diff --git a/src/components/views/rooms/BasicMessageComposer.tsx b/src/components/views/rooms/BasicMessageComposer.tsx
index 9d9e3a1ba0..f19b5903df 100644
--- a/src/components/views/rooms/BasicMessageComposer.tsx
+++ b/src/components/views/rooms/BasicMessageComposer.tsx
@@ -51,6 +51,7 @@ import {replaceableComponent} from "../../../utils/replaceableComponent";
 
 // matches emoticons which follow the start of a line or whitespace
 const REGEX_EMOTICON_WHITESPACE = new RegExp('(?:^|\\s)(' + EMOTICON_REGEX.source + ')\\s$');
+export const REGEX_EMOTICON = new RegExp('(?:^|\\s)(' + EMOTICON_REGEX.source + ')$');
 
 const IS_MAC = navigator.platform.indexOf("Mac") !== -1;
 
@@ -150,7 +151,7 @@ export default class BasicMessageEditor extends React.Component<IProps, IState>
         }
     }
 
-    private replaceEmoticon = (caretPosition: DocumentPosition) => {
+    public replaceEmoticon(caretPosition: DocumentPosition, regex: RegExp) {
         const {model} = this.props;
         const range = model.startRange(caretPosition);
         // expand range max 8 characters backwards from caretPosition,
@@ -161,7 +162,7 @@ export default class BasicMessageEditor extends React.Component<IProps, IState>
             n -= 1;
             return n >= 0 && (part.type === "plain" || part.type === "pill-candidate");
         });
-        const emoticonMatch = REGEX_EMOTICON_WHITESPACE.exec(range.text);
+        const emoticonMatch = regex.exec(range.text);
         if (emoticonMatch) {
             const query = emoticonMatch[1].replace("-", "");
             // try both exact match and lower-case, this means that xd won't match xD but :P will match :p
@@ -180,7 +181,7 @@ export default class BasicMessageEditor extends React.Component<IProps, IState>
                 return range.replace([partCreator.plain(data.unicode + " ")]);
             }
         }
-    };
+    }
 
     private updateEditorState = (selection: Caret, inputType?: string, diff?: IDiff) => {
         renderModel(this.editorRef.current, this.props.model);
@@ -567,8 +568,7 @@ export default class BasicMessageEditor extends React.Component<IProps, IState>
     };
 
     private configureEmoticonAutoReplace = () => {
-        const shouldReplace = SettingsStore.getValue('MessageComposerInput.autoReplaceEmoji');
-        this.props.model.setTransformCallback(shouldReplace ? this.replaceEmoticon : null);
+        this.props.model.setTransformCallback(this.transform);
     };
 
     private configureShouldShowPillAvatar = () => {
@@ -576,6 +576,11 @@ export default class BasicMessageEditor extends React.Component<IProps, IState>
         this.setState({ showPillAvatar });
     };
 
+    private transform = (documentPosition: DocumentPosition) => {
+        const shouldReplace = SettingsStore.getValue('MessageComposerInput.autoReplaceEmoji');
+        if (shouldReplace) this.replaceEmoticon(documentPosition, REGEX_EMOTICON_WHITESPACE);
+    }
+
     componentWillUnmount() {
         document.removeEventListener("selectionchange", this.onSelectionChange);
         this.editorRef.current.removeEventListener("input", this.onInput, true);
diff --git a/src/components/views/rooms/SendMessageComposer.js b/src/components/views/rooms/SendMessageComposer.js
index a3e841a0e2..703d409b00 100644
--- a/src/components/views/rooms/SendMessageComposer.js
+++ b/src/components/views/rooms/SendMessageComposer.js
@@ -28,7 +28,7 @@ import {
     stripPrefix,
 } from '../../../editor/serialize';
 import {CommandPartCreator} from '../../../editor/parts';
-import BasicMessageComposer from "./BasicMessageComposer";
+import BasicMessageComposer, {REGEX_EMOTICON} from "./BasicMessageComposer";
 import ReplyThread from "../elements/ReplyThread";
 import {parseEvent} from '../../../editor/deserialize';
 import {findEditableEvent} from '../../../utils/EventUtils';
@@ -334,6 +334,11 @@ export default class SendMessageComposer extends React.Component {
             return;
         }
 
+        // Replace emoticon at the end of the message
+        const caret = this._editorRef.getCaret();
+        const position = model.positionForOffset(caret.offset, caret.atNodeEnd);
+        this._editorRef.replaceEmoticon(position, REGEX_EMOTICON);
+
         const replyToEvent = this.props.replyToEvent;
         let shouldSend = true;
         let content;