diff --git a/website/client/components/chat/chatCard.vue b/website/client/components/chat/chatCard.vue
index e2db8411b1..687fa7457b 100644
--- a/website/client/components/chat/chatCard.vue
+++ b/website/client/components/chat/chatCard.vue
@@ -13,6 +13,8 @@ div
         .svg-icon(v-html="tierIcon", v-if='showShowTierStyle')
       p.time {{msg.timestamp | timeAgo}}
       .text(v-markdown='msg.text')
+      .reported(v-if="isMessageReported")
+        span(v-once) {{ $t('reportedMessage')}}
       hr
       .action(@click='like()', v-if='!inbox && msg.likes', :class='{active: msg.likes[user._id]}')
         .svg-icon(v-html="icons.like")
@@ -20,13 +22,13 @@ div
         span(v-if='msg.likes[user._id]') {{ $t('liked') }}
       span.action(v-if='!inbox', @click='copyAsTodo(msg)')
         .svg-icon(v-html="icons.copy", v-once)
-        | {{$t('copyAsTodo')}}
-      span.action(v-if='inbox || (user.flags.communityGuidelinesAccepted && msg.uuid !== "system")', @click='report(msg)')
+        span(v-once)  {{$t('copyAsTodo')}}
+      span.action(v-if='inbox || (user.flags.communityGuidelinesAccepted && msg.uuid !== "system" && !isMessageReported)', @click='report(msg)')
         .svg-icon(v-html="icons.report", v-once)
-        | {{$t('report')}}
+        span(v-once) {{$t('report')}}
       span.action(v-if='msg.uuid === user._id || inbox || user.contributor.admin', @click='remove()')
         .svg-icon(v-html="icons.delete", v-once)
-        | {{$t('delete')}}
+        span(v-once) {{$t('delete')}}
       span.action.float-right.liked(v-if='likeCount > 0')
         .svg-icon(v-html="icons.liked")
         | + {{ likeCount }}
@@ -34,6 +36,7 @@ div
 
 <style lang="scss" scoped>
   @import '~client/assets/scss/tiers.scss';
+  @import '~client/assets/scss/colors.scss';
 
   .mentioned-icon {
     width: 16px;
@@ -104,6 +107,10 @@ div
   .action.active, .active .svg-icon {
     color: #46a7d9
   }
+
+  .reported {
+    color: $maroon-50;
+  }
 </style>
 
 <script>
@@ -154,6 +161,7 @@ export default {
         tier9,
         tierNPC,
       }),
+      reported: false,
     };
   },
   directives: {
@@ -218,6 +226,9 @@ export default {
       }
       return this.icons[`tier${message.contributor.level}`];
     },
+    isMessageReported () {
+      return this.msg.reported || this.reported;
+    },
   },
   methods: {
     async like () {
@@ -239,7 +250,15 @@ export default {
     copyAsTodo (message) {
       this.$root.$emit('habitica::copy-as-todo', message);
     },
-    async report () {
+    report () {
+      this.$root.$on('habitica:report-result', data => {
+        if (data.ok) {
+          this.reported = true;
+        }
+
+        this.$root.$off('habitica:report-result');
+      });
+
       this.$root.$emit('habitica::report-chat', {
         message: this.msg,
         groupId: this.groupId || 'privateMessage',
diff --git a/website/client/components/chat/reportFlagModal.vue b/website/client/components/chat/reportFlagModal.vue
index 9d2e177987..884906a2b0 100644
--- a/website/client/components/chat/reportFlagModal.vue
+++ b/website/client/components/chat/reportFlagModal.vue
@@ -113,12 +113,22 @@ export default {
     async reportAbuse () {
       this.text('Thank you for reporting this violation. The moderators have been notified.');
 
-      await this.$store.dispatch('chat:flag', {
+      let result = await this.$store.dispatch('chat:flag', {
         groupId: this.groupId,
         chatId: this.abuseObject.id,
         comment: this.reportComment,
       });
 
+
+      console.info('error', result);
+      this.$root.$emit('habitica:report-result', result);
+
+      if (!result.ok && result.error) {
+        alert('errrorororor!');
+        console.info('error', result);
+        this.error(result.error);
+      }
+
       this.close();
     },
     async clearFlagCount () {
diff --git a/website/client/store/actions/chat.js b/website/client/store/actions/chat.js
index 509f6b33cf..80c909f8cb 100644
--- a/website/client/store/actions/chat.js
+++ b/website/client/store/actions/chat.js
@@ -80,6 +80,9 @@ export async function flag (store, payload) {
   const response = await axios.post(url, {
     comment: payload.comment,
   });
+
+  console.info('response', response.data.data);
+
   return response.data.data;
 }
 
diff --git a/website/common/locales/en/messages.json b/website/common/locales/en/messages.json
index 4bf55ff6c3..f1362df2fb 100644
--- a/website/common/locales/en/messages.json
+++ b/website/common/locales/en/messages.json
@@ -70,5 +70,7 @@
   "notificationsRequired": "Notification ids are required.",
   "unallocatedStatsPoints": "You have <span class=\"notification-bold-blue\"><%= points %> unallocated Stat Points</span>",
 
-  "beginningOfConversation": "This is the beginning of your conversation with <%= userName %>. Remember to be kind, respectful, and follow the Community Guidelines!"
+  "beginningOfConversation": "This is the beginning of your conversation with <%= userName %>. Remember to be kind, respectful, and follow the Community Guidelines!",
+
+  "reportedMessage": "You have reported this message to moderators."
 }
diff --git a/website/server/controllers/api-v3/members.js b/website/server/controllers/api-v3/members.js
index 151e64bc2d..d5d9d59b99 100644
--- a/website/server/controllers/api-v3/members.js
+++ b/website/server/controllers/api-v3/members.js
@@ -543,9 +543,19 @@ api.flagPrivateMessage = {
   url: '/members/flag-private-message/:messageId',
   middlewares: [authWithHeaders()],
   async handler (req, res) {
-    const chatReporter = chatReporterFactory('Inbox', req, res);
-    const message = await chatReporter.flag();
-    res.respond(200, message);
+    try {
+      const chatReporter = chatReporterFactory('Inbox', req, res);
+      const message = await chatReporter.flag();
+      res.respond(200, {
+        ok: true,
+        message,
+      });
+    } catch (e) {
+      res.respond(500, {
+        ok: false,
+        error: e,
+      });
+    }
   },
 };
 
diff --git a/website/server/libs/chatReporting/inboxChatReporter.js b/website/server/libs/chatReporting/inboxChatReporter.js
index e78ba8c0ad..36751d354f 100644
--- a/website/server/libs/chatReporting/inboxChatReporter.js
+++ b/website/server/libs/chatReporting/inboxChatReporter.js
@@ -61,32 +61,48 @@ export default class InboxChatReporter extends ChatReporter {
     });
   }
 
-  async flagInboxMessage (message) {
-    // Log user ids that have flagged the message
-    if (!message.flags) message.flags = {};
-    // TODO fix error type
-    if (message.flags[this.user._id] && !this.user.contributor.admin) throw new NotFound(this.res.t('messageGroupChatFlagAlreadyReported'));
-    message.flags[this.user._id] = true;
-
-    // Log total number of flags (publicly viewable)
-    if (!message.flagCount) message.flagCount = 0;
-    if (this.user.contributor.admin) {
-      // Arbitrary amount, higher than 2
-      message.flagCount = 5;
-    } else {
-      message.flagCount++;
-    }
+  updateMessageAndSave (message, updateFunc) {
+    updateFunc(message);
 
     this.user.inbox.messages[message.id] = message;
     this.user.markModified('inbox.messages');
 
-    await this.user.save();
+    return this.user.save();
+  }
+
+  flagInboxMessage (message) {
+    // Log user ids that have flagged the message
+    if (!message.flags) message.flags = {};
+    // TODO fix error type
+    if (message.flags[this.user._id] && !this.user.contributor.admin) {
+      throw new NotFound(this.res.t('messageGroupChatFlagAlreadyReported'));
+    }
+
+    return this.updateMessageAndSave(message, (m) => {
+      m.flags[this.user._id] = true;
+
+      // Log total number of flags (publicly viewable)
+      if (!m.flagCount) m.flagCount = 0;
+      if (this.user.contributor.admin) {
+        // Arbitrary amount, higher than 2
+        m.flagCount = 5;
+      } else {
+        m.flagCount++;
+      }
+    });
+  }
+
+  async markMessageAsReported (message) {
+    return this.updateMessageAndSave(message, (m) => {
+      m.reported = true;
+    });
   }
 
   async flag () {
     let {message, userComment} = await this.validate();
     await this.flagInboxMessage(message);
     await this.notify(message, userComment);
+    await this.markMessageAsReported(message);
     return message;
   }
 }