diff --git a/src/components/views/rooms/BasicMessageComposer.js b/src/components/views/rooms/BasicMessageComposer.js
index 2b4693646a..99e7b8ea07 100644
--- a/src/components/views/rooms/BasicMessageComposer.js
+++ b/src/components/views/rooms/BasicMessageComposer.js
@@ -24,7 +24,7 @@ import {setSelection} from '../../../editor/caret';
 import {
     formatRangeAsQuote,
     formatRangeAsCode,
-    formatInline,
+    toggleInlineFormat,
     replaceRangeAndMoveCaret,
 } from '../../../editor/operations';
 import {getCaretOffsetAndText, getRangeForSelection} from '../../../editor/dom';
@@ -457,13 +457,13 @@ export default class BasicMessageEditor extends React.Component {
         this.historyManager.ensureLastChangesPushed(this.props.model);
         switch (action) {
             case "bold":
-                formatInline(range, "**");
+                toggleInlineFormat(range, "**");
                 break;
             case "italics":
-                formatInline(range, "*");
+                toggleInlineFormat(range, "*");
                 break;
             case "strikethrough":
-                formatInline(range, "<del>", "</del>");
+                toggleInlineFormat(range, "<del>", "</del>");
                 break;
             case "code":
                 formatRangeAsCode(range);
diff --git a/src/editor/operations.js b/src/editor/operations.js
index 4645e7d805..e2661faf59 100644
--- a/src/editor/operations.js
+++ b/src/editor/operations.js
@@ -100,10 +100,27 @@ export function formatRangeAsCode(range) {
     replaceRangeAndExpandSelection(range, parts);
 }
 
-export function formatInline(range, prefix, suffix = prefix) {
+export function toggleInlineFormat(range, prefix, suffix = prefix) {
     const {model, parts} = range;
     const {partCreator} = model;
-    parts.unshift(partCreator.plain(prefix));
-    parts.push(partCreator.plain(suffix));
+
+    const isFormatted = parts.length &&
+        parts[0].text.startsWith(prefix) &&
+        parts[parts.length - 1].text.endsWith(suffix);
+
+    if (isFormatted) {
+        // remove prefix and suffix
+        const partWithoutPrefix = parts[0].serialize();
+        partWithoutPrefix.text = partWithoutPrefix.text.substr(prefix.length);
+        parts[0] = partCreator.deserializePart(partWithoutPrefix);
+
+        const partWithoutSuffix = parts[parts.length - 1].serialize();
+        const suffixPartText = partWithoutSuffix.text;
+        partWithoutSuffix.text = suffixPartText.substring(0, suffixPartText.length - suffix.length);
+        parts[parts.length - 1] = partCreator.deserializePart(partWithoutSuffix);
+    } else {
+        parts.unshift(partCreator.plain(prefix));
+        parts.push(partCreator.plain(suffix));
+    }
     replaceRangeAndExpandSelection(range, parts);
 }