr._id] = usr;
-  }
+  const usersQuery = {
+    _id: { $in: users },
+  };
 
-  // if a conversation doesn't have a response of the chat-partner,
-  // those won't be listed by the query above
-  const usersStillNeedToBeLoaded = users.filter(userId => !usersMap[userId]);
+  const loadedUsers = await User.find(usersQuery, {
+    _id: 1,
+    contributor: 1,
+    backer: 1,
+    items: 1,
+    preferences: 1,
+    stats: 1,
+    flags: 1,
+    inbox: 1,
+  }).exec();
 
-  if (usersStillNeedToBeLoaded.length > 0) {
-    const usersQuery = {
-      _id: { $in: usersStillNeedToBeLoaded },
+  for (const usr of loadedUsers) {
+    const loadedUserConversation = {
+      _id: usr._id,
+      backer: usr.backer,
+      contributor: usr.contributor,
+      optOut: usr.inbox.optOut,
+      blocks: usr.inbox.blocks || [],
     };
+    // map user values to conversation properties
+    setUserStyles(loadedUserConversation, usr);
 
-    const loadedUsers = await User.find(usersQuery, {
-      _id: 1,
-      contributor: 1,
-      backer: 1,
-      items: 1,
-      preferences: 1,
-      stats: 1,
-    }).exec();
-
-    for (const usr of loadedUsers) {
-      const loadedUserConversation = {
-        _id: usr._id,
-        backer: usr.backer,
-        contributor: usr.contributor,
-      };
-      // map user values to conversation properties
-      setUserStyles(loadedUserConversation, usr);
-
-      usersMap[usr._id] = loadedUserConversation;
-    }
+    usersMap[usr._id] = loadedUserConversation;
   }
 
   return usersMap;
@@ -98,7 +68,7 @@ export async function listConversations (owner) {
   const userIdList = conversationsList.map(c => c._id);
 
   // get user-info based on conversations
-  const usersMap = await usersMapByConversations(owner, userIdList);
+  const usersMap = await usersMapByConversations(userIdList);
 
   const conversations = conversationsList.map(res => {
     const uuid = res._id;
@@ -109,9 +79,15 @@ export async function listConversations (owner) {
     };
 
     if (usersMap[uuid]) {
-      conversation.userStyles = usersMap[uuid].userStyles;
-      conversation.contributor = usersMap[uuid].contributor;
-      conversation.backer = usersMap[uuid].backer;
+      const user = usersMap[uuid];
+
+      conversation.userStyles = user.userStyles;
+      conversation.contributor = user.contributor;
+      conversation.backer = user.backer;
+
+      const isOwnerBlocked = user.blocks.includes(owner._id);
+
+      conversation.canReceive = !(user.optOut || isOwnerBlocked) || owner.isAdmin();
     }
 
     return conversation;