diff --git a/src/components/views/elements/MessageEditor.js b/src/components/views/elements/MessageEditor.js
index b07eca22b6..cb5767b192 100644
--- a/src/components/views/elements/MessageEditor.js
+++ b/src/components/views/elements/MessageEditor.js
@@ -22,7 +22,7 @@ import dis from '../../../dispatcher';
 import EditorModel from '../../../editor/model';
 import {setCaretPosition} from '../../../editor/caret';
 import {getCaretOffsetAndText} from '../../../editor/dom';
-import {htmlSerialize, textSerialize, requiresHtml} from '../../../editor/serialize';
+import {htmlSerializeIfNeeded, textSerialize} from '../../../editor/serialize';
 import {parseEvent} from '../../../editor/deserialize';
 import Autocomplete from '../rooms/Autocomplete';
 import {PartCreator} from '../../../editor/parts';
@@ -128,9 +128,10 @@ export default class MessageEditor extends React.Component {
             msgtype: newContent.msgtype,
             body: ` * ${newContent.body}`,
         };
-        if (requiresHtml(this.model)) {
+        const formattedBody = htmlSerializeIfNeeded(this.model);
+        if (formattedBody) {
             newContent.format = "org.matrix.custom.html";
-            newContent.formatted_body = htmlSerialize(this.model);
+            newContent.formatted_body = formattedBody;
             contentBody.format = newContent.format;
             contentBody.formatted_body = ` * ${newContent.formatted_body}`;
         }
diff --git a/src/editor/serialize.js b/src/editor/serialize.js
index 1724e4a2b7..73fbbe5d01 100644
--- a/src/editor/serialize.js
+++ b/src/editor/serialize.js
@@ -15,21 +15,31 @@ See the License for the specific language governing permissions and
 limitations under the License.
 */
 
-export function htmlSerialize(model) {
+import Markdown from '../Markdown';
+
+export function mdSerialize(model) {
     return model.parts.reduce((html, part) => {
         switch (part.type) {
             case "newline":
-                return html + "<br />";
+                return html + "\n";
             case "plain":
             case "pill-candidate":
                 return html + part.text;
             case "room-pill":
             case "user-pill":
-                return html + `<a href="https://matrix.to/#/${part.resourceId}">${part.text}</a>`;
+                return html + `[${part.text}](https://matrix.to/#/${part.resourceId})`;
         }
     }, "");
 }
 
+export function htmlSerializeIfNeeded(model) {
+    const md = mdSerialize(model);
+    const parser = new Markdown(md);
+    if (!parser.isPlainText()) {
+        return parser.toHTML();
+    }
+}
+
 export function textSerialize(model) {
     return model.parts.reduce((text, part) => {
         switch (part.type) {