diff --git a/src/components/structures/UserSettings.js b/src/components/structures/UserSettings.js
index a172ca4dbf..45c52c7f1d 100644
--- a/src/components/structures/UserSettings.js
+++ b/src/components/structures/UserSettings.js
@@ -93,6 +93,10 @@ const SETTINGS_LABELS = [
         id: 'enableSyntaxHighlightLanguageDetection',
         label: 'Enable automatic language detection for syntax highlighting',
     },
+    {
+        id: 'MessageComposerInput.autoReplaceEmoji',
+        label: 'Automatically replace plain text Emoji',
+    },
 /*
     {
         id: 'useFixedWidthFont',
diff --git a/src/components/views/rooms/MessageComposerInput.js b/src/components/views/rooms/MessageComposerInput.js
index abe63ad491..acd49f6fb4 100644
--- a/src/components/views/rooms/MessageComposerInput.js
+++ b/src/components/views/rooms/MessageComposerInput.js
@@ -43,6 +43,11 @@ import Markdown from '../../../Markdown';
 import ComposerHistoryManager from '../../../ComposerHistoryManager';
 import MessageComposerStore from '../../../stores/MessageComposerStore';
 
+import {asciiRegexp, shortnameToUnicode, emojioneList, asciiList, mapUnicodeToShort} from 'emojione';
+const EMOJI_SHORTNAMES = Object.keys(emojioneList);
+const EMOJI_UNICODE_TO_SHORTNAME = mapUnicodeToShort();
+const REGEX_EMOJI_WHITESPACE = new RegExp('(' + asciiRegexp + ')\\s$');
+
 const TYPING_USER_TIMEOUT = 10000, TYPING_SERVER_TIMEOUT = 30000;
 
 const ZWS_CODE = 8203;
@@ -369,6 +374,32 @@ export default class MessageComposerInput extends React.Component {
             editorState = EditorState.forceSelection(editorState, currentSelection);
         }
 
+        // Automatic replacement of plaintext emoji to Unicode emoji
+        if (UserSettingsStore.getSyncedSetting('MessageComposerInput.autoReplaceEmoji', false)) {
+            // The first matched group includes just the matched plaintext emoji
+            const emojiMatch = REGEX_EMOJI_WHITESPACE.exec(text.slice(0, currentStartOffset));
+            if(emojiMatch) {
+                // plaintext -> hex unicode
+                const emojiUc = asciiList[emojiMatch[1]];
+                // hex unicode -> shortname -> actual unicode
+                const unicodeEmoji = shortnameToUnicode(EMOJI_UNICODE_TO_SHORTNAME[emojiUc]);
+                const newContentState = Modifier.replaceText(
+                    editorState.getCurrentContent(),
+                    currentSelection.merge({
+                        anchorOffset: currentStartOffset - emojiMatch[0].length,
+                        focusOffset: currentStartOffset,
+                    }),
+                    unicodeEmoji,
+                );
+                editorState = EditorState.push(
+                    editorState,
+                    newContentState,
+                    'insert-characters',
+                );
+                editorState = EditorState.forceSelection(editorState, newContentState.getSelectionAfter());
+            }
+        }
+
         /* Since a modification was made, set originalEditorState to null, since newState is now our original */
         this.setState({
             editorState,
diff --git a/src/i18n/strings/en_EN.json b/src/i18n/strings/en_EN.json
index e041649906..4841f2f0de 100644
--- a/src/i18n/strings/en_EN.json
+++ b/src/i18n/strings/en_EN.json
@@ -955,5 +955,6 @@
     "To join an exisitng group you'll have to know its group identifier; this will look something like <i>+example:matrix.org</i>.": "To join an exisitng group you'll have to know its group identifier; this will look something like <i>+example:matrix.org</i>.",
     "Featured Rooms:": "Featured Rooms:",
     "Error whilst fetching joined groups": "Error whilst fetching joined groups",
-    "Featured Users:": "Featured Users:"
+    "Featured Users:": "Featured Users:",
+    "Automatically replace plain text Emoji": "Automatically replace plain text Emoji"
 }